ethyl 3-<2-bromo-4-(trifluoromethyl)phenyl>-2-cyano-2-propenoate | 85118-34-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: ethyl 3-<2-bromo-4-(trifluoromethyl)phenyl>-2-cyano-2-propenoate
• 英文别名: ethyl 3-[2-bromo-4-(trifluoromethyl)phenyl]-2-cyanoacrylate；Ethyl 3-[2-bromo-4-(trifluoromethyl)phenyl]-2-cyano-2-propenoate；ethyl 3-[2-bromo-4-(trifluoromethyl)phenyl]-2-cyanoprop-2-enoate
• CAS: 85118-34-9
• 化学式: C₁₃H₉BrF₃NO₂
• 分子量: 348.119
• InChiKey: IQXGKIDXUFMKPE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  50.1
• 氢给体数：
  0
• 氢受体数：
  6

安全信息

• 海关编码：
  2926909090

反应信息

• 作为反应物：
  描述：

  ethyl 3-<2-bromo-4-(trifluoromethyl)phenyl>-2-cyano-2-propenoate 在 sodium tetrahydroborate 、 正丁基锂 、 氯化亚砜 、 硫酸 、 magnesium 、 溶剂黄146 作用下， 以 甲醇 、 乙醚 、 正己烷 、 甲苯 为溶剂， 反应 27.5h， 生成 3-氯-1-(4-氟苯基)-5-(三氟甲基)茚满
  参考文献：
  名称：

  Neuroleptic activity and dopamine-uptake inhibition in 1-piperazino-3-phenylindans

  摘要：

  A series of 1-piperazino-3-phenylindans was synthesized and tested for neuroleptic and thymoleptic activity. Neuroleptic activity was found only in trans racemates and was associated with one of the enantiomers only. The potent and long-acting neuroleptic compound trans-4-[3-(4-fluorophenyl)-6-(trifluoromethyl)indan-1-yl]-1-piperazineethanol (Lu 18-012, tefludazine) was developed by systematic variation of structural components. Thymoleptic activity was optimized, especially with respect to dopamine-uptake inhibition. No geometrical stereoselectivity was found with regard to dopamine-uptake inhibition, but a high enantioselectivity could be demonstrated for both cis and trans racemates. The most potent compounds were 1-piperazino-3-(3,4-dichlorophenyl)indans with IC50 values of about 2nM for inhibition of dopamine uptake.

  DOI：

  10.1021/jm00361a002
• 作为产物：
  描述：

  2-溴-4-三氟甲基苯甲醛 、 氰乙酸乙酯 在 哌啶 作用下， 以 甲苯 为溶剂， 反应 0.5h， 以82%的产率得到ethyl 3-<2-bromo-4-(trifluoromethyl)phenyl>-2-cyano-2-propenoate
  参考文献：
  名称：

  Neuroleptic activity and dopamine-uptake inhibition in 1-piperazino-3-phenylindans

  摘要：

  A series of 1-piperazino-3-phenylindans was synthesized and tested for neuroleptic and thymoleptic activity. Neuroleptic activity was found only in trans racemates and was associated with one of the enantiomers only. The potent and long-acting neuroleptic compound trans-4-[3-(4-fluorophenyl)-6-(trifluoromethyl)indan-1-yl]-1-piperazineethanol (Lu 18-012, tefludazine) was developed by systematic variation of structural components. Thymoleptic activity was optimized, especially with respect to dopamine-uptake inhibition. No geometrical stereoselectivity was found with regard to dopamine-uptake inhibition, but a high enantioselectivity could be demonstrated for both cis and trans racemates. The most potent compounds were 1-piperazino-3-(3,4-dichlorophenyl)indans with IC50 values of about 2nM for inhibition of dopamine uptake.

  DOI：

  10.1021/jm00361a002

文献信息

• Neuroleptic activity and dopamine-uptake inhibition in 1-piperazino-3-phenylindans
  作者：Klaus P. Boegesoe

  DOI：10.1021/jm00361a002

  日期：1983.7

  A series of 1-piperazino-3-phenylindans was synthesized and tested for neuroleptic and thymoleptic activity. Neuroleptic activity was found only in trans racemates and was associated with one of the enantiomers only. The potent and long-acting neuroleptic compound trans-4-[3-(4-fluorophenyl)-6-(trifluoromethyl)indan-1-yl]-1-piperazineethanol (Lu 18-012, tefludazine) was developed by systematic variation of structural components. Thymoleptic activity was optimized, especially with respect to dopamine-uptake inhibition. No geometrical stereoselectivity was found with regard to dopamine-uptake inhibition, but a high enantioselectivity could be demonstrated for both cis and trans racemates. The most potent compounds were 1-piperazino-3-(3,4-dichlorophenyl)indans with IC50 values of about 2nM for inhibition of dopamine uptake.