5-Methyl-2-(2-pyridyl)indole | 109809-21-4

• 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: 5-Methyl-2-(2-pyridyl)indole
• 英文别名: 5-Methyl-2-pyridyl-(2)-indol；5-methyl-2-pyridin-2-yl-indole；5-methyl-2-pyridin-2-yl-1H-indole
• CAS: 109809-21-4
• 化学式: C₁₄H₁₂N₂
• 分子量: 208.263
• InChiKey: KUFMLHYTDIVNJM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  28.7
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  反式硝基苯乙烯 、 5-Methyl-2-(2-pyridyl)indole 在 cerium(III) chloride heptahydrate 作用下， 以 乙醇 为溶剂， 反应 12.0h， 以88%的产率得到(5-methyl-2-(pyridin-2-yl)-1H-indol-3-yl)(phenyl)methanone
  参考文献：
  名称：

  铈（III）催化吲哚与硝基烯烃的C3-酰化反应

  摘要：

  首次开发了一种新型高效的铈（III）催化的硝基苯吲哚的C3选择性C3选择性酰化反应，该反应使用硝基烯烃作为酰化试剂。发现使用CeCl 3作为催化剂可实现意想不到且高效的C–C键裂解。

  DOI：

  10.1016/j.tetlet.2016.01.029
• 作为产物：
  描述：

  2-Acetylpyridine-p-tolylhydrazone 在 PPA 作用下， 以43%的产率得到5-Methyl-2-(2-pyridyl)indole
  参考文献：
  名称：

  Synthesis and pharmacological investigation of 9-methyl-1,2,3,4,6,7,12,12b-octahydro-7-oxo-indolo[2,3-a]quinolizine

  摘要：

  The title ketone, a supposed metabolite of 9-methyl-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizine (MIQ), was prepared and found different on chromatographic comparison from the isolated metabolite M-4. However, the pharmacological screening of this compound evidenced, among others, some interesting properties as inhibition of arachidonic acid induced platelet aggregation and protection from both hypobaric and cyanide induced hypoxia in mice. These activities suggest a possible cerebroprotective action to be further investigated. (C) 1999 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0014-827x(99)00056-7

文献信息

• Olefin Hydroarylation Catalyzed by (pyridyl-indolate)Pt(II) Complexes: Catalytic Efficiencies and Mechanistic Aspects
  作者：Benjamin A. Suslick、Allegra L. Liberman-Martin、Truman C. Wambach、T. Don Tilley

  DOI：10.1021/acscatal.7b01560

  日期：2017.7.7

  A series of Pt(II) complexes of the type (N–N)PtPh(SR2) (N–N = 2,2′-pyridyl-indolate) were prepared, and their performance as catalysts for the hydroarylation of olefins was assessed. Evidence that the catalysis is homogeneous and is Pt-mediated is provided by control experiments with added hindered base (2,6-di-tert-butyl-4-methylpyridine) and Hg(0). Two potential catalytic intermediates, (tBuPyInd)PtPh(C2H4)

  制备了一系列（N–N）PtPh（SR 2）（N–N = 2,2'-吡啶基-吲哚酸酯）类型的Pt（II）配合物，并评估了它们作为烯烃加氢芳基化反应的催化剂的性能。 。对照实验提供了添加受阻碱（2,6-二叔丁基-4-甲基吡啶）和Hg（0）的证据，证明了催化是均相的并且是Pt介导的。两种潜在的催化中间体（t BuPyInd）PtPh（C 2 H 4）和（t BuPyInd）Pt（CH 2 CH 2 Ph）（C 2 H 4），合成，并探索其催化功效。此外，还确定了分解和失活途径，包括通过β-氢化物消除和配体还原性脱金属形成苯乙烯。
• Cerium(III)-catalyzed C3-acylation of indoles with nitroolefins
  作者：Cheng-Tao Feng、Hui-Zhi Zhu、Zhong Li、Zaigang Luo、Song-Song Wu、Shi-Tang Ma

  DOI：10.1016/j.tetlet.2016.01.029

  日期：2016.2

  A novel and efficient cerium(III)-catalyzed C3-selective acylation of N–H indoles using nitroolefins as acylating reagents was first developed. It was found that the use of CeCl3 as a catalyst achieves an unexpected and highly efficient C–C bond cleavage.

  首次开发了一种新型高效的铈（III）催化的硝基苯吲哚的C3选择性C3选择性酰化反应，该反应使用硝基烯烃作为酰化试剂。发现使用CeCl 3作为催化剂可实现意想不到且高效的C–C键裂解。
• Synthesis and pharmacological investigation of 9-methyl-1,2,3,4,6,7,12,12b-octahydro-7-oxo-indolo[2,3-a]quinolizine
  作者：Teresa Grandi、Fabio Sparatore、Anna Sparatore

  DOI：10.1016/s0014-827x(99)00056-7

  日期：1999.7

  The title ketone, a supposed metabolite of 9-methyl-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizine (MIQ), was prepared and found different on chromatographic comparison from the isolated metabolite M-4. However, the pharmacological screening of this compound evidenced, among others, some interesting properties as inhibition of arachidonic acid induced platelet aggregation and protection from both hypobaric and cyanide induced hypoxia in mice. These activities suggest a possible cerebroprotective action to be further investigated. (C) 1999 Elsevier Science S.A. All rights reserved.