methyl (9Z,12Z,15E)-octadeca-9,12,15-trienoate | 37929-05-8

• 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: methyl (9Z,12Z,15E)-octadeca-9,12,15-trienoate
• 英文别名: octadeca-9c,12c,15t-trienoic acid methyl ester；9cis.12cis.15trans-Octadecatriensaeure-methylester
• CAS: 37929-05-8
• 化学式: C₁₉H₃₂O₂
• 分子量: 292.462
• InChiKey: DVWSXZIHSUZZKJ-IISVKSLHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  21
• 可旋转键数：
  14
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (8Z,11Z,14E)-1-bromoheptadeca-8,11,14-triene 在 盐酸 作用下， 以 二甲基亚砜 为溶剂， 反应 0.33h， 生成 methyl (9Z,12Z,15E)-octadeca-9,12,15-trienoate
  参考文献：
  名称：

  Synthesis of (9Z,12Z,15E)- and (9E,12Z,15Z)-octadecatrienoic acids and their [1-14C]-radiolabelled analogs

  摘要：

  In order to study the effect of the double bonds geometry of linolenic acid (18:3 n-3) on its biological activities, (9Z,12Z,15E)- and (9E,12Z,15Z)-octadecatrienoic acids, found in many refined vegetable oils, were made by total synthesis. Synthesis of 18:3 Delta 9c, 12c, 15t involves a Wittig reaction between 3-(2-tetrahydropyranyloxy)-propylphosphonium salt and (E)-3-hexenal which gave (3Z,6E)-1-(2-tetrahydropyranyloxy)-nonadiene in 66% yield. The transformation of the ether function to a phosphonium salt, followed by a Wittig reaction with 8-(t-butyldimethylsilyloxy)-octanal afforded a C17 trienic ether. A one-carbon homologation of its corresponding bromide with potassium cyanide followed by hydrolysis in basic medium furnished 18:3 Delta 9c, 12c, 15t in high isomeric purity and high radiochemical purity for its [1-C-14]-labelled analog. In the synthesis of 18:3 Delta 9t, 12c, 15c, a Wittig reaction between (E)-6-(2-tetrahydropyranyloxy)-hex-3-enylphosphonium salt, obtained in three steps from 6-(2-tetrahydropyranyloxy)-hex-3-yn-l-ol and (Z)-3-hexenal afforded a C12 (E,Z,Z)-trienic ether. After a six-carbon homologation of this ether, in three steps, the resulting nitrile was hydrolyzed to (9E,12Z, 15Z)-octadecatrienoic acid (99% purity) (99% radiochemical purity of its [1-C-14]-labelled analog).

  DOI：

  10.1016/0009-3084(94)90058-2

文献信息

• WO2007/12190
  申请人：——

  公开号：——

  公开（公告）日：——
• RAKOFF, H.;EMKEN, E. A., CHEM. AND PHYS. LIPIDS, 1982, 31, N 3, 215-225
  作者：RAKOFF, H.、EMKEN, E. A.

  DOI：——

  日期：——
• Synthesis of (9Z,12Z,15E)- and (9E,12Z,15Z)-octadecatrienoic acids and their [1-14C]-radiolabelled analogs
  作者：Thierry Eynard、Jean-Michel Vatèle、Didier Poullain、Jean-Pierre Noël、Jean-Michel Chardigny、Jean-Louis Sébédio

  DOI：10.1016/0009-3084(94)90058-2

  日期：1994.12

  In order to study the effect of the double bonds geometry of linolenic acid (18:3 n-3) on its biological activities, (9Z,12Z,15E)- and (9E,12Z,15Z)-octadecatrienoic acids, found in many refined vegetable oils, were made by total synthesis. Synthesis of 18:3 Delta 9c, 12c, 15t involves a Wittig reaction between 3-(2-tetrahydropyranyloxy)-propylphosphonium salt and (E)-3-hexenal which gave (3Z,6E)-1-(2-tetrahydropyranyloxy)-nonadiene in 66% yield. The transformation of the ether function to a phosphonium salt, followed by a Wittig reaction with 8-(t-butyldimethylsilyloxy)-octanal afforded a C17 trienic ether. A one-carbon homologation of its corresponding bromide with potassium cyanide followed by hydrolysis in basic medium furnished 18:3 Delta 9c, 12c, 15t in high isomeric purity and high radiochemical purity for its [1-C-14]-labelled analog. In the synthesis of 18:3 Delta 9t, 12c, 15c, a Wittig reaction between (E)-6-(2-tetrahydropyranyloxy)-hex-3-enylphosphonium salt, obtained in three steps from 6-(2-tetrahydropyranyloxy)-hex-3-yn-l-ol and (Z)-3-hexenal afforded a C12 (E,Z,Z)-trienic ether. After a six-carbon homologation of this ether, in three steps, the resulting nitrile was hydrolyzed to (9E,12Z, 15Z)-octadecatrienoic acid (99% purity) (99% radiochemical purity of its [1-C-14]-labelled analog).