(2-cyclohexylethyl)fumaric acid | 5469-50-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (2-cyclohexylethyl)fumaric acid
• 英文别名: (E)-2-(2-cyclohexylethyl)but-2-enedioic acid
• CAS: 5469-50-1
• 化学式: C₁₂H₁₈O₄
• 分子量: 226.273
• InChiKey: QTBWCJKDRVFXFZ-CSKARUKUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2-cyclohexylethyl)fumaric acid 、 (2R)-bornane-10,2-sultam 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 以66%的产率得到
  参考文献：
  名称：

  Asymmetric synthesis of 2-substituted butane-1,4-diols by hydrogenation of homochiral fumaramide derivatives

  摘要：

  Diastereoselective hydrogenation of homochiral fumaramides 1 derived from (2R)-Oppolzer's sultam was observed by analysis of the H-1 NMR spectra of the succinamide mixtures with de's of 77-88%. Reduction of these succinamides using LiAlH4 gave the corresponding (2S)-butane-1,4-diols and established that addition of hydrogen takes place selectively on the re-face of 14 fumaramides 1. The stereoselectivity was confirmed by estimating the ee's from the F-19 NMR spectra of the Mosher's diesters of the diols. This methodology was applied to the synthesis of selected pyrrolidine natural products in homochiral form. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.11.023
• 作为产物：
  描述：

  diethyl (2-cyclohexylethyl)fumarate 在 potassium carbonate 作用下， 以 乙醇 、 水 为溶剂， 生成 (2-cyclohexylethyl)fumaric acid
  参考文献：
  名称：

  Asymmetric synthesis of 2-substituted butane-1,4-diols by hydrogenation of homochiral fumaramide derivatives

  摘要：

  Diastereoselective hydrogenation of homochiral fumaramides 1 derived from (2R)-Oppolzer's sultam was observed by analysis of the H-1 NMR spectra of the succinamide mixtures with de's of 77-88%. Reduction of these succinamides using LiAlH4 gave the corresponding (2S)-butane-1,4-diols and established that addition of hydrogen takes place selectively on the re-face of 14 fumaramides 1. The stereoselectivity was confirmed by estimating the ee's from the F-19 NMR spectra of the Mosher's diesters of the diols. This methodology was applied to the synthesis of selected pyrrolidine natural products in homochiral form. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.11.023

文献信息

• Asymmetric synthesis of 2-substituted butane-1,4-diols by hydrogenation of homochiral fumaramide derivatives
  作者：Samaila Jawaid、Louis J. Farrugia、David J. Robins

  DOI：10.1016/j.tetasy.2004.11.023

  日期：2004.12

  Diastereoselective hydrogenation of homochiral fumaramides 1 derived from (2R)-Oppolzer's sultam was observed by analysis of the H-1 NMR spectra of the succinamide mixtures with de's of 77-88%. Reduction of these succinamides using LiAlH4 gave the corresponding (2S)-butane-1,4-diols and established that addition of hydrogen takes place selectively on the re-face of 14 fumaramides 1. The stereoselectivity was confirmed by estimating the ee's from the F-19 NMR spectra of the Mosher's diesters of the diols. This methodology was applied to the synthesis of selected pyrrolidine natural products in homochiral form. (C) 2004 Elsevier Ltd. All rights reserved.