3-(7-cyano-5-(2-(2,2,2-trifluoroacetamido)propyl)indolin-1-yl)propyl benzoate | 1566565-56-7

• 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: 3-(7-cyano-5-(2-(2,2,2-trifluoroacetamido)propyl)indolin-1-yl)propyl benzoate
• 英文别名: 3-[7-Cyano-5-[2-[(2,2,2-trifluoroacetyl)amino]propyl]-2,3-dihydroindol-1-yl]propyl benzoate；3-[7-cyano-5-[2-[(2,2,2-trifluoroacetyl)amino]propyl]-2,3-dihydroindol-1-yl]propyl benzoate
• CAS: 1566565-56-7
• 化学式: C₂₄H₂₄F₃N₃O₃
• 分子量: 459.468
• InChiKey: USRARHWWRFCGPH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  33
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  82.4
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  5-(2-氨基丙基)-1-[3-(苯甲酰氧基)丙基]-2,3-二氢-1H-吲哚-7-甲腈 、 三氟乙酸酐 在 4-二甲氨基吡啶 作用下， 以 乙二醇二甲醚 为溶剂， 反应 12.0h， 以61%的产率得到3-(7-cyano-5-(2-(2,2,2-trifluoroacetamido)propyl)indolin-1-yl)propyl benzoate
  参考文献：
  名称：

  Enzymatic asymmetric synthesis of the silodosin amine intermediate

  摘要：

  Various enantiocomplementary omega-transaminases (omega TAs) were investigated in kinetic resolution and asymmetric reductive amination reactions to prepare silodosin amine. Whilst the enzymatic kinetic resolution gave moderate to good results with respect to the yield and enantioselectivity, the asymmetric reductive amination proved to be superior. The best results were obtained with the omega TA originating from (R)-Arthrobacter sp. which afforded the desired bioactive (R)-enantiomer in enantiomerically pure form (ee >97%) at excellent conversion (cony. >97%) under mild and benign reaction conditions. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.12.012

文献信息

• EP2909327A1
  申请人：——

  公开号：EP2909327A1

  公开（公告）日：2015-08-26
• [EN] A PROCESS FOR PREPARING INDOLINE DERIVATIVES<br/>[FR] PROCÉDÉ DE PRÉPARATION DE DÉRIVÉS D'INDOLINE
  申请人：SANDOZ AG

  公开号：WO2014060571A1

  公开（公告）日：2014-04-24

  The present invention relates in general to the field of organic chemistry, and in particular to the preparation of indoline derivatives. These indoline derivatives can be used as intermediates in the synthesis of pharmaceutically active agents such as silodosin or derivatives thereof.
• Enzymatic asymmetric synthesis of the silodosin amine intermediate
  作者：Robert C. Simon、Johann H. Sattler、Judith E. Farnberger、Christine S. Fuchs、Nina Richter、Ferdinand Zepeck、Wolfgang Kroutil

  DOI：10.1016/j.tetasy.2013.12.012

  日期：2014.2

  Various enantiocomplementary omega-transaminases (omega TAs) were investigated in kinetic resolution and asymmetric reductive amination reactions to prepare silodosin amine. Whilst the enzymatic kinetic resolution gave moderate to good results with respect to the yield and enantioselectivity, the asymmetric reductive amination proved to be superior. The best results were obtained with the omega TA originating from (R)-Arthrobacter sp. which afforded the desired bioactive (R)-enantiomer in enantiomerically pure form (ee >97%) at excellent conversion (cony. >97%) under mild and benign reaction conditions. (C) 2013 Elsevier Ltd. All rights reserved.