4--2,3,4,9-tetrahydro-1H-carbazol-1-one | 174625-04-8

• 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: 4--2,3,4,9-tetrahydro-1H-carbazol-1-one
• 英文别名: N-(2-hydroxyethyl)-N-(1-oxo-2,3,4,9-tetrahydrocarbazol-4-yl)benzamide
• CAS: 174625-04-8
• 化学式: C₂₁H₂₀N₂O₃
• 分子量: 348.401
• InChiKey: LVJQHZYLXVQQMK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  73.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4--2,3,4,9-tetrahydro-1H-carbazol-1-one 在 草酰氯 、 sodium hydride 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 3.92h， 生成 2-benzoyl-4-hydroxy-1,2,3,4,5,7-hexahydro-1,5c-methanoazocino<4,3-b>indol-6-one
  参考文献：
  名称：

  A New Synthetic Route to the Tetracyclic Framework of Strychnos Alkaloids via Intramolecular Aldol Reaction

  摘要：

  By treatment of 2,3,4,9-tetrahydrospiro[1H-carbazole-1,2'-[1,3]dithiolan]-4(9H)- one (1) with ethanolamine, followed by reduction of the corresponding imine (6) with NaBH4 to the amine (7) and benzoylation, N-benzoyl-N-(2-hydroxyethyl)-{2,3,4,9-tetrahydrospiro-[1H-carbazole-1,2'-(1,3)dithiolan]-4-yl}amine (8) is formed, which can be deprotected to 4-[Benzoyl-(2-hydroxyethyl)amino]-2,3,4,9-tetrahydro-1H-carbazol-1-one (9). Oxidation of the primary hydroxyl group yields [benzoyl-(1-oxo-2,3,4,9-tetrahydrocarbazol-1-one-4-yl)amino]acetaldehyde (10), a key-intermediate for the cyclization to 2-benzoyl-4-hydroxy-1,2,3,4,5,7-hexahydro-1, 5c-methanoazocino[4,3-b]indol-6-one (11), which represents the tetracyclic skeleton of Strychnos-type alkaloids.

  DOI：

  10.3987/com-95-7060
• 作为产物：
  描述：

  N-benzoyl-N-(2-hydroxyethyl)-(2,3,4,9-tetrahydrospiro<1H-carbazole-1,2'-(1,3)dithiolan>-4-yl)amine 在 吡啶 、 苯亚硒酸酐 作用下， 以 氯仿 为溶剂， 反应 48.0h， 以62%的产率得到4--2,3,4,9-tetrahydro-1H-carbazol-1-one
  参考文献：
  名称：

  A New Synthetic Route to the Tetracyclic Framework of Strychnos Alkaloids via Intramolecular Aldol Reaction

  摘要：

  By treatment of 2,3,4,9-tetrahydrospiro[1H-carbazole-1,2'-[1,3]dithiolan]-4(9H)- one (1) with ethanolamine, followed by reduction of the corresponding imine (6) with NaBH4 to the amine (7) and benzoylation, N-benzoyl-N-(2-hydroxyethyl)-{2,3,4,9-tetrahydrospiro-[1H-carbazole-1,2'-(1,3)dithiolan]-4-yl}amine (8) is formed, which can be deprotected to 4-[Benzoyl-(2-hydroxyethyl)amino]-2,3,4,9-tetrahydro-1H-carbazol-1-one (9). Oxidation of the primary hydroxyl group yields [benzoyl-(1-oxo-2,3,4,9-tetrahydrocarbazol-1-one-4-yl)amino]acetaldehyde (10), a key-intermediate for the cyclization to 2-benzoyl-4-hydroxy-1,2,3,4,5,7-hexahydro-1, 5c-methanoazocino[4,3-b]indol-6-one (11), which represents the tetracyclic skeleton of Strychnos-type alkaloids.

  DOI：

  10.3987/com-95-7060

文献信息

• Intermediates for the synthesis of tetracyclic indole alkaloids. Synthesis of 4-aminotetrahydrocarbazole derivatives
  作者：Süleyman Patir、Görol Okay、Ahmet Gülce、Bekir Salih、Tuncer Hökelek

  DOI：10.1002/jhet.5570340423

  日期：1997.7

  An efficient method for the synthesis of 4-aminotetrahydrocarbazole derivatives from 2,3-dihydrospiro-[1H-carbazole-1,2′-(1,3)-dithiolan]-4-(9H)-one 1 is described. The structure of compound 6 has been confirmed by X-ray structure analysis.

  由2,3-二氢螺- [1为4- aminotetrahydrocarbazole衍生物的合成的有效方法ħ -4-（9 - （1,3） -咔唑-dithiolan-1,2'] ħ描述） -酮1。化合物6的结构已经通过X射线结构分析确认。
• A New Synthetic Route to the Tetracyclic Framework of Strychnos Alkaloids via Intramolecular Aldol Reaction
  作者：Süleyman Patir、Peter Rosenmund、Peter H. Götz

  DOI：10.3987/com-95-7060

  日期：——

  By treatment of 2,3,4,9-tetrahydrospiro[1H-carbazole-1,2'-[1,3]dithiolan]-4(9H)- one (1) with ethanolamine, followed by reduction of the corresponding imine (6) with NaBH4 to the amine (7) and benzoylation, N-benzoyl-N-(2-hydroxyethyl)-2,3,4,9-tetrahydrospiro-[1H-carbazole-1,2'-(1,3)dithiolan]-4-yl}amine (8) is formed, which can be deprotected to 4-[Benzoyl-(2-hydroxyethyl)amino]-2,3,4,9-tetrahydro-1H-carbazol-1-one (9). Oxidation of the primary hydroxyl group yields [benzoyl-(1-oxo-2,3,4,9-tetrahydrocarbazol-1-one-4-yl)amino]acetaldehyde (10), a key-intermediate for the cyclization to 2-benzoyl-4-hydroxy-1,2,3,4,5,7-hexahydro-1, 5c-methanoazocino[4,3-b]indol-6-one (11), which represents the tetracyclic skeleton of Strychnos-type alkaloids.