1,2,4,5-tetrakis(2-butynyl)benzene

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1,2,4,5-tetrakis(2-butynyl)benzene
• 英文别名: 1,2,4,5-Tetrakis(but-2-ynyl)benzene
• 化学式: C₂₂H₂₂
• 分子量: 286.417
• InChiKey: ZHMQAYODLVXIMK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  1,2,4,5-tetrakis(2-butynyl)benzene 、 丁炔二酸二甲酯 在 zirconocene dichloride 正丁基锂 、 copper(l) chloride 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 21.0h， 以17%的产率得到1,4,8,11-tetramethyl-2,3,9,10-tetrakis(methoxycarbonyl)-5,7,12,14-tetrahydropentacene
  参考文献：
  名称：

  Three-Step Synthesis of End-Substituted Pentacenes

  摘要：

  [GRAPHICS]A concise, three-step synthesis of 1,4,8, 11 -substituted 2,3,9,10-tetrakis(methoxycarbonyl)pentacenes from commercially available 1,2,4,5-tetrakis(bromomethyl)benzene was established. Efficient alkynylation, followed by formation of four fused rings via a zirconacyclopentadiene intermediate, and then oxidation with DDQ gave pentacenes la-c. The process was compatible with methyl, phenyl, and trimethylsilyl substituents, which have good solubility in various organic solvents.

  DOI：

  10.1021/jo7017284
• 作为产物：
  描述：

  1-丙炔溴化镁 、 四溴甲苯 在 copper(I) bromide 作用下， 以 四氢呋喃 为溶剂， 反应 96.5h， 以40%的产率得到1,2,4,5-tetrakis(2-butynyl)benzene
  参考文献：
  名称：

  Three-Step Synthesis of End-Substituted Pentacenes

  摘要：

  [GRAPHICS]A concise, three-step synthesis of 1,4,8, 11 -substituted 2,3,9,10-tetrakis(methoxycarbonyl)pentacenes from commercially available 1,2,4,5-tetrakis(bromomethyl)benzene was established. Efficient alkynylation, followed by formation of four fused rings via a zirconacyclopentadiene intermediate, and then oxidation with DDQ gave pentacenes la-c. The process was compatible with methyl, phenyl, and trimethylsilyl substituents, which have good solubility in various organic solvents.

  DOI：

  10.1021/jo7017284

文献信息

• Three-Step Synthesis of End-Substituted Pentacenes
  作者：Matthew T. Stone、Harry L. Anderson

  DOI：10.1021/jo7017284

  日期：2007.12.1

  [GRAPHICS]A concise, three-step synthesis of 1,4,8, 11 -substituted 2,3,9,10-tetrakis(methoxycarbonyl)pentacenes from commercially available 1,2,4,5-tetrakis(bromomethyl)benzene was established. Efficient alkynylation, followed by formation of four fused rings via a zirconacyclopentadiene intermediate, and then oxidation with DDQ gave pentacenes la-c. The process was compatible with methyl, phenyl, and trimethylsilyl substituents, which have good solubility in various organic solvents.