cis-4-benzyloxy-1-(2-hydroxyethyl)cyclohexan-1-ol | 894074-67-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: cis-4-benzyloxy-1-(2-hydroxyethyl)cyclohexan-1-ol
• CAS: 894074-67-0
• 化学式: C₁₅H₂₂O₃
• 分子量: 250.338
• InChiKey: SWPNKJVAJVGOCX-GASCZTMLSA-N

物化性质

• 熔点：
  102 °C(Solvent: Diisopropyl ether)
• 沸点：
  392.1±32.0 °C(Predicted)
• 密度：
  1.13±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.26
• 重原子数：
  18.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  49.69
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  cis-4-benzyloxy-1-(2-hydroxyethyl)cyclohexan-1-ol 在 palladium on activated charcoal 环己烯 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以99%的产率得到trans-1-(2-Hydroxyethyl)-1,4-cyclohexanediol
  参考文献：
  名称：

  Chemo enzymatic synthesis of Rengyol and Isorengyol

  摘要：

  Cyanohydrins 2 of O-protected 4-hydroxycyclohexanones 1 are excellent starting compounds for the synthesis of Isorengyol (I) and Rengyol (II). The cyano group of the O-benzyl derivative 2d is first converted into the corresponding aldehyde 4, which via Wittig olefination led to the vinyl Compound 6. Hydroboration of the trans-derivative (trans-6) leads, after debenzylation, to Isorengyol, whereas hydroboration and debenzylation of the cis-isomer (cis-6) gives Rengyol. With hydroxynitrile lyases (HNLs) as catalysts the stereoselective preparation of cis- as well as trans-cyanohydrin 2d is possible, which enables the selective preparation of Isorengyol or Rengyol, respectively. The trans-con figuration of Isorengyol and the cis-configuration of Rengyol were secured by X-ray crystal structure analysis. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.03.012
• 作为产物：
  描述：

  (4-benzyloxy-1-vinylcyclohexyloxy)trimethylsilane 在 四丁基氟化铵 、 diborane(6) 作用下， 以 四氢呋喃 为溶剂， 反应 2.5h， 生成 cis-4-benzyloxy-1-(2-hydroxyethyl)cyclohexan-1-ol
  参考文献：
  名称：

  Chemo enzymatic synthesis of Rengyol and Isorengyol

  摘要：

  Cyanohydrins 2 of O-protected 4-hydroxycyclohexanones 1 are excellent starting compounds for the synthesis of Isorengyol (I) and Rengyol (II). The cyano group of the O-benzyl derivative 2d is first converted into the corresponding aldehyde 4, which via Wittig olefination led to the vinyl Compound 6. Hydroboration of the trans-derivative (trans-6) leads, after debenzylation, to Isorengyol, whereas hydroboration and debenzylation of the cis-isomer (cis-6) gives Rengyol. With hydroxynitrile lyases (HNLs) as catalysts the stereoselective preparation of cis- as well as trans-cyanohydrin 2d is possible, which enables the selective preparation of Isorengyol or Rengyol, respectively. The trans-con figuration of Isorengyol and the cis-configuration of Rengyol were secured by X-ray crystal structure analysis. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.03.012