1-oxo-2-cyclohexen-4-yl hydroperoxide

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-oxo-2-cyclohexen-4-yl hydroperoxide
• 英文别名: 4-Hydroperoxy-4-propan-2-ylcyclohex-2-en-1-one
• 化学式: C₉H₁₄O₃
• 分子量: 170.208
• InChiKey: LNKLAYQCNWNXIN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-oxo-2-cyclohexen-4-yl hydroperoxide 在 20percent Pd(OH)2/C 叔丁基过氧化氢 、 potassium carbonate 作用下， 以 二氯甲烷 为溶剂， 生成 4-hydroxycryptone
  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
• 作为产物：
  描述：

  叔丁基过氧化氢 、 4-异丙基环己-2-烯-1-酮 在 palladium hydroxide - carbon 、 potassium carbonate 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以4%的产率得到1-oxo-2-cyclohexen-4-yl hydroperoxide
  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.