1-nitro-1-phenyl-2-(4-tolylsulfonyl)ethene | 137882-81-6

• 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: 1-nitro-1-phenyl-2-(4-tolylsulfonyl)ethene
• 英文别名: 1-nitro-1-phenyl-2-p-tolylthioethene；1-methyl-4-(2-nitro-2-phenylethenyl)sulfanylbenzene
• CAS: 137882-81-6
• 化学式: C₁₅H₁₃NO₂S
• 分子量: 271.34
• InChiKey: MROSMNSCUHRAPD-UHFFFAOYSA-N

物化性质

• 沸点：
  410.3±45.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-nitro-1-phenyl-2-(4-tolylsulfonyl)ethene 在 氨 、 水 作用下， 以 甲醇 为溶剂， 反应 0.08h， 以39%的产率得到(Z)-2-amino-1-nitro-1-phenylethene
  参考文献：
  名称：

  摘要：

  2-Arylthio- and 2-arylsulfonyl-1-nitro-1-phenylethenes react with an-tines to give the corresponding nitroenamines whose configuration (E or Z) depends on the amine structure. Primary amines gives rise to Z-nitroenamines, secondary cyclic amines with 2-arylthio-1-nitroalkenes form E-nitroenaniines, and with more reactive 2-arylsulfonyl-1-nitroalkenes E/Z-isomeric mixtures are obtained.

  DOI：

  10.1023/a:1023494629499
• 作为产物：
  描述：

  1,2-dinitro-1-phenylethene 以 甲醇 为溶剂， 反应 0.5h， 生成 1-nitro-1-phenyl-2-(4-tolylsulfonyl)ethene
  参考文献：
  名称：

  摘要：

  Reactions of 1-nitro-2-sulfonylalkenes with arenethiolates result in replacement of the sulfonyl group; the reactions with alkanethiolates are accompanied by subsequent addition of the reagent at the double bond to afford thioacetals. Less reactive alpha-nitro-beta-R-thiostyrenes with thiolates at reduced temperature form addition products which are converted into the corresponding substitution products on storage at room temperature, in keeping with the addition-elimination mechanism of nucleophilic vinyl substitution. Nitro(aryl-thio)- and nitro(heterylthio)alkenes react with alkanethiolates at room temperature, resulting in replacement of the arylthio (heterylthio) group by alkylthio.

  DOI：

  10.1023/a:1013119318658

文献信息

• Mukhina, E. S.; Pavlova, Z. F.; Berkova, G. A., Journal of Organic Chemistry USSR (English Translation), 1991, vol. 27, # 5, p. 785 - 791
  作者：Mukhina, E. S.、Pavlova, Z. F.、Berkova, G. A.、Lipina, E. S.、Mostyaeva, L. V.、et al.

  DOI：——

  日期：——
• ——
  作者：N. V. Kuz'mina、E. S. Lipina、T. Yu. Kropotova、G. A. Berkova、Z. F. Pavlova

  DOI：10.1023/a:1013119318658

  日期：——

  Reactions of 1-nitro-2-sulfonylalkenes with arenethiolates result in replacement of the sulfonyl group; the reactions with alkanethiolates are accompanied by subsequent addition of the reagent at the double bond to afford thioacetals. Less reactive alpha-nitro-beta-R-thiostyrenes with thiolates at reduced temperature form addition products which are converted into the corresponding substitution products on storage at room temperature, in keeping with the addition-elimination mechanism of nucleophilic vinyl substitution. Nitro(aryl-thio)- and nitro(heterylthio)alkenes react with alkanethiolates at room temperature, resulting in replacement of the arylthio (heterylthio) group by alkylthio.
• ——
  作者：N. V. Kuz'mina

  DOI：10.1023/a:1023494629499

  日期：——

  2-Arylthio- and 2-arylsulfonyl-1-nitro-1-phenylethenes react with an-tines to give the corresponding nitroenamines whose configuration (E or Z) depends on the amine structure. Primary amines gives rise to Z-nitroenamines, secondary cyclic amines with 2-arylthio-1-nitroalkenes form E-nitroenaniines, and with more reactive 2-arylsulfonyl-1-nitroalkenes E/Z-isomeric mixtures are obtained.