3-<(phenylthio)methyl>-1H-indole | 56366-43-9

• 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: 3-<(phenylthio)methyl>-1H-indole
• 英文别名: 3-(phenylsulfanyl-methyl)-indole；3-(Phenylmercapto-methyl)-indol；<3-Indolylmethyl>-phenylsulfid；(3-Indolylmethyl)-phenylsulfid；3-(phenylsulfanylmethyl)-1H-indole
• CAS: 56366-43-9
• 化学式: C₁₅H₁₃NS
• 分子量: 239.341
• InChiKey: AJRNAFUSNYAEGZ-UHFFFAOYSA-N

物化性质

• 熔点：
  80.5-81.5 °C(Solv: ligroine (8032-32-4))
• 沸点：
  435.7±28.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  41.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  芦竹碱 、 苯硫酚 生成 3-<(phenylthio)methyl>-1H-indole
  参考文献：
  名称：

  硫醇和硫醚的反应。第一部分：曼尼希反应的类似物，涉及硫醇，甲醛和活性亚甲基或亚甲基二炔化合物

  摘要：

  DOI：

  10.1039/jr9540001124

文献信息

• (1-Nosyl-5-nitroindol-3-yl)methyl Ester: A Novel Protective Group for Carboxylic Acids
  作者：Takuya Nishimura、Kouhei Yamada、Tohru Takebe、Satoshi Yokoshima、Tohru Fukuyama

  DOI：10.1021/ol8008655

  日期：2008.6.1

  (1-nosyl-5-nitroindol-3-yl)methyl esters as a novel protective group for carboxylic acid is fully demonstrated. The novel protective group is stable under a broad range of conditions and can easily be deprotected under the mild conditions used for removal of the nosyl (Ns) group. It is orthogonal to the existing protective groups for carboxylic acids such as t-butyl and allyl esters.

  充分证明了（1-戊基-5-硝基吲哚-3-基）甲基酯作为羧酸的新型保护基的有效性。该新型保护基在广泛的条件下是稳定的，并且在用于除去壬基（Ns）基团的温和条件下可以容易地被脱保护。它与现有的羧酸保护基团（例如叔丁基酯和烯丙基酯）正交。
• Reactions of thiols and thioethers. Part I. An analogue of the Mannich reaction involving thiols, formaldehyde, and active methylene or methylidyne compounds
  作者：F. Poppelsdorf、S. J. Holt

  DOI：10.1039/jr9540001124

  日期：——
• Free radical reactions initiated by organocobalt complexes. A new method for the degradation of carboxylic acids tofunctionalised nor-alkanes via acylcobalt salophen intermediates.
  作者：Vinod F. Patel、Gerald Pattenden

  DOI：10.1016/s0040-4039(00)80190-2

  日期：——
• Patel, Vinod F.; Pattenden, Gerald; Thompson, David M., Journal of the Chemical Society. Perkin transactions I, 1990, # 10, p. 2729 - 2734
  作者：Patel, Vinod F.、Pattenden, Gerald、Thompson, David M.

  DOI：——

  日期：——
• Methodology for the Efficient Synthesis of 3,4-Differentially Substituted Indoles. Fluoride Ion-induced Elimination-Addition Reaction of 1-Triisopropylsilylgramine Methiodides
  作者：M Iwao

  DOI：10.1016/00404-0399(50)1197p-

  日期：1995.8.14

  1-Triisopropylsilylgramine methiodide reacted smoothly with a variety of nucleophiles in the presence of tetrabutylammmonium fluoride to give 3-substituted indoles. The 3,4-disubstituted indoles were efficiently synthesized by sequential use of 4-selective lithiation of 1-triisopropylsilylgramine and this new substitution reaction.