Ethyl 3'-<1-(phenylsulfonyl)-2-methylindole-3-yl>acrylate | 856251-55-3

• 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'-<1-(phenylsulfonyl)-2-methylindole-3-yl>acrylate
• 英文别名: ethyl (E)-3-[1-(benzenesulfonyl)-2-methylindol-3-yl]prop-2-enoate
• CAS: 856251-55-3
• 化学式: C₂₀H₁₉NO₄S
• 分子量: 369.441
• InChiKey: DJQZTUHWUXTYRS-BUHFOSPRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  73.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Ethyl 3'-<1-(phenylsulfonyl)-2-methylindole-3-yl>acrylate 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 Ethyl 3'-<1-(phenylsulfonyl)-2-(2-bromomethyl)indole-3-yl>acrylate
  参考文献：
  名称：

  Stille carbonylation of N-protected bromomethylindoles

  摘要：

  A variety of N-protected indolylmethyl bromides are carbonylated using 5 mol % Pd(PPh3)(2)Cl-2 under Stille conditions in the presence of an alcohol to afford the corresponding methyl/ethyl esters. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.05.010
• 作为产物：
  描述：

  2-甲基吲哚-3-甲醛 在 sodium hydride 作用下， 以 四氢呋喃 、 乙二醇二甲醚 为溶剂， 反应 12.0h， 生成 Ethyl 3'-<1-(phenylsulfonyl)-2-methylindole-3-yl>acrylate
  参考文献：
  名称：

  A Versatile Construction of the 8H-Quino[4,3-b]carbazole Ring System as a Potential DNA Binder

  摘要：

  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.

  DOI：

  10.1021/jo00112a011

文献信息

• 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 efficient preparation of 1-phenylsulfonylindolyl methyl sulfoxides using KF/m-CPBA
  作者：Arasambattu K. Mohanakrishnan、Neelamegam Ramesh

  DOI：10.1016/j.tetlet.2005.04.067

  日期：2005.6

  A variety of 1-phenylsulfonylindolylmethyl sulfides are selectively oxidized to the corresponding sulfoxides using a hitherto unexplored KF/m-CPBA system. A major advantage is the absence of over-oxidation. (c) 2005 Elsevier Ltd. All rights reserved.
• Stille carbonylation of N-protected bromomethylindoles
  作者：Arasambattu K. Mohanakrishnan、Neelamegam Ramesh

  DOI：10.1016/j.tetlet.2005.05.010

  日期：2005.7

  A variety of N-protected indolylmethyl bromides are carbonylated using 5 mol % Pd(PPh3)(2)Cl-2 under Stille conditions in the presence of an alcohol to afford the corresponding methyl/ethyl esters. (c) 2005 Elsevier Ltd. All rights reserved.
• 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.