trans-2-<(benzyloxy)methyl>cyclohexanol | 138630-57-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: trans-2-<(benzyloxy)methyl>cyclohexanol
• 英文别名: trans-2-[(benzyloxy)methyl]cyclohexanol；(1S,2R)-2-(phenylmethoxymethyl)cyclohexan-1-ol
• CAS: 138630-57-6
• 化学式: C₁₄H₂₀O₂
• 分子量: 220.312
• InChiKey: LNDRAALFEONYKU-KGLIPLIRSA-N

物化性质

• 沸点：
  332.5±15.0 °C(Predicted)
• 密度：
  1.058±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-环己烯-1-甲醇 在 lithium aluminium tetrahydride 、 potassium tert-butylate 、 sodium hydride 、 N-溴代乙酰胺 作用下， 以 四氢呋喃 、 水 、 正戊烷 、 苯 为溶剂， 反应 6.0h， 生成 trans-2-<(benzyloxy)methyl>cyclohexanol
  参考文献：
  名称：

  Regiochemical control of the ring opening of 1,2-epoxides by means of chelating processes. 4. Synthesis and reactions of the cis- and trans-oxides derived from 3-[(benzyloxy)methyl]cyclohexene

  摘要：

  The synthesis and nucleophilic addition reactions of diastereoisomeric title epoxides cis-7 and trans-8 were studied. While the ring-opening reactions of trans epoxide 8 are rationalized by means of steric, stereolectronic, and conformational arguments, the analogous reactions of cis epoxide 7 indicate the ability of this isomer to react through chelated intermediates when metal salt catalyst is used. In 7 chelation reaction conditions led to a significant increase of nucleophilic attack on the C-1 oxirane carbon; the lack of reversal of the regiochemistry of the ring opening on passing from nonchelating to chelating reaction conditions suggests that cis epoxide 7 reacts through its more stable conformation in both of the two different operating conditions.

  DOI：

  10.1021/jo00032a022