isomenthol methyl ether | 34048-68-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: isomenthol methyl ether
• 英文别名: Methylaether v. Isomenthol；Methyl-isomenthylaether；Isomenthylmethylether；O-Methyl-isomenthol；Methoxy-isomenthan；(1R,2S,4R)-2-methoxy-4-methyl-1-propan-2-ylcyclohexane
• CAS: 34048-68-5
• 化学式: C₁₁H₂₂O
• 分子量: 170.295
• InChiKey: JDGJLPHFRJNJMN-MXWKQRLJSA-N

物化性质

• 沸点：
  191.5±8.0 °C(Predicted)
• 密度：
  0.84±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  isomenthol methyl ether 在 HOF* CH₃CN 、 sodium fluoride 作用下， 以 氯仿 、 水 、 乙腈 为溶剂， 以5%的产率得到(-)-薄荷酮
  参考文献：
  名称：

  Oxidative Cleavage of Methyl Ethers Using the HOF.cntdot.CH3CN Complex

  摘要：

  HOF . CH3CN complex, made easily by bubbling fluorine diluted with nitrogen through aqueous acetonitrile, proved to be a suitable oxidizer for various methyl ethers. Secondary ethers are oxidized to ketones and even to lactones via Baeyer-Villiger type of oxidation. The reaction is ionic, and the reagent's electrophilic oxygen attacks the relatively electron rich C-H bend alpha to the ether moiety. It was found that the more sterically hindered is the C-H bond in question, the slower the reaction. In cases where this bond is an electron poor one as in benzoin methyl ether (9), no reaction takes place. When labeled (HOF)-O-18 . CH3CN is used on a O-16 methyl ether, the resulting ketone possesses only the heavier oxygen isotope. Primary methyl ethers are somewhat slower to react, but they too were oxidized in very good yields to acids via the corresponding aldehydes.

  DOI：

  10.1021/jo00130a029
• 作为产物：
  描述：

  重氮甲烷 、 (+)-异薄荷醇 在 三氟化硼乙醚 作用下， 生成 isomenthol methyl ether
  参考文献：
  名称：

  Hueckel,W.; Jennewein,C.-M., Justus Liebigs Annalen der Chemie, 1965, vol. 683, p. 100 - 117

  摘要：

  DOI：

文献信息

• Hueckel,W. et al., Justus Liebigs Annalen der Chemie, 1961, vol. 645, p. 115 - 162
  作者：Hueckel,W. et al.

  DOI：——

  日期：——
• Hueckel,W.; Jennewein,C.-M., Justus Liebigs Annalen der Chemie, 1965, vol. 683, p. 100 - 117
  作者：Hueckel,W.、Jennewein,C.-M.

  DOI：——

  日期：——
• Oxidative Cleavage of Methyl Ethers Using the HOF.cntdot.CH3CN Complex
  作者：Shlomo Rozen、Sharon Dayan、Yifat Bareket

  DOI：10.1021/jo00130a029

  日期：1995.12

  HOF . CH3CN complex, made easily by bubbling fluorine diluted with nitrogen through aqueous acetonitrile, proved to be a suitable oxidizer for various methyl ethers. Secondary ethers are oxidized to ketones and even to lactones via Baeyer-Villiger type of oxidation. The reaction is ionic, and the reagent's electrophilic oxygen attacks the relatively electron rich C-H bend alpha to the ether moiety. It was found that the more sterically hindered is the C-H bond in question, the slower the reaction. In cases where this bond is an electron poor one as in benzoin methyl ether (9), no reaction takes place. When labeled (HOF)-O-18 . CH3CN is used on a O-16 methyl ether, the resulting ketone possesses only the heavier oxygen isotope. Primary methyl ethers are somewhat slower to react, but they too were oxidized in very good yields to acids via the corresponding aldehydes.