3-phenyl-1-(pyridin-2-yl)isoquinoline | 960054-13-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 3-phenyl-1-(pyridin-2-yl)isoquinoline
• 英文别名: 3-phenyl-1-(2-pyridyl)isoquinoline；3-phenyl-1-pyridin-2-ylisoquinoline
• CAS: 960054-13-1
• 化学式: C₂₀H₁₄N₂
• 分子量: 282.345
• InChiKey: HGSRJNQAZREXJF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  25.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3-苯基-1-(2-吡啶)-5,6,7,8-四氢异喹啉 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 邻二甲苯 为溶剂， 反应 10.0h， 以51%的产率得到3-phenyl-1-(pyridin-2-yl)isoquinoline
  参考文献：
  名称：

  A rational protocol for the synthesis of 1-(2-pyridyl)isoquinolines

  摘要：

  Aza-Diels-Alder reaction between 3-(2-pyridyl)-1,2,4-triazines and 1-morpholinocyclohexene followed by aromatization of the cyclohexene moiety affords 1-(2-pyridyl)isoquinolines. Crystal structures of two tetrahydroisoquinolines were confirmed by X-ray diffraction analysis.

  DOI：

  10.1016/j.mencom.2013.05.007

文献信息

• Synthesis of 6-phenyl-2,2′-bipyridine ligands bearing polyaromatic substituents
  作者：Stéphane Diring、Pascal Retailleau、Raymond Ziessel

  DOI：10.1016/j.tetlet.2007.09.011

  日期：2007.11

  substituted 6-phenyl-2,2′-bipyridine derivatives is described. An inverse Diels–Alder reaction between a 3-phenyl-5-pyridyl-1,2,4-triazine and an electron-rich ethynyl species at high temperature provides a mixture of two products easily separable by column chromatography. The most encumbered isomer is favoured, likely due to favourable π–π stacking interactions in the transition state. A variety of

  描述了一种有效制备取代的6-苯基-2,2'-联吡啶衍生物的简单方案。3-苯基-5-吡啶基-1，2，4-三嗪与富含电子的乙炔基之间的高温逆Diels-Alder反应提供了两种产品的混合物，可通过柱色谱法轻松分离。最易受干扰的异构体受到青睐，可能是由于过渡态中有利的π-π堆积相互作用所致。已经生产了多种适合于合成环金属化配合物的那些配体。
• A Rational Protocol for the Synthesis of Arylated Bipyridine Ligands via a Cycloaddition Pathway
  作者：Stéphane Diring、Pascal Retailleau、Raymond Ziessel

  DOI：10.1021/jo7019866

  日期：2007.12.1

  in low yields in most cases. The use of tert-butylacetylene or N,N-dimethylamino-2-propyne, however, drives the reaction exclusively to the para isomer. Di-N,N-dibutylaminophenyl or isoquinoline ligands can also be produced in a single step by reverse Diels−Alder reactions. Cross-coupling reactions of iodo-substituted ligands or their platinum(II) complexes under Pd(0) catalysis gives branched ligands

  描述了制备各种取代的苯基-聚吡啶配体的通用设计原理。这些配体很容易通过缺电子二烯（例如2,6-二取代-1,3,4-三嗪）与乙炔基-芳烃或乙炔基-烷烃之间的区域选择性[4 + 2]环加成而制备。对于带有乙炔基没食子酸酯或乙炔基苯基二丁基氨基的富含电子的亲二烯体，发现了出色的反应性。形成两个区域异构体，由于过渡态中有利的π-π相互作用，优选间位，而在大多数情况下以低收率形成对位异构体。然而，叔丁基乙炔或N，N-二甲基氨基-2-丙炔的使用仅将反应驱动为对位异构体。二ñ，N-二丁基氨基苯基或异喹啉配体也可以通过反向Diels-Alder反应一步生成。在Pd（0）催化下，碘取代的配体或其铂（II）配合物的交叉偶联反应产生带有石蜡链，电子给体或电子受体基团的支链配体和配合物。碘官能化配体的氯-Pt（II）配合物的使用允许通过使用不同的催化剂，两个卤素都被乙炔基取代。该方法易于容纳各种功能组，并已成功地
• A rational protocol for the synthesis of 1-(2-pyridyl)isoquinolines
  作者：Dmitry S. Kopchuk、Igor S. Kovalev、Albert F. Khasanov、Grigory V. Zyryanov、Pavel A. Slepukhin、Vladimir L. Rusinov、Oleg N. Chupakhin

  DOI：10.1016/j.mencom.2013.05.007

  日期：2013.5

  Aza-Diels-Alder reaction between 3-(2-pyridyl)-1,2,4-triazines and 1-morpholinocyclohexene followed by aromatization of the cyclohexene moiety affords 1-(2-pyridyl)isoquinolines. Crystal structures of two tetrahydroisoquinolines were confirmed by X-ray diffraction analysis.
• Preparation of (benzo)isoquinolines using in situ generated aryne intermediates
  作者：D. S. Kopchuk、G. V. Zyryanov、I. S. Kovalev、I. N. Egorov、V. L. Rusinov、O. N. Chupakhin

  DOI：10.1007/s10593-013-1222-4

  日期：2013.3
• Synthesis and characterizations of new cadmium complexes based on poly(aza)arene-annelated 2,2′-bipyridines
  作者：Dmitry S. Kopchuk、Pavel A. Slepukhin、Igor S. Kovalev、Albert F. Khasanov、Olga S. Taniya、Olga V. Shabunina、Grigory V. Zyryanov、Vladimir L. Rusinov、Oleg N. Chupakhin

  DOI：10.1016/j.poly.2016.02.047

  日期：2016.5

  We have developed an efficient synthesis of new cadmium(II)-containing complexes based on poly(aza) arene-annelated 2,2'-bipyridines. All the complexes were characterized by X-ray structural analysis. The influence of the type of the ligand at the structural properties of the complexes has been studied. (C) 2016 Elsevier Ltd. All rights reserved.