2-(Benzyloxy)-3-hydroxy-4,4-dimethyltetrahydropyran | 133871-99-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: 2-(Benzyloxy)-3-hydroxy-4,4-dimethyltetrahydropyran
• 英文别名: 4,4-dimethyl-2-phenylmethoxyoxan-3-ol
• CAS: 133871-99-5
• 化学式: C₁₄H₂₀O₃
• 分子量: 236.311
• InChiKey: UKSYXQZRIINHOZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.34
• 重原子数：
  17.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 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：

  4,4-dimethyltetrahydro-2H-pyran-2-ol 在 氢氧化钾 、 sodium hydroxide 、 对甲苯磺酸 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 74.5h， 生成 2-(Benzyloxy)-3-hydroxy-4,4-dimethyltetrahydropyran
  参考文献：
  名称：

  Chemistry of dioxiranes. 18. Deuterium isotope effects in the reaction of 4,4-dimethyldihydropyran with dimethyldioxirane

  摘要：

  The reaction of dimethyldioxirane (1) with 4,4-dimethyl-2,3-dihydro-gamma-pyran (2) gives the derived epoxide. Measured secondary deuterium isotope effects indicate that there is a greater degree of rehybridization at the beta position (5-carbon) than at the alpha position (6-carbon) in the transition state leading to epoxide. The results are compared to those reported earlier in which 2 was oxidized by singlet oxygen to give the dioxetane.

  DOI：

  10.1021/jo00011a043

文献信息

• MURRAY, ROBERT W.;SHIANG, DAWN L.;SINGH, MEGH, J. ORG. CHEM., 56,(1991) N1, C. 3677-3682
  作者：MURRAY, ROBERT W.、SHIANG, DAWN L.、SINGH, MEGH

  DOI：——

  日期：——
• Chemistry of dioxiranes. 18. Deuterium isotope effects in the reaction of 4,4-dimethyldihydropyran with dimethyldioxirane
  作者：Robert W. Murray、Dawn L. Shiang、Megh Singh

  DOI：10.1021/jo00011a043

  日期：1991.5

  The reaction of dimethyldioxirane (1) with 4,4-dimethyl-2,3-dihydro-gamma-pyran (2) gives the derived epoxide. Measured secondary deuterium isotope effects indicate that there is a greater degree of rehybridization at the beta position (5-carbon) than at the alpha position (6-carbon) in the transition state leading to epoxide. The results are compared to those reported earlier in which 2 was oxidized by singlet oxygen to give the dioxetane.