cis (4R,5S)-4,5-epoxynonane

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 环氧化物
• 英文名称: cis (4R,5S)-4,5-epoxynonane
• 英文别名: (2S,3R)-2-butyl-3-propyloxirane
• 化学式: C₉H₁₈O
• 分子量: 142.241
• InChiKey: IKNXPNNMKVOEMV-BDAKNGLRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  10
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  5-壬酮 在 磺酰氯 、 Rhodotorula glutinis 、 水 、 potassium carbonate 作用下， 以 四氯化碳 、 N,N-二甲基甲酰胺 为溶剂， 反应 73.0h， 生成 cis (4R,5S)-4,5-epoxynonane
  参考文献：
  名称：

  Chemoenzymatic synthesis of α-halogeno-3-octanol and 4-or 5-nonanols. Application to the preparation of chiral epoxides

  摘要：

  A study of the microbiological reduction of different alpha-halogenoketones (4-chloro-3-octanone, 4-chloro-5-nonanone, 5-bromo-4-nonanone and 5-chloro-4-nonanone) with several strains of microorganism showed great difficulty in reducing ketone functions located in the middle of carbon chains. However, by choosing the appropriate microorganism, several enantiomerically pure diastereoisomers of the corresponding halohydrins have been obtained and were transformed into chiral epoxides. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00470-4

文献信息

• Highly stereoselective reduction of β-oxosulfonium salts ---synthesis of trans epoxides---
  作者：Masayuki Shimagaki、Yuji Matsuzaki、Isaburo Hori、Tadashi Nakata、Takeshi Oishi

  DOI：10.1016/s0040-4039(01)81517-3

  日期：——
• Chemoenzymatic synthesis of α-halogeno-3-octanol and 4-or 5-nonanols. Application to the preparation of chiral epoxides
  作者：Pascale Besse、Tania Sokoltchik、Henri Veschambre

  DOI：10.1016/s0957-4166(98)00470-4

  日期：1998.12

  A study of the microbiological reduction of different alpha-halogenoketones (4-chloro-3-octanone, 4-chloro-5-nonanone, 5-bromo-4-nonanone and 5-chloro-4-nonanone) with several strains of microorganism showed great difficulty in reducing ketone functions located in the middle of carbon chains. However, by choosing the appropriate microorganism, several enantiomerically pure diastereoisomers of the corresponding halohydrins have been obtained and were transformed into chiral epoxides. (C) 1998 Elsevier Science Ltd. All rights reserved.