1-hydroxy-2-phenyl-3-[(n-propylthio)methyl]-1H-indole

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 1-hydroxy-2-phenyl-3-[(n-propylthio)methyl]-1H-indole
• 英文别名: 1-Hydroxy-2-phenyl-3-(propylsulfanylmethyl)indole；1-hydroxy-2-phenyl-3-(propylsulfanylmethyl)indole
• 化学式: C₁₈H₁₉NOS
• 分子量: 297.421
• InChiKey: FYNRFRUZJSVRDD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  50.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-(2-nitrophenyl)-1-phenylethanol 在 tin(II) chloride dihdyrate 、 sodium hydride 、 pyridinium chlorochromate 作用下， 以 乙二醇二甲醚 、 二氯甲烷 为溶剂， 反应 6.5h， 生成 1-hydroxy-2-phenyl-3-[(n-propylthio)methyl]-1H-indole
  参考文献：
  名称：

  Synthesis of New 3-Substituted 1-Hydroxy-2-phenylindoles Using Sulfur-Containing Nucleophiles

  摘要：

  The synthesis of new 3-[(acyl(or alkyl)thio)methyl]-1-hydroxy-2-phenylindoles 1 are presented. The substrates 2 obtained by each efficient three-step synthesis were treated, in the presence of SnCl2 center dot 2H(2)O, with nucleophiles such as thiocarboxylic acids and thiols to provide target compounds 1 by successive processes of nitro reduction and intramolecular condensation, followed by addition of nucleophile. Analyses of the reaction mechanism, including the effects of substituents along with the reactivity of nucleophiles, are described.

  DOI：

  10.3987/com-16-13544

文献信息

• Synthesis of New 3-Substituted 1-Hydroxy-2-phenylindoles Using Sulfur-Containing Nucleophiles
  作者：Sang Hyup Lee、Hyejin Kim

  DOI：10.3987/com-16-13544

  日期：——

  The synthesis of new 3-[(acyl(or alkyl)thio)methyl]-1-hydroxy-2-phenylindoles 1 are presented. The substrates 2 obtained by each efficient three-step synthesis were treated, in the presence of SnCl2 center dot 2H(2)O, with nucleophiles such as thiocarboxylic acids and thiols to provide target compounds 1 by successive processes of nitro reduction and intramolecular condensation, followed by addition of nucleophile. Analyses of the reaction mechanism, including the effects of substituents along with the reactivity of nucleophiles, are described.