6-(pyridin-3-yl)phenanthridine | 412336-64-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 6-(pyridin-3-yl)phenanthridine
• 英文别名: 6-Pyridin-3-ylphenanthridine
• CAS: 412336-64-2
• 化学式: C₁₈H₁₂N₂
• 分子量: 256.307
• InChiKey: HPMOWFZORAEMDR-UHFFFAOYSA-N

物化性质

• 熔点：
  125-126 °C
• 沸点：
  449.7±30.0 °C(Predicted)
• 密度：
  1.223±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  20
• 可旋转键数：
  1
• 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

• 作为反应物：
  描述：

  6-(pyridin-3-yl)phenanthridine 在 sodium hydroxide 、 potassium hexacyanoferrate(III) 、 苯 作用下， 生成 1-methyl-5-phenanthridin-6-yl-1H-pyridin-2-one
  参考文献：
  名称：

  267.对菲啶化学的贡献。第一部分。9-（3'-吡啶基）菲啶向其季盐的转化以及某些具有潜在生物学意义的衍生物的制备

  摘要：

  DOI：

  10.1039/jr9470001410
• 作为产物：
  描述：

  nicotineimidic acid biphenyl-2-ylamide 在 硝基苯 、 三氯氧磷 作用下， 生成 6-(pyridin-3-yl)phenanthridine
  参考文献：
  名称：

  150. Am。第十二部分。由N -2-二苯基嘧啶制备9-取代的菲啶

  摘要：

  DOI：

  10.1039/jr9490000703

文献信息

• Assembly of substituted phenanthridines via a cascade palladium-catalyzed coupling reaction, deprotection and intramolecular cyclization
  作者：Jun Ge、Xiaojian Wang、Tianqi Liu、Zeyu Shi、Qiong Xiao、Dali Yin

  DOI：10.1039/c6ra00249h

  日期：——

  is presented. In the presence of Pd(PPh3)4, accessible precursors undergo a Suzuki cross-coupling reaction with 2-(Boc-amino)benzeneboronic acid pinacol ester and then spontaneously undergo deprotection and intramolecular condensation to form the corresponding phenanthridines in one step. This reaction has a wide range of substrates with various functional groups, and the corresponding products have

  提出了一种一锅合成取代菲啶的通用方法的发现和发展。在Pd（PPh 3）4存在下，可及的前体与2-（Boc-氨基）苯硼酸频哪醇酯进行Suzuki交叉偶联反应，然后自发进行脱保护和分子内缩合以形成相应的菲啶。该反应具有多种具有各种官能团的底物，并且已经以良好的产率获得了相应的产物。
• A One-Pot Access to 6-Substituted Phenanthridines from Fluoroarenes and Nitriles via 1,2-Arynes
  作者：Jan Pawlas、Mikael Begtrup

  DOI：10.1021/ol026197c

  日期：2002.8.1

  [reaction: see text] A one-pot, t-BuLi-induced synthesis of 6-substituted phenanthridines from fluoroarenes and nitriles via 1,2-arynes is reported. Aryl- and hetaryl nitriles, cyanamides, and trimethylacetonitrile gave phenanthridine products. The method was extended to provide bisphenanthridine 10 by a one-pot bis-cyclization, using 1,3-dicyanobenzene and PhF in 1:5 ratio. Reaction of 1-fluoronaphthalene

  [反应：见正文]据报道，一锅t-BuLi诱导通过1,2-芳烃从氟代芳烃和腈中合成6位取代的菲啶。芳基和杂芳基腈，氰胺和三甲基乙腈得到菲啶产物。该方法扩展为使用1，3-二氰基苯和PhF以1：5的比例通过一锅双环进行双联吡啶10的制备。1-氟萘和4-氯氟苯与苄腈的反应分别得到区域异构纯产物11和12。
• Metal-Free Nitrogenation of 2-Acetylbiphenyls: Expeditious Synthesis of Phenanthridines
  作者：Conghui Tang、Yizhi Yuan、Ning Jiao

  DOI：10.1021/acs.orglett.5b00797

  日期：2015.5.1

  An intermolecular nitrogenation reaction toward the synthesis of phenanthridines has been developed. This metal-free protocol provides a novel nitrogen-incorporation transformation using azides as the nitrogen source. Phenanthridines, which are of great interest in pharmaceutical and medicinal chemistry, are synthesized efficiently in one step. Moreover, the byproducts derived from the Schmidt reaction are inhibited, which further demonstrated the high chemoselectivity of this transformation.
• Metal-free photocatalyzed cross coupling of aryl (heteroaryl) bromides with isonitriles
  作者：Xiangguang Li、Deqiang Liang、Wenzhong Huang、Huanli Sun、Lvsu Wang、Mengran Ren、Baoling Wang、Yinhai Ma

  DOI：10.1016/j.tet.2017.10.074

  日期：2017.12

  A visible-light-catalyzed synthesis of 6-aryl substituted phenanthridines from aryl bromides and 2-isocyanobiphenyls at room temperature has been discovered. This metal-free cross-coupling reaction offers rapid and sustainable access to a series of structurally complex and diverse phenanthridines. The usage of inexpensive Rhodamine 6G as the catalyst with easy operation makes this protocol very practical. (C) 2017 Elsevier Ltd. All rights reserved.