(Z)-1-(triethylsilyl)octadec-1-en-6-ol | 1346254-44-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (Z)-1-(triethylsilyl)octadec-1-en-6-ol
• 英文别名: (Z)-1-triethylsilyloctadec-1-en-6-ol
• CAS: 1346254-44-1
• 化学式: C₂₄H₅₀OSi
• 分子量: 382.746
• InChiKey: NXBMVDVJSVANBT-ATJXCDBQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.43
• 重原子数：
  26
• 可旋转键数：
  19
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (Z)-1-(triethylsilyl)octadec-1-en-6-ol 、 溶剂黄146 在 palladium diacetate 、 对苯醌 作用下， 以 水 、 丙酮 为溶剂， 反应 24.0h， 生成 (Z)-(2-(5-dodecyltetrahydrofuran-2-yl)vinyl)triethylsilane 、 (E)-(2-(5-dodecyltetrahydrofuran-2-yl)vinyl)triethylsilane
  参考文献：
  名称：

  Oxidant-Controlled Stereoselectivity in the Pd-Catalyzed Allylic Oxidation of cis-Vinylsilanes

  摘要：

  The allylic oxidation of cis-vinylsilanes is reported. The reaction requires a low catalyst loading of Pd(OAc)(2) without the need for an external ligand. Interestingly, trans-vinylsilanes are unreactive, whereas allylic oxidations of cis-vinylsilanes proceed in good yields giving a single diastereo- and regioisomer of the branched allylic acetate trans-vinylsilane when benzoquinone is employed. The use of PhI(OAc)(2) as oxidant in place of benzoquinone provides the branched, cis-vinylsilane as the major product. Additionally, the first intramolecular allylic C-H etherifications of cis-vinylsilanes to give oxygen heterocycles are also described.

  DOI：

  10.1021/ja2089102
• 作为产物：
  描述：

  5-己炔-1-醇 在 草酰氯 、 二氯乙基铝 、 二甲基亚砜 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 甲苯 为溶剂， 反应 8.42h， 生成 (Z)-1-(triethylsilyl)octadec-1-en-6-ol
  参考文献：
  名称：

  Oxidant-Controlled Stereoselectivity in the Pd-Catalyzed Allylic Oxidation of cis-Vinylsilanes

  摘要：

  The allylic oxidation of cis-vinylsilanes is reported. The reaction requires a low catalyst loading of Pd(OAc)(2) without the need for an external ligand. Interestingly, trans-vinylsilanes are unreactive, whereas allylic oxidations of cis-vinylsilanes proceed in good yields giving a single diastereo- and regioisomer of the branched allylic acetate trans-vinylsilane when benzoquinone is employed. The use of PhI(OAc)(2) as oxidant in place of benzoquinone provides the branched, cis-vinylsilane as the major product. Additionally, the first intramolecular allylic C-H etherifications of cis-vinylsilanes to give oxygen heterocycles are also described.

  DOI：

  10.1021/ja2089102

文献信息

• Oxidant-Controlled Stereoselectivity in the Pd-Catalyzed Allylic Oxidation of <i>cis</i>-Vinylsilanes
  作者：Christopher T. Check、William H. Henderson、Brenda C. Wray、Matthew J. Vanden Eynden、James P. Stambuli

  DOI：10.1021/ja2089102

  日期：2011.11.23

  The allylic oxidation of cis-vinylsilanes is reported. The reaction requires a low catalyst loading of Pd(OAc)(2) without the need for an external ligand. Interestingly, trans-vinylsilanes are unreactive, whereas allylic oxidations of cis-vinylsilanes proceed in good yields giving a single diastereo- and regioisomer of the branched allylic acetate trans-vinylsilane when benzoquinone is employed. The use of PhI(OAc)(2) as oxidant in place of benzoquinone provides the branched, cis-vinylsilane as the major product. Additionally, the first intramolecular allylic C-H etherifications of cis-vinylsilanes to give oxygen heterocycles are also described.