c-5-<(benzyloxy)methyl>-t-2-methoxy-r-1-cyclohexanol | 138008-11-4

• 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-5-<(benzyloxy)methyl>-t-2-methoxy-r-1-cyclohexanol
• 英文别名: c-5-[(benzyloxy)methyl]-t-2-methoxy-r-1-cyclohexanol；(1R,2R,5R)-2-methoxy-5-(phenylmethoxymethyl)cyclohexan-1-ol
• CAS: 138008-11-4
• 化学式: C₁₅H₂₂O₃
• 分子量: 250.338
• InChiKey: XMENYFNJRCTKNS-RBSFLKMASA-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

• 作为反应物：
  描述：

  c-5-<(benzyloxy)methyl>-t-2-methoxy-r-1-cyclohexanol 生成 (1R,2R,5R)-5-(hydroxymethyl)-2-methoxycyclohexan-1-ol
  参考文献：
  名称：

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

  摘要：

  The synthesis of the diastereoisomeric epoxides cis-1b-d and trans-2b-d and the products of their ring-opening by various nucleophiles are described. The results of the ring-openings of the trans-epoxides 2b-d can be rationalized by combining stereoelectronic and conformational arguments. However, the regioselectivity of the ring-openings of the cis-epoxides 1b-d can, in principle, be influenced by the chelation of a metal ion by the oxygen atom of the epoxy group and that of the substituent on the 4-position. The results of the reactions of the cis-epoxides 1b-d indicate that, to some degree, chelation is indeed a factor. How important a factor it is is dependent both on the reaction conditions and on the concentration and nature of the metal ion. In the ring-openings of the cis-epoxides 1b and 1d, chelation seems to be a larger factor than it is in the ring-openings of cis-epoxide 1c. However, in no case is chelation as large a factor as it was in the ring-openings of the cis-epoxide 1a, which was studied earlier. On the other hand, the autocatalyzed methanolysis, under neutral conditions, of epoxy acid 1e, followed by CH2N2 methylation of the crude product, afforded a mixture of the two regioisomeric hydroxy ethers in which the C-2-type compound predominates. This result suggests that intramolecular hydrogen bonding may determine the reactive conformation of 1e.

  DOI：

  10.1021/jo00031a018
• 作为产物：
  描述：

  (1R*,3R*,6S*)-7-oxabicyclo[4.1.0]hept-3-ylmethanol 在 lithium perchlorate 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 20.0h， 生成 c-5-<(benzyloxy)methyl>-t-2-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. 2. Synthesis and reactions of the cis- and trans-oxides of 4-[(benzyloxy)methyl]cyclohexene, 3-cyclohexenemethanol, and methyl 3-cyclohexenecarboxylate

  摘要：

  The synthesis of the diastereoisomeric epoxides cis-1b-d and trans-2b-d and the products of their ring-opening by various nucleophiles are described. The results of the ring-openings of the trans-epoxides 2b-d can be rationalized by combining stereoelectronic and conformational arguments. However, the regioselectivity of the ring-openings of the cis-epoxides 1b-d can, in principle, be influenced by the chelation of a metal ion by the oxygen atom of the epoxy group and that of the substituent on the 4-position. The results of the reactions of the cis-epoxides 1b-d indicate that, to some degree, chelation is indeed a factor. How important a factor it is is dependent both on the reaction conditions and on the concentration and nature of the metal ion. In the ring-openings of the cis-epoxides 1b and 1d, chelation seems to be a larger factor than it is in the ring-openings of cis-epoxide 1c. However, in no case is chelation as large a factor as it was in the ring-openings of the cis-epoxide 1a, which was studied earlier. On the other hand, the autocatalyzed methanolysis, under neutral conditions, of epoxy acid 1e, followed by CH2N2 methylation of the crude product, afforded a mixture of the two regioisomeric hydroxy ethers in which the C-2-type compound predominates. This result suggests that intramolecular hydrogen bonding may determine the reactive conformation of 1e.

  DOI：

  10.1021/jo00031a018

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。