(-) (4R)-6-(2-oxazolyl)-4-(di-n-propylamino)-1,3,4,5-tetrahydrobenz[cd]indole

• 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: (-) (4R)-6-(2-oxazolyl)-4-(di-n-propylamino)-1,3,4,5-tetrahydrobenz[cd]indole
• 英文别名: (4R)-6-(2-oxazolyl)-4-(di-n-propylamino)-1,3,4,5-tetrahydrobenz[cd]indole；(4R)-6-(2-oxazolyl)4-(di-n-propylamino)-1,3,4,5-tetrahydrobenz[c,d]indole；(4R)-6-(1,3-oxazol-2-yl)-N,N-dipropyl-1,3,4,5-tetrahydrobenzo[cd]indol-4-amine
• 化学式: C₂₀H₂₅N₃O
• 分子量: 323.438
• InChiKey: QEEUUCCJDYUBFJ-HNNXBMFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  45.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (+) (2aR,4S)-1-benzoyl-6-iodo-4-(di-n-propylamino)-1,2,2a,3,4,5-hexahydrobenz[cd]indole 在 bis-triphenylphosphine-palladium(II) chloride 、 sodium hydroxide 、 正丁基锂 、 草酰氯 、 三乙胺 、 zinc(II) chloride 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 1.5h， 生成 (-) (4R)-6-(2-oxazolyl)-4-(di-n-propylamino)-1,3,4,5-tetrahydrobenz[cd]indole
  参考文献：
  名称：

  Application of Palladium(0)-Catalyzed Processes to the Synthesis of Oxazole-Containing Partial Ergot Alkaloids

  摘要：

  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.

  DOI：

  10.1021/jo970374j

文献信息

• 6-heterocyclic-4-amino-1,3,4,5-tetrahydrobenz[CD]indoles
  申请人：Eli Lilly and Company

  公开号：US05364856A1

  公开（公告）日：1994-11-15

  6-heterocyclic-4-amino-1,3,4,5-tetrahydrobenz[cd]indoles are provided which are useful in modifying the function of serotonin in mammals.

  提供了对哺乳动物中的5-噻吩基-4-氨基-1,3,4,5-四氢苯并[cd]吲哚功能进行修改的化合物。
• 6-heterocyclic-4-amino-1,3,4,5-tetrahydrobenz[cd]indoles
  申请人：Eli Lilly and Company

  公开号：US05624944A1

  公开（公告）日：1997-04-29

  6-heterocyclic-4-amino-1,3,4,5-tetrahydrobenz[cd]indoles are provided which are useful in modifying the function of serotonin in mammals.

  提供了6-杂环-4-氨基-1,3,4,5-四氢苯[cd]吲哚，可用于修改哺乳动物中的血清素功能。
• 6-heterocyclic-4-amino-1,3,4,5-tetrahydrobenz[cd] indoles
  申请人：Eli Lilly and Company

  公开号：US05641797A1

  公开（公告）日：1997-06-24

  6-heterocyclic-4-amino-1,3,4,5-tetrahydrobenz-[cd]indoles are provided which are useful in modifying the function of serotonin in mammals.

  提供了6-杂环-4-氨基-1,3,4,5-四氢苯[c,d]吲哚，可用于修饰哺乳动物中的血清素功能。
• 6-heterocyclic-4-amino-1,3,4,5,-tetrahydrobenz [cd]indoles
  申请人：Eli Lilly and Company

  公开号：US05643930A1

  公开（公告）日：1997-07-01

  6-heterocyclic-4-amino-1,3,4,5-tetrahydrobenz-[cd]indoles are provided which are useful in modifying the function of serotonin in mammals.

  提供了6-杂环-4-氨基-1,3,4,5-四氢苯-[cd]吲哚，这些化合物在改变哺乳动物体内的血清素功能方面是有用的。
• 6-heterocyclic-4-amino-1,3,4,5-tetrahydrobenz[CD] indoles
  申请人：Eli Lilly and Company

  公开号：US05665743A1

  公开（公告）日：1997-09-09

  6-heterocyclic-4-amino-1,3,4,5-tetrahydrobenz[cd]indoles are provided which are useful in modifying the function of serotonin in mammals.

  提供了6-杂环-4-氨基-1,3,4,5-四氢苯[cd]吲哚，可用于修改哺乳动物中5-羟色胺的功能。