methyl 3-(1H-indol-2-yl)benzoate | 1059628-81-7

• 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: methyl 3-(1H-indol-2-yl)benzoate
• CAS: 1059628-81-7
• 化学式: C₁₆H₁₃NO₂
• 分子量: 251.285
• InChiKey: KYRGKTWKSJGGGT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  42.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  methyl 3-(1H-indol-2-yl)benzoate 在 吡啶 、 tris(acetonitrile)(η5-pentamethylcyclopentadienyl)rhodium(III) hexafluoroantimonate 、 氧气 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 20.0~100.0 ℃ 、101.33 kPa 条件下， 反应 0.17h， 生成 methyl 3'-oxo-2,3-diphenylspiro[indene-1,2'-indoline]-6-carboxylate
  参考文献：
  名称：

  Multi-site cyclization via initial C–H activation using a rhodium(iii) catalyst: rapid assembly of frameworks containing indoles and indolines

  摘要：

  通过Rh（III）催化的C–H活化触发的串联多位点环化反应已成功实现，用于高效合成螺环吲哚-3-酮（C2-环化）、苯并[a]咔唑（C3-环化）和一种不寻常的吲哧核心（N1-环化）。

  DOI：

  10.1039/c4cc07125e
• 作为产物：
  描述：

  3-碘苯甲酸甲酯 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 potassium carbonate 、 二异丙胺 、 L-脯氨酸 、 copper(I) bromide 作用下， 以 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 生成 methyl 3-(1H-indol-2-yl)benzoate
  参考文献：
  名称：

  Copper catalysed domino decarboxylative cross coupling-cyclisation reactions: synthesis of 2-arylindoles

  摘要：

  The efficient synthesis of 2-arylindoles and 6H-isoindolo[2,1-a]indol-6-one through copper catalysed domino sp-sp(2) decarboxylative cross-coupling and subsequent cyclisation reactions of arylpropiolic acids with 2-iodotrifluoroacetanilide has been described. This methodology also demonstrates that indolo[1,2-c]quinazolin-6(5H)-one can be obtained with the elimination of trifluoromethyl anion. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.06.023

文献信息

• Palladium-catalyzed intermolecular C-H amidation of indoles with sulfonyl azides
  作者：Ziwei Hu、Shuang Luo、Qiang Zhu

  DOI：10.1007/s11426-015-5369-y

  日期：2015.8

  A new kind of intermolecular indole C-H amidation reaction catalyzed by the most frequently used palladium catalyst has been developed. Sulfonyl azide was employed as an innovative nitrogen source and environmentally benign nitrogen was produced as the only byproduct.

  一种新型的分子间吲哚C-H酰胺化反应已被开发出来，该反应由最常用的钯催化剂催化进行。使用磺酰叠氮作为创新的氮源，并且唯一的副产品是环境友好的氮气。
• [EN] COMPOUNDS FOR MODULATING DDAH AND ADMA LEVELS, AS WELL AS METHODS OF USING THEREOF TO TREAT DISEASE<br/>[FR] COMPOSÉS DESTINÉS À MODULER LES NIVEAUX DE DDAH ET D'ADMA, AINSI QUE LEURS MÉTHODES D'UTILISATION POUR TRAITER UNE MALADIE
  申请人：VASCULONICS LLC

  公开号：WO2019213148A1

  公开（公告）日：2019-11-07

  Disclosed are compounds that can modulate DDAH and the amount of asymmetric dimethylarginine (ADMA) in a subject. Also provided are pharmaceutical compositions comprising these compounds, as well as methods of using these compositions to treat and/or prevent diseases associated with elevated or low levels of DDAH and ADMA.

  揭示了能够调节DDAH和主体中不对称二甲基精氨酸（ADMA）含量的化合物。还提供了包含这些化合物的药物组合物，以及使用这些组合物治疗和/或预防与DDAH和ADMA水平升高或降低相关的疾病的方法。
• Palladium-Catalyzed Tandem Nucleophilic Addition/C–H Functionalization of Anilines and Bromoalkynes for the Synthesis of 2-Phenylindoles
  作者：Caijin Zeng、Songjia Fang、Shuqi Guo、Huanfeng Jiang、Shaorong Yang、Wanqing Wu

  DOI：10.1021/acs.orglett.3c00137

  日期：2023.3.10

  A novel and efficient palladium-catalyzed annulation of anilines with bromoalkynes for the synthesis of 2-phenylindoles has been described. This approach features excellent regio- and stereoselectivities and good functional group tolerance. Preliminary mechanistic studies indicate that anilines undergo anti-nucleophilic addition to bromoalkynes to generate (Z)-N-(2-bromo-1-phenylvinyl) anilines, followed

  已经描述了用于合成 2-苯基吲哚的新型和有效的钯催化的苯胺与溴炔的环化。这种方法具有出色的区域选择性和立体选择性以及良好的官能团耐受性。初步的机理研究表明，苯胺对溴代炔烃进行反亲核加成反应生成 ( Z )- N -(2-bromo-1-phenylvinyl) 苯胺，然后依次进行 C-H 官能化以提供不同的取代 2-苯基吲哚。该方法为构建各种生物活性化合物提供了潜在的应用。
• Structure–activity relationships of 2-aryl-1H-indole inhibitors of the NorA efflux pump in Staphylococcus aureus
  作者：Joseph I. Ambrus、Michael J. Kelso、John B. Bremner、Anthony R. Ball、Gabriele Casadei、Kim Lewis

  DOI：10.1016/j.bmcl.2008.06.093

  日期：2008.8

  The synthesis of 22 2-aryl-1H-indoles, including 12 new compounds, has been achieved via Pd- or Rh-mediated methodologies, or selective electrophilic substitution. All three methods were based on elaborations from simple indole precursors. SAR studies on these indoles and 2-phenyl-1H-indole in Staphylococcus aureus as NorA efflux pump inhibitors indicated 5-nitro-2-(3-methoxycarbonyl)phenyl-1H-indole was a slightly more potent inhibitor than the lead INF55. A promising new antibacterial lead compound against S. aureus (2-phenyl-1H-indol-5-yl)-methanol, was also found. (c) 2008 Elsevier Ltd. All rights reserved.
• Synthesis of Berberine—Efflux Pump Inhibitor Hybrid Antibacterials
  作者：John B. Bremner、Michael J. Kelso

  DOI：10.1080/00397910903457415

  日期：2010.11.3

  This article describes the compact synthesis of two isomeric dual-action hybrid antimicrobials where the 13-position of the antibacterial berberine has been linked via 3'- and 4'-methylene bridges to INF55 (5-nitro-2-phenylindole), an inhibitor of the bacterial NorA multidrug-resistance pump.