(2R-trans)-3-<(Z)-pent-2-enyl>oxiranemethylchloride | 142795-86-6

• 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: (2R-trans)-3-<(Z)-pent-2-enyl>oxiranemethylchloride
• 英文别名: (2R-trans)-3-((Z)-pent-2-enyl)oxiranemethylchloride；(2R,3S)-2-(chloromethyl)-3-[(Z)-pent-2-enyl]oxirane
• CAS: 142795-86-6
• 化学式: C₈H₁₃ClO
• 分子量: 160.644
• InChiKey: URWNYAIZAQSWLH-FBJRUSGASA-N

物化性质

• 沸点：
  207.5±15.0 °C(Predicted)
• 密度：
  1.020±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (2R-trans)-3-<(Z)-pent-2-enyl>oxiranemethylchloride 在 Lindlar's catalyst 、 四(三苯基膦)钯 咪唑 、 copper(l) iodide 、 四丁基氟化铵 、 氢气 、 potassium carbonate 、 二乙胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 生成 (9Z,11E,13S,15Z)-13-羟基-9,11,15-十八碳三烯酸
  参考文献：
  名称：

  Stereoselective synthesis of (S)-13-hydroxy octadeca-(9Z, 11E)-di- and (9Z, 11E, 15Z)-trienoic acids : selfdefensive substances against rice blast disease

  摘要：

  A highly stereoselective synthesis of [(S)-coriolic acid] (1) and first total synthesis of (S)-15,16-didehydrocoriolic acid (2) by a Pd-degrees-CuI catalysed coupling of (S)-halovinylalcohol with acetylenic moiety is described. The required optically pure chlorovinylalcohols or bromovinylalcohols have been prepared from epoxy chlorides, obtained by Sharpless asymmetric epoxidation of allylic alcohols.

  DOI：

  10.1016/s0040-4020(01)80454-3
• 作为产物：
  描述：

  (2S-trans)-3-<(Z)-pent-2-enyl>oxirane methanol 在 四氯化碳 、 三苯基膦 作用下， 以88%的产率得到(2R-trans)-3-<(Z)-pent-2-enyl>oxiranemethylchloride
  参考文献：
  名称：

  Stereoselective synthesis of (S)-13-hydroxy octadeca-(9Z, 11E)-di- and (9Z, 11E, 15Z)-trienoic acids : selfdefensive substances against rice blast disease

  摘要：

  A highly stereoselective synthesis of [(S)-coriolic acid] (1) and first total synthesis of (S)-15,16-didehydrocoriolic acid (2) by a Pd-degrees-CuI catalysed coupling of (S)-halovinylalcohol with acetylenic moiety is described. The required optically pure chlorovinylalcohols or bromovinylalcohols have been prepared from epoxy chlorides, obtained by Sharpless asymmetric epoxidation of allylic alcohols.

  DOI：

  10.1016/s0040-4020(01)80454-3

文献信息

• Stereoselective synthesis of (S)-13-hydroxy octadeca-(9Z, 11E)-di- and (9Z, 11E, 15Z)-trienoic acids : selfdefensive substances against rice blast disease
  作者：J.S. Yadav、P.K. Deshpande、GVM Sharma

  DOI：10.1016/s0040-4020(01)80454-3

  日期：1992.1

  A highly stereoselective synthesis of [(S)-coriolic acid] (1) and first total synthesis of (S)-15,16-didehydrocoriolic acid (2) by a Pd-degrees-CuI catalysed coupling of (S)-halovinylalcohol with acetylenic moiety is described. The required optically pure chlorovinylalcohols or bromovinylalcohols have been prepared from epoxy chlorides, obtained by Sharpless asymmetric epoxidation of allylic alcohols.