N-((4-chlorophenyl)(2,4,6-trimethoxyphenyl)methyl)toluenesulfonamide | 778577-38-1

• 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-((4-chlorophenyl)(2,4,6-trimethoxyphenyl)methyl)toluenesulfonamide
• 英文别名: N-[(4-chlorophenyl)-(2,4,6-trimethoxyphenyl)methyl]-4-methylbenzenesulfonamide
• CAS: 778577-38-1
• 化学式: C₂₃H₂₄ClNO₅S
• 分子量: 461.966
• InChiKey: SSZFHNORPASOHU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  31
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  82.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-((4-chlorophenyl)(2,4,6-trimethoxyphenyl)methyl)toluenesulfonamide 、 二苯甲酰基甲烷 在 [Ir(COD)(SnCl3)Cl(μ-Cl)]2 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 2.0h， 以78%的产率得到2-((4-chlorophenyl)(2,4,6-trimethoxyphenyl)methyl)-1,3-diphenylpropane-1,3-dione
  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 C₁₆H₂₇Br₁₀Ir₂Sn₂ 作用下， 以 1,2-二氯乙烷 、 甲苯 为溶剂， 反应 12.42h， 生成 N-((4-chlorophenyl)(2,4,6-trimethoxyphenyl)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

• 一种N-二芳基甲基磺胺化合物的合成方法
  申请人：丽水学院

  公开号：CN111170899B

  公开（公告）日：2022-03-01

  本发明公开了一种N‑二芳基甲基磺胺化合物的合成方法，属于有机合成中间体技术领域，本发明利用串联反应合成N‑二芳基甲基磺胺化合物，具体包括如下步骤：①向反应管中加入摩尔比为1.0:1.0:1.0:0.1的芳香醛、磺酰胺、三甲氧基苯或其衍生物、Lewis酸，以1,2‑二氯乙烷为溶剂，室温下磁力搅拌反应8～24小时；②待反应结束后，减压蒸去大部分溶剂，以体积比为1:1～2:1的石油醚和乙酸乙酯为淋洗液对剩余的混合液进行柱层析分离提纯，即得产品；本发明合成的N‑二芳基甲基磺胺化合物在医药、农药等诸多领域有着广泛的应用。本发明的合成方法具有成本低、操作简单、收率高、条件温和等优点，具有很好的应用前景。
• Friedel−Crafts Arylation Reactions of <i>N</i>-Sulfonyl Aldimines or Sulfonamidesulfones with Electron-Rich Arenes Catalyzed by FeCl₃·6H₂O: Synthesis of Triarylmethanes and Bis-heteroarylarylmethanes
  作者：Ponnaboina Thirupathi、Sung Soo Kim

  DOI：10.1021/jo1010137

  日期：2010.8.6

  The FeCl3 center dot 6H(2)O-catalyzed Friedel-Crafts arylation reactions of N-sulfonyl aldimines or sulfonamidesulfones with electron-rich arenes and heteroarenes, which lead to the formation of triarylmethanes and bis-heteroarylarylmethanes, are developed. The use of mild reaction conditions, low catalytic loading, high yield, and single step synthesis are the advantages of the present procedure.
• RUTHENIUM PORPHYRIN CATALYZED FRIEDEL–CRAFTS TYPE REACTION OF ARENES WITH IMINES
  作者：Takuya Kurahashi、Seijiro Matsubara、Takuma Terada

  DOI：10.3987/com-12-12556

  日期：——

  Cationic ruthenium porphyrin complex was found to be an efficient catalyst for the Friedel-Crafts type reaction of arenes with imines. The use of a structurally rigid tetradentate porphyrin as the equatorial ligand and weakly coordinating axial ligand is the key to bring out the catalytic reactivity of ruthenium for the reaction.
• Design and Applications of Cyclopropenium Chalcogen Dihalides in Catalysis via C(sp³)–H···X Interactions
  作者：Junjie Yang、Yabin Zhang、Hong-Chai Fabio Wong、Jingxian Huang、Ying-Lung Steve Tse、Ying-Yeung Yeung

  DOI：10.1021/acscatal.4c00087

  日期：2024.3.1
• Heterobimetallic Ir–Sn catalysis: aza-Friedel–Crafts reaction of N-sulfonyl aldimines
  作者：Paresh Nath Chatterjee、Arnab Kumar Maity、Swapna Sarita Mohapatra、Sujit Roy

  DOI：10.1016/j.tet.2013.01.074

  日期：2013.4

  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.