Benzoic acid (Z)-(S)-1-formyl-hex-3-enyl ester | 853929-53-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Benzoic acid (Z)-(S)-1-formyl-hex-3-enyl ester
• 英文别名: [(Z,2S)-1-oxohept-4-en-2-yl] benzoate
• CAS: 853929-53-0
• 化学式: C₁₄H₁₆O₃
• 分子量: 232.279
• InChiKey: YFORJGWKLZFTEE-DXTPNHAXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Benzoic acid (Z)-(S)-1-formyl-hex-3-enyl ester 在 四(三苯基膦)钯 chromium dichloride 、 正丙胺 、 copper(l) iodide 、 silver nitrate 作用下， 以 四氢呋喃 、 甲醇 、 水 、 苯 为溶剂， 生成 C₃₇H₃₈O₆
  参考文献：
  名称：

  First total synthesis of 7(S),17(S)-Resolvin D5, a potent anti-inflammatory docosanoid

  摘要：

  The first total synthesis of 7(S),17(S)-Resolvin D5, a lipid mediator derived from docosahexacnoic acid, has been achieved. The chiral centers were generated via a Co-salen hydrolytic kinetic resolution of a terminal epoxide with > 99% ee. Key steps include Takai olefination, Pd-0/Cu-I coupling and simultaneous deprotection and ester cleavage with lipase from Candida rugosa. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.03.175
• 作为产物：
  描述：

  [(2S)-1-phenylmethoxyhept-4-yn-2-yl] benzoate 在 Lindlar catalyst 三氯化铝 、 氢气 、 三氧化硫吡啶 、 二甲基亚砜 、 三乙胺 、 乙硫醇 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 生成 Benzoic acid (Z)-(S)-1-formyl-hex-3-enyl ester
  参考文献：
  名称：

  First total synthesis of 7(S),17(S)-Resolvin D5, a potent anti-inflammatory docosanoid

  摘要：

  The first total synthesis of 7(S),17(S)-Resolvin D5, a lipid mediator derived from docosahexacnoic acid, has been achieved. The chiral centers were generated via a Co-salen hydrolytic kinetic resolution of a terminal epoxide with > 99% ee. Key steps include Takai olefination, Pd-0/Cu-I coupling and simultaneous deprotection and ester cleavage with lipase from Candida rugosa. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.03.175

文献信息

• First total synthesis of 7(S),17(S)-Resolvin D5, a potent anti-inflammatory docosanoid
  作者：Ana R. Rodríguez、Bernd W. Spur

  DOI：10.1016/j.tetlet.2005.03.175

  日期：2005.5

  The first total synthesis of 7(S),17(S)-Resolvin D5, a lipid mediator derived from docosahexacnoic acid, has been achieved. The chiral centers were generated via a Co-salen hydrolytic kinetic resolution of a terminal epoxide with > 99% ee. Key steps include Takai olefination, Pd-0/Cu-I coupling and simultaneous deprotection and ester cleavage with lipase from Candida rugosa. (c) 2005 Elsevier Ltd. All rights reserved.