4-(3-Cyano-phenyl)-5-oxo-2-trifluoromethyl-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid benzyl ester | 852613-33-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 4-(3-Cyano-phenyl)-5-oxo-2-trifluoromethyl-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid benzyl ester
• CAS: 852613-33-3
• 化学式: C₂₅H₁₉F₃N₂O₃
• 分子量: 452.433
• InChiKey: AQJJTPCDGXQCHS-UHFFFAOYSA-N

物化性质

• 沸点：
  557.2±50.0 °C(Predicted)
• 密度：
  1.38±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.81
• 重原子数：
  33.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  79.19
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  4-(3-Cyano-phenyl)-5-oxo-2-trifluoromethyl-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid benzyl ester 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 生成 (-)-4-(3-cyanophenyl)-2-trifluoromethyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylic acid
  参考文献：
  名称：

  Alternative esters in the synthesis of ZD0947

  摘要：

  Alternatives to the original iso-borneol and allyl esters were investigated in the synthesis of ZD0947 (1). Homologous allylic esters were prepared in higher yields and were more readily purified than for the existing route, but offered no further benefits later in the synthesis. However, the PNB-substituted ester series provided crystalline intermediates, higher yields and simplified isolations through-out, and utilised a heterogeneous hydrogenation, thus reducing the residual catalyst levels. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.03.057
• 作为产物：
  描述：

  3-氰基苯甲醛 在 ammonium acetate 、 对甲苯磺酸 作用下， 以 乙醇 、 溶剂黄146 为溶剂， 生成 4-(3-Cyano-phenyl)-5-oxo-2-trifluoromethyl-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid benzyl ester
  参考文献：
  名称：

  Alternative esters in the synthesis of ZD0947

  摘要：

  Alternatives to the original iso-borneol and allyl esters were investigated in the synthesis of ZD0947 (1). Homologous allylic esters were prepared in higher yields and were more readily purified than for the existing route, but offered no further benefits later in the synthesis. However, the PNB-substituted ester series provided crystalline intermediates, higher yields and simplified isolations through-out, and utilised a heterogeneous hydrogenation, thus reducing the residual catalyst levels. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.03.057