ethyl (6S,7E,9R,10S)-6,9,10-trihydroxyoctadecenoate | 1312759-19-5

• 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: ethyl (6S,7E,9R,10S)-6,9,10-trihydroxyoctadecenoate
• 英文别名: ethyl (E,6S,9R,10S)-6,9,10-trihydroxyoctadec-7-enoate
• CAS: 1312759-19-5
• 化学式: C₂₀H₃₈O₅
• 分子量: 358.519
• InChiKey: DNFAAFRTVHGGHV-ZCLIZIHASA-N

物化性质

• 沸点：
  507.7±50.0 °C(Predicted)
• 密度：
  1.026±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  25
• 可旋转键数：
  17
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  87
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl (6S,7E,9R,10S)-6,9,10-trihydroxyoctadecenoate 在 potassium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 4.0h， 以95%的产率得到(6S,7E,9R,10S)-6,9,10-trihydroxyoctadec-7-enoic acid
  参考文献：
  名称：

  First asymmetric synthesis of the oxylipin, (6S,9R,10S)-6,9,10-trihydroxyoctadeca-7E-enoic acid

  摘要：

  A brief and facile synthesis of the title compound has been developed using cyclohexylideneglyceraldehyde as a chiral template. The key steps in the synthesis were: (i) two highly diastereoselective organometallic addition reactions to the aldehyde to furnish the required synthons with the appropriate stereogenic centers, and (ii) their cross metathesis to give the E-olefin geometry of the target compound. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.02.008
• 作为产物：
  描述：

  octyllithium 在 吡啶 、 咪唑 、 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 4-二甲氨基吡啶 、 正丁基锂 、 四丁基氟化铵 、 水 、 potassium carbonate 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 为溶剂， 反应 99.0h， 生成 ethyl (6S,7E,9R,10S)-6,9,10-trihydroxyoctadecenoate
  参考文献：
  名称：

  First asymmetric synthesis of the oxylipin, (6S,9R,10S)-6,9,10-trihydroxyoctadeca-7E-enoic acid

  摘要：

  A brief and facile synthesis of the title compound has been developed using cyclohexylideneglyceraldehyde as a chiral template. The key steps in the synthesis were: (i) two highly diastereoselective organometallic addition reactions to the aldehyde to furnish the required synthons with the appropriate stereogenic centers, and (ii) their cross metathesis to give the E-olefin geometry of the target compound. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.02.008

文献信息

• First asymmetric synthesis of the oxylipin, (6S,9R,10S)-6,9,10-trihydroxyoctadeca-7E-enoic acid
  作者：Sucheta Chatterjee、Seema V. Kanojia、Subrata Chattopadhyay、Anubha Sharma

  DOI：10.1016/j.tetasy.2011.02.008

  日期：2011.2

  A brief and facile synthesis of the title compound has been developed using cyclohexylideneglyceraldehyde as a chiral template. The key steps in the synthesis were: (i) two highly diastereoselective organometallic addition reactions to the aldehyde to furnish the required synthons with the appropriate stereogenic centers, and (ii) their cross metathesis to give the E-olefin geometry of the target compound. (C) 2011 Elsevier Ltd. All rights reserved.