2-(2-methyl-2-propenyl)quinoxaline | 113477-51-3

• 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-(2-methyl-2-propenyl)quinoxaline
• 英文别名: 2-(2-methylallyl)quinoxaline；2-(2-Methylprop-2-enyl)quinoxaline
• CAS: 113477-51-3
• 化学式: C₁₂H₁₂N₂
• 分子量: 184.241
• InChiKey: BFVZZULRVSGORA-UHFFFAOYSA-N

物化性质

• 沸点：
  280.2±25.0 °C(Predicted)
• 密度：
  1.079±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  25.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  喹喔啉 、 3-溴-2-甲基丙烯 在 bis(2,2,6,6-tetramethylpiperidin-1-yl)magnesium-bis(lithium chloride) complex 、 zinc(II) chloride 、 copper(I) cyanide di(lithium chloride) 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以75%的产率得到2-(2-methyl-2-propenyl)quinoxaline
  参考文献：
  名称：

  An efficient and mild ortho-zincation of aromatics and heterocycles by using TMP2Mg·2LiCl in the presence of ZnCl2

  摘要：

  A variety range of functionalized aryl and heteroaryl zinc reagents were efficiently generated by using TMP2Mg center dot 2LiCl (TMP = 2,2,6,6-tetramethylpiperamidyl) in the presence of ZnCl2. The subsequently functionalization gave after reaction with electrophiles the expected polyfunctionalized products in good yields. A detailed study concerned on the point how we found the protocol and how we optimized it was depicted. (C) 2009 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2009.12.016

文献信息

• Reaction of quimoxalines with β,γ-unsaturated grignard reagents
  作者：Erbana Epifani、Saverio Florio、Giovanni Ingrosso、Riccardo Sgarra、Francesca Stasi

  DOI：10.1016/s0040-4020(01)86883-6

  日期：1987.1

  Mono- and bis-addition reactions of the β,γ-unsaturated Grignard reagents and to the C bonds of quinoxalines afford high yields of dihydroquinoxalines and tetrahydroquinoxalines . Dehydrogenation of and with DDQ leads to allylic quinoxalines and respectively in very good yields. Allylic and propargylic quinoxalines and can conveniently be synthesized by “cross-coupling” of 2-chloro-3-methylquinoxaline

  β，γ-不饱和格氏试剂的单加双反应和喹喔啉的C键的单加双反应可提供高产率的二氢喹喔啉和四氢喹喔啉。DDQ和DDQ的脱氢分别导致烯丙基喹喔啉，并分别以非常高的收率进行。烯丙基炔丙基和喹喔啉和可方便地通过2-氯-3-甲基喹喔啉与“交叉耦合”来合成和。
• EPIFANI, ERBANA;FLORIO, SAVERIO;INGROSSO, GIOVANNI;SGARRA, RICCARDO;STASI+, TETRAHEDRON, 43,(1987) N 12, 2769-2778
  作者：EPIFANI, ERBANA、FLORIO, SAVERIO、INGROSSO, GIOVANNI、SGARRA, RICCARDO、STASI+

  DOI：——

  日期：——