N-[(5-bromoindol-3-yl)-(phenyl)methyl]-4-methylbenzenesulfonamide | 1172116-64-1

• 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: N-[(5-bromoindol-3-yl)-(phenyl)methyl]-4-methylbenzenesulfonamide
• 英文别名: N-[(5-bromo-1H-indol-3-yl)-phenylmethyl]-4-methylbenzenesulfonamide
• CAS: 1172116-64-1；1257844-48-6
• 化学式: C₂₂H₁₉BrN₂O₂S
• 分子量: 455.375
• InChiKey: SSHOOBNUJVIKDM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  70.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-甲基吲哚 、 N-[(5-bromoindol-3-yl)-(phenyl)methyl]-4-methylbenzenesulfonamide 在 1,3-diTs-2,3-dihydro-2-oxo-benzo[1,3,2]-diaza-phosphole-2-ol 作用下， 以 甲苯 为溶剂， 反应 1.0h， 以74%的产率得到5-bromo-3-((1-methyl-1H-indol-3-yl)(phenyl)methyl)-1H-indole
  参考文献：
  名称：

  布朗斯台德酸催化合成不对称芳基双（3-吲哚基）-甲烷

  摘要：

  已通过布朗斯台德酸催化的 α-(3-吲哚基) 苄胺与 N-甲基吲哚的 Friedel-Crafts 烷基化合成了不对称的芳基双 (3-吲哚基) 甲烷。使用 5 mol% 的催化剂，反应在温和条件下顺利进行，以优异的产率（高达 98%）得到不对称的三芳基甲烷。

  DOI：

  10.1055/s-0028-1088109
• 作为产物：
  描述：

  对甲苯磺酰胺 在 磷酸二苯酯 、 硅酸四乙酯 作用下， 以 甲苯 为溶剂， 反应 12.0h， 生成 N-[(5-bromoindol-3-yl)-(phenyl)methyl]-4-methylbenzenesulfonamide
  参考文献：
  名称：

  Organic hydrogen phosphites and hydrogen phosphates catalyzed Friedel–Crafts amidoalkylation of indoles with aryl aldimines

  摘要：

  A highly efficient and selective Friedel-Crafts amidoalkylation reaction of indoles with N-Ts aryl aldimines has been developed utilizing dimethyl hydrogen phosphite or diphenyl hydrogen phosphate as the organocatalysts, providing a facile and cost-effective process for synthesis of 3-indolyl methanamine derivatives in good to excellent yields. This transformation displays a broad substrate scope and wide functional-group tolerability, regardless of the electronic and steric properties of N-Ts aryl aldimines. Given that the developed catalytic Friedel-Crafts amidoalkylation reaction exhibits several salient features such as metal-free catalysis, high efficiency, low cost and mild reaction condition, this process might have practical applications in the synthesis of 3-indolyl methanamine derivatives. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.07.010

文献信息

• Enantioselective Synthesis of Unsymmetrical Triarylmethanes by Chiral Brønsted Acids
  作者：Feng-Lai Sun、Xiao-Jian Zheng、Qing Gu、Qing-Li He、Shu-Li You

  DOI：10.1002/ejoc.200901164

  日期：2010.1

  Chiral Bronsted acid catalyzed Friedel-Crafts alkylation of electron-rich arenes with (3-indolyl)methanamines has been realized to provide an efficient synthesis of enantioenriched unsymmetrical triarylmethanes. With 5 mol-% of a newly developed chiral phosphoric acid, the enantioenriched unsymmetrical triarylmethanes were obtained in excellent yields with up to 91 % ee.

  手性布朗斯台德酸催化富电子芳烃与（3-吲哚基）甲胺的弗瑞德-克来福特烷基化已被实现，以提供对映体富集的不对称三芳基甲烷的有效合成。使用 5 mol-% 的新开发的手性磷酸，以高达 91% ee 的优异收率获得对映体富集的不对称三芳基甲烷。
• Organic hydrogen phosphites and hydrogen phosphates catalyzed Friedel–Crafts amidoalkylation of indoles with aryl aldimines
  作者：Bei-Lei Wang、Jin-Xin Zhang、Nai-Kai Li、Guo-Gui Liu、Qi Shen、Xing-Wang Wang

  DOI：10.1016/j.tetlet.2011.07.010

  日期：2011.9

  A highly efficient and selective Friedel-Crafts amidoalkylation reaction of indoles with N-Ts aryl aldimines has been developed utilizing dimethyl hydrogen phosphite or diphenyl hydrogen phosphate as the organocatalysts, providing a facile and cost-effective process for synthesis of 3-indolyl methanamine derivatives in good to excellent yields. This transformation displays a broad substrate scope and wide functional-group tolerability, regardless of the electronic and steric properties of N-Ts aryl aldimines. Given that the developed catalytic Friedel-Crafts amidoalkylation reaction exhibits several salient features such as metal-free catalysis, high efficiency, low cost and mild reaction condition, this process might have practical applications in the synthesis of 3-indolyl methanamine derivatives. (C) 2011 Elsevier Ltd. All rights reserved.
• Brønsted Acid Catalyzed Synthesis of Unsymmetrical Arylbis(3-indolyl)-methanes
  作者：Shu-Li You、Qing-Li He、Feng-Lai Sun、Xiao-Jian Zheng

  DOI：10.1055/s-0028-1088109

  日期：2009.4

  Jnsymmetrical arylbis(3-indolyl)methanes have been synthesized via a Bronsted acid catalyzed Friedel-Crafts alkylation of α-(3-indolyl)benzylamines with N-methylindole. With 5 mol% of the catalyst, the reaction proceeds smoothly under mild conditions, affording the unsymmetrical triarylmethanes in excellent yields (up to 98%).

  已通过布朗斯台德酸催化的 α-(3-吲哚基) 苄胺与 N-甲基吲哚的 Friedel-Crafts 烷基化合成了不对称的芳基双 (3-吲哚基) 甲烷。使用 5 mol% 的催化剂，反应在温和条件下顺利进行，以优异的产率（高达 98%）得到不对称的三芳基甲烷。