(-)-menthol-MOM | 121153-32-0

• 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: (-)-menthol-MOM
• 英文别名: (1S,2R,4R)-2-(methoxymethoxy)-4-methyl-1-propan-2-ylcyclohexane
• CAS: 121153-32-0
• 化学式: C₁₂H₂₄O₂
• 分子量: 200.321
• InChiKey: IMFNXDRFEFZAIK-GRYCIOLGSA-N

物化性质

• 沸点：
  226.3±8.0 °C(Predicted)
• 密度：
  0.89±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (-)-menthol-MOM 在 三甲基氯硅烷 、 zinc(II) tetrahydroborate 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 2.0h， 以87%的产率得到[1R-(1alpha,2beta,5alpha)]-1-(异丙基)-2-甲氧基-4-甲基环己烷
  参考文献：
  名称：

  Efficient method for the reductive cleavage of acetals and ketals with Zn(BH4)2/Me3SiCl

  摘要：

  DOI：

  10.1021/jo00388a049
• 作为产物：
  描述：

  二甲醇缩甲醛 、 L-薄荷醇 在 对甲苯磺酸 、 lithium bromide 作用下， 反应 24.0h， 以70%的产率得到(-)-menthol-MOM
  参考文献：
  名称：

  从有机三氟硼酸盐和缩醛合成二烷基醚

  摘要：

  在苛刻的碱性或酸性条件下通过 CO 键形成形成醚是有机化学中根深蒂固的合成断开。我们报告了一种战略替代方案，涉及 BF(3).OEt(2) 促进的稳定、易于制备的缩醛与广泛可用的芳基-、烯基-和炔基三氟硼酸钾的偶联。这种快速、操作简单的过程提供了直接获得二烷基醚的途径，其中许多使用经典方法难以制备。使用 MOM 保护的醇和缩醛保护的醛可以形成醚，而无需求助于保护基操作或强碱。

  DOI：

  10.1021/ja906514s

文献信息

• Lithium Bromide, a Novel and Highly Effective Catalyst for Monothioacetalization of Acetals under Mild Reaction Conditions
  作者：Fumiaki Ono、Ryojyu Negoro、Tsuneo Sato

  DOI：10.1055/s-2001-17477

  日期：——

  Lithium bromide is efficient as a catalyst for the monothioacetalization of acetals under mild reaction conditions to provide products in excellent yields with high chemoselectivity.

  溴化锂在温和反应条件下作为催化剂对醛的单硫醇缩合反应非常有效，能够以优异的产率和高的化学选择性提供反应产物。
• Organotin-Mediated Preparation of Monothioacetals
  作者：Tsuneo Sato、Takamitsu Kobayashi、Tamehisa Gojo、Enji Yoshida、Junzo Otera、Hitosi Nozaki

  DOI：10.1246/cl.1987.1661

  日期：1987.8.5

  Monothioacetals are obtained by treating the corresponding acetals with organotin thiophenoxides in the presence of BF2·OEt2. The reaction proceeds under mild conditions to provide the desired compounds with high selectivity.

  在 BF2·OEt2 存在下，用有机锡噻吩氧化物处理相应的缩醛得到一硫代缩醛。该反应在温和条件下进行，以高选择性提供所需化合物。
• Na-Y zeolite, an efficient catalyst for the methoxymethylation of alcohols
  作者：Pradeep Kumar、Satya V.N. Raju、Ravinder S. Reddy、Bipin Pandey

  DOI：10.1016/0040-4039(94)88046-8

  日期：1994.2

  A variety of hydroxy compounds react with methoxymethyl chloride in the presence of catalytic amount of Na-Y zeolite to afford the corresponding methoxymethyl ethers (MOM ethers) in excellent yields.

  在催化量的Na-Y沸石存在下，多种羟基化合物与甲氧基甲基氯反应，以优异的收率得到相应的甲氧基甲基醚（MOM醚）。
• Kantam, M. Lakshmi; Santhi, P. Lakshmi, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1996, vol. 35, # 3, p. 260 - 261
  作者：Kantam, M. Lakshmi、Santhi, P. Lakshmi

  DOI：——

  日期：——
• Expanded Substrate Scope and Improved Reactivity of Ether-Forming Cross-Coupling Reactions of Organotrifluoroborates and Acetals
  作者：Cam-Van T. Vo、T. Andrew Mitchell、Jeffrey W. Bode

  DOI：10.1021/ja205174c

  日期：2011.9.7

  Mixed acetals and organotrifluoroborates undergo BF3 center dot OEt2-promoted cross-couplings to give dialkyl ethers under simple, mild conditions. A survey of reaction partners identified a hydroxamate leaving group that improves the regioselectivity and product yield in the BF3 center dot OEt2-promoted coupling reaction of mixed acetals and potassium alkynyl-, alkenyl-, aryl- and heteroaryltrifluoroborates to access substituted dialkyl ethers. This leaving group enables the reaction to proceed rapidly under mild conditions (0 degrees C, 5-60 min) and permits reactions with electron-deficient potassium aryltrifluoroborates that are less reactive with other acetal substrates. A study of the reaction mechanism and characterization of key intermediates by NMR spectroscopy and X-ray crystallography identified a role for the hydroxamate moiety as a reversible leaving group that serves to stabilize the key oxocarbenium intermediate and the need for a slight excess of organodifluoroborane to serve as a catalyst. A secondary role for the boron nucleophile as an activating ligand was also considered. These studies provide the basis for a general class of reagents that lead to dialkyl ethers by a simple, predictable cross-coupling reaction.