1-benzyl-2-methyl-3-(phenylthio)indole

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 1-benzyl-2-methyl-3-(phenylthio)indole
• 英文别名: 1-Benzyl-2-methyl-3-phenylsulfanylindole
• 化学式: C₂₂H₁₉NS
• 分子量: 329.466
• InChiKey: DZZCPOCFUWJVEW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  30.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-benzyl-2-methyl-3-(phenylthio)indole 在 硫代水杨酸 、 三氟乙酸 作用下， 反应 1.0h， 以86%的产率得到1-苄基-2-甲基吲哚
  参考文献：
  名称：

  A general non-reductive method for the desulfenylation of 3-indolyl sulfides

  摘要：

  In trifluoroacetic acid, in the presence of thiosalicylic acid as a trapping agent, 3-indolyl sulfides bearing a wide variety of substituents are smoothly and rapidly desulfenylated to the corresponding 3-unsubstituted indoles.

  DOI：

  10.1016/s0040-4039(00)60345-3
• 作为产物：
  描述：

  2-methyl-3-phenylthioindole 以95%的产率得到
  参考文献：
  名称：

  Hamel Pierre, Zajac Nicolas, Atkinson Joseph G., Girard Yves, J. Org. Chem, 59 (1994) N 21, S 6372-6377

  摘要：

  DOI：

文献信息

• Indium chloride: a versatile Lewis acid catalyst for the synthesis of 3-sulfenylindoles
  作者：P. Praveen Kumar、Y. Dathu Reddy、Ch. Venkata Ramana Reddy、B. Rama Devi、P.K. Dubey

  DOI：10.1080/17415993.2013.879870

  日期：2014.7.4

  Indium chloride has been used as a versatile Lewis acid catalyst for the synthesis of 3-sulfenylindoles in good yields by the independent reaction of indoles and N-alkylindoles with N-(phenylthio)phthalimide in dimethyl formamide (DMF) at 100 degrees C for about 5-6 h.[GRAPHICS].(a) R = H (b) R = CH3 (c) R= Ph(a) R-1 = H (b)R-1 = CH3 (c) R-1 = CH2-Ph
• A general non-reductive method for the desulfenylation of 3-indolyl sulfides
  作者：Pierre Hamel、Nicolas Zajac、Joseph G. Atkinson、Yves Girard

  DOI：10.1016/s0040-4039(00)60345-3

  日期：1993.3

  In trifluoroacetic acid, in the presence of thiosalicylic acid as a trapping agent, 3-indolyl sulfides bearing a wide variety of substituents are smoothly and rapidly desulfenylated to the corresponding 3-unsubstituted indoles.
• Hamel Pierre, Zajac Nicolas, Atkinson Joseph G., Girard Yves, J. Org. Chem, 59 (1994) N 21, S 6372-6377
  作者：Hamel Pierre, Zajac Nicolas, Atkinson Joseph G., Girard Yves

  DOI：——

  日期：——
• Nonreductive Desulfenylation of 3-Indolyl Sulfides. Improved Syntheses of 2-Substituted Indoles and 2-Indolyl Sulfides
  作者：Pierre Hamel、Nicolas Zajac、Joseph G. Atkinson、Yves Girard

  DOI：10.1021/jo00100a045

  日期：1994.10

  Desulfenylation of 3-indolyl sulfides to the corresponding 3-unsubstituted indoles is usually carried out under reductive conditions, thus accommodating only substituents which are resistant to reduction. We have developed a nonreductive procedure for removal of a sulfide at the 3-position of indoles, using trifluoroacetic acid in the presence of a thiol as trapping agent, which is compatible with a large array of functionalities on the indole ring. In addition, the desulfenylation occurs selectively at the 3-position of the indole, and sulfide groups at other positions of the molecule remain untouched. Thus, indole 2,3-bis-sulfides are selectively desulfenylated at the 3-position, affording 3-unsubstituted 2-indolyl sulfides. This methodology broadens the use of sulfide as a protecting group for the 3-position of indoles.