3-((4-chlorophenyl)thio)-6-methoxy-1H-indole | 1224875-73-3

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 3-((4-chlorophenyl)thio)-6-methoxy-1H-indole
• 英文别名: 3-(4-chlorophenyl)sulfanyl-6-methoxy-1H-indole
• CAS: 1224875-73-3
• 化学式: C₁₅H₁₂ClNOS
• 分子量: 289.785
• InChiKey: KMKQWMVCVVKMTQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  19
• 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：
  50.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  6-甲氧基吲哚 、 2-(4-chlorophenylthio)isoindoline-1,3-dione 在 cerium(III) chloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.5h， 以88%的产率得到3-((4-chlorophenyl)thio)-6-methoxy-1H-indole
  参考文献：
  名称：

  The use of anhydrous CeCl3 as a catalyst for the synthesis of 3-sulfenyl indoles

  摘要：

  Anhydrous CeCl3 was successfully used as a catalyst for the synthesis of several 3-sulfenyl indoles in good to excellent yields through the reaction of indole with N-(alkylthio) and N-(arylthio)phthalimides in DMF. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.02.038

文献信息

• Nitrosonium ion catalysis: aerobic, metal-free cross-dehydrogenative carbon–heteroatom bond formation
  作者：Luis Bering、Laura D’Ottavio、Giedre Sirvinskaite、Andrey P. Antonchick

  DOI：10.1039/c8cc08328b

  日期：——

  coupling of heteroarenes with thiophenols and phenothiazines has been developed under mild and environmentally benign reaction conditions. For the first time, NOx+ was applied for catalytic C–S and C–N bond formation. A comprehensive scope for the C–H/S–H and C–H/N–H cross-dehydrogenative coupling was demonstrated with >60 examples. The sustainable cross-coupling conditions utilize ambient oxygen as the

  杂芳烃与硫酚和吩噻嗪的催化交叉脱氢偶联已在温和且环境友好的反应条件下得到发展。首次将NO x +用于催化C–S和C–N键的形成。用60多个例子证明了C–H / S–H和C–H / N–H交叉脱氢偶联的综合范围。可持续的交叉偶联条件利用环境氧作为末端氧化剂，而水是唯一的副产物。
• DBU-Catalyzed Aerobic CDC Reaction of Thiophenols
  作者：Xuemin Jia、Xiao Ma、Wei Feng、Ji-Quan Zhang、Yonglong Zhao、Bing Guo、Lei Tang、Yuan-Yong Yang

  DOI：10.1021/acs.joc.2c02207

  日期：2022.12.16

  A convenient method was developed for the preparation of thiolated compounds via a DBU-catalyzed aerobic cross-dehydrogenative coupling (CDC) reaction. The established protocol is environmentally friendly and operationally simple. Substrates like (hetero)aryl acetates, (hetero)aryl ketones, and indoles could be transformed into the corresponding thiolated products in moderate to high yields and further

  通过DBU 催化的有氧交叉脱氢偶联 (CDC) 反应，开发了一种制备硫醇化化合物的简便方法。已建立的协议对环境友好且操作简单。(杂)芳基乙酸酯、(杂)芳基酮和吲哚等底物可以中高产率转化为相应的硫醇化产物，并以无预功能化的方式进一步应用于生物活性化合物的制备。
• The use of anhydrous CeCl3 as a catalyst for the synthesis of 3-sulfenyl indoles
  作者：Claudio C. Silveira、Samuel R. Mendes、Lucas Wolf、Guilherme M. Martins

  DOI：10.1016/j.tetlet.2010.02.038

  日期：2010.4

  Anhydrous CeCl3 was successfully used as a catalyst for the synthesis of several 3-sulfenyl indoles in good to excellent yields through the reaction of indole with N-(alkylthio) and N-(arylthio)phthalimides in DMF. (C) 2010 Elsevier Ltd. All rights reserved.