(E)-3-(4-bromophenylamino)-1-(4-methoxyphenyl)-3-methylthioprop-2-ene-1-thione | 743353-82-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (E)-3-(4-bromophenylamino)-1-(4-methoxyphenyl)-3-methylthioprop-2-ene-1-thione
• 英文别名: (E)-3-(4-bromoanilino)-1-(4-methoxyphenyl)-3-methylsulfanylprop-2-ene-1-thione
• CAS: 743353-82-4
• 化学式: C₁₇H₁₆BrNOS₂
• 分子量: 394.356
• InChiKey: ZQKBIFWUQLYRPM-GZTJUZNOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  78.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-3-(4-bromophenylamino)-1-(4-methoxyphenyl)-3-methylthioprop-2-ene-1-thione 在 dirhodium(II) tetrakis(perfluorobutyrate) 4-二甲氨基吡啶 、 二碳酸二叔丁酯 、 mercury(II) diacetate 作用下， 以 四氢呋喃 、 二氯甲烷 、 苯 为溶剂， 反应 5.5h， 生成 4-(4-bromophenyl)-2-(4-methoxyphenyl)-5,6-dihydro-4H-thieno[3,2-b]pyrrol-5-one
  参考文献：
  名称：

  Facile Synthesis of 4-Alkyl (and Aryl)-2-aryl-6-diazo-4H- thieno[3,2-b]pyridine-5,7-diones

  摘要：

  Treatment of 3-{3-alkyl (and aryl)amino-5-arylthieno-2-yl}-2-diazo-3-oxopropanoates 8 with TMSOTf (3 equiv) in the presence of Et3N (6 equiv) in CH2Cl2 for 1 h at room temperature afforded 4-alkyl (and aryl)-2-aryl-6-diazo-4H-thieno[3,2-b]pyridine-5,7-diones 14 in excellent yields. On heating of 14 in the presence of a catalytic amount of Rh-2(CF3CF2CF2CO2)(4) in PhH for 4-10 h at reflux, corresponding ring contraction products, 4-alkyl (and aryl)-5,6-dihydro-4H-thieno[3,2-b]pyrrol-5-ones 16, were produced in good to excellent yields.

  DOI：

  10.1021/jo049769a
• 作为产物：
  描述：

  1-(4-甲氧基苯基)-3,3-二(甲硫基)-2-丙烯-1-酮 在 劳森试剂 、 三氟化硼乙醚 作用下， 以 甲苯 、 苯 为溶剂， 反应 2.5h， 生成 (E)-3-(4-bromophenylamino)-1-(4-methoxyphenyl)-3-methylthioprop-2-ene-1-thione
  参考文献：
  名称：

  Facile Synthesis of 4-Alkyl (and Aryl)-2-aryl-6-diazo-4H- thieno[3,2-b]pyridine-5,7-diones

  摘要：

  Treatment of 3-{3-alkyl (and aryl)amino-5-arylthieno-2-yl}-2-diazo-3-oxopropanoates 8 with TMSOTf (3 equiv) in the presence of Et3N (6 equiv) in CH2Cl2 for 1 h at room temperature afforded 4-alkyl (and aryl)-2-aryl-6-diazo-4H-thieno[3,2-b]pyridine-5,7-diones 14 in excellent yields. On heating of 14 in the presence of a catalytic amount of Rh-2(CF3CF2CF2CO2)(4) in PhH for 4-10 h at reflux, corresponding ring contraction products, 4-alkyl (and aryl)-5,6-dihydro-4H-thieno[3,2-b]pyrrol-5-ones 16, were produced in good to excellent yields.

  DOI：

  10.1021/jo049769a

文献信息

• Facile Synthesis of 4-Alkyl (and Aryl)-2-aryl-6-diazo-4<i>H</i>- thieno[3,2-<i>b</i>]pyridine-5,7-diones
  作者：Dong Joon Lee、Kyongtae Kim

  DOI：10.1021/jo049769a

  日期：2004.7.1

  Treatment of 3-3-alkyl (and aryl)amino-5-arylthieno-2-yl}-2-diazo-3-oxopropanoates 8 with TMSOTf (3 equiv) in the presence of Et3N (6 equiv) in CH2Cl2 for 1 h at room temperature afforded 4-alkyl (and aryl)-2-aryl-6-diazo-4H-thieno[3,2-b]pyridine-5,7-diones 14 in excellent yields. On heating of 14 in the presence of a catalytic amount of Rh-2(CF3CF2CF2CO2)(4) in PhH for 4-10 h at reflux, corresponding ring contraction products, 4-alkyl (and aryl)-5,6-dihydro-4H-thieno[3,2-b]pyrrol-5-ones 16, were produced in good to excellent yields.