3-(p-acetylphenyl)-1-methylindole

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(p-acetylphenyl)-1-methylindole
• 英文别名: 1-[4-(1-Methylindol-3-yl)phenyl]ethanone；1-[4-(1-methylindol-3-yl)phenyl]ethanone
• 化学式: C₁₇H₁₅NO
• 分子量: 249.312
• InChiKey: UBVCBSJAIGLTRG-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：
  0.12
• 拓扑面积：
  22
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  1-甲基吲哚-3-甲酸 、 4-溴苯乙酮 在 C₆₆H₆₂Cl₂N₄Pd₂ 、 potassium acetate 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 5.0h， 以78%的产率得到3-(p-acetylphenyl)-1-methylindole
  参考文献：
  名称：

  Abnormal NHC supported palladacycles: Regioselective arylation of heteroarenes via decarboxylation

  摘要：

  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.

  DOI：

  10.1016/j.jorganchem.2018.01.046

文献信息

• Catalytic Au(<scp>i</scp>)/Au(<scp>iii</scp>) arylation with the hemilabile MeDalphos ligand: unusual selectivity for electron-rich iodoarenes and efficient application to indoles
  作者：Jessica Rodriguez、Abdallah Zeineddine、E. Daiann Sosa Carrizo、Karinne Miqueu、Nathalie Saffon-Merceron、Abderrahmane Amgoune、Didier Bourissou

  DOI：10.1039/c9sc01954e

  日期：——

  electron-deprived substrates typically encountered with palladium. Based on DFT calculations and detailed analysis of the key transition states (using NBO, CDA and ETS-NOCV methods in particular), the different behavior of the two metals is proposed to result from inverse electron flow between the substrate and metal. Indeed, oxidative addition of iodobenzene is associated with a charge transfer from the substrate

  已充分研究了半不稳定（P，N）MeDalphos配体引发碘代芳烃向金的氧化加成的能力。竞争实验和Hammett相关性在化学计量氧化加成反应和与1,3,5-三甲氧基苯的催化C–C交叉偶联中都证明了金对于富电子底物的明显偏好。此特征与钯通常遇到的电子剥夺性底物的更高反应性形成鲜明对比。基于DFT计算和关键过渡状态的详细分析（特别是使用NBO，CDA和ETS-NOCV方法），提出了两种金属的不同行为，这是由于基底和金属之间的逆电子流导致的。的确，碘苯的氧化加成与金在过渡态时从基底到金属的电荷转移有关，而钯则相反。金中心的较高亲电性有利于富电子的基质，而钯的重要背向供稿则有利于电子贫乏的基质。碘代芳烃的简便氧化加成结合金的倾向（III）络合物易于与富电子（杂）芳烃反应，促使我们将（MeDalphos）AuCl络合物应用于吲哚的催化芳基化反应，这是一项具有挑战性但非常重要的转化。金络合物被证明是非常
• General Suzuki Coupling of Heteroaryl Bromides by Using Tri-<i>tert</i>-butylphosphine as a Supporting Ligand
  作者：Yinjun Zou、Guizhou Yue、Jianwei Xu、Jianrong Steve Zhou

  DOI：10.1002/ejoc.201402915

  日期：2014.9

  A general procedure for the fast Suzuki coupling of major families of heteroaryl bromides was realized by using Pd(OAc)2/PtBu3 as the catalyst. Many couplings were finished within minutes at room temperature in n-butanol. Different from previous studies, three typical heteroaryl bromides were systematically examined in couplings of various heteroaryl and aryl boronic acids.

  通过使用 Pd(OAc)2/PtBu3 作为催化剂，实现了主要家族杂芳基溴化物的快速 Suzuki 偶联的一般程序。许多偶联在室温下在正丁醇中几分钟内完成。与之前的研究不同，在各种杂芳基和芳基硼酸的偶联中系统地研究了三种典型的杂芳基溴化物。
• Direct C−H Arylation of (Hetero)arenes with Aryl Iodides via Rhodium Catalysis
  作者：Shuichi Yanagisawa、Tomoko Sudo、Ryoji Noyori、Kenichiro Itami

  DOI：10.1021/ja064500p

  日期：2006.9.1

  A new method for the catalytic C-H arylation of heteroarenes and arenes that manifests high activity paired with reasonably broad scope was developed. Under the catalytic influence of RhCl(CO)P[OCH(CF3)2]3}2 and Ag2CO3, the direct C-H arylation of heteroarenes/arenes with aryl/heteroaryl iodides took place to afford a range of biaryls in good to excellent yields with high regioselectivity. Thiophenes, furans, pyrroles, indoles, and alkoxybenzenes are applicable in this arylation protocol.
• Direct coupling of arenes and iodoarenes catalyzed by a rhodium complex with a strongly π-accepting phosphite ligand
  作者：Shuichi Yanagisawa、Tomoko Sudo、Ryoji Noyori、Kenichiro Itami

  DOI：10.1016/j.tet.2008.01.053

  日期：2008.6

  A new rhodium-based catalytic system for the direct C-H coupling of arenes and iodoarenes that shows high activity with reasonably broad scope was developed. Under the catalytic influence of RhCl(CO)P[OCH(CF3)(2)](3)}(2) and Ag2CO3, the direct C-H arylation of heteroarenes and arenes took place with iodoarenes to afford a range of biaryls in good to excellent yields with high regioselectivity. Thiophenes, furans, pyrroles, indoles, and alkoxybenzenes are applicable to this arylation protocol. (C) 2008 Elsevier Ltd. 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.