(Z,Z)-1-Iodo-1,4-heptadiene | 150698-23-0

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 乙烯基卤化物
• 英文名称: (Z,Z)-1-Iodo-1,4-heptadiene
• 英文别名: (1Z,4Z)-1-iodohepta-1,4-diene
• CAS: 150698-23-0
• 化学式: C₇H₁₁I
• 分子量: 222.069
• InChiKey: AWWIRAYCOKDYRD-CWWKMNTPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  8
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  threo-(2R,3R)-1,2-Epoxy-3-(tosyloxy)tetradecane 、 (Z,Z)-1-Iodo-1,4-heptadiene 生成 2-(Iodomethyl)-3-undecyloxirane
  参考文献：
  名称：

  Alkylative epoxide rearrangement. A stereospecific approach to chiral epoxide pheromones

  摘要：

  The alkylative rearrangement of 1,2-epoxy-3-alkanol tosylates is applied to the synthesis of chiral epoxide pheromones. Attack at the terminal carbon atom of epoxy tosylates by lithioacetylenes and cyclization of the intermediate tosyloxy alcohols produces internal epoxides in high yield. The method is stereospecific: threo-epoxy tosylates give eL's-epoxides, and erythro-epoxy tosylates yield trans-epoxides. Several diastereomerically pure epoxides were prepared in high optical purity from chiral pool intermediates derived from sugars. Pheromone components prepared include (+/-)-cis-epoxyalkene 20 and both enantiomers of cis-epoxy diene 16, a female sex pheromone component of a number of lepidopteran species. These results demonstrate that alkylative rearrangement of 1,2-epoxy-3-alkanol tosylates complements existing methods for stereoselective synthesis of epoxides, including the Payne rearrangement and Sharpless epoxidation.

  DOI：

  10.1021/jo00071a026
• 作为产物：
  描述：

  1,4-庚二炔 在 (Sia)2BH 、 乙基溴化镁 、 碘 、 溶剂黄146 作用下， 反应 24.75h， 生成 (Z,Z)-1-Iodo-1,4-heptadiene
  参考文献：
  名称：

  Alkylative epoxide rearrangement. A stereospecific approach to chiral epoxide pheromones

  摘要：

  The alkylative rearrangement of 1,2-epoxy-3-alkanol tosylates is applied to the synthesis of chiral epoxide pheromones. Attack at the terminal carbon atom of epoxy tosylates by lithioacetylenes and cyclization of the intermediate tosyloxy alcohols produces internal epoxides in high yield. The method is stereospecific: threo-epoxy tosylates give eL's-epoxides, and erythro-epoxy tosylates yield trans-epoxides. Several diastereomerically pure epoxides were prepared in high optical purity from chiral pool intermediates derived from sugars. Pheromone components prepared include (+/-)-cis-epoxyalkene 20 and both enantiomers of cis-epoxy diene 16, a female sex pheromone component of a number of lepidopteran species. These results demonstrate that alkylative rearrangement of 1,2-epoxy-3-alkanol tosylates complements existing methods for stereoselective synthesis of epoxides, including the Payne rearrangement and Sharpless epoxidation.

  DOI：

  10.1021/jo00071a026

文献信息

• [EN] FATTY ACID FUMARATE DERIVATIVES AND THEIR USES<br/>[FR] DÉRIVÉS FUMARATÉS D'ACIDES GRAS ET LEURS UTILISATIONS
  申请人：CATABASIS PHARMACEUTICALS INC

  公开号：WO2011085211A1

  公开（公告）日：2011-07-14

  The invention relates to Fatty Acid Fumarate Derivatives; compositions comprising an effective amount of a Fatty Acid Fumarate Derivative; and methods for treating or preventing cancer, a metabolic disorder or neurodegenerative disorder comprising the administration of an effective amount of a Fatty Acid Fumarate Derivative.