1,2-dimethyl-3-(phenylthio)-1H-indole | 340169-30-4

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 1,2-dimethyl-3-(phenylthio)-1H-indole
• 英文别名: 1,2-dimethyl-3-(phenylthio)indole；1,2-methyl-3-phenylthio-1H-indole；1,2-dimethyl-3-phenylthioindole；1,2-Dimethyl-3-phenylsulfanylindole
• CAS: 340169-30-4
• 化学式: C₁₆H₁₅NS
• 分子量: 253.368
• InChiKey: QFWPAQCYFGRAEU-UHFFFAOYSA-N

物化性质

• 沸点：
  400.6±25.0 °C(Predicted)
• 密度：
  1.11±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 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：

  1,2-dimethyl-3-(phenylthio)-1H-indole 在 硫代水杨酸 作用下， 以 三氟乙酸 为溶剂， 反应 0.5h， 以94%的产率得到1,2-二甲基吲哚
  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：

  4-(Benzenesulfinyl)-2,3,5,6-tetramethylphenol 在 三氟甲磺酸三甲基硅酯 、 对甲苯磺酸 作用下， 以 甲苯 、 乙腈 为溶剂， 反应 1.17h， 生成 1,2-dimethyl-3-(phenylthio)-1H-indole
  参考文献：
  名称：

  Facile and Efficient Sulfenylation Method Using Quinone Mono-O,S-Acetals under Mild Conditions

  摘要：

  A novel sulfenylation method induced by aromatization of quinone mono-O,S-acetals is described. These sulfenylation reagents readily react with silyl enolethers or electron rich aromatic compounds to give sulfenylation products under mild conditions. In particular, O,S-acetal 2j, which possesses a pentafluorophenylthio function, is the most effective reagent from the standpoint of the adaptability for various substrates.

  DOI：

  10.1021/jo001710q

文献信息

• <i>S</i>-Aryl Arenesulfonothioate and Copper Acetate Mediated Arylthiolation of 2-Arylpyridines and Heteroarenes
  作者：Poonam Sharma、Nidhi Jain

  DOI：10.1021/acs.joc.9b01954

  日期：2019.10.18

  Copper acetate mediated regioselective ortho-arylthiolation of 2-arylpyridines has been accomplished for the first time using S-aryl arenesulfonothioate as the arylthiolating agent. The reaction shows good functional group tolerance and gives thioarylated products in 67-89% yields. This reagent is a good alternative to unpleasant smelling arylthiols. Experimental evidence suggests an unprecedented

  乙酸铜介导的2-芳基吡啶的区域选择性邻芳基硫醇化是首次使用S-芳基芳基磺基硫代磺酸盐作为芳基硫醇化剂来完成的。该反应显示出良好的官能团耐受性，并以67-89％的产率得到硫代芳基化产物。该试剂是难闻的芳硫醇的良好替代品。实验证据表明，在乙酸铜存在下，从试剂的两个部分（SPh和对-TolSO2）中都插入了芳硫基单元，这是前所未有的。吲哚和咪唑并吡啶在C-3位也容易进行反应，并以高收率提供硫代芳基化衍生物。
• An efficient and clean CuI-catalyzed chalcogenylation of aromatic azaheterocycles with dichalcogenides
  作者：Zhen Li、Jianquan Hong、Xigeng Zhou

  DOI：10.1016/j.tet.2011.03.067

  日期：2011.5

  A highly efficient and environmentally friendly method for catalytic chalcogenylation of imidazopyridines, imidazopyrimidines, indoles, and pyrrolo[2,3-b]pyridines with dichalcogenides has been developed by using CuI as catalyst under air. The reactions proceed smoothly to give the desired products in moderate to excellent yields, without the presence of other additive.

  通过在空气中使用CuI作为催化剂，开发了一种高效的，环境友好的方法，该方法用于用二硫代甲烷催化咪唑并吡啶，咪唑并嘧啶，吲哚和吡咯并[2,3- b ]吡啶。反应平稳进行，以中等至优异的产率得到所需产物，而没有其他添加剂的存在。
• Micelle-mediated multicomponent cross-coupling in water: general construction of 3-chalcogenylindoles
  作者：Xi He、Weili Song、Xuemin Liu、Jiamin Huang、Ruilong Feng、Shaodong Zhou、Jianquan Hong、Xin Ge

  DOI：10.1039/d2gc03694k

  日期：——

  A general and sustainable multicomponent cross-coupling for the construction of 3-chalcogenylindoles from indoles with aryl iodides and elemental sulfur under the aqueous micellar condition was developed. Elemental sulfur is employed as an eco-friendly and easy-handling sulfur source of thiyl radicals. The synergic effect between Cu catalysts and micelles formed by the sugar-based surfactant GluM can

  开发了一种通用且可持续的多组分交叉偶联，用于在水性胶束条件下从吲哚与芳基碘化物和元素硫构建 3-硫属吲哚。元素硫被用作一种环保且易于处理的硫自由基硫源。Cu 催化剂和糖基表面活性剂 GluM 形成的胶束之间的协同作用可以稳定硫自由基，进一步通过单电子转移在容易获得的吲哚上引发 C-S 偶联。值得注意的是，水性胶束系统不仅可以回收再利用，收率高，而且还可以扩展到元素硒的转化。
• 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
• Development of a Novel, Highly Efficient Halide-Catalyzed Sulfenylation of Indoles
  作者：Matthew Tudge、Minoru Tamiya、Cecile Savarin、Guy R. Humphrey

  DOI：10.1021/ol052615c

  日期：2006.2.1

  The reaction of a variety of indoles with N-thioalkyl- and N-thioarylphthalimides to produce 3-thioindoles is reported. Catalytic quantities of halide-containing salts are crucial to the success of this reaction. This highly efficient reaction provides sulfenylated indoles from bench-stable, readily available starting materials in good to excellent yields.