(Z)-1-Amino-1-(2-pyridyl)-1,3-butadiene

• 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: (Z)-1-Amino-1-(2-pyridyl)-1,3-butadiene
• 英文别名: (1Z)-1-pyridin-2-ylbuta-1,3-dien-1-amine
• 化学式: C₉H₁₀N₂
• 分子量: 146.192
• InChiKey: LZOPNIVOOMISEX-YVMONPNESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  38.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (Z)-1-Amino-1-(2-pyridyl)-1,3-butadiene 以 氘代苯 为溶剂， 反应 0.92h， 生成 (E)-1-Amino-1-(2-pyridyl)-1,3-butadiene
  参考文献：
  名称：

  Preparation of Stable Primary Enamines: 1-Aminobutadienes by Allyl Grignard Addition to Aryl Cyanides Followed by Controlled Hydrolysis

  摘要：

  From thermochemical data it is suggested that 1-aminobutadienes are more stable than their nonconjugated imine tautomers by about 2 kcal mol(-1). High level ab initio calculations have established the thermodynamic preference of the conjugated primary enamines over their beta,gamma-unsaturated ketimine isomers in the gas phase. This general prediction of an increased stability of primary enamines by butadiene conjugation has been confirmed experimentally with a variety of representative examples. Allyl Grignard addition to a number of aryl or hetaryl cyanides followed by controlled hydrolysis yields the respective beta,gamma-unsaturated ketimine systems that subsequently rearrange completely to their 1-aminobutadiene isomers. Rearrangement to the thermodynamically more favored alpha,beta-unsaturated imine tautomers is kinetically inhibited and, hence, not observed in these systems. In some cases conjugated enamine formation is already observed at the stage of the organometallic intermediates.

  DOI：

  10.1021/jo00121a055
• 作为产物：
  描述：

  magnesium;1-pyridin-2-ylbut-3-enylideneazanide;chloride 在 ammonium hydroxide 作用下， 以 乙醚 为溶剂， 反应 0.17h， 生成 (Z)-1-Amino-1-(2-pyridyl)-1,3-butadiene
  参考文献：
  名称：

  Preparation of Stable Primary Enamines: 1-Aminobutadienes by Allyl Grignard Addition to Aryl Cyanides Followed by Controlled Hydrolysis

  摘要：

  From thermochemical data it is suggested that 1-aminobutadienes are more stable than their nonconjugated imine tautomers by about 2 kcal mol(-1). High level ab initio calculations have established the thermodynamic preference of the conjugated primary enamines over their beta,gamma-unsaturated ketimine isomers in the gas phase. This general prediction of an increased stability of primary enamines by butadiene conjugation has been confirmed experimentally with a variety of representative examples. Allyl Grignard addition to a number of aryl or hetaryl cyanides followed by controlled hydrolysis yields the respective beta,gamma-unsaturated ketimine systems that subsequently rearrange completely to their 1-aminobutadiene isomers. Rearrangement to the thermodynamically more favored alpha,beta-unsaturated imine tautomers is kinetically inhibited and, hence, not observed in these systems. In some cases conjugated enamine formation is already observed at the stage of the organometallic intermediates.

  DOI：

  10.1021/jo00121a055

文献信息

• Heterocyclic bridged biphenyls
  申请人：UDC IRELAND LIMITED

  公开号：US10934262B2

  公开（公告）日：2021-03-02

  The present invention relates electroluminescent devices, comprising a compound of the formula especially as host for phosphorescent compounds. The hosts may function with phosphorescent materials to provide improved efficiency, stability, manufacturability, or spectral characteristics of electroluminescent devices.

  本发明涉及电致发光装置，该装置包含式如下的化合物 特别是作为磷光化合物的宿主。宿主可与磷光材料一起发挥作用，提高电致发光装置的效率、稳定性、可制造性或光谱特性。
• US9716241B2
  申请人：——

  公开号：US9716241B2

  公开（公告）日：2017-07-25
• Preparation of Stable Primary Enamines: 1-Aminobutadienes by Allyl Grignard Addition to Aryl Cyanides Followed by Controlled Hydrolysis
  作者：Gerhard Erker、Michael Riedel、Sandra Koch、Tim Joedicke、Ernst-Ulrich Wuerthwein

  DOI：10.1021/jo00121a055

  日期：1995.8

  From thermochemical data it is suggested that 1-aminobutadienes are more stable than their nonconjugated imine tautomers by about 2 kcal mol(-1). High level ab initio calculations have established the thermodynamic preference of the conjugated primary enamines over their beta,gamma-unsaturated ketimine isomers in the gas phase. This general prediction of an increased stability of primary enamines by butadiene conjugation has been confirmed experimentally with a variety of representative examples. Allyl Grignard addition to a number of aryl or hetaryl cyanides followed by controlled hydrolysis yields the respective beta,gamma-unsaturated ketimine systems that subsequently rearrange completely to their 1-aminobutadiene isomers. Rearrangement to the thermodynamically more favored alpha,beta-unsaturated imine tautomers is kinetically inhibited and, hence, not observed in these systems. In some cases conjugated enamine formation is already observed at the stage of the organometallic intermediates.

表征谱图