c-2-<(benzyloxy)methyl>-t-6-methoxy-r-1-cyclohexanol | 138630-51-0

• 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: c-2-<(benzyloxy)methyl>-t-6-methoxy-r-1-cyclohexanol
• 英文别名: c-2-[(benzyloxy)methyl]-t-6-methoxy-r-1-cyclohexanol；(1R,2R,6S)-2-methoxy-6-(phenylmethoxymethyl)cyclohexan-1-ol
• CAS: 138630-51-0
• 化学式: C₁₅H₂₂O₃
• 分子量: 250.338
• InChiKey: WYSGABOWBSDPLM-RRFJBIMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.38
• 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：
  38.69
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  3-<(benzyloxy)methyl>cyclohexene 在 叔丁基过氧化氢 、 硫酸 、 potassium tert-butylate 、 四氯化钛 作用下， 以 异辛烷 、 二氯甲烷 、 苯 为溶剂， 反应 1.0h， 生成 c-2-<(benzyloxy)methyl>-t-6-methoxy-r-1-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

文献信息

• Regiochemical Control of the Ring Opening of 1,2-Epoxides by Means of Chelating Processes. Part 14: Regioselectivity of the Opening Reactions with MeOH of Remote O-Substituted 1,2-Epoxycyclohexanes under Gas-Phase Operating Conditions
  作者：Paolo Crotti、Valeria Di Bussolo、Lucilla Favero、Mauro Pineschi、Francesco Marianucci、Gabriele Renzi、Giuseppina Amici、Graziella Roselli

  DOI：10.1016/s0040-4020(00)00643-8

  日期：2000.9

  was determined in the gas-phase in opening reactions with MeOH, using a gaseous acid (D3+, CnH5+, Me2F+) as the promoting agent. The results obtained indicate the incursion in the opening process in the gas phase of H+(or D+)-mediated chelated bidentate species completely absent in the corresponding reactions (methanolysis) carried out in the condensed phase.

  使用气态酸（D 3 +，C n H 5 +，Me 2 F +）作为促进剂，在与MeOH进行开环反应的气相中，确定了具有远距离O-官能度的环己烯氧化物的区域化学行为。所获得的结果表明，在缩合相中进行的相应反应（甲烷分解）中完全不存在H +（或D +）介导的螯合双齿物质在气相中的打开过程。