trans-2-chloro-7-oxabicyclo<4.1.0>heptane | 137940-88-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧杂环己烷
• 英文名称: trans-2-chloro-7-oxabicyclo<4.1.0>heptane
• 英文别名: 3-chloro-trans-1,2-epoxycyclohexane；trans-3-chloro-1,2-epoxycyclohexane；trans-2-chloro-7-oxabicyclo[4.1.0]heptane；(1R,2R,6R)-2-chloro-7-oxabicyclo[4.1.0]heptane
• CAS: 137940-88-6
• 化学式: C₆H₉ClO
• 分子量: 132.59
• InChiKey: CHBHHVKAAFZYEQ-PBXRRBTRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.55
• 重原子数：
  8.0
• 可旋转键数：
  0.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  12.53
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  trans-2-chloro-7-oxabicyclo<4.1.0>heptane 在 sodium hydroxide 作用下， 以 异丙醇 、 苯 为溶剂， 反应 132.0h， 生成 trans-1-pyrrolidinyl-2,3-epoxycyclohexane
  参考文献：
  名称：

  Regioselective and stereoselective syntheses of 1,2,3-triaminocyclohexane derivatives

  摘要：

  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 triamines were converted to amide derivatives. The structure of one of these amides (23) was confirmed by single crystal X-ray analysis.

  DOI：

  10.1021/jo00067a042
• 作为产物：
  描述：

  3-氯环己烯 在 二甲基二环氧乙烷 作用下， 以 丙酮 为溶剂， 生成 cis-2-chloro-7-oxabicyclo<4.1.0>heptane 、 trans-2-chloro-7-oxabicyclo<4.1.0>heptane
  参考文献：
  名称：

  Diastereoselectivity in the Epoxidation of Substituted Cyclohexenes by Dimethyldioxirane^1,2

  摘要：

  Three series of compounds based on the cyclohexene framework. have been epoxidized by dimethyldioxirane. A pronounced dependence of epoxide diastereoselectivity on substituent has been observed. In addition there is a solvent influence on this stereoselectivity. The results have been explained by invoking steric, H-bonding, and dipole-dipole influences on the epoxide stereochemistry.

  DOI：

  10.1021/jo951864j

文献信息

• Radical reactions of epoxides. Chlorine-atom abstraction from .alpha.- and .beta.-chloro epoxides by the triphenyltin radical
  作者：Kevin W. Krosley、Gerald Jay Gleicher、Gary E. Clapp

  DOI：10.1021/jo00029a011

  日期：1992.1

  The four isomers of chloroepoxypropane have been prepared, and their relative reactivities with triphenyltin hydride have been determined. The three alpha-chloroepoxypropanes react at a much slower rate than does epichlorohydrin, the only beta-chloro epoxide of the four. The nature of the increased reactivity for the beta-chloro epoxides has been investigated by studying two pair of diastereomeric beta-chloro epoxides, and a single acyclic beta-chloro ether. The results are discussed in terms of the inductive, resonance, and stereoelectronic effects of the epoxide.