(+/-)-1,2-epoxycyclohexane-1-carboxylic acid

• 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: (+/-)-1,2-epoxycyclohexane-1-carboxylic acid
• 英文别名: 1,2-epoxycyclohexane-1-carboxylic acid；2,3-Epoxycyclohexancarboxylic acid；(1R,6S)-7-oxabicyclo[4.1.0]heptane-1-carboxylic acid
• 化学式: C₇H₁₀O₃
• 分子量: 142.155
• InChiKey: WGDYTLFJZZPJNS-CAHLUQPWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (+/-)-1,2-epoxycyclohexane-1-carboxylic acid 在 sodium azide 、 水 、 copper(II) nitrate 作用下， 反应 0.25h， 生成 trans-2-Azido-1-hydroxycyclohexan-1-carboxylic acid
  参考文献：
  名称：

  Fringuelli, Francesco; Pizzo, Ferdinando; Vaccaro, Luigi, Synlett, 2000, # 3, p. 311 - 314

  摘要：

  DOI：
• 作为产物：
  描述：

  sodium;(1R,6S)-7-oxabicyclo[4.1.0]heptane-1-carboxylate 生成 (+/-)-1,2-epoxycyclohexane-1-carboxylic acid
  参考文献：
  名称：

  LEMMENS, J. M.;BLOMMERDE, W. W. J. M.;THIJS, L.;ZWANENBURG, B., J. ORG. CHEM., 1984, 49, N 12, 2231-2235

  摘要：

  DOI：

文献信息

• First One<i>-</i>Pot Copper-Catalyzed Synthesis of α-Hydroxy-β-Amino Acids in Water. A New Protocol for Preparation of Optically Active Norstatines
  作者：Francesco Fringuelli、Ferdinando Pizzo、Mauro Rucci、Luigi Vaccaro

  DOI：10.1021/jo034752y

  日期：2003.9.1

  alpha-Hydroxy-beta-amino acids were synthesized with excellent yields for the first time in water and by a simple procedure based on a copper catalytic cycle, which included the recovery and reuse of the catalyst and is possible to realize by using only water as reaction medium.
• InCl₃-Catalyzed Regio- and Stereoselective Thiolysis of α,β-Epoxycarboxylic Acids in Water
  作者：Francesco Fringuelli、Ferdinando Pizzo、Simone Tortoioli、Luigi Vaccaro

  DOI：10.1021/ol051582y

  日期：2005.9.1

  The thiolysis of alpha,beta-epoxycarboxylic acids la-e by thiois 2a,b is more efficient in water than in dichloromethane or SFC. At pH 9.0 phenylthiolate generally attacks the C-alpha carbon while at pH 4.0, and in the presence of InCl3 (10 mol %), the thiolysis is exclusively C-beta regioselective. In all cases, the processes are completely anti-diasteroselective, and the corresponding products 3, 4, and 5 have been isolated in good yields. Both water and catalysts have been recovered and reused.