3-methyl-2-phenyl-1-(pyridin-2-yl)-1H-indole | 1283073-92-6

• 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: 3-methyl-2-phenyl-1-(pyridin-2-yl)-1H-indole
• 英文别名: 3-Methyl-2-phenyl-1-pyridin-2-ylindole
• CAS: 1283073-92-6
• 化学式: C₂₀H₁₆N₂
• 分子量: 284.36
• InChiKey: DMYSHBJVJYBWCX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  17.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  3-甲基吲哚 在 potassium phosphate 、 copper(l) iodide 、 [RhCl2(p-cymene)]2 、 copper(II) bis(trifluoromethanesulfonate) 、 silver(l) oxide 、 N,N'-二甲基乙二胺 作用下， 以 1,4-二氧六环 、 甲苯 为溶剂， 反应 30.0h， 生成 3-methyl-2-phenyl-1-(pyridin-2-yl)-1H-indole
  参考文献：
  名称：

  Ruthenium-Catalyzed Heteroatom-Directed Regioselective C–H Arylation of Indoles Using a Removable Tether

  摘要：

  A new approach to C-2 arylated indoles has been developed by utilizing a ruthenium-catalyzed, heteroatom-directed regioselective C-H arylation. The reaction is highly site-selective and results in very good yields. The highlight of the work is the use of a removable directing group and compatibility of the catalytic system with halogen functional groups in the substrates.

  DOI：

  10.1021/acs.orglett.5b00535

文献信息

• Cobalt(II)-Catalyzed Oxidative C–H Arylation of Indoles and Boronic Acids
  作者：Xinju Zhu、Jian-Hang Su、Cong Du、Zheng-Long Wang、Chang-Jiu Ren、Jun-Long Niu、Mao-Ping Song

  DOI：10.1021/acs.orglett.6b03746

  日期：2017.2.3

  Co(II)-catalyzed C–H C2 selective arylation of indoles with boronic acids through monodentate chelation assistance has been achieved for the first time. The unique features of this methodology include mild reaction conditions, highly C2 regioselectivity, and employment of a Grignard reagent-free catalytic system. A wide range of substrates, including unreactive arenes, are well tolerated, which enables

  首次通过单齿螯合助剂实现了Co（II）催化的吲哚与硼酸的C–H C2选择性芳基化。该方法的独特之处包括温和的反应条件，高度的C2区域选择性以及采用格氏试剂无催化体系。包括非反应性芳烃在内的各种基材均具有良好的耐受性，从而可以高效地构建偶联产物。该新策略提供了使用廉价的钴催化剂构建联芳基的另一种通用方法。
• Synthesis of<i>N</i>-(2-Pyridyl)indoles via Pd(II)-Catalyzed Oxidative Coupling
  作者：Jinlei Chen、Qingyu Pang、Yanbo Sun、Xingwei Li

  DOI：10.1021/jo1025546

  日期：2011.5.6

  Readily available Pd(II) chloride catalysts can catalyze selective and efficient oxidative coupling between N-aryl-2-aminopyridines and internal alkynes to yield N-(2-pyridyl)indoles. This process involves the ortho C−H activation of N-aryl-2-aminopyridines, and CuCl2 was used as an oxidant. Compared to our previously reported Rh(III)-catalyzed synthesis of this class of product, this method is advantageous

  容易获得的Pd（II）氯化物催化剂可以催化之间的选择性的和有效的氧化偶合ñ -芳基-2-氨基吡啶和内部炔烃，得到ñ - （2-吡啶基）吲哚。该过程涉及N-芳基-2-氨基吡啶的邻位CH活化，并且CuCl 2被用作氧化剂。与我们先前报道的Rh（III）催化的这类产物的合成相比，该方法在炔烃和成本效益较高的Pd（II）催化剂方面具有优势。分子氧可以用作末端氧化剂。
• Nanocrystalline magnesium oxide-stabilized palladium(0): an efficient and reusable catalyst for synthesis of N-(2-pyridyl)indoles
  作者：Police Vishnuvardhan Reddy、Manne Annapurna、Pottabathula Srinivas、Pravin R. Likhar、Mannepalli Lakshmi Kantam

  DOI：10.1039/c5nj00074b

  日期：——

  A selective and efficient catalytic process has been developed for the oxidative coupling between N-aryl-2-aminopyridines and alkynes using a nanocrystalline magnesium oxide (NAP–MgO)-supported palladium nanoparticle [NAP–Mg–Pd(0)] catalyst and CuCl2 as an oxidant. The process involves the ortho C–H activation of N-aryl-2-aminopyridines to give N-pyridyl indoles in excellent yields and the true heterogeneity

  已经开发出一种选择性和有效的催化方法，以使用纳米晶氧化镁（NAP–MgO）负载的钯纳米颗粒[NAP–Mg–Pd（0）]催化剂和CuCl催化N-芳基-2-氨基吡啶和炔烃之间的氧化偶联。2作为氧化剂。该过程涉及N-芳基-2-氨基吡啶的邻位C–H活化，从而以优异的收率得到N-吡啶基吲哚，并且通过研究四个循环的可回收性和可重复使用性而证实了催化剂的真正非均相性，而不会显着降低催化活性。 。
• Rhodium(<scp>iii</scp>)-catalyzed regioselective oxidative annulation of anilines and allylbenzenes <i>via</i> C(sp³)–H/C(sp²)–H bond cleavage
  作者：Yunqi Liu、Yudong Yang、Chunxia Wang、Zhishuo Wang、Jingsong You

  DOI：10.1039/c8cc09099h

  日期：——

  and directed C(sp2)–H activation into a single approach for discovering unprecedented chemical transformations. As a proof-of-concept, we disclose for the first time the rhodium-catalyzed regioselective oxidative annulation of anilines with allylbenzenes to deliver a variety of indoles. In this work, the C3 and C2 positions of the allylic segment are set to construct C–N and C–C bonds, respectively

  本文描述的是将烯丙基C（sp 3）-H激活和定向C（sp 2）-H激活合并为单一方法以发现前所未有的化学转化。作为概念验证，我们首次公开了铑催化的苯胺与烯丙基苯的区域选择性氧化环合反应，以释放出各种吲哚。在这项工作中，将烯丙基链段的C3和C2位置分别设置为构建C–N和C–C键。
• Ruthenium-Catalyzed Heteroatom-Directed Regioselective C–H Arylation of Indoles Using a Removable Tether
  作者：Virendra Kumar Tiwari、Neha Kamal、Manmohan Kapur

  DOI：10.1021/acs.orglett.5b00535

  日期：2015.4.3

  A new approach to C-2 arylated indoles has been developed by utilizing a ruthenium-catalyzed, heteroatom-directed regioselective C-H arylation. The reaction is highly site-selective and results in very good yields. The highlight of the work is the use of a removable directing group and compatibility of the catalytic system with halogen functional groups in the substrates.