19,19-dimethyleicosa-(8Z,11Z)-dienoic acid

• 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: 19,19-dimethyleicosa-(8Z,11Z)-dienoic acid
• 英文别名: (8Z,11Z)-19,19-dimethylicosa-8,11-dienoic acid
• 化学式: C₂₂H₄₀O₂
• 分子量: 336.558
• InChiKey: NNAJYCRHDZXUMQ-SFECMWDFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.3
• 重原子数：
  24
• 可旋转键数：
  16
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  methyl oct-7-ynoate 在 Lindlar's catalyst 喹啉 、 四氯化碳 、 lithium hydroxide 、 copper(l) iodide 、 锂硼氢 、 氢气 、 potassium carbonate 、 三苯基膦 、 sodium iodide 作用下， 以 四氢呋喃 、 甲醇 、 六甲基磷酰三胺 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 丙酮 、 苯 为溶剂， 反应 40.75h， 生成 19,19-dimethyleicosa-(8Z,11Z)-dienoic acid
  参考文献：
  名称：

  18-Iodooctadeca-(8 Z ,11 Z )-dienoic Acid as Useful Intermediate for the Synthesis of Special Lipoxygenase Substrates Bearing Bulky Substituents at the ω-Position

  摘要：

  18-Iodooctadeca-(8Z,11Z)-dienoic acid (7) was synthesized in five steps starting from methyl 10-bromodec-7-ynoate (2) in an overall yield of 53%. The synthetic procedure involves Cu(I)-catalyzed cross-coupling of propargylic bromide 2 with 7-octyn-1-ol (3), followed by hydrogenation of the coupling product 4 to Z,Z-diene 5 on Lindlar's catalyst and subsequent substitution of the OH- group of 5 with iodine. Coupling of the resulting iodide 7 with low-order organic cuprates [t-Bu2CuLi or (PhCH2)(2)CuMgCl] leads to 19,19-dimethyleicosa-(8Z,11Z)-dienoic acid (1a) and 19-phenylnonadeca-(8Z,11Z)-dienoic acid (1b), respectively. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)01032-7

文献信息

• 18-Iodooctadeca-(8 Z ,11 Z )-dienoic Acid as Useful Intermediate for the Synthesis of Special Lipoxygenase Substrates Bearing Bulky Substituents at the ω-Position
  作者：Igor V Ivanov、Nataliya V Groza、Stepan G Romanov、Hartmut Kuhn、Galina I Myagkova

  DOI：10.1016/s0040-4020(99)01032-7

  日期：2000.1

  18-Iodooctadeca-(8Z,11Z)-dienoic acid (7) was synthesized in five steps starting from methyl 10-bromodec-7-ynoate (2) in an overall yield of 53%. The synthetic procedure involves Cu(I)-catalyzed cross-coupling of propargylic bromide 2 with 7-octyn-1-ol (3), followed by hydrogenation of the coupling product 4 to Z,Z-diene 5 on Lindlar's catalyst and subsequent substitution of the OH- group of 5 with iodine. Coupling of the resulting iodide 7 with low-order organic cuprates [t-Bu2CuLi or (PhCH2)(2)CuMgCl] leads to 19,19-dimethyleicosa-(8Z,11Z)-dienoic acid (1a) and 19-phenylnonadeca-(8Z,11Z)-dienoic acid (1b), respectively. (C) 2000 Elsevier Science Ltd. All rights reserved.