sec-butyl (Z)-3-chloro-2-octenoate

• 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: sec-butyl (Z)-3-chloro-2-octenoate
• 英文别名: butan-2-yl (Z)-3-chlorooct-2-enoate
• 化学式: C₁₂H₂₁ClO₂
• 分子量: 232.751
• InChiKey: QDJBYZJKMHRMAX-LUAWRHEFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  15
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 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：

  1-庚炔 、 一氧化碳 、 仲丁醇 在 copper dichloride 、 palladium dichloride 作用下， 以 苯 为溶剂， 20.0 ℃ 、101.32 kPa 条件下， 反应 2.0h， 以49%的产率得到sec-butyl (Z)-3-chloro-2-octenoate
  参考文献：
  名称：

  Novel Stereospecific Synthesis of 3-Chloroacrylate Esters via Palladium-Catalyzed Carbonylation of Terminal Acetylenes

  摘要：

  A simple and effective method for the highly regio- and stereospecific synthesis of (Z)-3-chloroacrylate esters is described. Using terminal acetylenes and primary, secondary, and tertiary aliphatic alcohols as substrates, the carbonylation reactions were carried out under carbon monoxide (1 atm) at room temperature in the presence of a catalytic amount of PdCl2 and 3 equiv of cupric chloride. Isolated yields of (Z)-3-chloroacrylate esters ranging 6 om 30% to 72% were obtained. Our results show that the polarity of the alcohol-benzene solvent plays an important role in the stereochemistry of the products.

  DOI：

  10.1021/jo982345u

文献信息

• Novel Stereospecific Synthesis of 3-Chloroacrylate Esters via Palladium-Catalyzed Carbonylation of Terminal Acetylenes
  作者：Jinheng Li、Huanfeng Jiang、Aiqun Feng、Lanqi Jia

  DOI：10.1021/jo982345u

  日期：1999.8.1

  A simple and effective method for the highly regio- and stereospecific synthesis of (Z)-3-chloroacrylate esters is described. Using terminal acetylenes and primary, secondary, and tertiary aliphatic alcohols as substrates, the carbonylation reactions were carried out under carbon monoxide (1 atm) at room temperature in the presence of a catalytic amount of PdCl2 and 3 equiv of cupric chloride. Isolated yields of (Z)-3-chloroacrylate esters ranging 6 om 30% to 72% were obtained. Our results show that the polarity of the alcohol-benzene solvent plays an important role in the stereochemistry of the products.