1-((cyclohexyloxy)methyl)-2-methylbenzene | 1327239-11-1

• 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: 1-((cyclohexyloxy)methyl)-2-methylbenzene
• 英文别名: 1-(Cyclohexyloxymethyl)-2-methylbenzene；1-(cyclohexyloxymethyl)-2-methylbenzene
• CAS: 1327239-11-1
• 化学式: C₁₄H₂₀O
• 分子量: 204.312
• InChiKey: UBJMRMZRTNCQKZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  (methoxymethoxy)cyclohexane 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 0.08h， 生成 1-((cyclohexyloxy)methyl)-2-methylbenzene
  参考文献：
  名称：

  Expanded Substrate Scope and Improved Reactivity of Ether-Forming Cross-Coupling Reactions of Organotrifluoroborates and Acetals

  摘要：

  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.

  DOI：

  10.1021/ja205174c

文献信息

• Ether Synthesis through Reductive Cross-Coupling of Ketones with Alcohols Using Me2SiHCl as both Reductant and Lewis Acid
  作者：Bill Morandi、Yong Lee

  DOI：10.1055/s-0036-1590838

  日期：2017.11

  We report that a Lewis acidic silane, Me2SiHCl, can mediate the direct cross-coupling of a wide range of carbonyl compounds with alcohols to form dialkyl ethers. The reaction is operationally simple, tolerates a range of polar functional groups, can be utilized to make sterically hindered ethers, and is extendable to sulfur and nitrogen nucleo­philes.

  我们报告说，路易斯酸性硅烷 Me2SiHCl 可以介导各种羰基化合物与醇的直接交叉偶联，形成二烷基醚。该反应操作简单，可耐受一系列极性官能团，可用于制备位阻醚，并可扩展到硫和氮亲核试剂。
• SUBSTITUTED 5-CARBOXYAMIDE PYRAZOLES AND [1,2,4]TRIAZOLES AS ANTIVIRAL AGENTS
  申请人：Schering Corporation

  公开号：EP1814860B1

  公开（公告）日：2009-06-03
• 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.