2-allylphenyl formate | 1396690-31-5

• 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: 2-allylphenyl formate
• 英文别名: (2-Prop-2-enylphenyl) formate；(2-prop-2-enylphenyl) formate
• CAS: 1396690-31-5
• 化学式: C₁₀H₁₀O₂
• 分子量: 162.188
• InChiKey: KULBZNMMUYJTLC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 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：

  2-allylphenyl formate 在 十二羰基三钌 、 1-(1-phenylethyl)-1H-imidazole 作用下， 以 均三甲苯 为溶剂， 反应 24.0h， 以90%的产率得到3-ethylbenzofuran-2(3H)-one
  参考文献：
  名称：

  Remarkable Improvement Achieved by Imidazole Derivatives in Ruthenium-Catalyzed Hydroesterification of Alkenes Using Formates

  摘要：

  Imidazole derivatives are revealed to be effective ligands in the Ru-catalyzed hydroesterification of alkenes using formates, affording one-carbon-elongated esters in high yields. Further, intramolecular hydroesterification was successfully performed to give lactones for the first time. Imidazole derivatives can contribute to promote the reaction as well as to suppress the undesired decarbonylation of formate. Toxic CO gas, a directing group, and large excess alkenes are not required.

  DOI：

  10.1021/ol301850y
• 作为产物：
  描述：

  2-烯丙基酚 、 甲乙酐 在 碳酸氢钠 作用下， 以 neat (no solvent) 为溶剂， 生成 2-allylphenyl formate
  参考文献：
  名称：

  Remarkable Improvement Achieved by Imidazole Derivatives in Ruthenium-Catalyzed Hydroesterification of Alkenes Using Formates

  摘要：

  Imidazole derivatives are revealed to be effective ligands in the Ru-catalyzed hydroesterification of alkenes using formates, affording one-carbon-elongated esters in high yields. Further, intramolecular hydroesterification was successfully performed to give lactones for the first time. Imidazole derivatives can contribute to promote the reaction as well as to suppress the undesired decarbonylation of formate. Toxic CO gas, a directing group, and large excess alkenes are not required.

  DOI：

  10.1021/ol301850y

文献信息

• Imidazole Derivatives as Accelerators for Ruthenium-Catalyzed Hydroesterification and Hydrocarbamoylation of Alkenes: Extensive Ligand Screening and Mechanistic Study
  作者：Hideyuki Konishi、Takashi Muto、Tsuyoshi Ueda、Yayoi Yamada、Miyuki Yamaguchi、Kei Manabe

  DOI：10.1002/cctc.201402986

  日期：2015.3

  Imidazole derivatives are effective ligands for promoting the [Ru3(CO)12]‐catalyzed hydroesterification of alkenes using formates. Extensive ligand screening was performed to identify 2‐hydroxymethylated imidazole as the optimal ligand. Neither carbon monoxide gas nor a directing group was required, and the reaction also showed a wide substrate generality. The Ru–imidazole catalyst system also promoted

  咪唑衍生物是使用甲酸酯促进[Ru 3（CO）12 ]催化的烯烃加氢酯化反应的有效配体。进行了广泛的配体筛选，以确定2-羟甲基化的咪唑为最佳配体。既不需要一氧化碳气体也不需要引导基团，并且该反应还显示出广泛的底物通用性。Ru-咪唑催化剂体系还促进了分子内的氨基甲酰化作用，以提供内酰胺。通过X射线晶体学分析明确地分析了Ru-咪唑配合物，它具有源自[[Ru 3（CO）12 ]和两个配体的三核结构。该配合物也已成功用于加氢酯化。通过使用D详细检查了该机制－和13 C标记的甲酸酯，表明加氢酯化反应是通过脱羰基－再羰基化途径进行的。
• Palladium-Catalyzed Synthesis of Esters from Arenes through C–H Thianthrenation
  作者：Mengning Wang、Xiaomei Zhang、Mengtao Ma、Binlin Zhao

  DOI：10.1021/acs.orglett.2c02330

  日期：2022.8.19

  efficient palladium-catalyzed synthesis of esters from readily available arenes has been developed. These C–H bond esterifications were achieved relying on the regioselective thianthrenation to generate the aryl-TT salts, which were treated as reactive electrophilic substrates to couple with phenol formate and N-hydroxysuccinimide (NHS) formate giving access to phenol esters and NHS esters, respectively

  已经开发出从容易获得的芳烃中高效钯催化合成酯的方法。这些 C-H 键酯化是通过区域选择性噻蒽化反应生成芳基-TT 盐实现的，芳基-TT 盐被视为反应性亲电底物，与苯酚甲酸酯和 N-羟基琥珀酰亚胺 (NHS) 甲酸酯偶联，从而获得苯酚酯和 NHS酯，分别在没有一氧化碳的情况下。在这种氧化还原中性钯催化条件下，可以高效制备多种功能性酯。合成应用的后期功能化和研究证明了已建立平台和这些产品的潜在应用。
• US3976702A
  申请人：——

  公开号：US3976702A

  公开（公告）日：1976-08-24
• Remarkable Improvement Achieved by Imidazole Derivatives in Ruthenium-Catalyzed Hydroesterification of Alkenes Using Formates
  作者：Hideyuki Konishi、Tsuyoshi Ueda、Takashi Muto、Kei Manabe

  DOI：10.1021/ol301850y

  日期：2012.9.21

  Imidazole derivatives are revealed to be effective ligands in the Ru-catalyzed hydroesterification of alkenes using formates, affording one-carbon-elongated esters in high yields. Further, intramolecular hydroesterification was successfully performed to give lactones for the first time. Imidazole derivatives can contribute to promote the reaction as well as to suppress the undesired decarbonylation of formate. Toxic CO gas, a directing group, and large excess alkenes are not required.