N-((4-chlorophenyl)(1H-indol-3-yl)methyl)-4-methylbenzenesulfonamide | 1027231-16-8

• 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-((4-chlorophenyl)(1H-indol-3-yl)methyl)-4-methylbenzenesulfonamide
• 英文别名: N-[indol-3-yl-(4-chlorophenyl)methyl]-4-methylbenzenesulfonamide；N-((4-chlorophenyl)(1H-indol-3-yl)methyl)toluenesulfonamide；N-[(4-chlorophenyl)-(1H-indol-3-yl)methyl]-4-methylbenzenesulfonamide
• CAS: 1027231-16-8；886209-17-2；902773-95-9
• 化学式: C₂₂H₁₉ClN₂O₂S
• 分子量: 410.924
• InChiKey: GQFWEMHRAAIOGO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 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：

  吲哚 、 N-((4-chlorophenyl)(1H-indol-3-yl)methyl)-4-methylbenzenesulfonamide 在 [Ir(COD)(SnCl3)Cl(μ-Cl)]2 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 1.0h， 以83%的产率得到化合物C-DIM12
  参考文献：
  名称：

  Heterobimetallic Ir–Sn catalysis: aza-Friedel–Crafts reaction of N-sulfonyl aldimines

  摘要：

  The heterobimetallic complex [Ir(COD)(SnCl3)Cl(mu-Cl)](2) catalyzes the aza-Friedel Crafts reaction of 1,3,5-trimethoxybenzene, as well as substituted indoles with N-sulfonyl aldimines leading to the formation of diarylamines and triarylmethanes in good yields. The symmetrical triarylmethanes were also obtained from diarylamines and suitable nucleophiles via simultaneous cleavage of sp(3) C-N bond and elimination of 1,3,5-trimethoxybenzene. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.01.074
• 作为产物：
  描述：

  对甲苯磺酰胺 在 [Ir(COD)(SnCl3)Cl(μ-Cl)]2 作用下， 以 1,2-二氯乙烷 、 甲苯 为溶剂， 反应 12.33h， 生成 N-((4-chlorophenyl)(1H-indol-3-yl)methyl)-4-methylbenzenesulfonamide
  参考文献：
  名称：

  Heterobimetallic Ir–Sn catalysis: aza-Friedel–Crafts reaction of N-sulfonyl aldimines

  摘要：

  The heterobimetallic complex [Ir(COD)(SnCl3)Cl(mu-Cl)](2) catalyzes the aza-Friedel Crafts reaction of 1,3,5-trimethoxybenzene, as well as substituted indoles with N-sulfonyl aldimines leading to the formation of diarylamines and triarylmethanes in good yields. The symmetrical triarylmethanes were also obtained from diarylamines and suitable nucleophiles via simultaneous cleavage of sp(3) C-N bond and elimination of 1,3,5-trimethoxybenzene. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.01.074

文献信息

• Asymmetric Friedel−Crafts Addition of Indoles to <i>N</i>-Sulfonyl Aldimines:  A Simple Approach to Optically Active 3-Indolyl-methanamine Derivatives
  作者：Yi-Xia Jia、Jian-Hua Xie、Hai-Feng Duan、Li-Xin Wang、Qi-Lin Zhou

  DOI：10.1021/ol0602001

  日期：2006.4.1

  [reaction: see text] The enantioselective copper(II)-catalyzed Friedel-Crafts addition of indoles to N-sulfonyl aldimines was developed using chiral bisoxazoline as ligands, and high enantioselectivities (up to 96% ee) were achieved.

  [反应：见正文]使用手性双恶唑啉作为配体，开发了对映体选择性铜（II）催化的吲哚的弗里德-克来福特将吲哚添加到N-磺酰基醛亚胺中，并实现了高对映选择性（ee高达96％）。
• Access to Chiral Bisphenol Ligands (BPOL) through Desymmetrizing Asymmetric Ortho-Selective Halogenation
  作者：Xiaodong Xiong、Tianyu Zheng、Xinyan Wang、Ying-Lung Steve Tse、Ying-Yeung Yeung

  DOI：10.1016/j.chempr.2020.01.009

  日期：2020.4

  Privileged chiral catalyst scaffolds are highly useful in chemical synthesis such as drug preparation. Substituted phenol ligands are among the most frequently used scaffolds. However, the preparation of chiral phenol ligands commonly involves tedious synthetic procedures. Herein, we describe a facile strategy to prepare potent chiral bisphenols (BPOLs) through the desymmetrizing asymmetric ortho-halogenation

  特权手性催化剂支架在化学合成（例如药物制备）中非常有用。取代的酚配体是最常用的支架之一。但是，手性酚配体的制备通常涉及繁琐的合成程序。本文中，我们描述了一种通过去对称不对称邻位卤化制备有效手性双酚（BPOL）的简便策略。为了阐明机械原理，进行了理论和实验研究。操作BPOL产品中的卤素手柄可产生不对称的手性BPOL配体，该配体是潜在的优先催化剂支架，已应用于其他不对称催化反应中。
• Asymmetric Friedel−Crafts Reaction of Indoles with Imines by an Organic Catalyst
  作者：Yong-Qiang Wang、Jun Song、Ran Hong、Hongming Li、Li Deng

  DOI：10.1021/ja062700v

  日期：2006.6.1

  In this communication, we report an asymmetric Friedel-Crafts reaction of indoles with imines catalyzed by a bifunctional cinchona alkaloid catalyst. This is the first efficient organocatalytic asymmetric Friedel-Crafts reaction of indoles with imines. This reaction is operationally simple and, unprecedentedly, affords high enantioselectivity for a wide range of indoles and both aryl and alkyl imines

  在这篇通讯中，我们报告了由双功能金鸡纳生物碱催化剂催化的吲哚与亚胺的不对称弗里德尔-克拉夫茨反应。这是吲哚与亚胺的第一个有效的有机催化不对称弗里德尔-克拉夫茨反应。该反应操作简单，并且前所未有地为广泛的吲哚以及芳基和烷基亚胺提供了高对映选择性。这为光学活性 3-吲哚基甲胺建立了一种直接、收敛和通用的方法，这是一种嵌入在众多吲哚生物碱和合成吲哚衍生物中的结构基序。
• Vanadium-catalyzed enantioselective Friedel–Crafts-type reactions
  作者：Shinobu Takizawa、Fernando Arteaga Arteaga、Yasushi Yoshida、Junpei Kodera、Yoshihiro Nagata、Hiroaki Sasai

  DOI：10.1039/c2dt32202a

  日期：——

  Vanadium-mediated enantioselective Friedel–Crafts (FC)-type reactions were established using the dinuclear vanadium complex (Ra,S,S)-1a. The vanadium complex promoted the FC-type reaction of imines with 2-naphthols or indoles to give corresponding adducts with high enantioselectivities.

  使用二核钒配合物(Ra,S,S)-1a建立了钒介导的对映选择性Friedel-Crafts（FC）型反应。钒配合物促进了亚胺与2-萘醇或吲哚的FC型反应，生成相应的加合物，具有较高的对映选择性。
• Highly enantioselective Friedel–Crafts reaction of indoles with N-sulfonyl aldimines catalyzed by heteroarylidene malonate-type bis(oxazoline) copper(II) complexes
  作者：Lei Liu、Qiuying Zhao、Fengpei Du、Hongliang Chen、Zhaohai Qin、Bin Fu

  DOI：10.1016/j.tetasy.2011.10.017

  日期：2011.11

  The enantioselective Friedel–Crafts addition of indoles to N-sulfonyl aldimines was studied using a heteroarylidene malonate-type bis(oxazoline) as a chiral ligand. High to excellent enantioselectivities (up to >99% ee) were achieved using the complex of copper(II)–L1b with a benzyl group. The effects of ligand structure, solvent, temperature and substrate on the reaction were also investigated.

  使用杂芳基丙二酸酯型双（恶唑啉）作为手性配体，研究了吲哚向N-磺酰基醛亚胺中的吲哚的对映选择性Friedel-Crafts加成反应。使用铜（II）–L1b与苄基的配合物可实现高至优异的对映选择性（高达> 99％ee）。还研究了配体结构，溶剂，温度和底物对反应的影响。