2-(p-toluenesulfonyl)oxymethyl-1,2,3,9-tetrahydro-4H-carbazol-4-one | 221299-79-2

• 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: 2-(p-toluenesulfonyl)oxymethyl-1,2,3,9-tetrahydro-4H-carbazol-4-one
• 英文别名: (4-Oxo-1,2,3,9-tetrahydrocarbazol-2-yl)methyl 4-methylbenzenesulfonate
• CAS: 221299-79-2
• 化学式: C₂₀H₁₉NO₄S
• 分子量: 369.441
• InChiKey: KGIZUIZLTOSFQU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  84.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-氟-3-(哌啶-4-基)苯并[D]异恶唑 、 2-(p-toluenesulfonyl)oxymethyl-1,2,3,9-tetrahydro-4H-carbazol-4-one 在 N-甲基吡咯烷酮 作用下， 反应 48.0h， 以70%的产率得到QF 2004B
  参考文献：
  名称：

  Butyrophenone analogues in the carbazole series: Synthesis and determination of affinities at D2 and 5-HT2A receptors

  摘要：

  We describe a practical and efficient route for synthesis of 2-aminomethyl-1,2,3,9-tetrahydro-4H-carbazol-4-ones using an effective Fisher indole methodology. The most active compounds, 4b (QF 2003B) and 4c (QF 2003B), with pKi (5-HT2A/D-2) ratio of 1.28 show an antipsychotic profile according to Meltzer's classification, (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00639-8
• 作为产物：
  描述：

  1,4-二氢-3,5-二甲氧基苯甲醇 在 4-二甲氨基吡啶 、 硫酸 作用下， 以 吡啶 为溶剂， 反应 28.0h， 生成 2-(p-toluenesulfonyl)oxymethyl-1,2,3,9-tetrahydro-4H-carbazol-4-one
  参考文献：
  名称：

  Butyrophenone analogues in the carbazole series as potential atypical antipsychotics: synthesis and determination of affinities at D2, 5-HT2A, 5-HT2B and 5-HT2C receptors

  摘要：

  We describe practical and efficient routes for synthesis of 2-aminomethyl-1,2,3,9-tetrahydro-4H-carbazol-4-ones using the Fischer indole synthesis or palladium-catalysed cyclization methodologies, as well as their affinities for D-2, 5-HT2A and 5-HT2C receptors, and their activity at the 5-HT2B receptor. The most active compounds, 4b (QF 2003B) and 4c (QF 2004B), with a pK(i) (5-HT2A/D-2) ratio of 1.28 show a potential antipsychotic profile according to Meltzer's classification. (C) 2000 Editions scientifiques et medicales Elsevier SAS.

  DOI：

  10.1016/s0223-5234(00)00109-4

文献信息

• Butyrophenone analogues in the carbazole series: Synthesis and determination of affinities at D2 and 5-HT2A receptors
  作者：Christian F. Masaguer、Emilio Formoso、Enrique Raviña、Helena Tristán、M.Isabel Loza、Emilia Rivas、JoséAngel Fontenla

  DOI：10.1016/s0960-894x(98)00639-8

  日期：1998.12

  We describe a practical and efficient route for synthesis of 2-aminomethyl-1,2,3,9-tetrahydro-4H-carbazol-4-ones using an effective Fisher indole methodology. The most active compounds, 4b (QF 2003B) and 4c (QF 2003B), with pKi (5-HT2A/D-2) ratio of 1.28 show an antipsychotic profile according to Meltzer's classification, (C) 1998 Elsevier Science Ltd. All rights reserved.
• Butyrophenone analogues in the carbazole series as potential atypical antipsychotics: synthesis and determination of affinities at D2, 5-HT2A, 5-HT2B and 5-HT2C receptors
  作者：C Masaguer

  DOI：10.1016/s0223-5234(00)00109-4

  日期：2000.1

  We describe practical and efficient routes for synthesis of 2-aminomethyl-1,2,3,9-tetrahydro-4H-carbazol-4-ones using the Fischer indole synthesis or palladium-catalysed cyclization methodologies, as well as their affinities for D-2, 5-HT2A and 5-HT2C receptors, and their activity at the 5-HT2B receptor. The most active compounds, 4b (QF 2003B) and 4c (QF 2004B), with a pK(i) (5-HT2A/D-2) ratio of 1.28 show a potential antipsychotic profile according to Meltzer's classification. (C) 2000 Editions scientifiques et medicales Elsevier SAS.