2,2-Dimesityl-1-phenylethenyl acetate | 77787-83-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 2,2-Dimesityl-1-phenylethenyl acetate
• 英文别名: acetic acid-(2,2-dimesityl-1-phenyl-vinyl ester)；1-Acetoxy-1-phenyl-2.2-dimesityl-aethylen；(1-Phenyl-2.2-dimesityl-vinyl)-acetat；Essigsaeure-(2,2-dimesityl-1-phenyl-vinylester)；Essigsaeure-[1-phenyl-2.2-bis-(2.4.6-trimethyl-phenyl)-vinylester]；1-Acetoxy-1-phenyl-2.2-bis-(2.4.6-trimethyl-phenyl)-aethylen；[1-phenyl-2,2-bis(2,4,6-trimethylphenyl)ethenyl] acetate
• CAS: 77787-83-8
• 化学式: C₂₈H₃₀O₂
• 分子量: 398.545
• InChiKey: JJODCACQLQCJIA-UHFFFAOYSA-N

物化性质

• 沸点：
  490.4±44.0 °C(Predicted)
• 密度：
  1.058±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.8
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  3.0
• 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

• 作为反应物：
  描述：

  2,2-Dimesityl-1-phenylethenyl acetate 在 tris(4-bromophenyl)aminium hexafluoroantimonate 作用下， 以 乙腈 为溶剂， 生成 3-mesityl-2-phenyl-4,6,7-trimethylbenzo[b]furan
  参考文献：
  名称：

  Electroactive Protecting Groups and Reaction Units. Part 1. Mesolytic Cleavage of the O-CO Bond in Enol Acetate Cation Radicals with Direct Formation of .alpha.-Carbonyl Cations. Mechanistic and Synthetic Aspects

  摘要：

  For the first time, enol ester cation radicals are reversibly monitored in a cyclic voltammetry experiment. Preparative one-electron oxidation of enol acetates A1-A4 leads to the formation of benzofurans B1-B4 through mesolytic O-CO bond fragmentation to alpha-carbonyl cations and the acetyl radical. With A3(.+), the kinetics of the O-CO bond cleavage was investigated by cyclic voltammetry, providing Delta H double dagger = 17.0 kcal mol(-1) and Delta S double dagger = 11 cal mol(-1) K-1 in dichloromethane. The slightly increased rate of bond dissociation upon addition of acetonitrile is explained with charge localization in the transition state rather than with a solvent-assisted bond cleavage mechanism. The occurrence of curve crossings and isopotential points in the cyclic voltammograms of the model compounds A1-A4 at low scan rates can be rationalized by a multiparameter reaction scheme based on an ECCE(DISP) mechanism, digital simulation of which confirmed the cleavage selectivity and allowed for the determination of the involved rate constants of the homogeneous chemical reaction steps.

  DOI：

  10.1021/jo00114a020
• 作为产物：
  描述：

  2,4,6-trimethylmandelic acid 在 吡啶 、 氯化亚砜 、 乙醚 、 四氯化锡 、 苯 作用下， 生成 2,2-Dimesityl-1-phenylethenyl acetate
  参考文献：
  名称：

  Vinyl Alcohols. XV.¹ Trisubstituted Vinyl Alcohols

  摘要：

  DOI：

  10.1021/ja01219a010