(2R,4R,11R)-2,4-dimethyl-1,5-dioxaspiro[5.5]undecan-11-ol | 147168-86-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,4R,11R)-2,4-dimethyl-1,5-dioxaspiro[5.5]undecan-11-ol
• CAS: 147168-86-3
• 化学式: C₁₁H₂₀O₃
• 分子量: 200.278
• InChiKey: KITAJHJKYXBXMK-OPRDCNLKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2R,4R,11R)-2,4-dimethyl-1,5-dioxaspiro[5.5]undecan-11-ol 在 对甲苯磺酸 作用下， 以 乙醚 为溶剂， 生成 (R)-α-hydroxycyclohexanone
  参考文献：
  名称：

  Diastereoface differentiating peracid oxidation of the enol ether derived from cyclohexanone and 2,4-pentanediol: Preparation of optically pure 2-hydroxycyclohexanone acetal

  摘要：

  Diastereoface differentiating m-chloroperbenzoic acid oxidation of the chiral enol ether prepared from cyclohexanone and optically active 2,4-pentanediol proceeded from -72 to 39-degrees-C to give a diastereomeric mixture of the corresponding 2-hydroxycyclohexanone acetal. The diastereomeric excess of the product reached almost 100 % at -72-degrees-C.

  DOI：

  10.1016/s0957-4166(00)86013-9
• 作为产物：
  描述：

  (2R,4R)-4-(cyclohex-1-en-1-yloxy)pentan-2-ol 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 以61.6%的产率得到(2R,4R,11R)-2,4-dimethyl-1,5-dioxaspiro[5.5]undecan-11-ol
  参考文献：
  名称：

  Diastereoface-differentiating oxidation of 1-cyclohexenyl ether using a 2,4-pentanediol tether

  摘要：

  Diastereoface-differentiating oxidation of the chiral enol ether prepared from cyclohexanone and optically active 2,4-pentanediol gave a diastereomeric mixture of the corresponding 2-hydroxycyclohexanone acetal. The diastereomeric excess of the product reached over 99% by oxidation with m-chloroperbenzoic acid at -78 degrees C. Oxidation with t-butyl hydroperoxide in the presence of metal catalysts also resulted in high diastereomeric excesses of up to 97%. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00046-9