(1R,4R)-9-amino-1,4-diisopropyl-1,2,3,4-tetrahydroacridine | 1214747-74-6

• 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: (1R,4R)-9-amino-1,4-diisopropyl-1,2,3,4-tetrahydroacridine
• 英文别名: (1R,4R)-1,4-di(propan-2-yl)-1,2,3,4-tetrahydroacridin-9-amine
• CAS: 1214747-74-6
• 化学式: C₁₉H₂₆N₂
• 分子量: 282.429
• InChiKey: LGVDBJRQLJIUBB-ZIAGYGMSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  38.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (2R,5S)-2,5-diisopropylcyclohexanone 、 2-氨基苯甲腈 在 三氟化硼乙醚 、 水 、 sodium hydroxide 作用下， 以 甲苯 为溶剂， 反应 48.0h， 以48%的产率得到(1R,4R)-9-amino-1,4-diisopropyl-1,2,3,4-tetrahydroacridine
  参考文献：
  名称：

  Synthesis and AChE inhibitory activity of new chiral tetrahydroacridine analogues from terpenic cyclanones

  摘要：

  This work describes the enantioselective synthesis of a new series of terpenic chiral 9-aminotetrahydroacridine analogues. Several chiral ketones were synthesized from natural monoterpenes in an optically active form and subjected to the cyclodehydration reactions with anthranilonitrile in the presence of BF3 center dot Et2O as catalyst. The 9-aminotetrahydroacridine analogues were tested as acetylcholinesterase (AChE) inhibitors. Based on qualitative structure-activity relationship some trends are suggested. (C) 2009 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2009.10.039

文献信息

• Synthesis and AChE inhibitory activity of new chiral tetrahydroacridine analogues from terpenic cyclanones
  作者：Diego dos Santos Pisoni、Jessie Sobieski da Costa、Douglas Gamba、Cesar Liberato Petzhold、Antonio César de Amorim Borges、Marco Antonio Ceschi、Paula Lunardi、Carlos Alberto Saraiva Gonçalves

  DOI：10.1016/j.ejmech.2009.10.039

  日期：2010.2

  This work describes the enantioselective synthesis of a new series of terpenic chiral 9-aminotetrahydroacridine analogues. Several chiral ketones were synthesized from natural monoterpenes in an optically active form and subjected to the cyclodehydration reactions with anthranilonitrile in the presence of BF3 center dot Et2O as catalyst. The 9-aminotetrahydroacridine analogues were tested as acetylcholinesterase (AChE) inhibitors. Based on qualitative structure-activity relationship some trends are suggested. (C) 2009 Elsevier Masson SAS. All rights reserved.