(Z)-2-fluoro-3,5,5-trimethylhex-2-enoic acid ethyl ester | 113307-21-4

• 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: (Z)-2-fluoro-3,5,5-trimethylhex-2-enoic acid ethyl ester
• 英文别名: ethyl (Z)-2-fluoro-3,5,5-trimethylhex-2-enoate
• CAS: 113307-21-4
• 化学式: C₁₁H₁₉FO₂
• 分子量: 202.269
• InChiKey: GRIADKCQMKDFPD-HJWRWDBZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4,4-二甲基-2-戊酮 、 二溴氟乙酸乙酯 在 diethylzinc 、 氯化铵 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 12.0h， 生成 (E)-2-fluoro-3,5,5-trimethylhex-2-enoic acid ethyl ester 、 (Z)-2-fluoro-3,5,5-trimethylhex-2-enoic acid ethyl ester
  参考文献：
  名称：

  Diethylzinc-Mediated One-Step Stereoselective Synthesis of α-Fluoroacrylates from Aldehydes and Ketones. Two Different Pathways Depending on the Carbonyl Partner

  摘要：

  A efficient methodology allowing the one-pot stereoselective synthesis of alpha-fluoroacrylates, based on the addition of ethyl dibromofluoroacetate to a carbonyl derivative using diethylzinc as organometallic mediator, is described. Two different pathways have been identified depending on the involved carbonyl partner. In the case of aldehydes, an E2-type mechanism has been identified, whereas ketones go through an E1cb-type mechanism.

  DOI：

  10.1021/jo900422m

文献信息

• Diethylzinc-Mediated One-Step Stereoselective Synthesis of α-Fluoroacrylates from Aldehydes and Ketones. Two Different Pathways Depending on the Carbonyl Partner
  作者：G. Lemonnier、L. Zoute、G. Dupas、J.-C. Quirion、P. Jubault

  DOI：10.1021/jo900422m

  日期：2009.6.5

  A efficient methodology allowing the one-pot stereoselective synthesis of alpha-fluoroacrylates, based on the addition of ethyl dibromofluoroacetate to a carbonyl derivative using diethylzinc as organometallic mediator, is described. Two different pathways have been identified depending on the involved carbonyl partner. In the case of aldehydes, an E2-type mechanism has been identified, whereas ketones go through an E1cb-type mechanism.