diphenylhydroperoxyacetate | 691889-72-2

• 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: diphenylhydroperoxyacetate
• CAS: 691889-72-2
• 化学式: C₁₅H₁₄O₄
• 分子量: 258.274
• InChiKey: VKLMJPXFLVFGER-UHFFFAOYSA-N

物化性质

• 沸点：
  425.1±45.0 °C(Predicted)
• 密度：
  1.229±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.94
• 重原子数：
  19.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  55.76
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2,4,6-三叔丁基苯酚 、 diphenylhydroperoxyacetate 在 meso-tetraphenylporphyrin iron(III) chloride 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 2,4,6-tri-tert-butylphenoxyl 、 二苯乙醇酸甲酯
  参考文献：
  名称：

  Oxygen transfer from percarboxylic acids and alkyl hydroperoxides to (meso-tetraphenylporphinato)iron(III) and -chromium(III)

  摘要：

  DOI：

  10.1021/ja00221a029
• 作为产物：
  描述：

  diphenylcarbonyl oxide 、 溶剂黄146 以 乙腈 为溶剂， 生成 diphenylhydroperoxyacetate
  参考文献：
  名称：

  摘要：

  The kinetics of the reactions of acetic, benzoic, formic, oxalic, malic, tartaric, trifluoroacetic, and hydrochloric acids with diphenylcarbonyl oxide Ph2COO was studied. The carbonyl oxide Ph2COO was generated by flash photolysis of diphenyldiazomethane Ph2CN2 in solutions of acetonitrile and benzene at 295 K. The apparent rate constants of the reaction range from 4.6-10(8) for (COOH)(2) in MeCN to 7.5.10(9) L mol(-1) s(-1) for acetic acid in a benzene Solution. The reaction mechanism was proposed, according to which at the first stage the carbonyl oxide is reversibly solvated by the solvent. Then the solvated carbonyl oxide reacts with the acid molecule by the mechanism of insertion at the O-H bond.

  DOI：

  10.1023/a:1015851730981

文献信息

• Cyclic mechanism in the trapping of carbonyl oxides with alcohols and carboxylic acids
  作者：Hiroshi Hanaki、Yuta Fukatsu、Masaki Harada、Yasuhiko Sawaki

  DOI：10.1016/j.tetlet.2004.01.158

  日期：2004.3

  The reaction of diphenylcarbonyl oxide with alcohols and carboxylic acids, which has been classified as a nucleophilic trapping, is shown to be in the reactivity order: AcOH much greater than MeOH > CF3CH2OH > EtOH much greater than t-BuOH. A laser-flash spectroscopy indicated that the reaction of carboxylic acids is very fast, that is, one-tenth of the diffusion rate. These results suggest that the hydroxyl compounds react as an acid and a nucleophile at the same time and the major reaction is via the seven- and five-membered cyclic mechanism for RCO2H and ROH, respectively. (C) 2004 Elsevier Ltd. All rights reserved.