(2S,3R)-2-Chloromethyl-3-((Z)-nonadec-10-enyl)-oxirane | 439140-28-0

• 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: (2S,3R)-2-Chloromethyl-3-((Z)-nonadec-10-enyl)-oxirane
• 英文别名: (2S,3R)-2-(chloromethyl)-3-[(Z)-nonadec-10-enyl]oxirane
• CAS: 439140-28-0
• 化学式: C₂₂H₄₁ClO
• 分子量: 357.02
• InChiKey: YSUKEHQWUZNAIY-LUCICDSHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.6
• 重原子数：
  24
• 可旋转键数：
  18
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.91
• 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：

  (2S,3R)-2-Chloromethyl-3-((Z)-nonadec-10-enyl)-oxirane 在 lithium amide 作用下， 以 氨 为溶剂， 以95%的产率得到(R,Z)-docos-13-en-1-yn-3-ol
  参考文献：
  名称：

  First total synthesis of strongylodiol A

  摘要：

  A new cytotoxic long-chain acetylenic alcohol (R)-strongylodiol A, originally isolated from an Okinawan marine sponge of the genus Strongylophora, has been synthesized for the first time using commercially available 1,10-decanediol. The key step of this process involves the selective introduction of the (R)-configuration at C-6 which was achieved by P-elimination of epoxychlorides. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)00066-7
• 作为产物：
  描述：

  [(2R,3R)-((Z)-3-Nonadec-10-enyl)-oxiranyl]-methanol 在 四氯化碳 、 三苯基膦 作用下， 以80%的产率得到(2S,3R)-2-Chloromethyl-3-((Z)-nonadec-10-enyl)-oxirane
  参考文献：
  名称：

  First total synthesis of strongylodiol A

  摘要：

  A new cytotoxic long-chain acetylenic alcohol (R)-strongylodiol A, originally isolated from an Okinawan marine sponge of the genus Strongylophora, has been synthesized for the first time using commercially available 1,10-decanediol. The key step of this process involves the selective introduction of the (R)-configuration at C-6 which was achieved by P-elimination of epoxychlorides. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)00066-7

文献信息

• First total synthesis of strongylodiol A
  作者：J.S Yadav、Rajesh Kumar Mishra

  DOI：10.1016/s0040-4039(02)00066-7

  日期：2002.2

  A new cytotoxic long-chain acetylenic alcohol (R)-strongylodiol A, originally isolated from an Okinawan marine sponge of the genus Strongylophora, has been synthesized for the first time using commercially available 1,10-decanediol. The key step of this process involves the selective introduction of the (R)-configuration at C-6 which was achieved by P-elimination of epoxychlorides. (C) 2002 Elsevier Science Ltd. All rights reserved.