1-(methylsulfonyl)-3-phenyl-1H-indole | 1394913-01-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 1-(methylsulfonyl)-3-phenyl-1H-indole
• 英文别名: N-Ms-3-phenylindole；1H-Indole, 1-(methylsulfonyl)-3-phenyl-；1-methylsulfonyl-3-phenylindole
• CAS: 1394913-01-9
• 化学式: C₁₅H₁₃NO₂S
• 分子量: 271.34
• InChiKey: CJQOEKRIZWABRW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  47.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(methylsulfonyl)-3-phenyl-1H-indole 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 四氯化碳 为溶剂， 反应 10.0h， 生成 2-bromo-1-(methylsulfonyl)-3-phenyl-1H-indole
  参考文献：
  名称：

  Generation of α-Imino Gold Carbenes through Gold-Catalyzed Intermolecular Reaction of Azides with Ynamides

  摘要：

  The generation of a-imino gold carbenes via gold-catalyzed intermolecular reaction of azides and ynamides is disclosed. This new methodology allows for highly regioselective access to valuable 2,aminoindoles and 3-amino-beta-carbolines in generally good to excellent yields. A mechanistic rationale for this tandem reaction, especially for the observed high regioselectivity, is supported by DFT calculations.

  DOI：

  10.1021/jacs.5b06015
• 作为产物：
  描述：

  N-苯基甲磺酰胺 在 亚硝酸特丁酯 、 1,10-菲罗啉 、 copper(ll) sulfate pentahydrate 、 (IPr)Au(NTf₂) 、 palladium 10% on activated carbon 、 甲酸铵 、 六甲基二锡 、 potassium carbonate 、 对甲苯磺酸 作用下， 以 甲醇 、 乙酸乙酯 、 1,2-二氯乙烷 、 甲苯 为溶剂， 反应 34.0h， 生成 1-(methylsulfonyl)-3-phenyl-1H-indole
  参考文献：
  名称：

  Generation of α-Imino Gold Carbenes through Gold-Catalyzed Intermolecular Reaction of Azides with Ynamides

  摘要：

  The generation of a-imino gold carbenes via gold-catalyzed intermolecular reaction of azides and ynamides is disclosed. This new methodology allows for highly regioselective access to valuable 2,aminoindoles and 3-amino-beta-carbolines in generally good to excellent yields. A mechanistic rationale for this tandem reaction, especially for the observed high regioselectivity, is supported by DFT calculations.

  DOI：

  10.1021/jacs.5b06015

文献信息

• Palladium-Catalyzed Regioselective Synthesis of 3-Arylindoles from <i>N</i> -Ts-Anilines and Styrenes
  作者：So Won Youn、Tae Yun Ko、Young Ho Jang

  DOI：10.1002/anie.201702205

  日期：2017.6.1

  A Pd-catalyzed intermolecular oxidative annulation between N-Ts-anilines and styrenes was developed. This method offers a straightforward and robust approach to a wide range of 3-arylindoles using readily available starting materials with good functional-group tolerance and high regioselectivity and efficiency. Further elaboration of the products obtained from this process provided access to highly

  建立了N -Ts-苯胺和苯乙烯之间Pd催化的分子间氧化环。该方法使用容易获得的，具有良好的官能团耐受性和高区域选择性和效率的起始原料，为各种3-芳基吲哚提供了一种简单而稳健的方法。从该方法获得的产物的进一步精制提供了获得高度官能化且结构多样的吲哚的途径，例如3-（吲哚-3-基）咔唑，1,9-二氢吡咯并-[2,3-b]咔唑和3 '-芳基-3,5'-联吲哚。
• Electrochemical Oxidative [4+2] Annulation for the π‐Extension of Unfunctionalized Heterobiaryl Compounds
  作者：Xia Hu、Lei Nie、Guoting Zhang、Aiwen Lei

  DOI：10.1002/anie.202003656

  日期：2020.8.24

  biological activities, regioselective access to fused aromatic compounds is significantly important in the field of organic materials and pharmaceutical science. Herein, we developed electrochemical oxidative [4+2] annulation reactions of heterobiaryl compounds with alkynes or alkenes, leading to the formation of several polycyclic heteroaromatic compounds. This electrosynthetic methodology serves for

  考虑到它们独特的电子特性和多样的生物活性，在有机材料和药物科学领域中，区域选择性地获得稠合的芳族化合物非常重要。在本文中，我们开发了杂联芳基化合物与炔烃或烯烃的电化学氧化[4 + 2]环氧化反应，从而导致形成多种多环杂芳族化合物。这种电合成方法可用于未官能化杂二芳基化合物的直接π延伸。消除了对其他氧化剂和原料预官能化的要求。通过原位产生杂二芳基自由基阳离子中间体，可以以高收率和优异的区域选择性获得各种稠合的芳族化合物。
• Palladium-Catalyzed Sequential Vinylic C–H Arylation/Amination of 2-Vinylanilines with Aryl boronic Acids: Access to 2-Arylindoles
  作者：Ruixia Yu、Dejun Li、Fanlong Zeng

  DOI：10.1021/acs.joc.7b02728

  日期：2018.1.5

  A palladium-catalyzed selective and successive vinylic C–H arylation/amination of 2-vinylanilines with arylboronic acids to generate indoles has been developed. This procedure represents a straightforward and practical approach to valuable multifunctionalized indoles.

  已开发出钯催化的2-乙烯基苯胺与芳基硼酸的选择性和连续乙烯基C–H芳基化/胺化反应，生成吲哚。该程序代表了一种有价值的多功能吲哚的直接而实用的方法。
• Arylation of Rhodium(II) Azavinyl Carbenes with Boronic Acids
  作者：Nicklas Selander、Brady T. Worrell、Stepan Chuprakov、Subash Velaparthi、Valery V. Fokin

  DOI：10.1021/ja3062453

  日期：2012.9.12

  A highly efficient and stereoselective arylation of in situ-generated azavinyl carbenes affording 2,2-diaryl enamines at ambient temperatures has been developed. These transition-metal carbenes are directly produced from readily available and stable 1-sulfonyl-1,2,3-triazoles in the presence of a rhodium carboxylate catalyst. In several cases, the enamines generated in this reaction can be cyclized

  已经开发了一种在环境温度下原位生成的氮杂乙烯基卡宾的高效和立体选择性芳基化反应，提供 2,2-二芳基烯胺。在羧酸铑催化剂存在下，这些过渡金属卡宾直接由易得且稳定的 1-磺酰基-1,2,3-三唑制备。在一些情况下，该反应中生成的烯胺可以在铜催化下环化成取代的吲哚。
• Generation of α-Imino Gold Carbenes through Gold-Catalyzed Intermolecular Reaction of Azides with Ynamides
  作者：Chao Shu、Yong-Heng Wang、Bo Zhou、Xin-Ling Li、Yi-Fan Ping、Xin Lu、Long-Wu Ye

  DOI：10.1021/jacs.5b06015

  日期：2015.8.5

  The generation of a-imino gold carbenes via gold-catalyzed intermolecular reaction of azides and ynamides is disclosed. This new methodology allows for highly regioselective access to valuable 2,aminoindoles and 3-amino-beta-carbolines in generally good to excellent yields. A mechanistic rationale for this tandem reaction, especially for the observed high regioselectivity, is supported by DFT calculations.