(1R,2S)-2-(tetrahydropyranyloxy)cyclohexanol | 120053-19-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1R,2S)-2-(tetrahydropyranyloxy)cyclohexanol
• 英文别名: cis-2--cyclohexan-1-ol；cis-2-(Tetrahydropyran-2-yloxy)-cyclohexan-1-ol；(1R,2S)-2-(oxan-2-yloxy)cyclohexan-1-ol
• CAS: 120053-19-2
• 化学式: C₁₁H₂₀O₃
• 分子量: 200.278
• InChiKey: UIDCHJAVLYCSFH-JKIOLJMWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.83
• 重原子数：
  14.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 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：

  (1R,2S)-2-(tetrahydropyranyloxy)cyclohexanol 在 吡啶 、 chromium(VI) oxide 、 4-二甲氨基吡啶 、 4-甲基苯磺酸吡啶 作用下， 以 四氢呋喃 、 吡啶 、 二氯甲烷 、 水 为溶剂， 反应 6.25h， 生成 (+)-(2R)-2-乙酰氧基环己酮
  参考文献：
  名称：

  Enantiodifferentiating functionalization of cis-cycloalkane-1,2-diols and cis-endo-5-norbornen-2,3-ylenebis(methanol) via chiral spiroacetals derived from L-menthone

  摘要：

  DOI：

  10.1021/jo00272a027
• 作为产物：
  描述：

  cis-1,2-bis(trimethylsilyloxy)cyclohexane 在 三氟甲磺酸三甲基硅酯 、 potassium tert-butylate 、 4-甲基苯磺酸吡啶 、 四氯化钛 作用下， 以 二氯甲烷 为溶剂， 反应 65.0h， 生成 (1R,2S)-2-(tetrahydropyranyloxy)cyclohexanol
  参考文献：
  名称：

  Enantiodifferentiating functionalization of cis-cycloalkane-1,2-diols and cis-endo-5-norbornen-2,3-ylenebis(methanol) via chiral spiroacetals derived from L-menthone

  摘要：

  DOI：

  10.1021/jo00272a027

文献信息

• Selective Monotetrahydropyranylation of Symmetrical Diols Catalyzed by Ion-Exchange Resins
  作者：Takeshi Nishiguchi、Shizuo Fujisaki、Masahumi Kuroda、Kohtaro Kajisaki、Masahiko Saitoh

  DOI：10.1021/jo980659b

  日期：1998.11.1

  Primary and secondary symmetrical diols with 2-10 carbon atoms gave selectively monotetrahydropyranyl ethers in the reaction catalyzed by wet sulfonic acid-type ion-exchange resins in 3,4-dihydro-2H-pyran (DI-IP)/toluene or DHP/hexane. The yields of the monoethers were higher than 80% while those of the corresponding diethers were lower than 5%. In these reactions the rate of the formation of the diethers did not increase much even after most of the diols had been consumed. In the reaction of 1,10-decanediol in DHP/hexane, the yields of the monoether were increased by the addition of DMF or DMSO. Each diol was found to have a particular DHP/hydrocarbon ratio that gave the highest selectivity for the monoether. Generally, the larger the number of carbon atoms of the diols, the smaller the ratio of DHP in the solvents to give high selectivity for the monoether. This method of the selective etherification is quite simple and practical.
• HARADA, TOSHIRO;WADA, ISAO;OKU, AKIRA, J. ORG. CHEM., 54,(1989) N1, C. 2599-2605
  作者：HARADA, TOSHIRO、WADA, ISAO、OKU, AKIRA

  DOI：——

  日期：——