tert-butyl 4,4,4-trifluorobutynoate | 1379659-36-5

• 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: tert-butyl 4,4,4-trifluorobutynoate
• 英文别名: Tert-butyl 4,4,4-trifluorobut-2-ynoate
• CAS: 1379659-36-5
• 化学式: C₈H₉F₃O₂
• 分子量: 194.153
• InChiKey: DDCCPMCFOMEQSC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.89
• 重原子数：
  13.0
• 可旋转键数：
  0.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  tert-butyl 4,4,4-trifluorobutynoate 、 1-(4-methoxyphenyl)-1-methylsiletane 在 allyl(cyclopentadiene)palladium(II) 、 10,16-dimethyl-N,N-bis[(1S)-1-phenylethyl]-12,14-dioxa-13-phosphapentacyclo[13.8.0.02,11.03,8.018,23]tricosa-1(15),2(11),3(8),9,16,18(23)-hexaen-13-amine 作用下， 以 甲苯 为溶剂， 反应 14.0h， 生成 、 tert-butyl (S)-1-(4-methoxyphenyl)-1-methyl-2-(trifluoromethyl)-1,4,5,6-tetrahydrosiline-3-carboxylate
  参考文献：
  名称：

  Palladium-Catalyzed Desymmetrization of Silacyclobutanes with Alkynes: Enantioselective Synthesis of Silicon-Stereogenic 1-Sila-2-cyclohexenes and Mechanistic Considerations

  摘要：

  A palladium-catalyzed enantioselective desymmetrization of silacyclobutanes with alkynes has been developed to give silicon-stereogenic 1-sila-2-cyclohexenes with high enantioselectivity. The products thus obtained undergo further derivatizations with complete stereoselectivity, and a new catalytic cycle involving alkyne coordination (oxidative cyclization)-transmetalation (sigma-bond metathesis)-reductive elimination has also been proposed.

  DOI：

  10.1021/ol301191u
• 作为产物：
  描述：

  4,4,4-trifluoro-3-oxo-2-(triphenylphosphoranylidene)butanoic acid, 1,1-dimethylethyl ester 在 potassium carbonate 作用下， 反应 5.0h， 以21%的产率得到tert-butyl 4,4,4-trifluorobutynoate
  参考文献：
  名称：

  Palladium-Catalyzed Desymmetrization of Silacyclobutanes with Alkynes: Enantioselective Synthesis of Silicon-Stereogenic 1-Sila-2-cyclohexenes and Mechanistic Considerations

  摘要：

  A palladium-catalyzed enantioselective desymmetrization of silacyclobutanes with alkynes has been developed to give silicon-stereogenic 1-sila-2-cyclohexenes with high enantioselectivity. The products thus obtained undergo further derivatizations with complete stereoselectivity, and a new catalytic cycle involving alkyne coordination (oxidative cyclization)-transmetalation (sigma-bond metathesis)-reductive elimination has also been proposed.

  DOI：

  10.1021/ol301191u