(Z)-1-{1-[(S)-(1-phenylethyl)amino]ethylidene}indan-2-one | 1365254-20-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: (Z)-1-{1-[(S)-(1-phenylethyl)amino]ethylidene}indan-2-one
• CAS: 1365254-20-1
• 化学式: C₁₉H₁₉NO
• 分子量: 277.366
• InChiKey: CBAQXTUCSNNIOE-ISNHLSKGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.89
• 重原子数：
  21.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  29.1
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  (S)-(-)- α-甲基苄胺 、 2-(2-(2-oxopropyl)phenyl)acetic acid 以 甲苯 为溶剂， 120.0 ℃ 、500.01 kPa 条件下， 反应 2.0h， 生成 (Z)-1-{1-[(S)-(1-phenylethyl)amino]ethylidene}indan-2-one
  参考文献：
  名称：

  Microwave assisted synthesis of 3-benzazepin-2-ones as building blocks for 2,3-disubstituted tetrahydro-3-benzazepines

  摘要：

  Microwave assisted condensation of primary amines with keto acids 1a-c provided directly 3,4-disubstituted 1,3-dihydro-3-benzazepin-2-ones 2. Whereas small amine size, such as NH3 afforded high yields of secondary lactams 2a, 2d, and 2g, primary amines with larger substituents in alpha-position led to lower yields of 2 or even to regioisomeric indanone derivatives 4. However, subsequent alkylation of 2a, 2d, and 2g with various alkyl halides provided the corresponding N-substituted 3-benzazepin-2-ones 2 in good yields. Hydrogenation of 2 followed by BH3 reduction led to 3-benzazepines 9. 3-Benzyl-2-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine (9c) reveals high sigma(1) affinity and selectivity over sigma(2) and NMDA receptors. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.01.052