(E)-5-chloro-N-((4-methylstyryl)sulfonyl)thiophene-2-carboxamide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: (E)-5-chloro-N-((4-methylstyryl)sulfonyl)thiophene-2-carboxamide
• 英文别名: 5-chloro-N-[(E)-2-(4-methylphenyl)ethenyl]sulfonylthiophene-2-carboxamide
• 化学式: C₁₄H₁₂ClNO₃S₂
• 分子量: 341.839
• InChiKey: WPZLEWBGEILURD-CMDGGOBGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  99.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-5-chloro-N-((4-methylstyryl)sulfonyl)thiophene-2-carboxamide 在 碘 、 十六烷基三甲基溴化铵 作用下， 以 水 、 二甲基亚砜 为溶剂， 反应 0.25h， 生成 5-chloro-N-((1,3-diphenyl-5-(p-tolyl)-1H-pyrazol-4-yl)sulfonyl)thiophene-2-carboxamide
  参考文献：
  名称：

  Green approach for the synthesis of thiophenyl pyrazoles and isoxazoles by adopting 1,3-dipolar cycloaddition methodology and their antimicrobial activity

  摘要：

  A variety of N-((1,3-dipheny1-5-aryl-1H-pyrazol-4-yl)sulfonyl)thiophene-2-carboxamides (7) and N-((5ary1-3-phenylisoxazol-4-yl)sulfonyl)thiophene-2-carboxamides (8) were prepared from (E)-N-(aryl-ethenesulfonyl)thiophene-2-carboxamides (4) adopting 1,3 -dipolar cycloaddition of nitrile imines and nitrile oxides generated from araldehyde phenylhydrazones and araldoximes in the presence of iodosobenzene and CTAB followed by oxidation with 12 in DMSO. The compounds 4f, 7e, 7f, 8e and 8f showed potential antibacterial activity against B. subtilis whereas Se and 8f exhibited potential antifungal activity against A. niger. (C) 2017 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2017.11.093
• 作为产物：
  描述：

  2-(4-甲基苯基)乙烯磺酰氯 在 4-二甲氨基吡啶 、 ammonium hydroxide 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 (E)-5-chloro-N-((4-methylstyryl)sulfonyl)thiophene-2-carboxamide
  参考文献：
  名称：

  Green approach for the synthesis of thiophenyl pyrazoles and isoxazoles by adopting 1,3-dipolar cycloaddition methodology and their antimicrobial activity

  摘要：

  A variety of N-((1,3-dipheny1-5-aryl-1H-pyrazol-4-yl)sulfonyl)thiophene-2-carboxamides (7) and N-((5ary1-3-phenylisoxazol-4-yl)sulfonyl)thiophene-2-carboxamides (8) were prepared from (E)-N-(aryl-ethenesulfonyl)thiophene-2-carboxamides (4) adopting 1,3 -dipolar cycloaddition of nitrile imines and nitrile oxides generated from araldehyde phenylhydrazones and araldoximes in the presence of iodosobenzene and CTAB followed by oxidation with 12 in DMSO. The compounds 4f, 7e, 7f, 8e and 8f showed potential antibacterial activity against B. subtilis whereas Se and 8f exhibited potential antifungal activity against A. niger. (C) 2017 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2017.11.093

文献信息

• Green approach for the synthesis of thiophenyl pyrazoles and isoxazoles by adopting 1,3-dipolar cycloaddition methodology and their antimicrobial activity
  作者：D.V. Sowmya、G. Lakshmi Teja、A. Padmaja、V. Kamala Prasad、V. Padmavathi

  DOI：10.1016/j.ejmech.2017.11.093

  日期：2018.1

  A variety of N-((1,3-dipheny1-5-aryl-1H-pyrazol-4-yl)sulfonyl)thiophene-2-carboxamides (7) and N-((5ary1-3-phenylisoxazol-4-yl)sulfonyl)thiophene-2-carboxamides (8) were prepared from (E)-N-(aryl-ethenesulfonyl)thiophene-2-carboxamides (4) adopting 1,3 -dipolar cycloaddition of nitrile imines and nitrile oxides generated from araldehyde phenylhydrazones and araldoximes in the presence of iodosobenzene and CTAB followed by oxidation with 12 in DMSO. The compounds 4f, 7e, 7f, 8e and 8f showed potential antibacterial activity against B. subtilis whereas Se and 8f exhibited potential antifungal activity against A. niger. (C) 2017 Elsevier Masson SAS. All rights reserved.