N-pivaloylproline ethyl ester | 75041-78-0

• 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: N-pivaloylproline ethyl ester
• 英文别名: ethyl (2S)-1-(2,2-dimethylpropanoyl)pyrrolidine-2-carboxylate
• CAS: 75041-78-0
• 化学式: C₁₂H₂₁NO₃
• 分子量: 227.304
• InChiKey: CPXLUDFDHAUOKT-VIFPVBQESA-N

物化性质

• 沸点：
  328.2±35.0 °C(Predicted)
• 密度：
  1.058±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-pivaloylproline ethyl ester 在 劳森试剂 、 吡啶 作用下， 以 甲苯 为溶剂， 生成 (S)-ethyl 1-(2,2-dimethylpropanethioyl)pyrrolidine-2-carboxylate
  参考文献：
  名称：

  Dakin-West Reaction of N-Thioacylprolines Using Trifluoroacetic Anhydride: Novel Access to 5-Trifluoromethylthiazoles

  摘要：

  The reaction between N-thioacylprolines and trifluoro acetic anhydride in the presence of pyridine afforded a good yield of 5-trifluoromethylthiazoles. This reaction proceeded through mesoionic 1,3-thiazolium-5-olates, followed by cleavage of the pyrrolidine ring and the formation of thiazoles, introducing a trifluoromethyl group at position 5 in the thiazole ring.

  DOI：

  10.3987/com-13-12904
• 作为产物：
  描述：

  L-脯氨酸 在 氯化亚砜 、 三乙胺 、 sodium hydroxide 作用下， 以 水 为溶剂， 生成 N-pivaloylproline ethyl ester
  参考文献：
  名称：

  Dakin-West Reaction of N-Thioacylprolines Using Trifluoroacetic Anhydride: Novel Access to 5-Trifluoromethylthiazoles

  摘要：

  The reaction between N-thioacylprolines and trifluoro acetic anhydride in the presence of pyridine afforded a good yield of 5-trifluoromethylthiazoles. This reaction proceeded through mesoionic 1,3-thiazolium-5-olates, followed by cleavage of the pyrrolidine ring and the formation of thiazoles, introducing a trifluoromethyl group at position 5 in the thiazole ring.

  DOI：

  10.3987/com-13-12904

文献信息

• Dakin-West Reaction of N-Thioacylprolines Using Trifluoroacetic Anhydride: Novel Access to 5-Trifluoromethylthiazoles
  作者：Masami Kawase、Yuri Hagimoto、Ryosuke Saijo

  DOI：10.3987/com-13-12904

  日期：——

  The reaction between N-thioacylprolines and trifluoro acetic anhydride in the presence of pyridine afforded a good yield of 5-trifluoromethylthiazoles. This reaction proceeded through mesoionic 1,3-thiazolium-5-olates, followed by cleavage of the pyrrolidine ring and the formation of thiazoles, introducing a trifluoromethyl group at position 5 in the thiazole ring.