ethyl 1-phenylsulfonyl-5-methoxy-2-phenylthiomethylindole-3-carboxylate | 147848-01-9

• 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: ethyl 1-phenylsulfonyl-5-methoxy-2-phenylthiomethylindole-3-carboxylate
• 英文别名: Ethyl 1-(benzenesulfonyl)-5-methoxy-2-(phenylsulfanylmethyl)indole-3-carboxylate；ethyl 1-(benzenesulfonyl)-5-methoxy-2-(phenylsulfanylmethyl)indole-3-carboxylate
• CAS: 147848-01-9
• 化学式: C₂₅H₂₃NO₅S₂
• 分子量: 481.593
• InChiKey: PHSINVIARFIQHK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  33
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  108
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ethyl 1-phenylsulfonyl-5-methoxy-2-phenylthiomethylindole-3-carboxylate 在 氢氟酸 、 双氧水 作用下， 以 水 、 乙腈 为溶剂， 反应 2.0h， 以85%的产率得到ethyl 5-methoxy-2-phenylsulfinylmethyl-1-phenylsulfonylindole-3-carboxylate
  参考文献：
  名称：

  Facile Preparation of Indolyl-2/3-methylsulfoxides Using HF/H₂O₂

  摘要：

  A variety of indolyl-2/3-methylsulfides tethered with sensitive functionalities were oxidized to the corresponding sulfoxides using a hitherto unexplored HF/H2O2 system.

  DOI：

  10.1080/00397910802517848
• 作为产物：
  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) 、 sodium hydride 、 过氧化苯甲酰 作用下， 以 四氯化碳 为溶剂， 反应 6.0h， 生成 ethyl 1-phenylsulfonyl-5-methoxy-2-phenylthiomethylindole-3-carboxylate
  参考文献：
  名称：

  An efficient preparation of 1-phenylsulfonylindolyl methyl sulfoxides using KF/m-CPBA

  摘要：

  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.

  DOI：

  10.1016/j.tetlet.2005.04.067

文献信息

• Synthesis of di-, tri-, and tetra-substituted carbazole analogs involving annulation methodology
  作者：Neelamegam Ramesh、Ganesan Gobi Rajeshwaran、Arasambattu K. Mohanakrishnan

  DOI：10.1016/j.tet.2009.03.009

  日期：2009.5

  Synthesis of substituted carbazole analogs was achieved via Michael addition followed by intramolecular cyclization and subsequent aromatization. (C) 2009 Elsevier Ltd. All rights reserved.
• One pot synthesis of 4-hydroxy-3-substituted carbazoles via sulfoxide stabilised carbanion
  作者：Arasambattu I. Mohanakrishnan、Panayencheri C. Srinivasan

  DOI：10.1016/s0040-4039(00)91791-x

  日期：1993.2

  A convenient method for the synthesis of 4-hydroxy-3-substitutedcarbazoles (Potential intermediate for pyridocarbazole alkaloids) from ethyl 5-methoxy-2-phenylsulfinylmethyl-1-phenylsulfonylindole-3-carboxylate is reported.
• Facile Preparation of Indolyl-2/3-methylsulfoxides Using HF/H₂O₂
  作者：Ganesan Gobi Rajeshwaran、Neelamegam Ramesh、Arasambattu K. Mohanakrishnan

  DOI：10.1080/00397910802517848

  日期：2009.3.10

  A variety of indolyl-2/3-methylsulfides tethered with sensitive functionalities were oxidized to the corresponding sulfoxides using a hitherto unexplored HF/H2O2 system.
• 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.