6-(furan-2-yl)phenanthridine

• 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-(furan-2-yl)phenanthridine
• 英文别名: 6-(2-furyl)-phenanthridine；6-(2-furyl)phenanthridine；6-[2]furyl-phenanthridine；6-[2]Furyl-phenanthridin
• 化学式: C₁₇H₁₁NO
• 分子量: 245.28
• InChiKey: QZLPNQDAZREYMJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  19
• 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：
  26
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  菲啶 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 27.0h， 生成 6-(furan-2-yl)phenanthridine
  参考文献：
  名称：

  Regioselective Metal-Free Cross-Coupling of Quinoline N-Oxides with Boronic Acids

  摘要：

  A novel and operationally simple one-step C-H bond functionalization of quinoline N-oxides to 2-substituted quinolines was developed. This approach enables the regioselective functionalization under external oxidant- and metal-free conditions. The developed transformation represents the first application of the Petasis reaction in functionalization of heterocycles.

  DOI：

  10.1021/acs.orglett.5b01456

文献信息

• 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。
• Coupling N–H Deprotonation, C–H Activation, and Oxidation: Metal-Free C(sp³)–H Aminations with Unprotected Anilines
  作者：Christopher J. Evoniuk、Gabriel dos Passos Gomes、Sean P. Hill、Satoshi Fujita、Kenneth Hanson、Igor V. Alabugin

  DOI：10.1021/jacs.7b07519

  日期：2017.11.15

  An intramolecular oxidative C(sp3)–H amination from unprotected anilines and C(sp3)–H bonds readily occurs under mild conditions using t-BuOK, molecular oxygen and N,N-dimethylformamide (DMF). Success of this process, which requires mildly acidic N–H bonds and an activated C(sp3)–H bond (BDE < 85 kcal/mol), stems from synergy between basic, radical, and oxidizing species working together to promote

  使用t -BuOK，分子氧和N，N-二甲基甲酰胺（DMF）在温和条件下容易发生未保护的苯胺和C（sp 3）-H键的分子内氧化C（sp 3）-H胺化反应。此过程的成功需要弱酸性的N–H键和活化的C（sp 3）–H键（BDE <85 kcal / mol），这是由于碱性，自由基和氧化性物种之间的协同作用共同促进了协调质子化的顺序：H原子的转移和氧化形成了一个新的C–N键。此过程适用于多种N的合成-杂环，从小分子到扩展的芳族化合物，无需过渡金属或强氧化剂。计算结果揭示了组成该反应级联的各个步骤序列的机械细节和能量分布。在此过程中，碱的重要性源于相对于反应物而言，形成2c，3e C–N键的过渡态和产物的酸性要高得多。在这种情况下，选择性去质子化为该过程提供了驱动力。
• Buu-Hoi; Hoan, Recueil des Travaux Chimiques des Pays-Bas, 1949, vol. 68, p. 5,29
  作者：Buu-Hoi、Hoan

  DOI：——

  日期：——
• 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.
• Regioselective Metal-Free Cross-Coupling of Quinoline <i>N</i>-Oxides with Boronic Acids
  作者：Luis Bering、Andrey P. Antonchick

  DOI：10.1021/acs.orglett.5b01456

  日期：2015.6.19

  A novel and operationally simple one-step C-H bond functionalization of quinoline N-oxides to 2-substituted quinolines was developed. This approach enables the regioselective functionalization under external oxidant- and metal-free conditions. The developed transformation represents the first application of the Petasis reaction in functionalization of heterocycles.