2-(furan-2-yl)-4,6-diphenylpyridine

• 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: 2-(furan-2-yl)-4,6-diphenylpyridine
• 英文别名: 2-(2-Furyl)-4,6-diphenylpyridine
• 化学式: C₂₁H₁₅NO
• 分子量: 297.356
• InChiKey: QVASQCKSOZIXLB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  23
• 可旋转键数：
  3
• 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：

  2-氰基呋喃 在 正丁基锂 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 2-(furan-2-yl)-4,6-diphenylpyridine
  参考文献：
  名称：

  由金属化的烷基膦酸酯，腈和α，β-不饱和酮“一锅”合成多取代的吡啶

  摘要：

  描述了一种简单有效的多取代吡啶的合成方法。关键步骤是基于将锂化的β-烯氨基膦酸酯5的区域选择性加成到不饱和羰基化合物3上。当这些化合物金属化后，通过添加腈和不饱和羰基化合物，也可在“一锅”反应中从膦酸酯6获得吡啶1。

  DOI：

  10.1016/0040-4039(96)00850-7

文献信息

• Regiocontrolled synthesis of 2,4,6-triarylpyridines from methyl ketones, electron-deficient acetylenes and ammonium acetate
  作者：Dmitrii A. Shabalin、Marina Yu. Dvorko、Elena Yu. Schmidt、Boris A. Trofimov

  DOI：10.1039/d1ob00193k

  日期：——

  A novel one-pot two-step approach for the synthesis of 2,4,6-triarylpyridines via t-BuOK/DMSO-promoted C-vinylation of a variety of methyl ketones with electron-deficient acetylenes (alkynones) followed by a cyclization of the in situ generated unsaturated 1,5-dicarbonyl species with ammonium acetate has been developed. This approach possesses competitive advantages such as high regioselectivity, available

  一种新颖的一锅两步方法，通过t -BuOK / DMSO促进的多种甲基酮的C-乙烯基与电子缺陷型乙炔（炔烃）的合成，然后环化环戊二烯，合成2,4,6-三芳基吡啶在原位用乙酸铵生成的不饱和的1,5-二羰基物种已经研制成功。该方法具有竞争优势，例如区域选择性高，可用的起始原料以及不存在过渡金属催化剂，氧化剂和不良副产物。三取代，四取代和稠合吡啶的合成证明了该开发方法的广泛合成效用。
• Synthesis of Highly Substituted Pyridines through Copper-Catalyzed Condensation of Oximes and α,β-Unsaturated Imines
  作者：Wei Wen Tan、Yew Jin Ong、Naohiko Yoshikai

  DOI：10.1002/anie.201704378

  日期：2017.7.3

  A copper-catalyzed condensation reaction of oxime acetates and α,β-unsaturated ketimines to give pyridine derivatives is reported. The reaction features mild conditions, high functional-group compatibility, and high regioselectivity with respect to unsymmetrical oxime acetates, thus allowing the preparation of a wide range of polysubstituted pyridines, many of which are not readily accessible by conventional

  据报道，乙酸肟肟和α，β-不饱和酮亚胺在铜催化下缩合反应生成吡啶衍生物。该反应具有温和的条件，相对于不对称肟肟酸酯的高官能团相容性和高的区域选择性，因此可以制备多种多取代的吡啶，其中许多不易通过常规缩合方法获得。
• Synthesis of Multisubstituted Pyridines
  作者：Zhi He、Dennis Dobrovolsky、Piera Trinchera、Andrei K. Yudin

  DOI：10.1021/ol303246b

  日期：2013.1.18

  By utilizing amino allenes, aldehydes, and aryl iodides as readily available building blocks, a simple and modular synthesis of multisubstituted pyridines with flexible control over the substitution pattern has been achieved. The method employs a two-step procedure involving the preparation of "skipped" allenyl imines and a subsequent palladium-catalyzed cyclization.
• A “one pot” synthesis of polysubstituted pyridines from metallated alkylphosphonates, nitriles and α,β-unsaturated ketones
  作者：Francisco Palacios、Ana M. Ochoa de Retana、Julen Oyarzabal

  DOI：10.1016/0040-4039(96)00850-7

  日期：1996.6

  A simple and efficient synthesis of polysubstituted pyridines is described. The key step is based on the regioselective addition of lithiated β-enaminophosphonates 5 to unsaturated carbonyl compounds 3. Pyridines 1 can also be obtained in “one pot” reaction from phosphonates 6 when these compounds are metallated followed by addition of nitriles and unsaturated carbonyl compounds.

  描述了一种简单有效的多取代吡啶的合成方法。关键步骤是基于将锂化的β-烯氨基膦酸酯5的区域选择性加成到不饱和羰基化合物3上。当这些化合物金属化后，通过添加腈和不饱和羰基化合物，也可在“一锅”反应中从膦酸酯6获得吡啶1。