2-methoxy-4,6-bis(4-methoxyphenyl)nicotinonitrile | 50549-13-8

• 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-methoxy-4,6-bis(4-methoxyphenyl)nicotinonitrile
• 英文别名: 2-methoxy-4,6-bis(4-methoxyphenyl)pyridine-3-carbonitrile；2-Methoxy-4,6-bis(4-methoxyphenyl)pyridine-3-carbonitrile
• CAS: 50549-13-8
• 化学式: C₂₁H₁₈N₂O₃
• 分子量: 346.386
• InChiKey: KPARUYODVUEYDM-UHFFFAOYSA-N

物化性质

• 沸点：
  508.8±50.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  64.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-methoxy-4,6-bis(4-methoxyphenyl)nicotinonitrile 在 磷酸 、 吡啶溴化氢盐 、 三溴氧磷 作用下， 以 1,4-二氧六环 为溶剂， 反应 18.0h， 以92%的产率得到2-bromo-4,6-bis(4-methoxyphenyl)nicotinonitrile
  参考文献：
  名称：

  Overcoming Paradoxical Kinase Priming by a Novel MNK1 Inhibitor

  摘要：

  DOI：

  10.1021/acs.jmedchem.1c01941
• 作为产物：
  描述：

  甲醇 、 4,4’-二甲氧基查耳酮 、 丙二腈 在 potassium carbonate 作用下， 反应 0.07h， 以82%的产率得到2-methoxy-4,6-bis(4-methoxyphenyl)nicotinonitrile
  参考文献：
  名称：

  Synthesis of polysubstituted pyridines under combined microwave and ultrasound irradiation: K2CO3-promoted tandem addition/cyclization/hydrogen shift process

  摘要：

  A convenient and efficient K2CO3-promoted tandem reaction of chalcone, malononitrile, and methanol for the synthesis of highly functionalized pyridines has been developed. This multi-component reaction employing the weak nucleophilic agent methanol proceeded smoothly under combined microwave and ultrasound irradiation (CMUI). The reaction mechanism was proposed to consist of a Michael addition. a methoxylation of C N bond, a cyclization to a 1,4-dihydropyridine and an intermolecular hydrogen shift between 1,4-dihydropyridine and initial chalcone. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.12.103

文献信息

• Microwave-Assisted, One-Pot Multicomponent Synthesis of Some New Cyanopyridines
  作者：Amer A. Amer、Antar A. Abdelhamid

  DOI：10.1002/jhet.2926

  日期：2017.11

  An efficient and facile synthesis of cyanopyridines via a one‐pot four‐component reaction of aromatic aldehydes, acetophenones, malononitrile, or 2‐aminoprop‐1‐ene‐1,1,3‐tricarbonitrile in presence of sodium alkoxide or ammonium acetate under both microwave and thermal reaction conditions was introduced.

  在芳烃醛，苯乙酮，丙二腈或2-氨基丙-1-烯-1,1,3-三腈的单锅四组分反应下，在烷氧基钠或乙酸铵存在下，高效，简便地合成氰基吡啶介绍了微波和热反应条件。
• Synthesis of polysubstituted pyridines under combined microwave and ultrasound irradiation: K2CO3-promoted tandem addition/cyclization/hydrogen shift process
  作者：Huangdi Feng、Yuan Li、Erik V. Van der Eycken、Yanqing Peng、Gonghua Song

  DOI：10.1016/j.tetlet.2011.12.103

  日期：2012.2

  A convenient and efficient K2CO3-promoted tandem reaction of chalcone, malononitrile, and methanol for the synthesis of highly functionalized pyridines has been developed. This multi-component reaction employing the weak nucleophilic agent methanol proceeded smoothly under combined microwave and ultrasound irradiation (CMUI). The reaction mechanism was proposed to consist of a Michael addition. a methoxylation of C N bond, a cyclization to a 1,4-dihydropyridine and an intermolecular hydrogen shift between 1,4-dihydropyridine and initial chalcone. (C) 2011 Elsevier Ltd. All rights reserved.
• Overcoming Paradoxical Kinase Priming by a Novel MNK1 Inhibitor
  作者：Elisabeth Bou-Petit、Stefan Hümmer、Helena Alarcon、Konstantin Slobodnyuk、Marta Cano-Galietero、Pedro Fuentes、Pedro J. Guijarro、María José Muñoz、Leticia Suarez-Cabrera、Anna Santamaria、Roger Estrada-Tejedor、José I. Borrell、Santiago Ramón y Cajal

  DOI：10.1021/acs.jmedchem.1c01941

  日期：2022.4.28