(4R)-4-(dipropylamino)-1,3,4,5-tetrahydrobenzo[cd]indole-6-carbaldehyde | 197888-21-4

• 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)-4-(dipropylamino)-1,3,4,5-tetrahydrobenzo[cd]indole-6-carbaldehyde
• CAS: 197888-21-4
• 化学式: C₁₈H₂₄N₂O
• 分子量: 284.401
• InChiKey: BYRKFQUXPHGAKS-HNNXBMFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  36.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  对甲基苯磺酰甲基异腈 、 (4R)-4-(dipropylamino)-1,3,4,5-tetrahydrobenzo[cd]indole-6-carbaldehyde 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 5.0h， 以81%的产率得到(4R)-6-(5-oxazolyl)4-(di-n-propylamino)-1,3,4,5-tetrahydrobenz[c,d]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
• 作为产物：
  描述：

  (S)-dipropyl-(6-iodo-1,3,4,5-tetra-hydrobenz-[cd]-indol-4-yl)amine 在 四(三苯基膦)钯 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 3.5h， 生成 (4R)-4-(dipropylamino)-1,3,4,5-tetrahydrobenzo[cd]indole-6-carbaldehyde
  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.