(R)-4-Dipropylamino-1,3,4,5-tetrahydro-benzo[cd]indole-6-carbonitrile | 132619-33-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: (R)-4-Dipropylamino-1,3,4,5-tetrahydro-benzo[cd]indole-6-carbonitrile
• 英文别名: (4R)-4-(dipropylamino)-1,3,4,5-tetrahydrobenzo[cd]indole-6-carbonitrile
• CAS: 132619-33-1
• 化学式: C₁₈H₂₃N₃
• 分子量: 281.401
• InChiKey: VBHKKUWTLDEBRY-HNNXBMFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  42.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (R)-4-Dipropylamino-1,3,4,5-tetrahydro-benzo[cd]indole-6-carbonitrile 在 PPA 作用下， 生成 (4R)-4-(二丙基氨基)-1,3,4,5-四氢苯并[cd]吲哚-6-甲酰胺
  参考文献：
  名称：

  The synthesis of (+)- and (−)-1-benzoyl-1,2,2a,3,4,5-hexahydrobenz[cd]indol-4-amine, and preparation of LY228729.

  摘要：

  Racemic epoxide 5 was reacted with S-Phenylethylamine to afford diastereomers 6 and 7, from which amino alcohol 6 could be isolated directly. Aziridine formation and tandem-hydrogenolysis provided optically pure primary amine 2 (31% from racemic 4), which was further elaborated to LY228729 (15), an interesting 5HT1a receptor agonist.

  DOI：

  10.1016/s0040-4039(00)97303-9
• 作为产物：
  描述：

  (+)-1-Benzoyl-1,2,2a,3,4,5-hexahydrobenzindol-4-amine 在 manganese(IV) oxide 、 正丁基锂 、 溴 、 sodium acetate 、 potassium carbonate 作用下， 以 溶剂黄146 、 乙腈 为溶剂， 生成 (R)-4-Dipropylamino-1,3,4,5-tetrahydro-benzo[cd]indole-6-carbonitrile
  参考文献：
  名称：

  The synthesis of (+)- and (−)-1-benzoyl-1,2,2a,3,4,5-hexahydrobenz[cd]indol-4-amine, and preparation of LY228729.

  摘要：

  Racemic epoxide 5 was reacted with S-Phenylethylamine to afford diastereomers 6 and 7, from which amino alcohol 6 could be isolated directly. Aziridine formation and tandem-hydrogenolysis provided optically pure primary amine 2 (31% from racemic 4), which was further elaborated to LY228729 (15), an interesting 5HT1a receptor agonist.

  DOI：

  10.1016/s0040-4039(00)97303-9

文献信息

• Application of Palladium(0)-Catalyzed Processes to the Synthesis of Oxazole-Containing Partial Ergot Alkaloids
  作者：Benjamin A. Anderson、Lisa M. Becke、Richard N. Booher、Michael E. Flaugh、Nancy K. Harn、Thomas J. Kress、David L. Varie、James P. Wepsiec

  DOI：10.1021/jo970374j

  日期：1997.12.1

  Syntheses of the potent 5-HT1A agonists 2 and 3 were accomplished in several steps from the 6-iodo partial ergoline alkaloid 8. Disparate tactics available for construction of differentially substituted oxazoles led to the development of new and general methodology critical to the efficient preparations of 2 and 3. A novel palladium(0)- and copper(I)-cocatalyzed cyanation reaction provided efficient access to the nitrile 10, a key intermediate in the synthesis of 2. A palladium(0)-catalyzed cross-coupling reaction of 16 with oxazol-2-ylzinc chloride formed the potent 6.HT1A agonist 3.
• The synthesis of (+)- and (−)-1-benzoyl-1,2,2a,3,4,5-hexahydrobenz[cd]indol-4-amine, and preparation of LY228729.
  作者：Michael J. Martinelli、M. Robert Leanna、David L. Varie、Barry C. Peterson、Thomas J. Kress、James P. Wepsiec、Vien V. Khau

  DOI：10.1016/s0040-4039(00)97303-9

  日期：——

  Racemic epoxide 5 was reacted with S-Phenylethylamine to afford diastereomers 6 and 7, from which amino alcohol 6 could be isolated directly. Aziridine formation and tandem-hydrogenolysis provided optically pure primary amine 2 (31% from racemic 4), which was further elaborated to LY228729 (15), an interesting 5HT1a receptor agonist.