1-苯磺酰基-5-甲氧基-2-甲基吲哚-3-羧酸乙酯 | 80191-95-3

• 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
• 中文名称: 1-苯磺酰基-5-甲氧基-2-甲基吲哚-3-羧酸乙酯
• 英文名称: Ethyl 1-benzenesulphonyl-5-methoxy-2-methylindole-3-carboxylate
• 英文别名: Ethyl 1-benzenesulfonyl-5-methoxy-2-methylindole-3-carboxylate；Ethyl 1-(benzenesulfonyl)-5-methoxy-2-methylindole-3-carboxylate
• CAS: 80191-95-3
• 化学式: C₁₉H₁₉NO₅S
• 分子量: 373.43
• InChiKey: DFVJWBVTIXMEMV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  83
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-苯磺酰基-5-甲氧基-2-甲基吲哚-3-羧酸乙酯 在 N-溴代丁二酰亚胺(NBS) 、 过氧化苯甲酰 作用下， 以 四氯化碳 为溶剂， 生成 1-苯磺酰基-2-溴甲基-5-甲氧基吲哚-3-羧酸乙酯
  参考文献：
  名称：

  使用改良的Hass程序轻松制备N保护的吲哚醛

  摘要：

  通过使用NaH / DMF使N-保护的溴甲基吲哚与2-硝基丙烷反应，报道了各种N-保护的吲哚醛的制备。

  DOI：

  10.1016/j.tetlet.2005.09.121
• 作为产物：
  描述：

  1-苯磺酰基-2-溴甲基-5-甲氧基吲哚-3-羧酸乙酯 在 sodium hydride 作用下， 以 甲苯 、 苯 为溶剂， 反应 18.0h， 生成 1-苯磺酰基-5-甲氧基-2-甲基吲哚-3-羧酸乙酯
  参考文献：
  名称：

  Nagarathnam, D.; Srinivasan, P. C., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1983, vol. 22, # 10, p. 1050 - 1051

  摘要：

  DOI：

文献信息

• A facile preparation of N-protected indolaldehydes using a modified Hass procedure
  作者：Arasambattu K. Mohanakrishnan、Ramalingam Balamurugan、Neelamegam Ramesh

  DOI：10.1016/j.tetlet.2005.09.121

  日期：2005.11

  The preparation of a variety of N-protected indolaldehydes is reported via the reaction of N-protected bromomethylindoles with 2-nitropropane using NaH/DMF.

  通过使用NaH / DMF使N-保护的溴甲基吲哚与2-硝基丙烷反应，报道了各种N-保护的吲哚醛的制备。
• Unusual Oxidation of 2 (or 3)-Methylindole Derivatives with Active Manganese Dioxide
  作者：Arasambattu K. Mohanakrishnan、Panayencheri C. Srinivasan

  DOI：10.1080/00397919508015444

  日期：1995.8

  Abstract Oxidation of 5-methoxy-1-phenylsulfonyl-2-methyl indole-3-aldehyde (3) with active manganese dioxide to the corresponding indole-2,3-dialdehyde (4) and similar reactions are reported.

  摘要 5-甲氧基-1-苯基磺酰基-2-甲基吲哚-3-醛(3) 与活性二氧化锰氧化成相应的吲哚-2,3-二醛(4) 和类似的反应。
• A Versatile Construction of the 8H-Quino[4,3-b]carbazole Ring System as a Potential DNA Binder
  作者：Arasambattu K. Mohanakrishnan、Panayencheri C. Srinivasan

  DOI：10.1021/jo00112a011

  日期：1995.4

  A short synthesis of the quino[4,3-b]- and quino[3,4-b]carbazoles is reported. The key step of the synthesis involves the preparation of suitable 2,3-divinylindoles by consecutive Wittig reactions. The thermal electrocyclic reaction of the divinylindole with concomitant dehydrogenation in the presence of Pd-C gave the (nitroaryl)carbazole which on reductive cyclization led to the quinocarbazole. The cleavage of the phenylsulfonyl group followed by phosphorus oxychloride treatment and subsequent displacement of the chlorine with 3-(dimethylamino)-1-propylamine gave the title compound in 25% overall yield.
• Synthesis of N-protected indolaldehydes using modified Hass procedure
  作者：Ramalingam Balamurugan、Arasambattu K. Mohanakrishnan

  DOI：10.1016/j.tet.2007.08.035

  日期：2007.11

  A detailed study on oxidation of N-protected bromomethylindoles into the respective aldehydes was carried out. Using a modified Hass procedure, synthesis of aryl-/hetero-aryl aldehydes in particular indolaldehydes is achieved in reasonable yields. (c) 2007 Elsevier Ltd. All rights reserved.
• Unusual dimerization of N-protected bromomethylindoles/benzyl bromide with arylmetal halides: generation of indolylmethyl/benzyl radical
  作者：Neelamegam Ramesh、Chandran Prakash、Radhakrishnan Sureshbabu、Vasudevan Dhayalan、Arasambattu K. Mohanakrishnan

  DOI：10.1016/j.tet.2007.12.047

  日期：2008.2

  A detailed study on the interaction of N-protected bromomethylindoles with various types of aryl/alkyl Grignard is reported. Full experimental details on the mechanism of the unusual dimerization reaction are presented. (c) 2007 Elsevier Ltd. All rights reserved.