(E)-3,7-dimethyl-1-methylsulfanylmethoxy-octa-2,6-diene | 72323-36-5

• 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: (E)-3,7-dimethyl-1-methylsulfanylmethoxy-octa-2,6-diene
• 英文别名: Geranylmethylthiomethylether；O-methylsulfanylmethyl-geraniol；(2E)-3,7-dimethyl-1-(methylsulfanylmethoxy)octa-2,6-diene
• CAS: 72323-36-5
• 化学式: C₁₂H₂₂OS
• 分子量: 214.372
• InChiKey: SJHCQVIWOJZXNI-XYOKQWHBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  14
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  34.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-3,7-dimethyl-1-methylsulfanylmethoxy-octa-2,6-diene 在 4-二甲氨基吡啶 、 磺酰氯 、 三氟化硼乙醚 、 N,N-二异丙基乙胺 、 环己烯 作用下， 以 二氯甲烷 为溶剂， 反应 25.0h， 生成 (E)-(3-((3,7-dimethylocta-2,6-dien-1-yl)oxy)prop-1-yn-1-yl)benzene
  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
• 作为产物：
  描述：

  香叶醇 、 氯甲基甲硫醚 在 silver nitrate 、 三乙胺 作用下， 以 苯 为溶剂， 生成 (E)-3,7-dimethyl-1-methylsulfanylmethoxy-octa-2,6-diene
  参考文献：
  名称：

  一种制备甲基硫代甲基醚的温和方便的方法：保护羟基

  摘要：

  使用氯甲基甲基硫化物和硝酸银在温和条件下制备了各种醇的甲硫基甲基（MTM）醚。

  DOI：

  10.1246/cl.1979.1277

文献信息

• A mild method for the conversion of alcohols to methylthiomethyl ethers
  作者：Julio C. Medina、Magalie Salomon、Keith S. Kyler

  DOI：10.1016/s0040-4039(00)82111-5

  日期：1988.1

  Alcohols can be easily transformed to their corresponding methylthiomethyl ethers under mild conditions by treatment with methyl sulfide and benzoyl peroxide in acetonitrile.

  通过在乙腈中用甲基硫和过氧化苯甲酰处理，可以在温和条件下将醇轻松转化为相应的甲硫基甲基醚。
• SUZUKI KENJI; INANAGA JUNJI; YAMAGUSHI MASARU, CHEM. LETT., 1979, NO 10, 1277-1278
  作者：SUZUKI KENJI、 INANAGA JUNJI、 YAMAGUSHI MASARU

  DOI：——

  日期：——
• MEDINA, JULIO C.;SALOMON, MAGALIE;KYLER, KEITH S., TETRAHEDRON LETT., 29,(1988) N 31, C. 3773-3776
  作者：MEDINA, JULIO C.、SALOMON, MAGALIE、KYLER, KEITH S.

  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.
• A MILD AND CONVENIENT METHOD FOR THE PREPARATION OF METHYLTHIOMETHYL ETHERS: PROTECTION OF HYDROXYL GROUPS
  作者：Kenji Suzuki、Junji Inanaga、Masaru Yamaguchi

  DOI：10.1246/cl.1979.1277

  日期：1979.10.5

  Methylthiomethyl (MTM) ethers of various types of alcohols were prepared under mild conditions by using chloromethyl methyl sulfide and silver nitrate.

  使用氯甲基甲基硫化物和硝酸银在温和条件下制备了各种醇的甲硫基甲基（MTM）醚。