(2aR,4S)-6-iodo-N,N-dipropyl-1,2,2a,3,4,5-hexahydrobenzo[cd]indol-4-amine | 197888-22-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: (2aR,4S)-6-iodo-N,N-dipropyl-1,2,2a,3,4,5-hexahydrobenzo[cd]indol-4-amine
• CAS: 197888-22-5
• 化学式: C₁₇H₂₅IN₂
• 分子量: 384.303
• InChiKey: QBBHMEFTIKXMLF-STQMWFEESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  15.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2aR,4S)-6-iodo-N,N-dipropyl-1,2,2a,3,4,5-hexahydrobenzo[cd]indol-4-amine 在 manganese(IV) oxide 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以92%的产率得到(S)-dipropyl-(6-iodo-1,3,4,5-tetra-hydrobenz-[cd]-indol-4-yl)amine
  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
• 作为产物：
  描述：

  ((2aR,4S)-4-Amino-6-iodo-2a,3,4,5-tetrahydro-2H-benzo[cd]indol-1-yl)-phenyl-methanone 在 sodium hydroxide 、 potassium carbonate 作用下， 以 乙醇 、 乙腈 为溶剂， 反应 17.0h， 生成 (2aR,4S)-6-iodo-N,N-dipropyl-1,2,2a,3,4,5-hexahydrobenzo[cd]indol-4-amine
  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

• 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.