2-(1-hydroxy-2-methylpropyl)cyclohexanol | 99850-76-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(1-hydroxy-2-methylpropyl)cyclohexanol
• 英文别名: 2-(α-Hydroxy-isobutyl)-cyclohexanol；2-(1-hydroxy-2-methylpropyl)cyclohexan-1-ol
• CAS: 99850-76-7
• 化学式: C₁₀H₂₀O₂
• 分子量: 172.268
• InChiKey: ZCYYSEWHSGFBKE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-(2-甲基-1-氧代丙烷)环己酮 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 2-(1-hydroxy-2-methylpropyl)cyclohexanol
  参考文献：
  名称：

  Asymmetric synthesis of new chiral 1,2- and 1,3-diols

  摘要：

  Seven chiral 1,2-diols and six chiral 1,3-diols were synthesized by the asymmetric reduction of the corresponding 1,2-diketones and 1,3-diketones using oxazaborolidine-BH3 catalyst. The 13 corresponding racemic 1,2- and 1,3-diols were synthesized by reducing the diketones with NaBH4 and they were used for determining the ee values through their chiral resolution on HPLC and GC. Five starting diketones, four racemic 1,2-diols, five chiral 1,2-diols, and two chiral 1,3-diols are novel compounds. The new chiral compounds were characterized by IR, H-1 and C-13 NMR, MS, and elemental analysis. The asymmetric reduction method, oxazaborolidine-BH3, was applied to these diketones for the first time in this study. The relationship between the structure of the diketone and the yield, diastereoselectivity, and enantiomeric excess was discussed.

  DOI：

  10.1007/s00706-012-0792-7

文献信息

• DE956948
  申请人：——

  公开号：——

  公开（公告）日：——
• Asymmetric synthesis of new chiral 1,2- and 1,3-diols
  作者：Tülay Yıldız、Ayşe Yusufoğlu

  DOI：10.1007/s00706-012-0792-7

  日期：2013.2

  Seven chiral 1,2-diols and six chiral 1,3-diols were synthesized by the asymmetric reduction of the corresponding 1,2-diketones and 1,3-diketones using oxazaborolidine-BH3 catalyst. The 13 corresponding racemic 1,2- and 1,3-diols were synthesized by reducing the diketones with NaBH4 and they were used for determining the ee values through their chiral resolution on HPLC and GC. Five starting diketones, four racemic 1,2-diols, five chiral 1,2-diols, and two chiral 1,3-diols are novel compounds. The new chiral compounds were characterized by IR, H-1 and C-13 NMR, MS, and elemental analysis. The asymmetric reduction method, oxazaborolidine-BH3, was applied to these diketones for the first time in this study. The relationship between the structure of the diketone and the yield, diastereoselectivity, and enantiomeric excess was discussed.