N-((5-bromo-1H-indol-3-yl)(4-chlorophenyl)methyl)toluenesulfonamide | 1426243-75-5

• 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-bromo-1H-indol-3-yl)(4-chlorophenyl)methyl)toluenesulfonamide
• 英文别名: N-((5-bromo-1H-indol-3-yl)(4-chlorophenyl)methyl)-4-methylbenzenesulfonamide；N-[(5-bromo-1H-indol-3-yl)-(4-chlorophenyl)methyl]-4-methylbenzenesulfonamide
• CAS: 1426243-75-5
• 化学式: C₂₂H₁₈BrClN₂O₂S
• 分子量: 489.82
• InChiKey: LZNNTZUKKXENJU-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：
  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：

  5-溴吲哚 、 N-((5-bromo-1H-indol-3-yl)(4-chlorophenyl)methyl)toluenesulfonamide 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89%的产率得到5-bromo-3-((5-bromo-1H-indol-3-yl)(4-chlorophenyl)methyl)-1H-indole
  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-((5-bromo-1H-indol-3-yl)(4-chlorophenyl)methyl)toluenesulfonamide
  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。