Regioselective and stereoselective syntheses of 1,2,3-triaminocyclohexane derivatives
Regioselective and stereoselective syntheses of 1,2,3-triaminocyclohexane derivatives
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1,2,3-三氨基环己烷衍生物的区域选择性和立体选择性合成
DOI：
10.1021/jo00067a042
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发表时间：
1993
影响因子：
3.6
通讯作者：
J. Szmuszkovicz
中科院分区：
文献类型：
--
作者：
Shikai Zhao;J. Freeman;C. Chidester;P. Vonvoigtlander;S. Mizsak;J. Szmuszkovicz
介绍了反式和顺式-3-溴-1,2-环氧环己烷与吡咯烷的反应。而在反式环氧化物2的情况下，二氨基醇3是在苯中得到的，顺式环氧化物5意外地在苯中得到溴氨基醇7。化合物7可以在DMF中用吡咯烷转化为3。反式3-氯-1,2-环氧环己烷11是异构二氨基醇4的来源。二氨基醇3和4被用来生产含有两个吡咯烷和一个甲胺残基的三胺（14,15,22）。溴氨基醇7用于制备含有两个甲胺和一个吡咯烷残基的三胺（25）。其中一种酰胺的结构通过单晶x射线分析得到了证实
The reactions of trans- and cis-3-bromo-1,2-epoxycyclohexanes with pyrrolidine are described. While in the case of the trans-epoxide 2 the diamino alcohol 3 was obtained in benzene, the cis-epoxide 5 unexpectedly led to bromo amino alcohol 7 in benzene. Compound 7 could be converted to 3 using pyrrolidine in DMF. The trans-3-chloro-1,2-epoxycyclohexane 11 was the source of the isomeric diamino alcohol 4. The diamino alcohols 3 and 4 were used to produce triamines containing two pyrrolidine and one methylamine residues (14, 15, 22). The bromo amino alcohol 7 was used to prepare a triamine containing two methylamine and one pyrrolidine residues (25). The structures of one of these amides was confirmed by single crystal X-ray analysis