3-mesityl-1-methylindole | 1469989-29-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 3-mesityl-1-methylindole
• 英文别名: N-methyl-3-(2-mesityl)indole；3-mesityl-N-methylindole；1-Methyl-3-(2,4,6-trimethylphenyl)indole
• CAS: 1469989-29-4
• 化学式: C₁₈H₁₉N
• 分子量: 249.356
• InChiKey: BEKZCEXHJFNGLO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  4.9
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  1-甲基吲哚 在 溴 、 palladium diacetate 、 sodium t-butanolate 、 tri tert-butylphosphoniumtetrafluoroborate 作用下， 以 2-甲基-2-丁醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 3-mesityl-1-methylindole
  参考文献：
  名称：

  3-溴吲哚与受阻苯硼酸的Suzuki偶联反应合成2-芳基吲哚

  摘要：

  开发了一种新的2-芳基吲哚合成方法，Pd（OAc）2 / PCy 3催化3-溴吲哚与受阻硼酸的Suzuki偶联反应，合成了一系列中等程度的2-芳基吲哚。高产。

  DOI：

  10.1016/j.tetlet.2017.01.014

文献信息

• Mild and selective base-free C–H arylation of heteroarenes: experiment and computation
  作者：Hannes P. L. Gemoets、Indrek Kalvet、Alexander V. Nyuchev、Nico Erdmann、Volker Hessel、Franziska Schoenebeck、Timothy Noël

  DOI：10.1039/c6sc02595a

  日期：——

  A mild and selective C–H arylation strategy for indoles, benzofurans and benzothiophenes is described. The arylation method engages aryldiazonium salts as arylating reagents in equimolar amounts. The protocol is operationally simple, base free, moisture tolerant and air tolerant. It utilizes low palladium loadings (0.5 to 2.0 mol% Pd), short reaction times, green solvents (EtOAc/2-MeTHF or MeOH) and

  描述了吲哚、苯并呋喃和苯并噻吩的温和选择性 C-H 芳基化策略。芳基化方法使用等摩尔量的芳基重氮盐作为芳基化试剂。该方案操作简单、无碱、耐湿且耐空气。它利用低钯负载量（0.5 至 2.0 mol% Pd）、短反应时间、绿色溶剂（EtOAc/2-MeTHF 或 MeOH）并在室温下进行，提供广泛的底物范围（47 个示例）和出色的选择性（吲哚和苯并呋喃的C-2芳基化，苯并噻吩的C-3芳基化。机理实验和 DFT 计算支持 Heck-Matsuda 型耦合机制。
• 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。
• Aromatic C–H coupling with hindered arylboronic acids by Pd/Fe dual catalysts
  作者：Kazuya Yamaguchi、Hiroki Kondo、Junichiro Yamaguchi、Kenichiro Itami

  DOI：10.1039/c3sc51206a

  日期：——

  An aerobic oxidative coupling of arenes/alkenes with arylboronic acids (C–H/C–B coupling) using catalytic Pd(II)–sulfoxide–oxazoline (sox) ligand and iron–phthalocyanine (FePc) has been developed. This dual catalyst system enables the synthesis of sterically hindered heterobiaryls and styrene derivatives under air without stoichiometric co-oxidants. Additionally, this chemistry demonstrated an advance

  芳烃/烯烃与芳基硼酸的好氧氧化偶联（C–H / C–B偶联），使用催化的Pd（II）–亚砜–恶唑啉 （含氧）配体和铁酞菁（FePc）已开发。这种双催化剂体系能够在没有化学计量助氧化剂的情况下在空气中合成位阻杂联芳基和苯乙烯衍生物。此外，这种化学方法还证明了通过C–H官能化对映选择性联芳基的进展。
• Palladium-Catalysed Direct Desulfitative Arylation of Pyrroles using Benzenesulfonyl Chlorides as Alternative Coupling Partners
  作者：Rongwei Jin、Kedong Yuan、Emmanuelle Chatelain、Jean-François Soulé、Henri Doucet

  DOI：10.1002/adsc.201400736

  日期：2014.12.15

  AbstractThe reactivity of pyrrole derivatives for palladium‐catalysed desulfitative arylation has been investigated. 1‐Methyl‐, 1‐phenyl‐ and 1‐benzylpyrroles were successfully coupled with a variety of benzenesulfonyl chlorides using a phosphine‐free catalyst. Highly regioselective arylations at carbon C2 of pyrroles were observed in all cases. A wide variety of substituents on the benzenesulfonyl derivative was tolerated.It should be noted that even bromo‐ and iodo‐benzenesulfonyl chlorides were successfully coupled with pyrrole derivatives without cleavage of the CBr or CI bonds, allowing further transformations. Surprisingly, with indoles, mixtures of C2‐ and C3‐arylation products were obtained.magnified image