methyl 2-methyl-9-(phenylsulfonyl)-9H-carbazole-3-carboxylate

• 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: methyl 2-methyl-9-(phenylsulfonyl)-9H-carbazole-3-carboxylate
• 英文别名: Methyl 9-(benzenesulfonyl)-2-methylcarbazole-3-carboxylate；methyl 9-(benzenesulfonyl)-2-methylcarbazole-3-carboxylate
• 化学式: C₂₁H₁₇NO₄S
• 分子量: 379.436
• InChiKey: WFGYMHWYBFEXHU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  73.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1,1-二甲氧基-N,N-二甲基乙胺 、 2-methyl-3-vinylindole 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以68%的产率得到methyl 2-methyl-9-(phenylsulfonyl)-9H-carbazole-3-carboxylate
  参考文献：
  名称：

  Synthesis of substituted carbazoles via electrocyclization of in situ generated enamines from 1-phenylsulfonyl-2/(3)-methyl-3/(2)-vinylindoles and DMF·DMA/DMA·DMA

  摘要：

  Interaction of 2/(3)-methyl-3/(2)-vinylindoles and DMF center dot DMA/DMA center dot DMA at 110 degrees C led to the in situ generation of enamines, which on concurrent electrocyclization followed by subsequent aromatization afforded substituted carbazoles. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.03.010

文献信息

• Synthesis of substituted carbazoles via electrocyclization of in situ generated enamines from 1-phenylsulfonyl-2/(3)-methyl-3/(2)-vinylindoles and DMF·DMA/DMA·DMA
  作者：Radhakrishnan Sureshbabu、Ramalingam Balamurugan、Arasambattu K. Mohanakrishnan

  DOI：10.1016/j.tet.2009.03.010

  日期：2009.5

  Interaction of 2/(3)-methyl-3/(2)-vinylindoles and DMF center dot DMA/DMA center dot DMA at 110 degrees C led to the in situ generation of enamines, which on concurrent electrocyclization followed by subsequent aromatization afforded substituted carbazoles. (C) 2009 Elsevier Ltd. All rights reserved.
• A novel synthesis of N-protected carbazoles involving electrocyclization of in situ generated enamines
  作者：Arasambattu K. Mohanakrishnan、Ramalingam Balamurugan

  DOI：10.1016/j.tetlet.2005.04.016

  日期：2005.6

  A new route for the synthesis of carbazoles has been realized through the intermediacy of 2,3-divinylindoles involving an electrocyclization followed by aromatization. (c) 2005 Elsevier Ltd. All rights reserved.
• An Improved Synthesis of Carbazoles<i>via</i>Domino Reaction of<i>N</i>-Protected-2-methylindoles with DMF-DMA/DMA-DMA
  作者：Radhakrishnan Sureshbabu、Arasambattu K. Mohanakrishnan

  DOI：10.1002/jhet.899

  日期：2012.7

  An efficient synthesis of carbazole analogs has been achieved via interaction of N‐protected‐2‐methylindoles with N,N‐dimethylformamide dimethylacetal as well as N,N‐dimethylacetamide dimethylacetal in the presence of pyrrolidine or 1,4‐diazabicyclo(2.2.2)octane (DABCO).