4-(3-Cyano-phenyl)-5-oxo-2-trifluoromethyl-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid allyl ester | 571178-39-7

• 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 allyl ester
• 英文别名: prop-2-enyl 4-(3-cyanophenyl)-5-oxo-2-(trifluoromethyl)-4,6,7,8-tetrahydro-1H-quinoline-3-carboxylate
• CAS: 571178-39-7
• 化学式: C₂₁H₁₇F₃N₂O₃
• 分子量: 402.373
• InChiKey: AXTRVZDYVGHHMI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  79.2
• 氢给体数：
  1
• 氢受体数：
  8

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 allyl ester 在 Wilkinson's catalyst 溶剂黄146 作用下， 以 乙醇 、 水 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 allyl 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

文献信息

• Method
  申请人：Jones Andrew

  公开号：US20050080104A1

  公开（公告）日：2005-04-14

  Process for preparing 3-[(4S)-5-oxo-2-(trifluoromethyl)-1,4,5,6,7,8-hexahydroquinolin-4-yl]benzonitrile, pharmaceutical compositions containing the compound and methods of treatment using the same.

  制备3-[(4S)-5-氧代-2-(三氟甲基)-1,4,5,6,7,8-六氢喹啉-4-基]苯甲腈的过程，含有该化合物的制药组合物以及使用该化合物的治疗方法。
• US7012145B2
  申请人：——

  公开号：US7012145B2

  公开（公告）日：2006-03-14
• Alternative esters in the synthesis of ZD0947
  作者：Jonathan D. Moseley

  DOI：10.1016/j.tetlet.2005.03.057

  日期：2005.5

  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.