N-[(4-methylphenylsulfonyl)]-2,4-dichlorobenzamide

• 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-methylphenylsulfonyl)]-2,4-dichlorobenzamide
• 英文别名: 2,4-dichloro-N-(4-methylphenyl)sulfonylbenzamide
• 化学式: C₁₄H₁₁Cl₂NO₃S
• 分子量: 344.218
• InChiKey: HUJQPYATBOSOGN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 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：

  2-叠氮丙二酸二甲酯 、 N-[(4-methylphenylsulfonyl)]-2,4-dichlorobenzamide 在 dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer 、 silver(I) acetate 作用下， 以 甲醇 为溶剂， 反应 1.5h， 以91%的产率得到dimethyl 2-(3,5-dichloro-2-(tosylcarbamoyl)phenyl)malonate
  参考文献：
  名称：

  Selective Gram-Scale C–H Carbenoid Functionalization of N-Sulfonylarylamides with a Rhodium Catalyst

  摘要：

  DOI：

  10.1021/acs.joc.1c01182
• 作为产物：
  描述：

  对甲苯磺酰叠氮 、 2,4-二氯苯甲酸 在 copper(l) iodide 、 3-丁炔-2-酮 作用下， 以 乙腈 为溶剂， 反应 4.0h， 以92%的产率得到N-[(4-methylphenylsulfonyl)]-2,4-dichlorobenzamide
  参考文献：
  名称：

  Ñ磺酰acetylketenimine作为合成高反应性的中间Ñ -Aroylsulfonamides

  摘要：

  高反应活性的中间体N-磺酰基乙酰酮亚胺是通过参与炔酮的CuAAC /开环方法生成的。它独特的结构使其能够与芳基羧酸反应，通过新颖的Mumm型重排反应生成N-芳酰基磺酰胺。

  DOI：

  10.1016/j.tet.2018.12.005

文献信息

• DE2744137
  申请人：——

  公开号：——

  公开（公告）日：——
• Acyl Sulfonamide Anti-Proliferatives:  Benzene Substituent Structure−Activity Relationships for a Novel Class of Antitumor Agents
  作者：Karen L. Lobb、Philip A. Hipskind、James A. Aikins、Enrique Alvarez、Yiu-Yin Cheung、Eileen L. Considine、Alfonso De Dios、Gregory L. Durst、Rafael Ferritto、Cora Sue Grossman、Deborah D. Giera、Beth A. Hollister、Zhongping Huang、Philip W. Iversen、Kevin L. Law、Tiechao Li、Ho-Shen Lin、Beatriz Lopez、Jose E. Lopez、Luisa M. Martin Cabrejas、Denis J. McCann、Victoriano Molero、John E. Reilly、Michael E. Richett、Chuan Shih、Beverly Teicher、James H. Wikel、Wesley T. White、Mary M. Mader

  DOI：10.1021/jm030594r

  日期：2004.10.1

  Two closely related diaryl acylsulfonamides were recently reported as potent antitumor agents against a broad spectrum of human tumor xenografts (colon, lung, breast, ovary, and prostate) in nude mice. Especially intriguing was their activity against colorectal cancer xenografts. In this paper, rapid parallel synthesis along with traditional medicinal chemistry techniques were used to quickly delineate the structure-activity relationships of the substitution patterns in both phenyl rings of the acylsufonamide anti-proliferative scaffold. Although the molecular target of the compounds remains unclear, we determined that the vascular endothelial growth factor-dependent human umbilical vein endothelial cells assay in combination with a soft agar disk diffusion assay allowed for optimization of potency in the series. The pharmacokinetic properties and in vivo activity in an HCT116 xenograft model are reported for representative compounds.
• BENZOYLSULFONAMIDES AND SULFONYLBENZAMIDINES FOR USE AS ANTITUMOUR AGENTS
  申请人：ELI LILLY AND COMPANY

  公开号：EP1401806B1

  公开（公告）日：2006-08-09
• N-Sulfonyl acetylketenimine as a highly reactive intermediate for synthesis of N-Aroylsulfonamides
  作者：Weiguang Yang、Dayun Huang、Xiaobao Zeng、Jianlan Zhang、Xinyan Wang、Yuefei Hu

  DOI：10.1016/j.tet.2018.12.005

  日期：2019.1

  A highly reactive intermediate N-sulfonyl acetylketenimine was generated from an ynone-participated CuAAC/ring-opening method. Its unique structure allowed it to react with aryl carboxylic acids to give N-aroylsulfonamides via a novel Mumm-type rearrangement.

  高反应活性的中间体N-磺酰基乙酰酮亚胺是通过参与炔酮的CuAAC /开环方法生成的。它独特的结构使其能够与芳基羧酸反应，通过新颖的Mumm型重排反应生成N-芳酰基磺酰胺。
• Selective Gram-Scale C–H Carbenoid Functionalization of <i>N</i>-Sulfonylarylamides with a Rhodium Catalyst
  作者：Yi Dong、Bo Mei、Xue-Peng Zhang、Heng Xu

  DOI：10.1021/acs.joc.1c01182

  日期：2021.9.3