1-benzyl-2,3-bis(phenylthio)indole | 108698-81-3

• 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-2,3-bis(phenylthio)indole
• 英文别名: 2,3-bis(phenylthio)-1-benzylindole；N-benzyl-2,3-bisphenylthioindole；1-Benzyl-2,3-bis(phenylsulfanyl)indole
• CAS: 108698-81-3
• 化学式: C₂₇H₂₁NS₂
• 分子量: 423.602
• InChiKey: JKKSRLCVDYNNQX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.1
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  55.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-benzyl-2,3-bis(phenylthio)indole 在 硫代水杨酸 作用下， 以 三氟乙酸 为溶剂， 反应 0.25h， 以87%的产率得到1-benzyl-2-(phenylsulfanyl)-1H-indole
  参考文献：
  名称：

  Nonreductive Desulfenylation of 3-Indolyl Sulfides. Improved Syntheses of 2-Substituted Indoles and 2-Indolyl Sulfides

  摘要：

  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.

  DOI：

  10.1021/jo00100a045
• 作为产物：
  描述：

  2,3-bis-phenyl-sulphenylindole 以86%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

• Iodine-catalysed versatile sulfenylation of indoles with thiophenols: controllable synthesis of mono- and bis-arylthioindoles
  作者：Hailei Zhang、Xiaoze Bao、Yuming Song、Jingping Qu、Baomin Wang

  DOI：10.1016/j.tet.2015.09.070

  日期：2015.11

  A versatile method for the synthesis of mono- and bis-arylthioindoles via I2 catalysed direct oxidative sulfenylation of indoles with thiophenols (especially mercaptobenzoic acids) has been presented. This system features environmental friendliness, easy operation, and mild reaction conditions, and shows a broad functional group tolerance furnishing good to excellent yields.

  通过I单-和双- arylthioindoles的合成的通用方法2催化直接氧化的吲哚与苯硫酚（尤其是巯基氨基酸）亚磺酰已经呈现。本系统的特点是对环境友好，操作方便，和温和的反应条件，并示出了广泛的官能团耐受性家具良好至优异的产量。
• 1,2,3-trisubstituted indoles for treatment of inflammation
  申请人：Syntex (U.S.A.) Inc.

  公开号：US04654360A1

  公开（公告）日：1987-03-31

  Disclosed are compounds of the formula ##STR1## wherein the several groups are defined herein. These compounds are useful for treating inflammation.

  揭示了以下化合物的结构式 ##STR1## 其中各个基团在此处定义。这些化合物可用于治疗炎症。
• Controllable Synthesis of Mono‐ and Bis‐sulfenylindoles from Indoles and Various Sulfenylation Agents Using KI/SeO ₂ System
  作者：Thewika Benchawan、Rungnapha Saeeng

  DOI：10.1002/ejoc.202200752

  日期：2022.10.13

  An efficient method for selective and controllable sulfenylation of indoles to synthesize mono- and bis-sulfenylindoles was reported by using a novel aerobic catalytic oxidation system KI/SeO2 for sulfenylation of indoles with disulfide/thiols. The method is scalable, not sensitive to moisture, and can proceed without metal catalyst.

  报道了一种有效的选择性和可控的吲哚亚磺酰化合成单和双亚磺酰吲哚的方法，该方法是使用新型好氧催化氧化系统 KI/SeO 2对二硫化物/硫醇对吲哚进行亚磺酰化。该方法具有可扩展性，对水分不敏感，并且可以在没有金属催化剂的情况下进行。
• US4654360A
  申请人：——

  公开号：US4654360A

  公开（公告）日：1987-03-31
• 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.