N-benzoyl-2-chlorobenzenesulfonamide | 143105-07-1

• 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-benzoyl-2-chlorobenzenesulfonamide
• 英文别名: Benzamide, N-[(2-chlorophenyl)sulfonyl]-；N-(2-chlorophenyl)sulfonylbenzamide
• CAS: 143105-07-1
• 化学式: C₁₃H₁₀ClNO₃S
• 分子量: 295.746
• InChiKey: DTNPMIRWOVXSPP-UHFFFAOYSA-N

物化性质

• 密度：
  1.399±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  71.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-benzoyl-2-chlorobenzenesulfonamide 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 以86%的产率得到3-phenyl-7-chloro-1,2-benzisothiazole 1,1-dioxide
  参考文献：
  名称：

  Aromatic heteroannulation via metalation-cyclization of N-acyl-2-chlorobenzenesulfonamides and N-acylbenzenesulfonamides

  摘要：

  N-Acyl-2-chlorobenzenesulfonamides 7a-d undergo competitive metal-halogen exchange and or alpha-deprotonation reactions when treated sequentially with sodium hydride and n-butyllithium. The o-lithio intermediates derived from metal-halogen exchange and ortho-deprotonation undergo cyclization to afford 3-substituted 1,2-benzisothiazole 1,1-dioxides 10a-d and 3-substituted 7-chloro-1,2-benzisothiazole 1,1-dioxides 14a-d, respectively. Reaction time-temperature data show evidence for the slow conversion of the lateral dianion of N-acetyl-2-chlorobenzenesulfonamide (7a) to the corresponding N,ortho-dialkali salt. 1,2-Benzisothiazole 1,1-dioxides 14a-d were obtained in good yield and free from products resulting from metal-halogen exchange by treatment of sulfonamides 7a-d with 2 equiv of LDA in THF. In the presence of 2 equiv of LDA, N-acylbenzenesulfonamides devoid of or containing only weakly acidic alpha-hydrogens undergo alpha-deprotonation-cyclization to afford the respective 1,2-benzoisothiazole 1,1-dioxides.

  DOI：

  10.1021/jo00046a012
• 作为产物：
  描述：

  邻氯苯磺酰胺 、 苯甲酸 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 生成 N-benzoyl-2-chlorobenzenesulfonamide
  参考文献：
  名称：

  N-酰基磺酰胺的电化学迁移环化

  摘要：

  N-酰基磺酰胺的电化学迁移环化已被开发用于轻松制备各种具有生物学意义但合成具有挑战性的苯并噻嗪二氧化物。

  DOI：

  10.1002/anie.202206058

文献信息

• Facile synthesis of acyl sulfonamides from carboxyic acids using the Mukaiyama reagent
  作者：Ling Chen、Guanglin Luo

  DOI：10.1016/j.tetlet.2018.12.030

  日期：2019.1

  A fast and convenient method using the Mukaiyama reagent was developed to prepare acyl sulfonamides from carboxylic acids and sulfonamides. This methodology is effective for a range of acids and sulfonamides proceeding in moderate to good yields with the majority of reactions complete within one hour under the optimized condition.

  开发了使用Mukaiyama试剂的快速便捷的方法，以从羧酸和磺酰胺制备酰基磺酰胺。该方法对于以中等至良好收率进行一系列酸和磺酰胺反应有效，并且大多数反应在优化条件下在一小时内即可完成。
• Palladium-Catalyzed CH Activation and Intermolecular Annulation with Allenes
  作者：Xiao-Feng Xia、Yu-Qi Wang、Lu-Lu Zhang、Xian-Rong Song、Xue-Yuan Liu、Yong-Min Liang

  DOI：10.1002/chem.201304300

  日期：2014.4.22

  A new and efficient PdII‐catalyzed intermolecular annulation of N‐benzoylsulfonamide with allenes for the synthesis of 3,4‐dihydroisoquinolin‐1(2H)‐ones is reported. This CH functionalization is compatible with ambient air and moisture, and it can be applied to terminal or internal allenes with different synthetically attractive functional groups. Control experiments and a kinetic isotope effect study

  报道了一种新的高效Pd II催化的N-苯甲酰磺酰胺与烯丙基的分子间环化反应，用于合成3,4-二氢异喹啉-1（2 H）-酮。这种CH官能化可与周围的空气和湿气兼容，并且可用于具有不同合成吸引力的官能团的末端或内部烯丙基。进行了控制实验和动力学同位素效应研究，并提出了合理的机理。
• A convenient method for the preparation of acylsulfonamide libraries
  作者：Claudio F Sturino、Marc Labelle

  DOI：10.1016/s0040-4039(98)01240-4

  日期：1998.8

  The preparation of an acylsulfonamide library is described using resin bound EDC (1-(3 dimethylaminopropyl)-3-ethylcarbodiimide). A polymer supported sulfonic acid (A-15) is used as a scavenger to remove dimethylaminopyridine and purification only involves filtration of the reaction mixture. This method provides the acylsulfonamides products in good yields and purity. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Aromatic heteroannulation via metalation-cyclization of N-acyl-2-chlorobenzenesulfonamides and N-acylbenzenesulfonamides
  作者：Christine K. F. Hermann、James A. Campbell、Thomas D. Greenwood、Judith A. Lewis、James F. Wolfe

  DOI：10.1021/jo00046a012

  日期：1992.9

  N-Acyl-2-chlorobenzenesulfonamides 7a-d undergo competitive metal-halogen exchange and or alpha-deprotonation reactions when treated sequentially with sodium hydride and n-butyllithium. The o-lithio intermediates derived from metal-halogen exchange and ortho-deprotonation undergo cyclization to afford 3-substituted 1,2-benzisothiazole 1,1-dioxides 10a-d and 3-substituted 7-chloro-1,2-benzisothiazole 1,1-dioxides 14a-d, respectively. Reaction time-temperature data show evidence for the slow conversion of the lateral dianion of N-acetyl-2-chlorobenzenesulfonamide (7a) to the corresponding N,ortho-dialkali salt. 1,2-Benzisothiazole 1,1-dioxides 14a-d were obtained in good yield and free from products resulting from metal-halogen exchange by treatment of sulfonamides 7a-d with 2 equiv of LDA in THF. In the presence of 2 equiv of LDA, N-acylbenzenesulfonamides devoid of or containing only weakly acidic alpha-hydrogens undergo alpha-deprotonation-cyclization to afford the respective 1,2-benzoisothiazole 1,1-dioxides.
• Electrochemical Migratory Cyclization of <i>N</i> ‐Acylsulfonamides
  作者：Zhaojiang Shi、Yuanyuan Li、Nan Li、Wei‐Zhen Wang、Hao‐Kuan Lu、Hong Yan、Yaofeng Yuan、Jun Zhu、Ke‐Yin Ye

  DOI：10.1002/anie.202206058

  日期：2022.7.25

  Electrochemical migratory cyclization of N-acylsulfonamides has been developed for the facile preparation of a diverse array of biologically interesting yet synthetically challenging benzoxathiazine dioxides.

  N-酰基磺酰胺的电化学迁移环化已被开发用于轻松制备各种具有生物学意义但合成具有挑战性的苯并噻嗪二氧化物。