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YUKIO SUGIMURA, KIMIO IINO, HARUMITSU KUWANO, NOBUO SOMA, YUKICHI KISH ...
1972 Volume 20 Issue 12 Pages
2515-2521
Published: December 25, 1972
Released on J-STAGE: March 31, 2008
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4, 5-Benzotropone reacted with malononitrile in acetic anhydride or in ethanol-piperidine to afford 8, 8-dicyano-3, 4-benzoheptafulvene (6a). On the other hand, 2, 3-benzotropone reacted with malononitrile in acetic anhydride to afford 8, 8-dicyano-1, 2-benzoheptafulvene (8a) and 6-cyano-7-amino-3, 4-benzobicyclo[3, 2, 2]nona-3, 5, 8-trien-2-one (9a). The reaction mechanism revealed that 8a was afforded not only by Knoevenagel reaction but also by Michael addition at 4-position of 2, 3-benzotropone.
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YOSHIO SASAKI, MIYOKO SUZUKI
1972 Volume 20 Issue 12 Pages
2522-2527
Published: December 25, 1972
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The eigenvalues and eigenvectors of the MeR (R=F, OH, NH
2, Me, H, CN, CHO and NO
2) series were presented by the CNDO/2 method. There values were applied to the theoretical treatment of C-13 chemical shift under the three conditions, namely, (2) ΔE=10 eV, (b) ΔE=the ionization potential, (c) ΔE=ε
i-ε
j, and compared with the experimental data. Of the three conditions, the method (a)and (b) afford the perturbation effect of the substituent group.
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AKIRA TSUJI, TSUKINAKA YAMANA, YUZO MIZUKAMI
1972 Volume 20 Issue 12 Pages
2528-2541
Published: December 25, 1972
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pH-Rate profiles for the hydrolyses of o-hydroxyphenylacetamide (I) and o-hydroxyphenylpropionamide (II) have been determined at 90.0° (μ=0.6). At pH region between 4 and 8, I and II were found to have their pH-independent reactions to form the corresponding lactones. The kinetic evidence indicates that the rate-determining step for the lactonizations of these amides is the breakdown of the tetrahedral intermediate. The mechanisms of intramolecular alcoholyses of amides were compared with alcoholic-and phenolic-hydroxyl amides, and the relative reactivities of these hydroxyamides were discussed.
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TARO OGISO, MAMORU SUGIURA, YOSHIO KATO
1972 Volume 20 Issue 12 Pages
2542-2550
Published: December 25, 1972
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Mucor lipase purified was transformed into water-insoluble forms by attaching the enyzme to insoluble carriers covalently and with ionic bond, and some characteristics and kinetics behavior of DEAE-cellulose-lipase were studied in comparing to the soluble form. There was very little difference between the free and bound forms of the lipase with respect to optimum pH, optimum temperature, substrate specificity, action pattern, Km value and the energy of activation, indicating that the immobilization did not alter the substantial properties of the lipase. However, a highly increase in pH and heat stability, a decrease in inhibitory effect of n-bromosuccinimide and iodine, and of the susceptibility towards the action of some proteases were found by the immobilization. The lipolytic activity of the bound lipase was enhanced 4-6 times higher at lower concentration of bile salts, whereas the activity was inhitited at higher concentration. The bound lipase little released from the carrier during lipolysis at 37° for 12-48 hr, although the inactivation caused on it.
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TEISUKE OKANO, MIKIO GOTO, HITOSHI MATSUMOTO, AKIRA TAKADATE
1972 Volume 20 Issue 12 Pages
2551-2560
Published: December 25, 1972
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Near-ultraviolet and visible absorption spectra of quinoline 1-oxides in aqueous and nonaqueous solutions were measured, with emphasis on 10 kinds of compounds known to be carcinogenic or non-carcinogenic, and the absorption bands were classified according to Platt's nomenclature system. Absorption spectra of 4-nitroquinoline 1-oxide and its derivatives in nonaqueous solution were separately assigned to the
1L
b and
1L
a bands, in addition to
1B
b band. Molecular orbitals of quinoline 1-oxides were calculated by the simple LCAO-MO method. From the energy difference between molecular orbitals, each of the absorption bands was assigned to the electronic transition between specified molecular orbitals. The following relationship between band assignment and electronic transition was found for 4-nitroquinoline 1-oxide and its 2-methyl, 6-chloro, 6-carboxy, and 6-nitro derivatives :
1L
b band, ψ
m→ψ
m+1 ;
1L
a band, ψ
m-1→ψ
m+1 ;
1B
b band, ψ
m→ψ
m+2 ;
1B
a band (for 6-nitro derivative), ψ
m-1→ψ
m+2.
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KENSAKU KINOSHITA, TAKESHI FUJITA
1972 Volume 20 Issue 12 Pages
2561-2569
Published: December 25, 1972
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The metabolic fate of
57Co-methylcobalamin after oral or intraperitoneal administration to rats and guinea pigs (25 μg/kg) have been studied. From fecal excretion test, the intestinal absorption of
57Co-methylcobalamin seems to be less than 5% of dose and the time course of fecal excretion was differed in both species. The fecal excretion in guinea pig was slower and more continuous than in rat. The urinary excretion of radioactivity after intraperitoneal administration was lower in rat (41% of dose during the first 24 hr) than in guinea pig (68%) and the main excretion form in urine was
57Co-methylcobalamin itself in both species.
57Co-methylcobalamin might be stable in intestinal tract and transfered through intestinal wall in unchanged form. Tissue distribution of radioactivity after intraperitoneal administration was higher in rat than in guinea pig generally and the highest uptake in rat was found in kidney, while the trend of higher uptake in guinea pig was found in liver. The biological conversion of
57Co-methylcobalamin incorporated in liver and kidney into other cobamide analogues has been studied and it has been evident that
57Co-methylcobalamin was transformed to 5, 6-dimethylbenzimidazolylcobamide coenzyme and hydroxocobalamin in both species.
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TETSUJI KAMETANI, SHIROSHI SHIBUYA, SHOJI HIRATA, KEIICHIRO FUKUMOTO
1972 Volume 20 Issue 12 Pages
2570-2574
Published: December 25, 1972
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Treatment of 5, 6, 13, 13a-tetrahydro-10-hydroxy-2, 3, 11-trimethoxy-8H-dibenzo[a, g]-quinolizine (10) with trifluoroacetic anhydride afforded 2-(2-trifluoroacetaminoethyl-4, 5-dimethoxyphenyl)-6-hydroxy-5-methoxyindene (13). 5, 6, 13, 13a-Tetrahydro-12-hydroxy-2, 3, 11-trimethoxy-8H-dibezo[a, g]quinolizie (11) under the same conditions as in the case of 10 yielded 2-(2-trifluoroacetaminoethyl-4, 5-dimethoxyphenyl)-4-hydroxy-5-methoxyindene (18).
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TAKUZO HISANO, MASATAKA ICHIKAWA, GO KITO, TOMOYUKI NISHI
1972 Volume 20 Issue 12 Pages
2575-2584
Published: December 25, 1972
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The preparation of series of 2-pyridyl-4(3H)-quinazolinones is described. Some of them showed a hypnotic action in mice when given orally. Studies on the structure-activity relationship demonstrated that 2-pyridyl, 3-pyridyl, and 4-pyridyl substitution at 2 position of quinazolinone ring, and o-, m-, and p-substitution of the aromatic ring at 3 position are suitable for manifestation of hypnotic activity. The order of potency of activities produced by the difference in the position of substitution of substituents at 2 and 3 position decreased in the order of 4-pyridyl, o-tolyl>3-pyridyl, o-tolyl>2-pyridyl, o-tolyl. The anthranilates of these 4(3H)-quinazolinones were inactive. A maximum hypnotic effect accompanied with other potent pharmacological properties was observed in 2-(4-pyridyl)-3-o-tolyl-4(3H)-quinazolinone (14), the potency of which was equal to or stronger than Methaqualone in mice.
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KOUICHI KATAYAMA, TAKESHI FUJITA
1972 Volume 20 Issue 12 Pages
2585-2592
Published: December 25, 1972
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The intestinal absorption of 1', 2', -(
3H)-coenzyme Q
10 (
3H-Q-10) was studied in rats with cannulated thoracic duct and the effect of surface-active agents on the lymphatic absorption of
3H-Q-10 was determined. The amount of radioactivity absorbed via lymphatics during the first 48 hr was 1 % of the dose after oral administration of
3H-Q-10 dissolved in sesame oil or 20 mM sodium taurocholate, and was 1.5% of the dose of
3H-Q-10 dissolved by HCO-60. Assuming that the amount of radioactivity recovered from urine (0.481%) and liver (0.004%) might come from the radioactivity absorbed via portal vein, the total amount of the radioactivity absorbed via portal vein and lymphatics was approximately 2% of the dose of
3H-Q-10 dissolved by HCO-60 and the main route in absorption of
3H-Q-10 was lymphatics. The model for lymphatic absorption of
3H-Q-10 was proposed by kinetic analysis of the data.
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MASAFUMI YOSHIMOTO, NOBORU ISHIDA, YUKICHI KISHIDA
1972 Volume 20 Issue 12 Pages
2593-2602
Published: December 25, 1972
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Novel 2-ethynylcyclopropanecarboxylates were synthesized by the reaction of acetylene sulfonium ylids with α, β-unsaturated esters. An unequivocal synthesis and degradation were performed to determine the structure and stereochemistry.
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HITOSHI UNO, AKIRA IRIE, KATSUHIKO HINO
1972 Volume 20 Issue 12 Pages
2603-2606
Published: December 25, 1972
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Thiazolo[2, 3-f]theophyllines were synthesized by ring closure of 8-(acylmethyl)-thiotheophyllines. And their structures were determined by desulfurization with Raney Ni. Their Mass Spectrum fragmentations were also described.
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TOSHIO NAMBARA, YASUHIKO MATSUKI, MOTOKO KURATA
1972 Volume 20 Issue 12 Pages
2607-2612
Published: December 25, 1972
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Biosynthesis of 16-epiestriol glucosiduronate was attempted with liver and small intestine preparations from several different species. Incubation of
3H-16-epiestriol with microsomal or supernatant fractions in the presence of UDPGA yielded the glucosiduronates whose separation was readily attained by column chromatography on Amberlite XAD-2 resin. The structure of 16-epiestriol glucosiduronates was elucidated by direct comparison with the synthetic samples on the thin-layer chromatogram, leading to the acetate-methyl ester for the reverse isotope dilution method and hyrolytic cleavage with β-glucuronidase. There could be seen the distinct difference in the position of conjugation depending upon the species and organ as listed in Table IV and V. The specificity and multiplicity of UDP-glucuronyltranferase toward 16-epiestriol as an acceptor have been discussed.
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YOSHIHISA IWAMOTO, ICHIJI MIFUCHI
1972 Volume 20 Issue 12 Pages
2613-2617
Published: December 25, 1972
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A mutant of Candida utilis containing about five fold amount of cytochrome c than that of a parental strain was induced by N-methyl-N'-nitro-N-nitrosoguanidine. In this mutant (I-35), repression of cytochrome c synthesis by glucose was not observed, while the parental strain was repressed cytochrome c content by glucose in medium. The amount of cytochrome c in the mutant varied from phase to phase in its growth stage. Iso-2-cytochrome c was found both in the parent and the cytochrome c abundant mutant, and was about 10% of total amount of cytochrome c in the both strains.
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MITSUO NAGANO, JUNZO TOBITSUKA, TAKASHI MATSUI, KOZO OYAMADA
1972 Volume 20 Issue 12 Pages
2618-2625
Published: December 25, 1972
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The reactions of some alkoxycarbonyl isothiocyanates (2) with 2-aminothiazol (15) afforded thiazolo[3, 2-a]-S-triazine-4-thio-2-one (27), N-alkoxycarbonyl-N'-(2-thiazolyl)-thuoureas (A), alkyl-N-(2-thiazolyl)carbamates (B), N-alkoxycarbonyl thiocarbamates (C) and thiocyanic acid (31). However, in the case using phenoxycarbonyl isothiocyanate (59), the corresponding 1 : 1 adduct of (59) and (15) could not be obtained, but thiazolo-[3, 2-a]-s-thiazine-2-thio-4-one (32) was isolated, besides the cyclic compound (27), thiazolyl carbamate (60) and phenol.
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MITSUO NAGANO, TAKASHI MATSUI, JUNZO TOBITSUKA, KOZO OYAMADA
1972 Volume 20 Issue 12 Pages
2626-2633
Published: December 25, 1972
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The Reactions of ethoxycarbonyl isothiocyanate (23) with 4, 5-substituted 2-amino-thiazoles (24) afforded thiazolo [3, 2-a]-s-triazine-4-thio-2-ones (25), N-alkoxycarbonyl-N'-(2-thiazolyl)thioureas (26), alkyl-N-(2-thiazolyl)carbamates (27), ethyl-N-ethoxycarbonyl thiocarbamate (28) and thiocyanic acid (7). However, in the cases of the amines whose pKa values were smaller than that of 2-aminothiazole (24-a) or the amines which had some substituents on the 4-position of 24, the corresponding cyclic compounds (25) could not be obtained. A series of these phenomena was discussed in connection with basicities of 2-aminothiazoles (24) and the steric hindrance of the substituents on the 4-position of 24.
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SADAO OIDA, YOSHIHIKO OHASHI, AKIRA YOSHIDA, EIJI OHKI
1972 Volume 20 Issue 12 Pages
2634-2641
Published: December 25, 1972
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Refering to the previous work,
2) tetracyclic diol (3a) derived from siccanin (1), an antifungal antibiotic, was converted back into 1; and 3a was shown as an important synthetic intermediate for 1. On the other hand, as a preliminary study on synthesis of 1, cyclization of 1-methyl-2-(2, 6-dihydroxy-4-methylbenzyl)cyclohexanol (19 or 20) or 1-methylene-2-(2, 6-dihydroxy-4-methylbenzyl)cyclohexane (21) was carried out, forming a hexahydroxanthene derivative (23) whose structure involves the B, C, and D rings of siccanin (1).
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AKIRA YOSHIDA, SADAO OIDA, YOSHIHIKO OHASHI, CHIHIRO TAMURA, EIJI OHKI
1972 Volume 20 Issue 12 Pages
2642-2650
Published: December 25, 1972
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A synthesis of a perhydrobenzo[a]xanthene related to the skeleton of siccanin (3), an antifungal antibiotic, was described. A series of reactions starting from Δ
1(9)-octal-2-one (5) gave 1-(2-hydroxy-6-methoxy-4-methylbenzyl)-2-methylene-9-vinyl-cis-decalin (19), whose acid-catalysed cyclization reaction yielded a perhydrobenzo[a]xanthene (20a) with cis/anti/cis ring junctures. The structure of the latter compound was determined by three dimensional X-ray analysis of its brosyl derivative (20c)
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YUTAKA KIRINO, TAKAO KWAN
1972 Volume 20 Issue 12 Pages
2651-2660
Published: December 25, 1972
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One-electron oxidations of L-ascorbic acid and its analogs or derivatives were investigated by electron spin resonance (ESR). ESR spectra were obtained from compounds not substituted at 3-hydroxyl group. Two types of spectra were observed when Ti
3+-H
2O
2 system was used as the oxidizing agent. On the basis of the comparison of the ESR spectra obtained from the compounds examined with one another and their pH-profile, the radical structures and hyperfine couplings were determined. One type of spectrum corresponds to an anion radical and the other corresponds to a neutral species. Variation in line width and the finding that only an anion radical was detected when oxidizing reagents other than Ti
3+-H
2O
2 system was used, were interpreted in terms of the complex formation of radicals with metal ions coexisting in the reaction system.
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MINORU SEKIYA, SHUICHI TAKAYAMA, KEIICHI ITO, JIRO SUZUKI, KUNIO SUZUK ...
1972 Volume 20 Issue 12 Pages
2661-2668
Published: December 25, 1972
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Conversion of varied N-methyl and N-formyl derivatives of p-phenylenediamine to other kinds of analogous compounds with increase and decrease of N-methyl has been found to occur on heating at 175-180° with the high-boiling liquid formates composed of formic acid and trialkylamine. From investigation on this reaction the formate reagents have been introduced to affect N-methylation of formanilides in a course entirely different from the known demethylation by the same reagents.
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MINORU SEKIYA, SHUICHI TAKAYAMA, JIRO SUZUKI, KUNIO SUZUKI
1972 Volume 20 Issue 12 Pages
2669-2677
Published: December 25, 1972
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Mechanistic investigation on the previously reported N-methylation of formanilides effected by the constant-boiling liquid of the formates composed of formic acid and trialkylamine has been made by introducing isotopic tracer method into the representative reaction of p-phenylenediamine derivatives. In accord with the isotopic tracer results a mechanism of this formate reaction has been proposed. It has been revealed that the formate reagents affect the conversion of N-formyul, which suffers interchange in the formate medium, into N-methyl acting as reducing agent.
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YOSHIO ITO, YOSHIKI HAMADA, MINORU HIROTA
1972 Volume 20 Issue 12 Pages
2678-2685
Published: December 25, 1972
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Nitration of 2-anilinopyridine (II) with a mixed acid afforded 2-(2-nitroanilino)pyridine (III), 2-(4'-nitroanilino)pyridine (V), and 2-(2', 4'-dinitroanilino)pyridine (VI), in a poor yield, but that with excess nitric acid gave VI alone in a high yield. Nitration of II with acetyl nitrate gave VI, 2-(2', 4'-dinitroanilino)-5-nitropyridine (IX), and 2-(2', 4'-dinitroanilino)-3, 5-dinitropyridine (X). II showed different reactivity in nitration with a strong acidic medium and a mild medium like nitric acid in acetic anhydride. In order to elucidate the reactivity of II in each case, it was assumed that II takes an anilinopyridinium ion form in a strongly acidic medium and a neutral anilinopyridine form in the mild acidic medium.
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YOSHIKI HAMADA, YOSHIO ITO, TOKUO MIZUNO, MINORU HIROTA
1972 Volume 20 Issue 12 Pages
2686-2693
Published: December 25, 1972
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Simple LCAO-MO calculations were carried out on 2-anilinopyridine and several of the nitro derivatives, and the reaction path of the nitration of the parent anilinopyridine is estimated. The nitration takes place exclusively on the ortho and the para positions of the benzene nucleus when it is carried out in mixed acid, so the reactive species in this condition is estimated to be the monoprotonated species (i.e. 2-anilinopyridinium ion). On the other hand, the reactive species for the nitration by acetyl nitrate in inert aprotic solvents must be the 2-anilinopyridine, not the 2-pyridone-anil, tautomer of the neutral molecule. The reaction intermediate to form polynitrated products is also discussed.
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MUSHADJI SUTAMIHARADJA TJANG, AKIHIRO ISHIKURA, JUNKO NAITO, ISAO ISHI ...
1972 Volume 20 Issue 12 Pages
2694-2700
Published: December 25, 1972
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(1) A new metabolite was isolated in crystalline form from urine of rats injected with anthranilic acid. (2) This compound was identified as anthranilamide by chemical and physical analyses. (3) It has been found that the urine from rats injected with anthranilic acid contained anthranilamide in the range of 1.2-2.5%. (4) It was found that a large part of anthranilamide was transformed into other metabolites, and onlu 5% of the dose could be found as free anthranilamide. (5) The possible new metabolic pathway of anthranilic acid was discussed.
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TERUO KUTSUMA, YASUO SEKINE, KAZUO HUJIYAMA, YOSHIRO KOBAYASHI
1972 Volume 20 Issue 12 Pages
2701-2706
Published: December 25, 1972
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2-(Methoxycarbonylmethyl)- (I), 2-cyanomethyl- (VIII), and 2-phenacyl-isoquinoli nium bromide (XII) react with dimethyl acetylenedicarboxylate, in the presence of tri-ethylamine, and form the corresponding 1, 10b-dihydropyrrolo[2, 1-a]isoquinoline (IV, X, and XIV) and aromatized compounds (V, XI, and XV). Treatment of IV, X, and XIV with hydrogen chloride in benzene, with subsequent neutralization with potassium carbonate, results in isomerization to stable 2, 3-trans-2, 3-dihydropyrrolo[2, 1-a]isoquinolines (VII, XX, and XXI).
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HATSUMI NIIZATO, YOSHIO UENO, SHOJI TAKEMURA
1972 Volume 20 Issue 12 Pages
2707-2709
Published: December 25, 1972
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A convenient method for β-bromo-formyloxylation of olefins with N, N-dibromobenzenesulfonamide and formic acid was developed. Cyclohexene, styrene, trans-β-methyl-styrene, and 1-hexene were made to react to give trans-2-brmocyclohexyl formate (I), 2-bormo-1-phenylethyl formate (II), erythro-2-bromo-1-phenylpropyl formate (III), and 1-bromo-2-hexyl fromate (IV).
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ISAO INGAKI, SUEO HISADA, SANSEI NISHIBE
1972 Volume 20 Issue 12 Pages
2710-2718
Published: December 25, 1972
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As the components of the stems of Trachelospermum asiaticum NAKAI var. intermedium NAKAI, arctiin (I), matairesinoside(VI) and tracheloside(VIII) were isolated. VI was elucidated as 4, 4'-dihydroxy-3, 3'-dimethoxy-lignan-olid(9, 9')-4'-β-D-glucopyranoside. In addition the formula of VIII established by T.Takano, et al. as C
36H
50O
18 was reexamined and revised to C
27H
34O
12·1/2H
2O. VIII gave trachelogenin(X), C
21H
24O
7, mp 139-141° and D-glucose by acid or emulsin hydrolysis. From chemical and physical data structure of X was proposed as 4', 8'-dihydroxy-3, 4, 3'-trimethoxy-lignan-olid(9, 9')(Xa) or 4, 8'-dihydroxy-3, 3', 4'-trimethoxylignan-olid(9, 9')(Xb). In this paper structure of methyltranchelogenin(XI) with absolute configuration was determined to be 8(S), 8'(S)-8'-dihydroxy-3, 4, 3', 4'-tetramethoxy-lignan-olid(9, 9'). Now we suggest two possible structures for VIII; 8(S), 8'(S)-4', 8'-dihydroxy-3, 4, 3', -trimethoxy-lignan-olid(9, 9')-4'-β-D-glucopyranoside(VIIIa) or 8(S), 8'(S)-4, 8'-dihydroxy-3, 3', 4'-trimethoxy-lignan-olid(9, 9')-4-β-D-glucopyranoside(VIIIb).
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EIICHI FUJIHIRA, NORIMITSU TAKAHASHI, AKIRA MINATO, KYOKO UENOYAMA, TA ...
1972 Volume 20 Issue 12 Pages
2719-2721
Published: December 25, 1972
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TERUO TAKAYANAGI, KENICHI YAMAMOTO, TAKAO KWAN
1972 Volume 20 Issue 12 Pages
2721-2723
Published: December 25, 1972
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TATUSO OZAWA, SHIN-ICHI SAITO, ISAO TOMITA
1972 Volume 20 Issue 12 Pages
2723-2727
Published: December 25, 1972
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KUNITOSHI YOSHIHIRA, CHIKAKO TAKAHASHI, SETSUKO SEKITA(SAKAKI), SHINSA ...
1972 Volume 20 Issue 12 Pages
2727-2728
Published: December 25, 1972
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MASASHI OKADA, KYOKO KIMURA, YUKIO SAITO
1972 Volume 20 Issue 12 Pages
2729-2731
Published: December 25, 1972
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TOKUJI SUZUKI, YUKIYA SAITOH, SADAO ISOZAKI, RYOZO ISHIDA
1972 Volume 20 Issue 12 Pages
2731-2735
Published: December 25, 1972
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MITSURU FURUKAWA, YOKO KOJIMA, SEISHI TSUIJI, SEIGORO HAYASHI
1972 Volume 20 Issue 12 Pages
2738-2739
Published: December 25, 1972
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YASUO OHTSUKA, HIROYUKI AKITA, AKIRA TAHARA
1972 Volume 20 Issue 12 Pages
2740-2741
Published: December 25, 1972
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KOICHI NAKAZAWA, KUMIKO WADA(IMAGAWA)
1972 Volume 20 Issue 12 Pages
2741-2743
Published: December 25, 1972
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