2,3-di(hex-1-ynyl)quinoxaline | 1416917-50-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 2,3-di(hex-1-ynyl)quinoxaline
• 英文别名: 2,3-Bis(hex-1-ynyl)quinoxaline；2,3-bis(hex-1-ynyl)quinoxaline
• CAS: 1416917-50-4
• 化学式: C₂₀H₂₂N₂
• 分子量: 290.408
• InChiKey: VAMAKMLLBILZFL-UHFFFAOYSA-N

物化性质

• 沸点：
  454.7±45.0 °C(Predicted)
• 密度：
  1.06±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  25.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,3-di(hex-1-ynyl)quinoxaline 在 溴 作用下， 以 氯仿 为溶剂， 反应 20.0h， 以73%的产率得到(E)-3-bromo-1-(1-bromopentylidene)-2-butyl-1H-cyclopenta[b]quinoxaline
  参考文献：
  名称：

  Electrophilic cyclizations of 2,3-dialkynylquinoxalines and 1,2-dialkynylbenzenes: a comparative study

  摘要：

  The reactivity of 2,3-dialkynylquinoxalines towards electrophiles (Br-2, I-2, ICI, NBS, HBr) has been studied. All tested reactions, except one with HBr, start with the addition of an electrophile to the carbon-carbon triple bond that promotes further 5-exo-dig carbocyclization ultimately yielding a mixture of stereoisomeric cyclopenta[b]quinoxaline derivatives. The nature of substituents on the C C bonds of the starting molecule influence the stereochemical result of the reaction. The ratio of isomeric cyclization products also depends on the electrophile used. ortho-Dialkynylbenzenes and ortho-dialkynylquinoxalines demonstrate rather similar reactivity towards halogen electrophiles, but differ in their reactions with hydrobromic acid, which is caused by the basic nature of the aza group of the quinoxaline substrate. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.10.098
• 作为产物：
  描述：

  2,3-二氯喹喔啉 、 1-己炔 在 copper(l) iodide 、 trans-bis(triphenylphosphine)palladium dichloride 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.33h， 以68%的产率得到2,3-di(hex-1-ynyl)quinoxaline
  参考文献：
  名称：

  Electrophilic cyclizations of 2,3-dialkynylquinoxalines and 1,2-dialkynylbenzenes: a comparative study

  摘要：

  The reactivity of 2,3-dialkynylquinoxalines towards electrophiles (Br-2, I-2, ICI, NBS, HBr) has been studied. All tested reactions, except one with HBr, start with the addition of an electrophile to the carbon-carbon triple bond that promotes further 5-exo-dig carbocyclization ultimately yielding a mixture of stereoisomeric cyclopenta[b]quinoxaline derivatives. The nature of substituents on the C C bonds of the starting molecule influence the stereochemical result of the reaction. The ratio of isomeric cyclization products also depends on the electrophile used. ortho-Dialkynylbenzenes and ortho-dialkynylquinoxalines demonstrate rather similar reactivity towards halogen electrophiles, but differ in their reactions with hydrobromic acid, which is caused by the basic nature of the aza group of the quinoxaline substrate. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.10.098

文献信息

• Electrophilic cyclizations of 2,3-dialkynylquinoxalines and 1,2-dialkynylbenzenes: a comparative study
  作者：Anna V. Gulevskaya、Roman Yu Lazarevich、Alexander F. Pozharskii

  DOI：10.1016/j.tet.2012.10.098

  日期：2013.1

  The reactivity of 2,3-dialkynylquinoxalines towards electrophiles (Br-2, I-2, ICI, NBS, HBr) has been studied. All tested reactions, except one with HBr, start with the addition of an electrophile to the carbon-carbon triple bond that promotes further 5-exo-dig carbocyclization ultimately yielding a mixture of stereoisomeric cyclopenta[b]quinoxaline derivatives. The nature of substituents on the C C bonds of the starting molecule influence the stereochemical result of the reaction. The ratio of isomeric cyclization products also depends on the electrophile used. ortho-Dialkynylbenzenes and ortho-dialkynylquinoxalines demonstrate rather similar reactivity towards halogen electrophiles, but differ in their reactions with hydrobromic acid, which is caused by the basic nature of the aza group of the quinoxaline substrate. (C) 2012 Elsevier Ltd. All rights reserved.