ethyl 5-(4-bromophenyl)-2,2,2-triphenyl-5-(trifluoromethyl)-2,5-dihydro-1,2λ⁵-oxaphosphole-4-carboxylate | 1418009-88-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: ethyl 5-(4-bromophenyl)-2,2,2-triphenyl-5-(trifluoromethyl)-2,5-dihydro-1,2λ⁵-oxaphosphole-4-carboxylate
• 英文别名: Ethyl 5-(4-bromophenyl)-2,2,2-triphenyl-5-(trifluoromethyl)-1,2lambda5-oxaphosphole-4-carboxylate；ethyl 5-(4-bromophenyl)-2,2,2-triphenyl-5-(trifluoromethyl)-1,2λ5-oxaphosphole-4-carboxylate
• CAS: 1418009-88-7
• 化学式: C₃₁H₂₅BrF₃O₃P
• 分子量: 613.411
• InChiKey: IWXKKXZMANMGKN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.9
• 重原子数：
  39
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  4'-溴-2,2,2-三氟苯乙酮 、 三苯基膦 、 丙炔酸乙酯 以 乙酸乙酯 为溶剂， 反应 8.0h， 以90%的产率得到ethyl 5-(4-bromophenyl)-2,2,2-triphenyl-5-(trifluoromethyl)-2,5-dihydro-1,2λ⁵-oxaphosphole-4-carboxylate
  参考文献：
  名称：

  Synthesis of 5-(Trifluoromethyl)-2,5-dihydro-1,2λ5-oxaphospholes by a One-Pot Three-Component Reaction

  摘要：

  A series of trifluoromethyl-substituted 1,2 lambda(5)-oxaphospholes were prepared in yields of up to 95% by a one-pot three-component reaction under mild conditions. The zwitterionic intermediate generated by attack of triphenylphosphine on an alkyl propiolate reacts with an aryl or styryl trifluoromethyl ketone to form the 1,2 lambda(5)-oxaphosphole ring. All the new products were characterized by IR, NMR, and mass spectroscopy and the structure of one of them, ethyl 2,2,2-triphenyl-5-[(E)-2-phenylvinyl]-5-(trifluoromethyl)-2,5-dihydro-1,2 lambda(5)-oxaphosphole-4-carboxylate, was confirmed by X-ray single-crystal diffraction analysis.

  DOI：

  10.1055/s-0032-1316799

文献信息

• Synthesis of 5-(Trifluoromethyl)-2,5-dihydro-1,2λ5-oxaphospholes by a One-Pot Three-Component Reaction
  作者：Jin-Ming Gao、Shi-Zheng Zhu、Hua-Fang Fan、Xiao-Wei Wang、Jing-Wei Zhao、Xin-Jin Li

  DOI：10.1055/s-0032-1316799

  日期：——

  A series of trifluoromethyl-substituted 1,2 lambda(5)-oxaphospholes were prepared in yields of up to 95% by a one-pot three-component reaction under mild conditions. The zwitterionic intermediate generated by attack of triphenylphosphine on an alkyl propiolate reacts with an aryl or styryl trifluoromethyl ketone to form the 1,2 lambda(5)-oxaphosphole ring. All the new products were characterized by IR, NMR, and mass spectroscopy and the structure of one of them, ethyl 2,2,2-triphenyl-5-[(E)-2-phenylvinyl]-5-(trifluoromethyl)-2,5-dihydro-1,2 lambda(5)-oxaphosphole-4-carboxylate, was confirmed by X-ray single-crystal diffraction analysis.