苯磺酰胺,N-(5-氯-2-硝基苯基)-4-甲基- | 198839-44-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 苯磺酰胺,N-(5-氯-2-硝基苯基)-4-甲基-
• 英文名称: N-(5-chloro-2-nitrophenyl)-4-methylbenzenesulfonamide
• 英文别名: toluene-4-sulfonic acid-(5-chloro-2-nitro-anilide)；Toluol-4-sulfonsaeure-(5-chlor-2-nitro-anilid)
• CAS: 198839-44-0
• 化学式: C₁₃H₁₁ClN₂O₄S
• 分子量: 326.76
• InChiKey: XOHJMPZUIUVGJM-UHFFFAOYSA-N

物化性质

• 熔点：
  133-135 °C(Solv: ethyl ether (60-29-7))
• 沸点：
  476.4±55.0 °C(Predicted)
• 密度：
  1.494±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.36
• 重原子数：
  21.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  89.31
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  苯磺酰胺,N-(5-氯-2-硝基苯基)-4-甲基- 在 盐酸 、 水 、 锌 作用下， 以 乙醇 为溶剂， 以87%的产率得到N-(2-amino-5-chlorophenyl)-4-methylbenzenesulfonamide
  参考文献：
  名称：

  Novel 1,3-dihydro-benzimidazol-2-ones and their analogues as potent non-nucleoside HIV-1 reverse transcriptase inhibitors

  摘要：

  A series of novel benzimidazolones and their analogues, characterized by the presence of one or more methyl groups or other bioisosteric moieties at different positions of the phenyl ring at N-1, were synthesized and evaluated as inhibitors of human immunodeficiency virus type-1 (HIV-1). Most of the new compounds proved to be highly effective in inhibiting both HIV-1 replication in MT4 cells with minimal cytotoxicity and RT enzyme at nanomolar concentrations. Some derivatives were also tested against RTs containing single amino acid mutations responsible for resistance to non-nucleoside reverse transcriptase inhibitors (NNRTIs). The different potencies displayed by the new compounds were studied using molecular modeling. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.12.059
• 作为产物：
  描述：

  N-(5-chloro-2-nitrophenyl)-N-(p-tolylsulfonyl) toluene-p-sulfonyl chloride 在 苄基三乙基溴化铵 、 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以56%的产率得到苯磺酰胺,N-(5-氯-2-硝基苯基)-4-甲基-
  参考文献：
  名称：

  Broggini, Gianluigi; Garanti, Luisa; Molteni, Giorgio, Journal of Chemical Research, Miniprint, 1997, # 10, p. 2215 - 2226

  摘要：

  DOI：

文献信息

• Direct oxidative nitration of aromatic sulfonamides under mild conditions
  作者：Ying-Xiu Li、Lian-Hua Li、Yan-Fang Yang、Hui-Liang Hua、Xiao-Biao Yan、Lian-Biao Zhao、Jin-Bang Zhang、Fa-Jin Ji、Yong-Min Liang

  DOI：10.1039/c4cc03784g

  日期：——

  This efficient reaction proceeds under very mild conditions with low cost nitration reagents and can be applied in gram-scale preparation.

  这种高效反应在非常温和的条件下进行，使用成本低廉的硝化试剂，可用于克级制备。
• Tandem Reduction, Ammonolysis, Condensation, and Deamination Reaction for Synthesis of Benzothiadiazines and 1-(Phenylsulfonyl)-1<i>H</i>-benzimidazoles
  作者：Xiao Yu、Zhihong Ma、Wenjing Zhu、Hongyan Liu、Zenghui Zhang、Yi Liu、Mei Zhang、Jinbo Zhao、Pengfei Zhang、Chengcai Xia

  DOI：10.1021/acs.joc.2c02071

  日期：2022.11.4

  A novel route for a SnCl2-promoted tandem reduction, ammonolysis, condensation, and deamination reaction which uses nitrile and 2-nitro-N-phenylbenzenesulfonamide/N-(2-nitrophenyl)benzenesulfonamide to synthesize derivatives of benzothiadiazine/1-(phenylsulfonyl)-1H-benzimidazole has been developed. The method features convenient operation and good functional group tolerance. In addition, it employs

  SnCl 2促进串联还原、氨解、缩合和脱氨反应的新路线以腈和2-硝基-N-苯基苯磺酰胺/ N- (2-硝基苯基)苯磺酰胺合成苯并噻二嗪/1-(苯磺酰基)衍生物开发了-1H-苯并咪唑。该方法操作方便，官能团耐受性好。此外，它采用不敏感且廉价的 SnCl 2 / i -PrOH 作为反应试剂，为合成重要的药学靶标提供了直接途径。
• CCCXXII.—The interaction of nitroaminophenols with sulphonyl chlorides
  作者：Frank Bell

  DOI：10.1039/jr9310002343

  日期：——