N-((4-bromophenyl)(1H-indol-3-yl)methyl)-4-methylbenzenesulfonamide | 1027323-29-0

• 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-bromophenyl)(1H-indol-3-yl)methyl)-4-methylbenzenesulfonamide
• 英文别名: N-[indol-3-yl-(4-bromophenyl)methyl]-4-methylbenzenesulfonamide；N-((4-bromophenyl)(1H-indol-3-yl)methyl)toluenesulfonamide；N-[(4-bromophenyl)-(1H-indol-3-yl)methyl]-4-methylbenzenesulfonamide
• CAS: 1027323-29-0
• 化学式: C₂₂H₁₉BrN₂O₂S
• 分子量: 455.375
• InChiKey: HCKUMHGCFDRPBX-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：

  吲哚 、 N-((4-bromophenyl)(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88%的产率得到bis(1H-indol-3-yl)-(4-bromophenyl)methane
  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-bromophenyl)(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

• 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。
• 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。
• Cavity-induced enantioselectivity reversal in a chiral metal–organic framework Brønsted acid catalyst
  作者：Min Zheng、Yan Liu、Cheng Wang、Shubin Liu、Wenbin Lin

  DOI：10.1039/c2sc20379k

  日期：——

  A pair of highly porous chiral metal–organic frameworks (CMOFs 1 and 2) were constructed from [Cu2(carboxylate)4] secondary building units (SBUs) and chiral 3,3′,6,6′- or 4,4′,6,6′-tetra(benzoate) ligands derived from 1,1′-binaphthyl-2,2′-phosphoric acid. Both 1 and 2 were active catalysts for Friedel–Crafts reactions between indole and imines. Interestingly, the 1-catalyzed asymmetric reactions yielded the major enantiomers of the opposite chirality to those afforded by the corresponding homogeneous catalyst. Structural analyses and QM/MM calculations revealed that the flip of product handedness results from the chiral environment of CMOF-1 cavity, similar to enzymatic catalysis in which the product stereoselectivity is determined by the enzyme pocket.

  一对高度多孔的手性金属有机框架（CMOF 1 和 2）由 [Cu2(羧酸盐) 4] 二级结构单元 (SBU) 和手性 3,3 , 6,6 或 4 构建而成，衍生自 1,1-联萘-2,2-磷酸的 4-,6,6-四（苯甲酸酯）配体。 1 和 2 都是吲哚和亚胺之间弗里德尔·克拉夫茨反应的活性催化剂。有趣的是，1-催化的不对称反应产生了与相应均相催化剂所提供的手性相反的主要对映体。结构分析和QM/MM计算表明，产物旋向性的翻转是由CMOF-1空腔的手性环境引起的，类似于酶催化中产物的立体选择性由酶袋决定。
• 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。