(Z)-triethyl(5-methoxypent-1-en-1-yl)silane | 1346254-29-2

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (Z)-triethyl(5-methoxypent-1-en-1-yl)silane
• 英文别名: triethyl-[(Z)-5-methoxypent-1-enyl]silane
• CAS: 1346254-29-2
• 化学式: C₁₂H₂₆OSi
• 分子量: 214.423
• InChiKey: HLJFSSUIMZAVQU-BENRWUELSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.02
• 重原子数：
  14
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 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：

  碘苯二乙酸 、 (Z)-triethyl(5-methoxypent-1-en-1-yl)silane 在 palladium diacetate 作用下， 以 溶剂黄146 为溶剂， 反应 1.5h， 生成 (Z)-5-methoxy-1-(triethylsilyl)pent-1-en-3-yl acetate 、 (E)-5-methoxy-1-(triethylsilyl)pent-1-en-3-yl acetate
  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：

  三乙基硅烷 在 二氯乙基铝 、 sodium hydride 作用下， 以 四氢呋喃 、 正己烷 、 甲苯 、 mineral oil 为溶剂， 反应 9.75h， 生成 (Z)-triethyl(5-methoxypent-1-en-1-yl)silane
  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