ethyl 3-(2-(methyl)-1-(phenylsulfonyl)-1H-indol-3-yl)acrylate | 164261-32-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: ethyl 3-(2-(methyl)-1-(phenylsulfonyl)-1H-indol-3-yl)acrylate
• 英文别名: ethyl 2-methyl-1-phenylsulfonylindol-3-ylacrylate；ethyl 3-[1-(benzenesulfonyl)-2-methylindol-3-yl]prop-2-enoate
• CAS: 164261-32-9
• 化学式: C₂₀H₁₉NO₄S
• 分子量: 369.441
• InChiKey: DJQZTUHWUXTYRS-UHFFFAOYSA-N

物化性质

• 沸点：
  564.0±42.0 °C(Predicted)
• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.76
• 重原子数：
  26.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  65.37
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  ethyl 3-(2-(methyl)-1-(phenylsulfonyl)-1H-indol-3-yl)acrylate 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 四氯化碳 为溶剂， 生成 ethyl 3-(2-(bromomethyl)-1-(phenylsulfonyl)-1H-indol-3-yl)acrylate
  参考文献：
  名称：

  Synthesis of di-, tri-, and tetra-substituted carbazole analogs involving annulation methodology

  摘要：

  Synthesis of substituted carbazole analogs was achieved via Michael addition followed by intramolecular cyclization and subsequent aromatization. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.03.009

文献信息

• A Versatile Synthesis of Annulated Carbazole Analogs Involving a Domino Reaction of Bromomethylindoles with Arenes/Heteroarenes
  作者：Vasudevan Dhayalan、J. Arul Clement、Radhakrishnan Jagan、Arasambattu K. Mohanakrishnan

  DOI：10.1002/ejoc.200801018

  日期：2009.2

  A ZnBr2-mediated arylation of aryl/heteroaryl methyl bromides with arenes at 80 °C led to the formation of arylated products, which underwent subsequent 1,5-sigmatropic rearrangement followed by electrocyclization and aromatization with loss of a diethylmalonate unit to afford the corresponding annulated products. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

  ZnBr2 介导的芳基/杂芳基甲基溴与芳烃在 80°C 的芳基化形成芳基化产物，随后进行 1,5-σ 重排，然后进行电环化和芳构化，失去丙二酸二乙酯单元，得到相应的环化产物。产品。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
• Synthetic Approach to Dictyodendrins: A Facile Synthesis of Pyrrolo[2,3-<i>c</i>]carbazole, Pyrrolodibenzothiophene, and Benzo[<i>e</i>]indole
  作者：Potharaju Raju、Arasambattu K. Mohanakrishnan

  DOI：10.1002/ejoc.201600674

  日期：2016.9

  A facile synthesis of the pyrrolo[2,3‐c]carbazole core unit of dictyodendrins has been achieved by using an intramolecular cyclization reaction of a triene precursor. The method was also applied to the syntheses of pyrrolodibenzothiophene and benzo[e]indole derivatives.

  通过使用三烯前体的分子内环化反应，可以轻松合成双齿yo草的吡咯并[2,3- c ]咔唑核心单元。该方法还应用于吡咯二苯并噻吩和苯并[ e ]吲哚衍生物的合成。
• Synthesis of 3-Indolylpyrroles via Base-Mediated Cycloaddition of TOSMIC with Activated Indole-2/3-vinylenes
  作者：Ramalingam Balamurugan、Radhakrishnan Sureshbabu、Ganesan Gobi Rajeshwaran、Arasambattu K. Mohanakrishnan

  DOI：10.1080/00397910802406703

  日期：2009.1.13

  A synthesis of various types of 3-indolylpyrroles is reported involving a base-mediated 1,3-dipolar cycloaddition of TOSMIC with activated indole-2-3-vinylenes.
• 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.
• 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).