2-Methyl-3-[3-phenyl-1-(toluene-4-sulfonyl)-propyl]-1H-indole | 911303-05-4

• 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: 2-Methyl-3-[3-phenyl-1-(toluene-4-sulfonyl)-propyl]-1H-indole
• 英文别名: 2-methyl-3-[1-(4-methylphenyl)sulfonyl-3-phenylpropyl]-1H-indole
• CAS: 911303-05-4
• 化学式: C₂₅H₂₅NO₂S
• 分子量: 403.545
• InChiKey: SNOPDDTXJNNIGP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  58.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-Methyl-3-[3-phenyl-1-(toluene-4-sulfonyl)-propyl]-1H-indole 在 polymer-supported sodium borohydride 作用下， 以 2-甲基四氢呋喃 、 乙醇 为溶剂， 反应 0.67h， 以75%的产率得到2-methyl-3-(3-phenylpropyl)-1H-indole
  参考文献：
  名称：

  通过在流动化学条件下还原磺酰基吲哚来制备 3-烷基化吲哚

  摘要：

  在流动化学条件下使用聚合物负载的硼氢化钠还原 3-（1-芳基磺酰基烷基）吲哚（磺酰基吲哚）可以有效合成 3-烷基吲哚，显着减少废物并减少溶剂消耗。流动条件也适用于磺酰吲哚的合成，磺酰吲哚可以通过吲哚与醛和对甲苯亚磺酸的三组分偶联获得。使用两步流动化学方法，3-烷基吲哚可以直接从它们的远程吲哚和醛前体中获得。

  DOI：

  10.24820/ark.5550190.p010.882
• 作为产物：
  描述：

  [3-Phenyl-1-(toluene-4-sulfonyl)-propyl]-carbamic acid ethyl ester 、 2-甲基吲哚 在 montmorillonite K-10 作用下， 反应 6.0h， 以90%的产率得到2-Methyl-3-[3-phenyl-1-(toluene-4-sulfonyl)-propyl]-1H-indole
  参考文献：
  名称：

  Solventless Clay-Promoted Friedel−Crafts Reaction of Indoles with α-Amido Sulfones:  Unexpected Synthesis of 3-(1-Arylsulfonylalkyl) Indoles

  摘要：

  Friedel-Crafts reaction of indoles with alpha-amido sulfones in the presence of montmorillonite K-10 leads unexpectedly to 3-(1-arylsulfonylalkyl) indoles in good yield. The obtained products can be further desulfonylated under reductive or alkylative conditions giving linear and branched 3-substituted indoles.

  DOI：

  10.1021/ol061604w

文献信息

• Synthesis of Unsymmetrical Bisindolylmethanes by Reaction of Indolylmagnesium Bromides with Sulfonyl Indoles
  作者：Lixia Yuan、Alessandro Palmieri、Marino Petrini

  DOI：10.1002/adsc.201901357

  日期：2020.4.8

  functionalized indole derivatives upon reaction with nucleophiles. In this paper reaction of sulfonyl indoles with indolylmagnesium bromides is used to access unsymmetrical bisindolylmethanes. The target compounds are obtained in satisfactory yields starting from a wide range of substrate/reagent combinations. The utilization of pyrrolylmagnesium bromides for the same reaction also affords the expected adducts

  磺酰基吲哚被广泛认为是亚烷基亚吲哚烯前体，其可在与亲核试剂反应后提供官能化的吲哚衍生物。在本文中，磺酰基吲哚与吲哚基溴化镁的反应用于获得不对称的双吲哚基甲烷。从多种底物/试剂组合开始，以令人满意的产率获得目标化合物。将吡咯基溴化镁用于相同反应也可提供预期的加合物，尽管产率中等。
• Solvent-Free Non-Covalent Organocatalysis: Enantioselective Addition of Nitroalkanes to Alkylideneindolenines as a Flexible Gateway to Optically Active Tryptamine Derivatives
  作者：Mariafrancesca Fochi、Lucia Gramigna、Andrea Mazzanti、Sara Duce、Stefano Fantini、Alessandro Palmieri、Marino Petrini、Luca Bernardi

  DOI：10.1002/adsc.201100737

  日期：2012.5.7

  A catalytic asymmetric addition of nitroalkanes to alkylideneindolenines, generated in situ from arylsulfonylindoles, is presented. Despite the weakness of the non‐covalent H‐bond interactions between catalyst and substrates, the performance of the bifunctional organocatalyst used was found to be essentially unaffected by the polarity of the reaction medium. Nitroalkanes, mostly used in nearly stoichiometric

  提出了从芳基磺酰亚油酰胺原位生成的亚烷基链烷烃亚胺催化硝基不对称加成反应。尽管催化剂和底物之间的非共价氢键相互作用较弱，但发现所用双功能有机催化剂的性能基本上不受反应介质极性的影响。因此，几乎以化学计量形式使用的硝基烷烃既可以用作溶剂也可以用作试剂，从而实现了真正的无溶剂反应。本转化所显示的广泛的底物范围允许制备一些光学活性的色胺盐前体，而这些是以前的催化不对称方法无法达到的。
• Synthesis of 3-(2-nitroalkyl) indoles by reaction of 3-(1-arylsulfonylalkyl) indoles with nitroalkanes
  作者：Alessandro Palmieri、Marino Petrini、Elisabetta Torregiani

  DOI：10.1016/j.tetlet.2007.06.027

  日期：2007.8

  Sulfonyl indoles act as effective precursors of vinylogous imino derivatives in the reaction with nitroalkanes under basic conditions leading to the corresponding nitro indoles in good yield. This procedure represents an effective option to the classical conjugate addition of indoles to nitroalkenes.

  在碱性条件下，磺酰吲哚是乙烯基亚氨基亚氨基衍生物的有效前体，可与硝基烷反应，从而以高收率得到相应的硝基吲哚。该方法代表了吲哚向硝基烯烃的经典共轭加成的有效选择。
• Synthesis of indolylalkylphosphonates and 3-(1-diphenylphosphinoalkyl) indoles by reaction of 3-(1-arylsulfonylalkyl) indoles with phosphorus derivatives
  作者：Marino Petrini、Rafik R. Shaikh

  DOI：10.1016/j.tetlet.2008.07.077

  日期：2008.9

  Dialkyl phosphites as well as diphenylphosphine react with 3-(1-arylsulfonylalkyl) indoles under basic conditions leading to a formal substitution of the arylsulfonyl group through a reactive 3-alkylidene indole intermediate. (C) 2008 Elsevier Ltd. All rights reserved.
• Solventless Clay-Promoted Friedel−Crafts Reaction of Indoles with α-Amido Sulfones:  Unexpected Synthesis of 3-(1-Arylsulfonylalkyl) Indoles
  作者：Roberto Ballini、Alessandro Palmieri、Marino Petrini、Elisabetta Torregiani

  DOI：10.1021/ol061604w

  日期：2006.8.1

  Friedel-Crafts reaction of indoles with alpha-amido sulfones in the presence of montmorillonite K-10 leads unexpectedly to 3-(1-arylsulfonylalkyl) indoles in good yield. The obtained products can be further desulfonylated under reductive or alkylative conditions giving linear and branched 3-substituted indoles.