(E)-3-(2,5-dimethylphenyl)allyl acetate | 945030-96-6

• 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: (E)-3-(2,5-dimethylphenyl)allyl acetate
• 英文别名: acetic acid-(2,5-dimethyl-cinnamyl ester)；3-Acetoxy-1-(2.5-dimethyl-phenyl)-propen-(1)；Essigsaeure-(2,5-dimethyl-cinnamylester)；3-Acetoxy-1-[2.5]xylyl-propen-(1)；(2.5-Dimethyl-cinnamyl)-acetat；[(E)-3-(2,5-dimethylphenyl)prop-2-enyl] acetate
• CAS: 945030-96-6
• 化学式: C₁₃H₁₆O₂
• 分子量: 204.269
• InChiKey: ZKSOFISCNASFFC-SNAWJCMRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-3-(2,5-dimethylphenyl)allyl acetate 在 alkaline solution 作用下， 生成 (E)-3-(2,5-dimethylphenyl)prop-2-en-1-ol
  参考文献：
  名称：

  Bert; Dorier, Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1930, vol. 191, p. 378

  摘要：

  DOI：
• 作为产物：
  描述：

  3-chloro-1-(2,5-dimethyl-phenyl)-propene 在 sodium acetate 、 溶剂黄146 作用下， 生成 (E)-3-(2,5-dimethylphenyl)allyl acetate
  参考文献：
  名称：

  Bert; Dorier, Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1930, vol. 191, p. 378

  摘要：

  DOI：

文献信息

• Pd(II)-Catalyzed Direct Olefination of Arenes with Allylic Esters and Ethers
  作者：Zhongquan Liu、Xiaojie Shang、Yun Xiong、Yuexia Zhang、Lei Zhang

  DOI：10.1055/s-0031-1290078

  日期：2012.1

  A convenient Pd(II)-catalyzed direct olefination of unactivated arenes with allylic esters and ethers via C-H activation was demonstrated. Under the typical conditions, various aryl-substituted allylic esters and ethers can be prepared.

  展示了一种便捷的钯(II)催化下，通过C-H活化实现非活化芳烃与烯丙基酯和醚的直接烯化反应。在典型条件下，可以制备各种含有芳基取代的烯丙基酯和醚。
• [(NHC)Au^I]-Catalyzed Rearrangement of Allylic Acetates
  作者：Nicolas Marion、Ronan Gealageas、Steven P. Nolan

  DOI：10.1021/ol070843w

  日期：2007.7.1

  [(NHC)AuCl] complexes (NHC = N-heterocyclic carbene), in conjunction with a silver salt, were found to efficiently catalyze the rearrangement of allylic acetates under both conventional and microwave-assisted heating. The optimization of several reaction parameters (solvent, silver salt, and ligand) as well as a study of the reaction scope are reported. The steric hindrance of the ligand bound to gold was

  发现[（NHC）AuCl]配合物（NHC = N-杂环卡宾）与银盐一起可有效催化常规加热和微波辅助加热下乙酸烯丙酯的重排。报告了几种反应参数（溶剂，银盐和配体）的优化以及对反应范围的研究。发现与金结合的配位体的空间位阻对于反应的结果至关重要，因为只有极大的配体才允许异构化。
• PdII-Catalyzed Highly Selective Arylation of Allyl Esters via CH Functionalization of Unreactive Arenes with Retention of the Traditional Leaving Group
  作者：Delin Pan、Miao Yu、Wei Chen、Ning Jiao

  DOI：10.1002/asia.200900558

  日期：2010.5.3

  A highly selective Fujiwara–Moritani oxidative Heck reaction of allyl esters with unreactive arenes via CH bond activation was developed, in which β‐H elimination is highly chemo‐, regio‐ and stereoselective. Moreover, even electron‐deficient arenes are tolerated in this type of CH activation.

  通过C selective H键活化，开发了具有非反应性芳烃的烯丙基酯的高度选择性藤原-莫里塔尼氧化Heck反应，其中β-H消除具有高度的化学，区域和立体选择性。此外，这种CH活化作用甚至可以耐受电子缺乏的芳烃。
• Access to Cinnamyl Derivatives from Arenes and Allyl Esters by a Biomimetic Aerobic Oxidative Dehydrogenative Coupling
  作者：Nicolas Gigant、Jan-E. Bäckvall

  DOI：10.1021/ol500326g

  日期：2014.3.21

  An efficient biomimetic aerobic oxidative dehydrogenative alkenylation of arenes with allyl esters is presented. The reaction proceeds under an ambient pressure of oxygen with relatively low catalyst loading of palladium acetate, employing catalytic amounts of electron-transfer mediators (ETMs). This study represents a new environmentally friendly method for the synthesis of cinnamyl derivatives.

  提出了一种有效的仿生用烯丙基酯的拟氧好氧氧化脱氢烯基化方法。反应在氧气的环境压力下，使用催化量的电子转移介体（ETM），在乙酸钯的催化剂负载量相对较低的情况下进行。这项研究代表了一种新的合成肉桂基衍生物的环境友好方法。
• Pd-catalyzed oxidative olefination of arenes with olefins via C–H activation: Retention of the leaving group
  作者：Jincheng Mao、Xiaojiang Yang、Dingli Wang、Yang Zhang

  DOI：10.1134/s1070427215012023x

  日期：2015.12

  Pd-catalyzed direct oxidative olefination of arenes with olefins via C–H activation is described in the absence of any chelating directing groups. For Pd-catalyzed oxidative coupling between arenes and allyl acetate, it was observed the retention of the leaving group.

  描述了在不存在任何螯合导向基团的情况下，钯经钯催化的芳烃经C–H活化的直接氧化烯烃化反应。对于芳烃和乙酸烯丙酯之间的Pd催化的氧化偶联，观察到离去基团的保留。