2-chloro-4-phenyl-pent-2-enoic acid isopropyl ester

• 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: 2-chloro-4-phenyl-pent-2-enoic acid isopropyl ester
• 英文别名: propan-2-yl (Z)-2-chloro-4-phenylpent-2-enoate
• 化学式: C₁₄H₁₇ClO₂
• 分子量: 252.741
• InChiKey: WSDHHUDOKAALBZ-LCYFTJDESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 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：

  二氯乙酸异丙酯 在 samarium diiodide 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 3.17h， 生成 2-chloro-4-phenyl-pent-2-enoic acid isopropyl ester
  参考文献：
  名称：

  Synthesis of ( Z )-α-chloro-α,β-unsaturated esters with complete stereoselectivity promoted by samarium diiodide

  摘要：

  Stereoselective beta-elimination in alpha,alpha-dichloro-beta-hydroxyesters 2 was achieved by using samarium diiodide, yielding (Z)-alpha-chloro-alpha, beta-unsaturated esters 1. The starting compounds 2 were easily prepared by reaction of the lithium enolate of ethyl dichloroacetate with different aldehydes at -78 degreesC. A mechanism to explain this process is proposed. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.04.101

文献信息

• Synthesis of ( Z )-α-chloro-α,β-unsaturated esters with complete stereoselectivity promoted by samarium diiodide
  作者：José M. Concellón、Mónica Huerta、Ricardo Llavona

  DOI：10.1016/j.tetlet.2004.04.101

  日期：2004.6

  Stereoselective beta-elimination in alpha,alpha-dichloro-beta-hydroxyesters 2 was achieved by using samarium diiodide, yielding (Z)-alpha-chloro-alpha, beta-unsaturated esters 1. The starting compounds 2 were easily prepared by reaction of the lithium enolate of ethyl dichloroacetate with different aldehydes at -78 degreesC. A mechanism to explain this process is proposed. (C) 2004 Elsevier Ltd. All rights reserved.