2-cyclohexyl-6-hydroperoxy-6-methyl-2H-pyran-3(6H)-one | 358741-05-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: 2-cyclohexyl-6-hydroperoxy-6-methyl-2H-pyran-3(6H)-one
• 英文别名: 2-Cyclohexyl-6-hydroperoxy-6-methylpyran-3-one
• CAS: 358741-05-6
• 化学式: C₁₂H₁₈O₄
• 分子量: 226.273
• InChiKey: KPALXTQKDAPIFB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-cyclohexyl-6-hydroperoxy-6-methyl-2H-pyran-3(6H)-one 在 二甲基硫 作用下， 以 乙醚 为溶剂， 以100%的产率得到2-cyclohexyl-6-hydroxy-6-methyl-2H-pyran-3(6H)-one
  参考文献：
  名称：

  New procedures for the enantioselective oxidation of sulfides under stoichiometric and catalytic conditions

  摘要：

  Acid-catalyzed oxidation of 2-furylcarbinols with hydrogen peroxide affords alternatively 2-(1-hydroperoxyalkyl)furans 2 or 6-hydroperoxy-2H-pyran-3(6H)-ones 3. Compounds of the type 2 and 3 have been used Lis oxygen donors in efficient stoichiometric or catalytic procedures for the asymmetric sulfoxidation of prochiral sulfides in the presence of Ti(O-i-Pr)(4)/L-DET or Ti(O-i-Pr)(4)/(R)-BINOL/H2O systems. Positive non linear effects, (+)-NLE, were observed in the enantioselective oxidation of methyl p-tolyl sulfide, promoted by enantiomierically enriched Ti(IV)/BINOL/H2O complexes. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00326-9
• 作为产物：
  描述：

  环己基溴化镁 在 双氧水 、 对甲苯磺酸 作用下， 以 乙二醇二甲醚 、 水 为溶剂， 反应 23.0h， 生成 2-cyclohexyl-6-hydroperoxy-6-methyl-2H-pyran-3(6H)-one
  参考文献：
  名称：

  New procedures for the enantioselective oxidation of sulfides under stoichiometric and catalytic conditions

  摘要：

  Acid-catalyzed oxidation of 2-furylcarbinols with hydrogen peroxide affords alternatively 2-(1-hydroperoxyalkyl)furans 2 or 6-hydroperoxy-2H-pyran-3(6H)-ones 3. Compounds of the type 2 and 3 have been used Lis oxygen donors in efficient stoichiometric or catalytic procedures for the asymmetric sulfoxidation of prochiral sulfides in the presence of Ti(O-i-Pr)(4)/L-DET or Ti(O-i-Pr)(4)/(R)-BINOL/H2O systems. Positive non linear effects, (+)-NLE, were observed in the enantioselective oxidation of methyl p-tolyl sulfide, promoted by enantiomierically enriched Ti(IV)/BINOL/H2O complexes. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00326-9

文献信息

• A convenient approach to renewable hydroperoxides
  作者：Antonio Massa、Laura Palombi、Arrigo Scettri

  DOI：10.1016/s0040-4039(01)00794-8

  日期：2001.7

  2-(1-Hydroperoxyalkyl)-furans and 6-hydroperoxy-2H-pyran-3(6H)-ones are alternatively accessible by acid-catalyzed oxidation of 2-furyl alcohols with hydrogen peroxide under appropriate conditions. Representative compounds of both classes of hydroperoxides have been used, as easily renewable oxygen donors, in asymmetric sulfoxidation reactions. (C) 2001 Published by Elsevier Science Ltd.