4-(1-methyl-1H-indol-3-yl)benzonitrile | 1175772-37-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 4-(1-methyl-1H-indol-3-yl)benzonitrile
• 英文别名: 4-(1-Methylindol-3-yl)benzonitrile
• CAS: 1175772-37-8
• 化学式: C₁₆H₁₂N₂
• 分子量: 232.285
• InChiKey: UYYVDPHKKPQOAD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  28.7
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  4-[2-(N-methylanilino)acetyl]benzonitrile 反应 0.67h， 以73%的产率得到4-(1-methyl-1H-indol-3-yl)benzonitrile
  参考文献：
  名称：

  微波辐射下 HFIP 促进的 Bischler 吲哚合成

  摘要：

  发现 1,1,1,3,3,3-Hexafluoropropan-2-ol (HFIP) 在没有金属催化剂的情况下在微波辐射下对 Bischler 吲哚合成有效。在HFIP的催化下，广泛的α-氨基芳基丙酮成功地转化为吲哚衍生物，产率中等至良好。

  DOI：

  10.3390/molecules23123317

文献信息

• Ascorbic Acid as an Aryl Radical Inducer in the Gold‐Mediated Arylation of Indoles with Aryldiazonium Chlorides
  作者：Ignacio Medina‐Mercado、Eric Omar Asomoza‐Solís、Eduardo Martínez‐González、Victor Manuel Ugalde‐Saldívar、Lydia Gabriela Ledesma‐Olvera、José Enrique Barquera‐Lozada、Virginia Gómez‐Vidales、Joaquín Barroso‐Flores、Bernardo A. Frontana‐Uribe、Susana Porcel

  DOI：10.1002/chem.201904413

  日期：2020.1.13

  the development of protocols that facilitate the oxidative addition of gold to access mild cross-coupling processes mediated by this metal has increased. In this context, we report herein that ascorbic acid, a natural and readily accessible antioxidant, can be used to accelerate the oxidative addition of aryldiazonium chlorides onto AuI . The aryl-AuIII species generated in this way, has been used

  近年来，对促进金的氧化添加以进入由该金属介导的温和的交叉偶联过程的方案的兴趣增加了。在此背景下，我们在本文中报道抗坏血酸是一种天然且易于获得的抗氧化剂，可用于加速芳基重氮氯化物到AuI上的氧化加成。以这种方式产生的芳基-AuIII物种已被用于以一锅法从苯胺和对位，间位和邻位取代的芳基重氮鎓氯化物制备3-芳基吲哚。基于EPR分析，循环伏安法和DFT计算，详细研究了氧化加成的潜在机理。有趣的是，我们发现在该方案中，氯化物原子诱导了AuII / AuIII氧化步骤。
• Well-Defined Palladium N-Heterocyclic Carbene Complexes: Direct C–H Bond Arylation of Heteroarenes
  作者：Anuj Kumar、Manoj Kumar、Akhilesh K. Verma

  DOI：10.1021/acs.joc.0c02024

  日期：2020.11.6

  A series of palladium N-heterocyclic carbene (NHC) complexes of type trans-(NHC)PdCl2L} (L = C5H5N, 3-ClC5H4N, and PPh3) (3–5) have been developed as efficient precatalysts for direct C–H bond arylation of various heteroarenes. In particular, an in situ generated new NHC ligand derived from 1,3-di-(2,6-diethylphenyl)acenaphtho[1,2-d] imidazolium} chloride (2) is used for the stabilization of the

  反式-（NHC）PdCl 2 L}（L = C 5 H 5 N，3-ClC 5 H 4 N和PPh 3）的一系列钯N-杂环卡宾（NHC）配合物（3 – 5）已经开发出作为各种杂芳烃直接C–H键芳基化的有效预催化剂。特别地，使用由1,3-二-（2,6-二乙基苯基）ac [1,2- d ]咪唑鎓}氯化物（2）衍生的原位生成的新NHC配体来稳定钯金属中心。在筛选出的钯预催化剂中（3 – 5），最活跃的PEPPSI主题复合物（3）已成功用于各种杂芳烃和芳基溴化物的直接C–H键芳基化。在整个标准反应条件下，芳基溴化物和杂芳烃上的一系列官能团均可轻松获得各种芳基化杂环化合物。重要的是，该协议的实用性通过有效合成雷洛昔芬（一种选择性雌激素受体调节剂）的前体来证明。
• Abnormal NHC supported palladacycles: Regioselective arylation of heteroarenes via decarboxylation
  作者：Anex Jose、Gonela Vijaykumar、Pavan K. Vardhanapu、Swadhin K. Mandal

  DOI：10.1016/j.jorganchem.2018.01.046

  日期：2018.6

  We report synthesis of two new palladium(II) complexes of abnormal N-heterocyclic carbene ligands. The catalytic activity of these palladium(II) complexes was examined for the decarboxylative arylation of N-methylindole-carboxylic acids. An exclusive regioselectivity and very good yields were obtained with a variety of aryl halide partners. (C) 2018 Elsevier B.V. All rights reserved.
• Pd(0)-Catalyzed Decarboxylative Coupling and Tandem C–H Arylation/Decarboxylation for the Synthesis of Heteroaromatic Biaryls
  作者：Debkumar Nandi、Yang-Ming Jhou、Jhen-Yi Lee、Bing-Chiuan Kuo、Chien-Yu Liu、Pei-Wen Huang、Hon Man Lee

  DOI：10.1021/jo3015837

  日期：2012.10.19

  An effective Pd(0) carbene complex was successfully employed in the decarboxylative coupling of the heteroaromatic carboxylic acids (imidazo[1,2-a]pyridine and isoxazole) with aryl halides. For carboxyindoles, either decarboxylative coupling or tandem C-H arylation and decarboxylation occurred, leading to the formation of C2-monoarylated indoles.
• HFIP-Promoted Bischler Indole Synthesis under Microwave Irradiation
  作者：Guangkai Yao、Zhi-Xiang Zhang、Cheng-Bei Zhang、Han-Hong Xu、Ri-Yuan Tang

  DOI：10.3390/molecules23123317

  日期：——

  1,1,1,3,3,3-Hexafluoropropan-2-ol (HFIP) was found to be effective for the Bischler indole synthesis under microwave irradiation in the absence of a metal catalyst. Under the catalysis of HFIP, a wide range of α-amino arylacetones were successfully transformed into indole derivatives with moderate to good yields.

  发现 1,1,1,3,3,3-Hexafluoropropan-2-ol (HFIP) 在没有金属催化剂的情况下在微波辐射下对 Bischler 吲哚合成有效。在HFIP的催化下，广泛的α-氨基芳基丙酮成功地转化为吲哚衍生物，产率中等至良好。