1-phenylsulfonyl-3-phenylthio-2-chloromethylindole | 868081-88-3

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 1-phenylsulfonyl-3-phenylthio-2-chloromethylindole
• 英文别名: 1-(Benzenesulfonyl)-2-(chloromethyl)-3-phenylsulfanylindole；1-(benzenesulfonyl)-2-(chloromethyl)-3-phenylsulfanylindole
• CAS: 868081-88-3
• 化学式: C₂₁H₁₆ClNO₂S₂
• 分子量: 413.949
• InChiKey: LERMWNHJBLMSSM-UHFFFAOYSA-N

物化性质

• 沸点：
  601.5±65.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  72.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-phenylsulfonyl-3-phenylthio-2-chloromethylindole 在 2-硝基丙烷 、 sodium hydride 、 sodium iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 1-(苯磺酰基)-3-甲基吲哚-2-甲醛
  参考文献：
  名称：

  Synthesis of N-protected indolaldehydes using modified Hass procedure

  摘要：

  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.

  DOI：

  10.1016/j.tet.2007.08.035
• 作为产物：
  描述：

  1-phenylsulfonyl-3-phenylthio-2-bromomethylindole 在 N-氯代丁二酰亚胺 、 过氧化苯甲酰 作用下， 以 四氢呋喃 、 四氯化碳 为溶剂， 生成 1-phenylsulfonyl-3-phenylthio-2-chloromethylindole
  参考文献：
  名称：

  Unusual dimerization of N-protected bromomethylindoles using phenylmagnesium chloride

  摘要：

  A novel dimerization of N-protected bromornethylindoles involving an exchange reaction with phenylmagnesium chloride is reported. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.08.068

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。
• Lewis Acid-Mediated Michaelis−Arbuzov Reaction at Room Temperature: A Facile Preparation of Arylmethyl/Heteroarylmethyl Phosphonates
  作者：Ganesan Gobi Rajeshwaran、Meganathan Nandakumar、Radhakrishnan Sureshbabu、Arasambattu K Mohanakrishnan

  DOI：10.1021/ol1029436

  日期：2011.3.18

  A facile preparation of arylmethyl and heteroarylmethyl phosphonate esters was achieved involving a Lewis acid mediated Michaelis-Arbuzov reaction at room temperature. Interaction of arylmethyl halides/alcohols with triethyl phosphite in the presence of Lewis acid at room temperature afforded phosphonate esters in good yields.
• 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.
• 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 using phenylmagnesium chloride
  作者：Arasambattu K. Mohanakrishnan、Neelamegam Ramesh、Chandran Prakash

  DOI：10.1016/j.tetlet.2005.08.068

  日期：2005.10

  A novel dimerization of N-protected bromornethylindoles involving an exchange reaction with phenylmagnesium chloride is reported. (c) 2005 Elsevier Ltd. All rights reserved.