5-methoxy-2-(2-pyridyl)indole | 475993-69-2

• 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-methoxy-2-(2-pyridyl)indole
• 英文别名: 5-methoxy-2-pyridin-2-yl-1H-indole
• CAS: 475993-69-2
• 化学式: C₁₄H₁₂N₂O
• 分子量: 224.262
• InChiKey: ZNXSAEORQMPNCF-UHFFFAOYSA-N

物化性质

• 熔点：
  128-129 °C
• 沸点：
  442.4±30.0 °C(Predicted)
• 密度：
  1.216±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  37.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-methoxy-2-(2-pyridyl)indole 在 三溴化硼 、 N,N-二异丙基乙胺 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.75h， 生成 3-bromo-1-[tert-butyl(dimethyl)silyl]-4-[5-[tert-butyl(dimethyl)silyl]oxy-2-pyridin-2-yl-1H-indol-3-yl]pyrrole-2,5-dione
  参考文献：
  名称：

  Pyrido[2,3-a]pyrrolo[3,4-c]carbazole-5,7(6H)-diones: Synthesis, Cyclometalation, and Protein Kinase Inhibition

  摘要：

  本研究公开了吡啶并[2,3-a]吡咯并[3,4-c]咔唑-5,7(6H)-二酮的合成路线，并介绍了随后将其转化为环甲基蛋白激酶抑制剂的实例。

  DOI：

  10.1055/s-2005-865331
• 作为产物：
  描述：

  4-methoxy-N-[(E)-1-pyridin-2-ylethylideneamino]aniline 在 三甲基硅基二氢化磷酸酯 作用下， 反应 18.0h， 以63%的产率得到5-methoxy-2-(2-pyridyl)indole
  参考文献：
  名称：

  Pyrido[2,3-a]pyrrolo[3,4-c]carbazole-5,7(6H)-diones: Synthesis, Cyclometalation, and Protein Kinase Inhibition

  摘要：

  本研究公开了吡啶并[2,3-a]吡咯并[3,4-c]咔唑-5,7(6H)-二酮的合成路线，并介绍了随后将其转化为环甲基蛋白激酶抑制剂的实例。

  DOI：

  10.1055/s-2005-865331

文献信息

• Total synthesis of new indolo[2,3-a]quinolizine alkaloids sempervirine type, potential pharmaceuticals
  作者：Teodozja M. Lipińska

  DOI：10.1016/j.tet.2006.03.085

  日期：2006.6

  the AB–DE synthons, has been obtained. The final stages: desulfuration, and formation of the C-ring via the Gribble method have led to the expected zwitterionic alkaloids. Model syntheses of the indolopyridocoline and its methoxy analogue from 2-acetylpyridine have been performed for investigation of the microwave-induced Fischer synthesis of sensitive indoles and for obtaining compounds for comparative

  从5-乙酰基-3-甲硫基-1分五个步骤详细阐述了两个系列的新五环杂环[ g ]吲哚并[2,3- a ]喹诺嗪生物碱（改性的sempervirine具有广泛的活性）的全合成。，2,4-三嗪（得自简单的无环材料）。在两个关键步骤中：电子逆需求Diors–Alder反应与环烯胺反应的前体，以及随后的3-乙酰基-1-甲基硫代环烷基的费歇尔吲哚化反应[ c已经获得了AB-DE合成子]吡啶。最后阶段：脱硫和通过Gribble方法形成C环已导致预期的两性离子生物碱。已经进行了吲哚吡咯啉及其从2-乙酰基吡啶的甲氧基类似物的模型合成，以研究敏感的吲哚的微波诱导费歇尔合成，并获得用于光谱数据比较研究的化合物。
• Microwave-induced solid-supported Fischer indolization, a key step in the total synthesis of the sempervirine type methoxy analogues
  作者：Teodozja Lipińska

  DOI：10.1016/j.tetlet.2004.10.008

  日期：2004.11

  A general protocol for the synthesis of 2-heteroaryl-5-methoxyindoles has been developed utilizing a microwave-induced solid-supported Fischer indolization under controlled conditions This route uses 2-acetylpyridine as a model and 3-acetyl derivatives of cycloalkeno[c]fused pyridines as the synthetic building blocks towards new 9-methoxyindolo[2,3-a]quinolizine alkaloids.

  对于2 -杂芳基-5- methoxyindoles合成的一般协议已被开发利用在受控条件下微波诱导的固体负载的Fischer吲哚此路线使用2-乙酰基作为cycloalkeno的模型和3-乙酰基衍生物[ C ^ ]熔融吡啶作为合成原料，可阻止新的9-甲氧基吲哚并[2,3- a ]喹诺嗪生物碱。
• 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。
• Tuning the Luminescence and Electroluminescence of Diphenylboron Complexes of 5-Substituted 2-(2‘-Pyridyl)indoles
  作者：Qinde Liu、Maria S. Mudadu、Hartmut Schmider、Randolph Thummel、Ye Tao、Suning Wang

  DOI：10.1021/om020446j

  日期：2002.10.1

  To examine the effect of substituent groups on the luminescence of BPh2(X-2-PI) complexes, three new air-stable boron complexes BPh2(F-2-PI) (5a), BPh2(Cl-2-PI) (5b), and BPh2(CH3O2-PI) (5c) were synthesized and characterized, where F-2-PI = 5-fluoro-2-(2'-pyridyl)indole, Cl-2-PI = 5-chloro-2-(2'-pyridyl)indole, and CH3O-2-PI = 5-methoxyl-2-(2'-pyridyl)indole. In these complexes, the 5-substituted 2-PI ligand chelates in a tretrahedral fashion to the boron center. Compounds 5a-c are luminescent, with 5a having the highest emission efficiency. Compared with the emission maximum of BPh2(2-PI) (516 nm), the emission maximum of 5a and 5b is blue-shifted to 490 and 487 nm, respectively, while the emission of 5c is red-shifted to 532 nm, indicating the possibility of tuning the luminescence of these complexes by varying the substituent groups on the 2-PI ligand. An electroluminescent device using compound 5a as the emitter and the electron transport material has been fabricated.
• Pyrido[2,3-<i>a</i>]pyrrolo[3,4-<i>c</i>]carbazole-5,7(6<i>H</i>)-diones: Synthesis, Cyclometalation, and Protein Kinase Inhibition
  作者：Eric Meggers、Howard Bregman、Douglas S. Williams

  DOI：10.1055/s-2005-865331

  日期：——

  Synthetic routes to pyrido[2,3-a]pyrrolo[3,4-c]carbazole-5,7(6H)-diones are disclosed and examples for their subsequent transformations into cyclometalated protein kinase inhibitors are presented.

  本研究公开了吡啶并[2,3-a]吡咯并[3,4-c]咔唑-5,7(6H)-二酮的合成路线，并介绍了随后将其转化为环甲基蛋白激酶抑制剂的实例。