4-Methoxyphenyl-(5-methyl-2-thienyl)methanol

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-Methoxyphenyl-(5-methyl-2-thienyl)methanol
• 英文别名: (4-methoxyphenyl)-(5-methylthiophen-2-yl)methanol
• 化学式: C₁₃H₁₄O₂S
• 分子量: 234.319
• InChiKey: XWAYUWSSWOPKMQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  57.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-硝基苯甲醚 、 4-Methoxyphenyl-(5-methyl-2-thienyl)methanol 在 T406石油添加剂 、 potassium tert-butylate 作用下， 生成 2-[(3-Methoxy-4-nitrophenyl)-(4-methoxyphenyl)methyl]-5-methylthiophene
  参考文献：
  名称：

  First General Synthesis of (p-Nitroaryl)diarylmethanes via Vicarious Nucleophilic Substitution of Hydrogen

  摘要：

  A general regiospecific method for the synthesis of (p-nitroaryl)diarylmethanes has been developed starting from diarylmethanols and 2- and/or 3-substituted nitrobenzenes. This utilizes the quantitative condensation between benzotriazole and diarylmethanols under acidic catalysis and in the presence of perfluorocarbon fluids, followed by vicarious nucleophilic substitution of the resulting diarylmethylbenzotriazoles upon nitrobenzenes in moderate to high yield. Oxidative nucleophilic substitution of hydrogen is observed as a side process. These vicarious nucleophilic substitutions complement Friedel-Crafts reactions for the synthesis of triarylmethanes.

  DOI：

  10.1021/jo9624197
• 作为产物：
  描述：

  2-甲基噻吩 、 4-甲氧基苯甲醛 在 正丁基锂 作用下， 生成 4-Methoxyphenyl-(5-methyl-2-thienyl)methanol
  参考文献：
  名称：

  First General Synthesis of (p-Nitroaryl)diarylmethanes via Vicarious Nucleophilic Substitution of Hydrogen

  摘要：

  A general regiospecific method for the synthesis of (p-nitroaryl)diarylmethanes has been developed starting from diarylmethanols and 2- and/or 3-substituted nitrobenzenes. This utilizes the quantitative condensation between benzotriazole and diarylmethanols under acidic catalysis and in the presence of perfluorocarbon fluids, followed by vicarious nucleophilic substitution of the resulting diarylmethylbenzotriazoles upon nitrobenzenes in moderate to high yield. Oxidative nucleophilic substitution of hydrogen is observed as a side process. These vicarious nucleophilic substitutions complement Friedel-Crafts reactions for the synthesis of triarylmethanes.

  DOI：

  10.1021/jo9624197

文献信息

• First General Synthesis of (<i>p</i>-Nitroaryl)diarylmethanes <i>via</i> Vicarious Nucleophilic Substitution of Hydrogen
  作者：Alan R. Katritzky、Dorin Toader

  DOI：10.1021/jo9624197

  日期：1997.6.13

  A general regiospecific method for the synthesis of (p-nitroaryl)diarylmethanes has been developed starting from diarylmethanols and 2- and/or 3-substituted nitrobenzenes. This utilizes the quantitative condensation between benzotriazole and diarylmethanols under acidic catalysis and in the presence of perfluorocarbon fluids, followed by vicarious nucleophilic substitution of the resulting diarylmethylbenzotriazoles upon nitrobenzenes in moderate to high yield. Oxidative nucleophilic substitution of hydrogen is observed as a side process. These vicarious nucleophilic substitutions complement Friedel-Crafts reactions for the synthesis of triarylmethanes.