3-buten-2-yl fluoroacetate | 98064-41-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 3-buten-2-yl fluoroacetate
• 英文别名: But-3-en-2-yl 2-fluoroacetate
• CAS: 98064-41-6
• 化学式: C₆H₉FO₂
• 分子量: 132.135
• InChiKey: YTOREGNFMJJWFF-UHFFFAOYSA-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：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  3-丁烯-2-醇 、 氟代乙酰氯 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 以87%的产率得到3-buten-2-yl fluoroacetate
  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
• WELCH, JOHN T.;PLUMMER, JANET S.;CHOU, TSO-SHENG, J. ORG. CHEM., 56,(1991) N, C. 353-359
  作者：WELCH, JOHN T.、PLUMMER, JANET S.、CHOU, TSO-SHENG

  DOI：——

  日期：——
• WELCH, J. T.;SAMARTINO, J. S., J. ORG. CHEM., 1985, 50, N 19, 3663-3665
  作者：WELCH, J. T.、SAMARTINO, J. S.

  DOI：——

  日期：——
• 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.

表征谱图