(3Z)-3,4-diphenyl-1-(3-pyridyl)-2-azabuta-1,3-diene

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (3Z)-3,4-diphenyl-1-(3-pyridyl)-2-azabuta-1,3-diene
• 英文别名: N-[(Z)-1,2-diphenylethenyl]-1-pyridin-3-ylmethanimine
• 化学式: C₂₀H₁₆N₂
• 分子量: 284.36
• InChiKey: HGDOYKCIODHUMN-JVIJOZEYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  25.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (3Z)-3,4-diphenyl-1-(3-pyridyl)-2-azabuta-1,3-diene 以 xylene 为溶剂， 反应 15.0h， 以82%的产率得到3-phenyl-1-(3-pyridyl)isoquinoline
  参考文献：
  名称：

  Aza-Wittig Reaction of N-Vinylic Phosphazenes with Carbonyl Compounds. Azadiene-Mediated Synthesis of Isoquinolines and 5,6-Dihydro-2H-1,3-oxazines

  摘要：

  N-Vinylic phosphazenes 4 are obtained by reaction of phosphorus ylide 5 and nitriles 6. Aza-Wittig reaction of phosphazenes 4 with aldehydes leads to the formation of 2-azadienes 1, which are easily converted into isoquinolines 2. Reaction of conjugated phosphazenes 4 with ethyl glyoxalate affords 5,6-dihydro-2H-1,3-oxazines 9 in a regio- and stereoselective fashion, while heterodienes 1 react with ethyl glyoxalate and diethyl ketomalonate giving 1,3-oxazines 11 and 12.

  DOI：

  10.1021/jo961664n

文献信息

• Cycloaddition Reactions of Neutral 2-Azadienes with Enamines − Regiospecific Synthesis of Highly Substituted Dihydropyridines and Pyridines
  作者：Francisco Palacios、Concepción Alonso、Gloria Rubiales、Jose María Ezpeleta

  DOI：10.1002/1099-0690(200106)2001:11<2115::aid-ejoc2115>3.3.co;2-g

  日期：2001.6
• Aza-Wittig Reaction of <i>N</i>-Vinylic Phosphazenes with Carbonyl Compounds. Azadiene-Mediated Synthesis of Isoquinolines and 5,6-Dihydro-2<i>H</i>-1,3-oxazines
  作者：Francisco Palacios、Concepción Alonso、Gloria Rubiales

  DOI：10.1021/jo961664n

  日期：1997.2.1

  N-Vinylic phosphazenes 4 are obtained by reaction of phosphorus ylide 5 and nitriles 6. Aza-Wittig reaction of phosphazenes 4 with aldehydes leads to the formation of 2-azadienes 1, which are easily converted into isoquinolines 2. Reaction of conjugated phosphazenes 4 with ethyl glyoxalate affords 5,6-dihydro-2H-1,3-oxazines 9 in a regio- and stereoselective fashion, while heterodienes 1 react with ethyl glyoxalate and diethyl ketomalonate giving 1,3-oxazines 11 and 12.