2-fluorohex-4-enoic acid | 98064-44-9

• 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-fluorohex-4-enoic acid
• 英文别名: (E)-2-fluorohex-4-enoic acid
• CAS: 98064-44-9
• 化学式: C₆H₉FO₂
• 分子量: 132.135
• InChiKey: NONDFGAXGWFOQH-NSCUHMNNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  9
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-buten-2-yl fluoroacetate 在 三甲基氯硅烷 、 lithium diisopropyl amide 作用下， 生成 2-fluorohex-4-enoic acid
  参考文献：
  名称：

  Ester enolate Claisen rearrangements of allyl .alpha.-fluoroacetates and .alpha.-fluoropropanoates

  摘要：

  The ester enolate Claisen rearrangement of allyl alpha-fluoroacetates 1 forms 2-fluoroalkenoic acids 2 in good to excellent yield with good internal asymmetric induction. This selectivity was unexpected as stereoselective deprotonation of fluoroacetates is not normally possible. The selective formation of the required alpha-fluoro silyl ketene acetal 3 was found to result from the stereoselective rearrangement of the allyl alpha-fluoro-alpha-silylacetate isomer. Although silyl ketene acetals derived from alpha-fluoropropanoates 7 also rearranged, control of internal asymmetric induction was not possible.

  DOI：

  10.1021/jo00001a065

文献信息

• Facile diastereoselective ester enolate Claisen rearrangements of allyl fluoroacetates
  作者：John T. Welch、Janet S. Samartino

  DOI：10.1021/jo00219a056

  日期：1985.9
• Ester enolate Claisen rearrangements of allyl .alpha.-fluoroacetates and .alpha.-fluoropropanoates
  作者：John T. Welch、Janet S. Plummer、Tso Sheng Chou

  DOI：10.1021/jo00001a065

  日期：1991.1

  The ester enolate Claisen rearrangement of allyl alpha-fluoroacetates 1 forms 2-fluoroalkenoic acids 2 in good to excellent yield with good internal asymmetric induction. This selectivity was unexpected as stereoselective deprotonation of fluoroacetates is not normally possible. The selective formation of the required alpha-fluoro silyl ketene acetal 3 was found to result from the stereoselective rearrangement of the allyl alpha-fluoro-alpha-silylacetate isomer. Although silyl ketene acetals derived from alpha-fluoropropanoates 7 also rearranged, control of internal asymmetric induction was not possible.