5-methyl-5-t-butylperoxy-3-hexen-2-one

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-methyl-5-t-butylperoxy-3-hexen-2-one
• 英文别名: (E)-5-tert-butylperoxy-5-methylhex-3-en-2-one
• 化学式: C₁₁H₂₀O₃
• 分子量: 200.278
• InChiKey: YHNPRLJRCAWHSQ-BQYQJAHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  叔丁基过氧化氢 、 (E)-5-甲基己-3-烯-2-酮 在 20percent Pd(OH)2/C potassium carbonate 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 以81%的产率得到5-methyl-5-t-butylperoxy-3-hexen-2-one
  参考文献：
  名称：

  A Mild, Catalytic, and Highly Selective Method for the Oxidation of α,β-Enones to 1,4-Enediones

  摘要：

  A new and simple method is described for the one-step oxidation of alpha,beta-enones to 1,4-enediones in good yields (generally 80-90%) using t-butylhydroperoxide as stoichiometric oxidant and 20% Pd(OH)2 on carbon (5 mol %) as catalyst in CH2Cl2 solution. The same reagents have been used to convert ethylene ketals of alpha,beta-enones to the corresponding monoethylene ketals of 1,4-enediones. Seven representative examples are presented in Table 1. All of the available evidence on these oxidations points to a radical-chain mechanism initiated by the tert-butylperoxy radical (see Scheme 1). gamma-tert-Butylperoxy ethers are formed as major products in the oxidation of alpha,beta-enones possessing only a single gamma-hydrogen.

  DOI：

  10.1021/ja0340735

文献信息

• A Mild, Catalytic, and Highly Selective Method for the Oxidation of α,β-Enones to 1,4-Enediones
  作者：Jin-Quan Yu、E. J. Corey

  DOI：10.1021/ja0340735

  日期：2003.3.1

  A new and simple method is described for the one-step oxidation of alpha,beta-enones to 1,4-enediones in good yields (generally 80-90%) using t-butylhydroperoxide as stoichiometric oxidant and 20% Pd(OH)2 on carbon (5 mol %) as catalyst in CH2Cl2 solution. The same reagents have been used to convert ethylene ketals of alpha,beta-enones to the corresponding monoethylene ketals of 1,4-enediones. Seven representative examples are presented in Table 1. All of the available evidence on these oxidations points to a radical-chain mechanism initiated by the tert-butylperoxy radical (see Scheme 1). gamma-tert-Butylperoxy ethers are formed as major products in the oxidation of alpha,beta-enones possessing only a single gamma-hydrogen.