3-((perfluorophenyl)thio)-1H-indole | 32884-77-8

• 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-((perfluorophenyl)thio)-1H-indole
• 英文别名: 3-(2,3,4,5,6-pentafluorophenyl)sulfanyl-1H-indole
• CAS: 32884-77-8
• 化学式: C₁₄H₆F₅NS
• 分子量: 315.266
• InChiKey: XIOXETMXXFIJNL-UHFFFAOYSA-N

物化性质

• 沸点：
  357.6±42.0 °C(Predicted)
• 密度：
  1.56±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  41.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2,3,5,6-Tetramethyl-4-(2,3,4,5,6-pentafluorophenyl)sulfinylphenol 在 三氟甲磺酸三甲基硅酯 作用下， 以 乙腈 为溶剂， 反应 0.17h， 生成 3-((perfluorophenyl)thio)-1H-indole
  参考文献：
  名称：

  An efficient sulfenylation of aromatics using highly active quinone mono O , S -acetal bearing a pentafluorophenylthio group

  摘要：

  A facile sulfenylation of various aromatic nuclei was achieved by use of the novel sulfenylation reagent, the quinone mono O,S-acetal bearing a pentafluorophenylthio group. This reagent functions below 0 degreesC in the presence of a catalytic amount of TMSOTf. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)02186-9

文献信息

• Organophosphorus‐Catalyzed Deoxygenation of Sulfonyl Chlorides: Electrophilic (Fluoroalkyl)sulfenylation by P ^III /P ^V =O Redox Cycling
  作者：Avipsa Ghosh、Morgan Lecomte、Shin‐Ho Kim‐Lee、Alexander T. Radosevich

  DOI：10.1002/anie.201813919

  日期：2019.2.25

  lyzed deoxygenative O‐atom transfer from sulfonyl chlorides is reported. This C−S bond‐forming reaction is catalyzed by a readily available small‐ring phosphine (phosphetane) in conjunction with a hydrosilane terminal reductant to afford a general entry to sulfenyl electrophiles, including valuable trifluoromethyl, perfluoroalkyl, and heteroaryl derivatives that are otherwise difficult to access. Mechanistic

  报道了一种通过有机磷催化的磺酰氯转移O-原子进行亲电亚磺酰化的方法。这种C-S键形成反应由易于获得的小环膦（磷杂环丁烷）与氢硅烷末端还原剂共同催化，可普遍进入亚硫基亲电子试剂，包括有价值的三氟甲基，全氟烷基和杂芳基衍生物，而这些原本很难做到的访问。机理研究表明，磺酰底物的双重脱氧是通过非循环静态硫磷鎓离子的干预而进行的。催化方法代表使用稳定的氧化膦作为预催化剂的操作简单方案，并且具有宽泛的官能团耐受性。
• Synergistic Effect of Squaric Acid in Bromine-Catalyzed Deoxygenation of Sulfonyl Derivatives: Mechanistic Investigations and Synthetic Applications in Electrophilic (Fluoroalkyl)sulfenylation
  作者：Haonan Xiang、Jie Liu、Jieping Wang、Lvqi Jiang、Wenbin Yi

  DOI：10.1021/acs.orglett.1c03813

  日期：2022.1.14

  A method for electrophilic (fluoroalkyl)sulfenylation of nucleophiles by collaborative CTAB- and squaric acid-promoted deoxygenation of sulfonyl derivatives is reported. Mechanistic studies indicate that squaric acid dramatically decreased the energy barrier in the first step of deoxygenation. The mild deoxygenation process enables the reduction of a wide range of functionalized sulfonyl chlorides

  报道了一种通过协同 CTAB 和方酸促进的磺酰基衍生物脱氧对亲核试剂进行亲电（氟烷基）亚磺酰化的方法。机理研究表明，方酸在脱氧的第一步中显着降低了能量屏障。温和的脱氧过程能够还原多种功能化磺酰氯以及磺酸酐。这种新方法代表了一种使用现成试剂的操作简单的协议，并表现出广泛的官能团耐受性。
• Potassium Persulfate‐Glucose Mediated Synthesis of (3)‐<i>S</i>‐Arylthioindoles from Indole and Thiophenols in Water
  作者：Nitin Kumar、Rapelly Venkatesh、Sundaram Singh、Jeyakumar Kandasamy

  DOI：10.1002/ejoc.202300679

  日期：2023.10.2

  An efficient and eco‐friendly method has been developed for the preparation of functionalized 3‐(S)‐arylthioindoles in good to excellent yields from indoles and aryl thiols in water. The coupling reaction was prompted by K₂S₂O₈ in the presence of glucose at room temperature. Broad substrate scope, functional group tolerance, room temperature reactions and metal‐free conditions are the salient features of the developed methodology.

  摘要 开发了一种高效、环保的方法，用于以吲哚和芳基硫醇为原料在水中制备官能化的 3-(S)-芳基硫代吲哚，收率从良好到极佳。K2S2O8 在葡萄糖存在下于室温促进了偶联反应。底物范围广、官能团耐受性好、室温反应和无金属条件是所开发方法的显著特点。
• Facile and Efficient Sulfenylation Method Using Quinone Mono-<i>O,S</i>-Acetals under Mild Conditions
  作者：Masato Matsugi、Kenji Murata、Kentoku Gotanda、Hisanori Nambu、Gopinathan Anilkumar、Keita Matsumoto、Yasuyuki Kita

  DOI：10.1021/jo001710q

  日期：2001.4.1

  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.