(E)-1-methoxy-4-(4,5-dimethyl-1,4-hexadienyl)benzene

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (E)-1-methoxy-4-(4,5-dimethyl-1,4-hexadienyl)benzene
• 英文别名: 1-(4,5-dimethylhexa-1,4-dien-1-yl)-4-methoxybenzene；1-[(1E)-4,5-dimethylhexa-1,4-dienyl]-4-methoxybenzene
• 化学式: C₁₅H₂₀O
• 分子量: 216.323
• InChiKey: PKBKAGBOTUSHKR-FNORWQNLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  4-甲氧基苯乙烯 、 2,3-二甲基-1,3-丁二烯 在 (η6-naphthalene)(η4-1,5-cyclooctadiene)ruthenium(0) 作用下， 以 甲苯 为溶剂， 反应 8.0h， 生成 (E)-1-methoxy-4-(4,5-dimethyl-1,4-hexadienyl)benzene
  参考文献：
  名称：

  Mechanistic insights into catalytic linear cross-dimerization between conjugated dienes and styrenes by a ruthenium(0) complex

  摘要：

  The mechanistic studies for linear cross-dimerization between 2,3-dimethylbuta-1,3-diene and styrene by a Ru(0) complex, Ru(eta(6)-naphthalene)(eta(4)-1,5-COD) (1), are performed both by kinetic and computational studies. This reaction is basically zero-order to both of the diene and styrene concentrations and first-order to the catalyst concentration. The Hammett plot using p-substituted styrenes gives a linear relationship with a positive slope (rho = +0.482). The deuterium isotope experiment clearly shows the present reaction being a formal 1,4-addition of a C-H bond in styrene to cisoid-1,3-diene. These kinetic studies show the reaction proceeding via oxidative coupling mechanism that is also supported by the DFT calculations. (C) 2015 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2015.08.022

文献信息

• Direct Cross-Coupling of Allylic C(sp³ )−H Bonds with Aryl- and Vinylbromides by Combined Nickel and Visible-Light Catalysis
  作者：Long Huang、Magnus Rueping

  DOI：10.1002/anie.201805118

  日期：2018.8.6

  An efficient protocol for the direct allylic C(sp3)−H bond activation of unactivated tri‐ and tetrasubstituted alkenes and their functionalization with aryl‐ and vinylbromides by nickel and visible‐light photocatalysis has been developed. The method allows C(sp2)−C(sp3) formation under mild reaction conditions with good functional‐group tolerance and excellent regioselectivity.

  已经开发了一种有效的协议，用于未活化的三取代和四取代的烯烃的直接烯丙基C（sp 3）-H键活化以及镍和可见光光催化作用将它们用芳基和乙烯基溴官能化。该方法可以在温和的反应条件下形成C（sp 2）-C（sp 3），具有良好的官能团耐受性和极好的区域选择性。
• Mechanistic insights into catalytic linear cross-dimerization between conjugated dienes and styrenes by a ruthenium(0) complex
  作者：Masafumi Hirano、Takao Ueda、Nobuyuki Komine、Sanshiro Komiya、Saki Nakamura、Hikaru Deguchi、Susumu Kawauchi

  DOI：10.1016/j.jorganchem.2015.08.022

  日期：2015.11

  The mechanistic studies for linear cross-dimerization between 2,3-dimethylbuta-1,3-diene and styrene by a Ru(0) complex, Ru(eta(6)-naphthalene)(eta(4)-1,5-COD) (1), are performed both by kinetic and computational studies. This reaction is basically zero-order to both of the diene and styrene concentrations and first-order to the catalyst concentration. The Hammett plot using p-substituted styrenes gives a linear relationship with a positive slope (rho = +0.482). The deuterium isotope experiment clearly shows the present reaction being a formal 1,4-addition of a C-H bond in styrene to cisoid-1,3-diene. These kinetic studies show the reaction proceeding via oxidative coupling mechanism that is also supported by the DFT calculations. (C) 2015 Elsevier B.V. All rights reserved.