tert-butyl N-methyl-(6-methoxy-2,3,4,9-tetrahydro-1H-carbazol-3-yl)carbamate | 1414848-10-4

• 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: tert-butyl N-methyl-(6-methoxy-2,3,4,9-tetrahydro-1H-carbazol-3-yl)carbamate
• 英文别名: tert-butyl (6-methoxy-2,3,4,9-tetrahydro-1H-carbazol-3-yl)(methyl)carbamate；tert-butyl N-(6-methoxy-2,3,4,9-tetrahydro-1H-carbazol-3-yl)-N-methylcarbamate
• CAS: 1414848-10-4
• 化学式: C₁₉H₂₆N₂O₃
• 分子量: 330.427
• InChiKey: YGWBQGVVPGXARG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  54.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  tert-butyl N-methyl-(6-methoxy-2,3,4,9-tetrahydro-1H-carbazol-3-yl)carbamate 、 3-三氟甲基苯磺酰氯 在 potassium hydride 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 反应 3.0h， 生成 tert-butyl N-methyl-[6-methoxy-9-(3-trifluoromethyl phenylsulfonyl)-2,3,4,9-tetrahydro-1H-carbazol-3-yl] carbamate
  参考文献：
  名称：

  N,N-Dimethyl-[9-(arylsulfonyl)-2,3,4,9-tetrahydro-1H-carbazol-3-yl]amines as novel, potent and selective 5-HT6 receptor antagonists

  摘要：

  The design, synthesis and SAR of novel tetrahydrocarbazole derivatives having 5-HT6 receptor antagonist activity is presented. The racemic compound 15e was found to possess desirable pharmacokinetic properties, adequate brain penetration and activity in animal models of cognition. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.06.002
• 作为产物：
  描述：

  N-甲基-1,4-二噁螺[4.5]-8-癸胺 在 硫酸 、 三乙胺 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 2.0h， 生成 tert-butyl N-methyl-(6-methoxy-2,3,4,9-tetrahydro-1H-carbazol-3-yl)carbamate
  参考文献：
  名称：

  N,N-Dimethyl-[9-(arylsulfonyl)-2,3,4,9-tetrahydro-1H-carbazol-3-yl]amines as novel, potent and selective 5-HT6 receptor antagonists

  摘要：

  The design, synthesis and SAR of novel tetrahydrocarbazole derivatives having 5-HT6 receptor antagonist activity is presented. The racemic compound 15e was found to possess desirable pharmacokinetic properties, adequate brain penetration and activity in animal models of cognition. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.06.002

文献信息

• A Halogen-Atom Transfer (XAT)-Based Approach to Indole Synthesis Using Aryl Diazonium Salts and Alkyl Iodides
  作者：Sebastian Govaerts、Kento Nakamura、Timothée Constantin、Daniele Leonori

  DOI：10.1021/acs.orglett.2c02840

  日期：2022.11.4

  among the most important N-heterocycles in pharmaceuticals. Here, we present an alternative to the classic Fischer indole synthesis based on the radical coupling between aryl diazoniums and alkyl iodides. This iron-mediated strategy features a double role for the aryl diazoniums that sequentially activate the alkyl iodides through halogen-atom transfer and then serve as radical acceptors. The process

  吲哚是药物中最重要的N-杂环化合物之一。在这里，我们提出了一种基于芳基重氮和烷基碘之间的自由基偶联的经典 Fischer 吲哚合成的替代方法。这种铁介导的策略具有芳基重氮盐的双重作用，芳基重氮盐通过卤素原子转移依次激活烷基碘，然后充当自由基受体。该过程在温和的条件下运行，可以制备致密功能化的吲哚。