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Journal of The Chemical Society C: Organic最新文献

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Stobbe condensation with dimethyl glutarate. Syntheses of some polycyclic compounds 与戊二酸二甲酯缩合。一些多环化合物的合成
Journal of The Chemical Society C: Organic Pub Date : 1971-01-01 DOI: 10.1039/J39710000661
A. Chatterjee, S. Banerjee, A. Sarker, B. Hazra
{"title":"Stobbe condensation with dimethyl glutarate. Syntheses of some polycyclic compounds","authors":"A. Chatterjee, S. Banerjee, A. Sarker, B. Hazra","doi":"10.1039/J39710000661","DOIUrl":"https://doi.org/10.1039/J39710000661","url":null,"abstract":"Dimethyl glutarate has been successfully utilised in the Stobbe condensation with some typical keto-esters such as (1), (2), (18), and (23). The Stobbe products, isolated in reasonably good yield, have subsequently been utilised for the preparation of polycyclic compounds.","PeriodicalId":17245,"journal":{"name":"Journal of The Chemical Society C: Organic","volume":"11 1","pages":"661-667"},"PeriodicalIF":0.0,"publicationDate":"1971-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"78780591","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 1
Syntheses of 6-deoxy-3-O-methyl-D-gulose and 6-deoxy-3-O-methyl-L-mannose(L-acofriose) 6-脱氧-3- o -甲基-d -葡萄糖和6-脱氧-3- o -甲基- l-甘露糖(l- acofose)的合成
Journal of The Chemical Society C: Organic Pub Date : 1971-01-01 DOI: 10.1039/J39710000613
J. S. Brimacombe, N. Robinson, J. M. Webber
{"title":"Syntheses of 6-deoxy-3-O-methyl-D-gulose and 6-deoxy-3-O-methyl-L-mannose(L-acofriose)","authors":"J. S. Brimacombe, N. Robinson, J. M. Webber","doi":"10.1039/J39710000613","DOIUrl":"https://doi.org/10.1039/J39710000613","url":null,"abstract":"A new and convenient synthesis of 6-deoxy-3-O-methyl-D-gulose (16) has been achieved by a route involving methylation and partial hydrolysis of 1,2 : 5,6-di-O-isopropylidene-α-D-gulofuranose (9) with acid to give 1,2-O-isopropylidene-3-O-methyl-α-D-gulofuranose (11). The diol (11) was converted into 6-deoxy-3-O-methyl-D-gulose (16) by ring-opening of the derived epoxide (14) with lithium aluminium hydride followed by hydrolysis with acid of the 6-deoxy-1,2-O-isopropylidene-3-O-methyl-α-D-gulofuranose (15) so formed. L-Acofriose (6-deoxy-3-O-methyl-L-mannose)(25), a sugar found in certain cardiac glycosides, has been synthesised for the first time. Treatment of either 6-O-benzoyl-1,2-O-isopropylidene-3-O-methyl-5-O-methyl-sulphonyl-α-D-gulofuranose (21) or the debenzoylated compound (22) with sodium methoxide afforded 5,6-an-hydro-1,2-O-isopropylidene-3-O-methyl-β-L-mannofuranose (23), which yielded L-acofriose (25) on reductive ring-opening and hydrolysis with acid. Attempts to obtain entry into the L-mannose series by means of a benzoate displacement reaction on the 6-deoxy-1,2-O-isopropylidene-3-O-methyl-α-D-gulofuranose 5-sulphonates (17) and (18) were unsuccessful.","PeriodicalId":17245,"journal":{"name":"Journal of The Chemical Society C: Organic","volume":"8 1","pages":"613-618"},"PeriodicalIF":0.0,"publicationDate":"1971-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"76312431","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 3
Heterocyclic studies. Part XVII. Some 2,3-dihydroimidazo-[1,2-a]- and [1,2-c]-pyrimidines 杂环的研究。第十七章的一部分。一些2,3-二氢咪唑-[1,2-a]-和[1,2-c]-嘧啶
Journal of The Chemical Society C: Organic Pub Date : 1971-01-01 DOI: 10.1039/J39710000679
J. Clark, T. Ramsden
{"title":"Heterocyclic studies. Part XVII. Some 2,3-dihydroimidazo-[1,2-a]- and [1,2-c]-pyrimidines","authors":"J. Clark, T. Ramsden","doi":"10.1039/J39710000679","DOIUrl":"https://doi.org/10.1039/J39710000679","url":null,"abstract":"A number of 7-substituted 2,3-dihydro-5-methyl-8-nitroimidazo[1,2-c]pyrimidines (III; X = OH, OMe, SH, NH2, NHMe, NMe2, or NH·CH2Ph) were synthesised by treatment of 4-chloro-6-(2-chloroethylamino)-2-methyl-5-nitropyrimidine with nucleophilic reagents and cyclisation of the resulting intermediates. Some 5-(substituted amino)-2,3-dihydro-7-methyl-8-nitroimidazo[1,2-c]pyrimidines (V; X = NHEt or NH·CH2Ph) were similarly prepared from 2-chloro-4-(2-chloroethylamino)-6-methyl-5-nitropyrimidine.Cyclisation of 4-(substituted amino)-2-(2-chloroethylamino)-6-methyl-5-nitropyrimidines gave 7-(substituted amino)-2,3-dihydro-5-methyl-6-nitroimidazo[1,2-a]pyrimidines (VII; X = NH2, NHMe, NHEt, or NH·CH2Ph) rather than the 7-methyl isomers (VIII). One of the 7-methyl isomers (VIII; X = NHEt) was synthesised by an alternative route. 1 H N.m.r. spectra of 14 of the compounds are recorded.","PeriodicalId":17245,"journal":{"name":"Journal of The Chemical Society C: Organic","volume":"69 1","pages":"679-683"},"PeriodicalIF":0.0,"publicationDate":"1971-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"76363584","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 5
Benzyne reaction. Part XI. Novel syntheses of 2-(3-substituted phenyl)cycloalkanones by the benzyne reaction 苯炔的反应。苯基反应合成2-(3-取代苯基)环烷酮的新方法
Journal of The Chemical Society C: Organic Pub Date : 1971-01-01 DOI: 10.1039/J39710001051
T. Kametani, K. Kigasawa, M. Hiiragi, T. Hayasaka, O. Kusama
{"title":"Benzyne reaction. Part XI. Novel syntheses of 2-(3-substituted phenyl)cycloalkanones by the benzyne reaction","authors":"T. Kametani, K. Kigasawa, M. Hiiragi, T. Hayasaka, O. Kusama","doi":"10.1039/J39710001051","DOIUrl":"https://doi.org/10.1039/J39710001051","url":null,"abstract":"The benzyne reaction of o-halogenoanisole with cyclic carbonyl compounds (II)–(VII) gave 2-(3-substituted phenyl)cycloalkanones.","PeriodicalId":17245,"journal":{"name":"Journal of The Chemical Society C: Organic","volume":"17 1","pages":"1051-1052"},"PeriodicalIF":0.0,"publicationDate":"1971-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"87695332","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 5
The Dimroth rearrangement. Part XIII. The small effect of p-substitution on rearrangement rates for 1,2-dihydro-2-imino-1-methyl-5-phenylpyrimidines 迪姆罗斯重排。十三。对取代对1,2-二氢-2-亚胺-1-甲基-5-苯基嘧啶重排速率的影响较小
Journal of The Chemical Society C: Organic Pub Date : 1971-01-01 DOI: 10.1039/J39710000250
D. J. Brown, B. England
{"title":"The Dimroth rearrangement. Part XIII. The small effect of p-substitution on rearrangement rates for 1,2-dihydro-2-imino-1-methyl-5-phenylpyrimidines","authors":"D. J. Brown, B. England","doi":"10.1039/J39710000250","DOIUrl":"https://doi.org/10.1039/J39710000250","url":null,"abstract":"Rates have been measured for the Dimroth rearrangements of 1,2-dihydro-2-imino-1-methyl-5-(p-substituted phenyl)pyrimidines. Although the mesomeric effects of the p-substituents are severely attenuated by the presence of a considerable interplanar angle between the benzene and pyrimidine rings, rearrangement rates decrease in the order NO2 > F > Cl > Br > Me > OMe > NH2 > NMe2, following qualitatively the σρ values for the groups. 1,2-Dihydro-2-imino-1,4,6-trimethyl-5-phenylpyrimidine and its p-nitro- and p-amino-derivatives, for which u.v. spectra and pKa values indicate even less through-conjugation, behave similarly.Syntheses are described for the three trimethylated imines and their products of rearrangement; for 1,2-dihydro-2-imino-1,6-dimethylpyrimidine, which rearranges more rapidly than its 1,4-dimethyl-isomer; and for 1,2-dihydro-2-imino-5-methoxy-1-methylpyrimidine, required for comparison of its rearrangement with that of the p-methoxyphenyl analogue and with those of quinazoline analogues. Structures were confirmed by 1H n.m.r. spectra.","PeriodicalId":17245,"journal":{"name":"Journal of The Chemical Society C: Organic","volume":"22 1","pages":"250-256"},"PeriodicalIF":0.0,"publicationDate":"1971-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"87703314","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 4
Chemistry of hop constituents. Part XXXVII. Separation and characterisation of cis- and trans-isohumulone and deduction of absolute configurations 啤酒花成分的化学。37章部分。顺式和反式异葎草酮的分离、表征及绝对构型的推导
Journal of The Chemical Society C: Organic Pub Date : 1971-01-01 DOI: 10.1039/J39710002412
D. Laws, J. Elvidge
{"title":"Chemistry of hop constituents. Part XXXVII. Separation and characterisation of cis- and trans-isohumulone and deduction of absolute configurations","authors":"D. Laws, J. Elvidge","doi":"10.1039/J39710002412","DOIUrl":"https://doi.org/10.1039/J39710002412","url":null,"abstract":"Superior conditions for the isomerisation of (–)-humulone into (+)-cis- and (–)-trans-isohumulone are described, together with a highly effective separation on Kieselgel H. The isohumulones are fully characterised for the first time, the mechanism of their formation is discussed, and their absolute configuration is deduced. That of the cis- and trans-humulinic acids follows.","PeriodicalId":17245,"journal":{"name":"Journal of The Chemical Society C: Organic","volume":"22 1","pages":"2412-2415"},"PeriodicalIF":0.0,"publicationDate":"1971-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"87831335","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 4
Organic reactions in strong alkalis. Part V. Alkali fusion of epoxides and ethers 强碱中的有机反应。第五部分环氧化物和醚的碱熔合
Journal of The Chemical Society C: Organic Pub Date : 1971-01-01 DOI: 10.1039/J39710001840
M. Ansell, I. Shepherd, B. Weedon
{"title":"Organic reactions in strong alkalis. Part V. Alkali fusion of epoxides and ethers","authors":"M. Ansell, I. Shepherd, B. Weedon","doi":"10.1039/J39710001840","DOIUrl":"https://doi.org/10.1039/J39710001840","url":null,"abstract":"The results obtained from the alkali fusion of long-chain epoxy-acids indicate the occurrence of at least four different reaction pathways, one of which, a β-elimination reaction, appears to be novel for unactivated epoxides. This particular reaction is also shown to occur with simple acylic ethers, as exemplified by 11-alkoxyundecanoic acids.","PeriodicalId":17245,"journal":{"name":"Journal of The Chemical Society C: Organic","volume":"24 1","pages":"1840-1846"},"PeriodicalIF":0.0,"publicationDate":"1971-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"87060200","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 3
Circular dichroism of some optically active steroidal iodides 某些旋光性甾体碘化物的圆二色性
Journal of The Chemical Society C: Organic Pub Date : 1971-01-01 DOI: 10.1039/J39710001466
R. Cookson, J. Coxon
{"title":"Circular dichroism of some optically active steroidal iodides","authors":"R. Cookson, J. Coxon","doi":"10.1039/J39710001466","DOIUrl":"https://doi.org/10.1039/J39710001466","url":null,"abstract":"A series of steroid iodides show the expected absorption maximum at 260–270 nm in their u.v. spectra, and a corresponding maximum in their circular dichroism curves at slightly shorter wavelengths, the sign of which for the secondary iodides usually agrees with that recently reported for alkyl iodides. However, adjacent hetero-substituents or unsaturation may reverse the sign.","PeriodicalId":17245,"journal":{"name":"Journal of The Chemical Society C: Organic","volume":"2016 1","pages":"1466-1468"},"PeriodicalIF":0.0,"publicationDate":"1971-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"88267088","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 3
The preparation of derivatives of dibenz[b,d]oxepin 二苯并[b,d]氧平衍生物的制备
Journal of The Chemical Society C: Organic Pub Date : 1971-01-01 DOI: 10.1039/J39710002098
T. A. Harrow, C. Harrison, W. Williamson
{"title":"The preparation of derivatives of dibenz[b,d]oxepin","authors":"T. A. Harrow, C. Harrison, W. Williamson","doi":"10.1039/J39710002098","DOIUrl":"https://doi.org/10.1039/J39710002098","url":null,"abstract":"A wide range of derivatives of dibenz[b,d]oxepin have been prepared from the 7(6H)-ketone, which is readily obtained from biphenyl-2-yloxyacetic acid.","PeriodicalId":17245,"journal":{"name":"Journal of The Chemical Society C: Organic","volume":"11 1","pages":"2098-2104"},"PeriodicalIF":0.0,"publicationDate":"1971-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"88357573","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 3
Diels–Alder reactions with alkyl coumalates 与烷基甲酸酯的Diels-Alder反应
Journal of The Chemical Society C: Organic Pub Date : 1971-01-01 DOI: 10.1039/J39710002268
A. Bahl, W. Kemp
{"title":"Diels–Alder reactions with alkyl coumalates","authors":"A. Bahl, W. Kemp","doi":"10.1039/J39710002268","DOIUrl":"https://doi.org/10.1039/J39710002268","url":null,"abstract":"Alkyl coumalates (methyl and ethyl 2-oxopyran-5-carboxylates) have been treated with a wide variety of dienophiles in Diels–Alder reactions. In all cases, extrusion of carbon dioxide occurred and multiple adducts were usually obtained; in one case a spontaneous loss of molecular hydrogen was observed. Thus methyl coumalate reacted with p-benzoquinone to give dimethyl anthraquinone-2,6-dicarboxylate (or the 2,7-analogue); with acetylenedicarboxylates, benzene-1,2,4-tricarboxylates were obtained; with benzyne, methyl naphthalene-2-carboxylate was formed. The adducts with maleic anhydride were 7-methoxycarbonylbicyclo[2,2,2]oct-7-ene-2,3;5,6-tetracarboxylic dianhydride and the 2-ethoxycarbonyl homologue. An analogous reaction with azodicarboxylate esters led (for example) to pentamethyl 2,3,5,6-tetra-azabicyclo[2,2,2]oct-7-ene-2,3,5,6,7-pentacarboxylate.","PeriodicalId":17245,"journal":{"name":"Journal of The Chemical Society C: Organic","volume":"466 1","pages":"2268-2271"},"PeriodicalIF":0.0,"publicationDate":"1971-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"86156329","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 4
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