methyl (E)-4-p-tolylbut-2-enoate | 1250907-45-9

• 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: methyl (E)-4-p-tolylbut-2-enoate
• 英文别名: methyl (E)-4-(4-methylphenyl)but-2-enoate
• CAS: 1250907-45-9
• 化学式: C₁₂H₁₄O₂
• 分子量: 190.242
• InChiKey: BMQNKUFTTNRSQH-HWKANZROSA-N

物化性质

• 沸点：
  284.0±19.0 °C(Predicted)
• 密度：
  1.027±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：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3-丁烯酸甲酯 、 2-对甲苯-1,3,2-二噁硼烷 在 Pd(IiPr)(OTs)2 、 氧气 、 copper(II) bis(trifluoromethanesulfonate) 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 24.0h， 生成 methyl (E)-4-p-tolylbut-2-enoate 、 methyl (E)-4-(p-tolyl)but-3-enoate
  参考文献：
  名称：

  A Highly Selective and General Palladium Catalyst for the Oxidative Heck Reaction of Electronically Nonbiased Olefins

  摘要：

  A general, highly selective oxidative Heck reaction is reported. The reaction is high-yielding under mild conditions without the need for base or high temperatures, and the selectivity is excellent, without the requirement for electronically biased olefins or other specific directing groups. A preliminary mechanistic investigation suggests that the unusually high selectivity may be due to the catalyst's sensitivity to C-H bond strength in the selectivity-determining beta-hydride elimination step.

  DOI：

  10.1021/ja1060998

文献信息

• Bicatalytic Allylation–Cross-Metathesis Reactions as γ-Carbonyl Cation Equivalents
  作者：James Green、Jake Henkie、Sugadar Dhaliwal

  DOI：10.1055/s-0032-1317045

  日期：——

  The products corresponding to the reactions of arenes and γ-carbonyl cations may be obtained by a one-pot, bicatalytic process involving InCl3-catalyzed arene allylation and cross metathesis with electron-deficient alkenes. The process is successful with electronically neutral and electron-rich arenes, and modestly Lewis basic donor groups are tolerated with an increase in InCl3 loading from 10 mol%

  对应于芳烃和γ-羰基阳离子反应的产物可以通过涉及InCl3催化芳烃烯丙基化和与缺电子烯烃交叉复分解的一锅双催化过程获得。该过程对于电子中性和富电子芳烃是成功的，并且在 InCl3 负载量从 10 mol% 增加到 15 mol%，在一种情况下，20 mol% 增加时，适度的路易斯碱性给体基团是可以容忍的。
• A Highly Selective and General Palladium Catalyst for the Oxidative Heck Reaction of Electronically Nonbiased Olefins
  作者：Erik W. Werner、Matthew S. Sigman

  DOI：10.1021/ja1060998

  日期：2010.10.13

  A general, highly selective oxidative Heck reaction is reported. The reaction is high-yielding under mild conditions without the need for base or high temperatures, and the selectivity is excellent, without the requirement for electronically biased olefins or other specific directing groups. A preliminary mechanistic investigation suggests that the unusually high selectivity may be due to the catalyst's sensitivity to C-H bond strength in the selectivity-determining beta-hydride elimination step.