3-((4-bromophenyl)thio)-2-phenyl-1H-indole | 1285494-73-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 3-((4-bromophenyl)thio)-2-phenyl-1H-indole
• 英文别名: 3-(4-bromophenyl)sulfanyl-2-phenyl-1H-indole
• CAS: 1285494-73-6
• 化学式: C₂₀H₁₄BrNS
• 分子量: 380.308
• InChiKey: BCIPFMSRLDKIBK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  4.0
• 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：
  1

反应信息

• 作为产物：
  描述：

  4-溴苯硫酚 在 copper(l) iodide 、 碘 、 二异丙胺 、 三苯基膦 、 palladium dichloride 作用下， 以 二甲基亚砜 、 乙腈 为溶剂， 生成 3-((4-bromophenyl)thio)-2-phenyl-1H-indole
  参考文献：
  名称：

  一锅 C-C、C-N 和 C-S 键结构，用于直接从未活化的苯胺合成 3-亚苯基吲哚，涉及双钯催化和 DFT 的机理洞察

  摘要：

  开发了一种有效的双 Pd 催化系统，用于在温和反应条件下直接从未活化的 2-碘 ( NH ) 苯胺通过C-C、C-N 和 C-S 键构建一锅法合成 3-亚苯基吲哚。此外，3-硒基/卤素/碳官能化吲哚以良好的产率和较短的反应时间合成。还证明了 3-sulfenylindole 的合成效用。DFT 揭示了溶剂在钯催化中的关键作用。

  DOI：

  10.1039/d2ob01606k

文献信息

• B(C₆F₅)₃-Catalyzed Electron Donor–Acceptor Complex-Mediated Aerobic Sulfenylation of Indoles under Visible-Light Conditions
  作者：Wenkai Yuan、Jie Huang、Xin Xu、Long Wang、Xiang-Ying Tang

  DOI：10.1021/acs.orglett.1c02553

  日期：2021.9.17

  efficient B(C6F5)3-catalyzed aerobic oxidative C–S cross-coupling reaction of thiophenol with indoles was developed, affording a wide range of diaryl sulfides in good yields. An electron donor–acceptor complex between B(C6F5)3 and indoles was formed, facilitating the photoinduced single-electron transfer (SET) from indole substrates to the B(C6F5)3 catalyst. This protocol demonstrates a new reaction model

  开发了一种高效的 B(C 6 F 5 ) 3催化的苯硫酚与吲哚的有氧氧化 C-S 交叉偶联反应，以良好的收率提供了范围广泛的二芳基硫化物。B(C 6 F 5 ) 3和吲哚之间形成了电子供体-受体复合物，促进了从吲哚底物到B(C 6 F 5 ) 3催化剂的光诱导单电子转移(SET) 。该协议展示了使用 B(C 6 F 5 ) 3作为单电子氧化剂的新反应模型。
• Visible-Light-Mediated Eosin Y Photoredox-Catalyzed Vicinal Thioamination of Alkynes: Radical Cascade Annulation Strategy for 2-Substituted-3-sulfenylindoles
  作者：Shrikant D. Tambe、Rajendra S. Rohokale、Umesh A. Kshirsagar

  DOI：10.1002/ejoc.201800287

  日期：2018.5.15

  An efficient, mild, and metal‐free radical cascade annulation strategy for 2‐substituted‐3‐sulfenylindoles from 2‐alkynyl‐azidoarenes by vicinal thioamination of alkynes, catalyzed by a eosin Y photoredox catalyst mediated by visible light in the presence of air as mild oxidant.

  一种有效的，温和的，金属自由基的级联环化策略，其通过炔烃的邻位硫代胺化反应制得的2-炔基-叠氮基芳烃中的2-取代的3-亚磺酰基吲哚，由曙红Y光氧化还原催化剂催化，可见光在空气存在下介导。温和的氧化剂。
• Microwave assisted metal-/oxidant-free cascade electrophilic sulfenylation/5-endo-dig cyclization of 2-alkynylanilines to generate diversified 3-sulfenylindoles
  作者：Shivani Sharma、Ramdas S. Pathare、Sukanya、Antim K. Maurya、Bhagyashree Goswami、Vijai K. Agnihotri、Devesh M. Sawant、Ram T. Pardasani

  DOI：10.1016/j.tetlet.2017.08.046

  日期：2017.10

  A metal-/oxidant-free sustainable protocol for the synthesis of 3-sulfenylindoles based on electrophilic cyclization of 2-alkynylanilines has been developed under microwave irradiation. Herein, catalytic amount of iodine and stoichiometric amount of sulfonyl hydrazides were employed as catalyst and electrophiles respectively to induce the 5-endo-dig cyclization of 2-alkynylanilines. This strategy allows a wide substrate scope, demonstrates good functional group tolerance, utilizes easily available reagents and overcome multistep synthesis. (C) 2017 Elsevier Ltd. All rights reserved.
• Copper-catalyzed chalcogenoamination of 2-alkynylanilines with dichalcogenides for one-step synthesis of 3-sulfenylindoles and 3-selenylindoles
  作者：Zhen Li、Longcheng Hong、Ruiting Liu、Jianzhong Shen、Xigeng Zhou

  DOI：10.1016/j.tetlet.2011.01.052

  日期：2011.3

  The copper-catalyzed chalcogenoamination of 2-alkynylanilines with dichalcogenides has been achieved under mild reaction conditions using the weak base Cs2CO3 in combination with air oxidant, providing a convenient and efficient method for synthesis of 3-sulfenylindoles and 3-selenylindoles, including complex products bearing two attached 3-sulfenylindole rings. (C) 2011 Elsevier Ltd. All rights reserved.
• One-pot C–C, C–N, and C–S bond construction for synthesis of 3-sulfenylindoles directly from unactivated anilines involving dual palladium catalysis and mechanistic insights from DFT
  作者：Sumit K. Rastogi、Richa Singh、Santosh Kumar、Abhishek Kumar Mishra、Mini Bharati Ahirwar、Milind M. Deshmukh、Arun K. Sinha、Ravindra Kumar

  DOI：10.1039/d2ob01606k

  日期：——

  An efficient dual Pd-catalytic system was developed for one-pot synthesis of 3-sulfenylindoles via C–C, C–N and C–S bond construction directly from unactivated 2-iodo(NH)anilines under mild reaction conditions. Furthermore, 3-selenyl/halo/carbon-functionalized indoles were synthesized in good yields and a short reaction time. The synthetic utility of 3-sulfenylindole was also demonstrated. The key

  开发了一种有效的双 Pd 催化系统，用于在温和反应条件下直接从未活化的 2-碘 ( NH ) 苯胺通过C-C、C-N 和 C-S 键构建一锅法合成 3-亚苯基吲哚。此外，3-硒基/卤素/碳官能化吲哚以良好的产率和较短的反应时间合成。还证明了 3-sulfenylindole 的合成效用。DFT 揭示了溶剂在钯催化中的关键作用。