trimethyl[(E)-3,7-dimethyl(phenylthio)octa-2,6-dienyl]silane | 88415-65-0

• 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: trimethyl[(E)-3,7-dimethyl(phenylthio)octa-2,6-dienyl]silane
• 英文别名: E-(3,7-dimethyl-1-phenylsulfanyl-octa-2,6-dienyl)-trimethyl-silane；[(2E)-3,7-dimethyl-1-phenylsulfanylocta-2,6-dienyl]-trimethylsilane
• CAS: 88415-65-0
• 化学式: C₁₉H₃₀SSi
• 分子量: 318.599
• InChiKey: QITFPPJUQSPQAF-BMRADRMJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.72
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  25.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  香叶醇 在 吡啶 、 三丁基膦 、 LiDBB 作用下， 以 四氢呋喃 为溶剂， 反应 1.08h， 生成 trimethyl[(E)-3,7-dimethyl(phenylthio)octa-2,6-dienyl]silane
  参考文献：
  名称：

  Synthesis of Allylsilanes by Reductive Lithiation of Thioethers

  摘要：

  Although much work in reductive lithiation has been done, the utilization of allylthioethers bearing various substituents to prepare allylsilanes has not been explored. The main reason clearly stems from the anticipated lack of regioselectivity. We describe herein the first study on the regioselectivity of the reductive silylation involving dissymmetric allylthioethers. We surveyed a broad spectrum of parameters and showed that this process displays a great dependence of the reaction conditions. We also discovered that an electron transporter, DBB or naphthalene, can cleave THF at room temperature by sonication, to generate a strong base, 4-lithiobutoxide. This feature was successfully exploited to the straightforward synthesis of bis-silanes in one pot. Examples are provided for maximizing both the chemical yield and the regioselectivity of the reductive silylation through the tuning of the reaction conditions. By changing these conditions, several allylsilanes can be selectively synthesized from one thioether.

  DOI：

  10.1021/jo049237u

文献信息

• New transformations of substituted allene sulphoxides
  作者：Ian Cutting、Philip J. Parsons

  DOI：10.1016/s0040-4039(00)85927-4

  日期：1983.1

  The preparation and reactions of trimethylsilyl substituted allene sulphoxides are described. Allenes (2) rearrange on warming to give α,β-unsaturated thiol esters.

  描述了三甲基甲硅烷基取代的烯丙基亚砜的制备和反应。丙二烯（2）在升温时重新排列，得到α，β-不饱和硫醇酯。
• Unexpected cleavage of tetrahydrofuran by catalytic reductive lithiation
  作者：Stéphane Streiff、Nigel Ribeiro、Laurent Désaubry

  DOI：10.1039/b312972a

  日期：——

  DBB, an electron transporter, can open THF at room temperature under sonication without any Lewis acid activation. This feature was successfully exploited in the straightforward synthesis of bis-silanes.

  DBB 是一种电子传递器，可在室温下通过超声打开四氢呋喃，而无需任何路易斯酸活化。利用这一特点，我们成功地合成了双硅烷。
• CUTTING, I.;PARSONS, P. J., TETRAHEDRON LETT., 1983, 24, N 41, 4463-4464
  作者：CUTTING, I.、PARSONS, P. J.

  DOI：——

  日期：——
• Synthesis of Allylsilanes by Reductive Lithiation of Thioethers
  作者：Stéphane Streiff、Nigel Ribeiro、Laurent Désaubry

  DOI：10.1021/jo049237u

  日期：2004.10.1

  Although much work in reductive lithiation has been done, the utilization of allylthioethers bearing various substituents to prepare allylsilanes has not been explored. The main reason clearly stems from the anticipated lack of regioselectivity. We describe herein the first study on the regioselectivity of the reductive silylation involving dissymmetric allylthioethers. We surveyed a broad spectrum of parameters and showed that this process displays a great dependence of the reaction conditions. We also discovered that an electron transporter, DBB or naphthalene, can cleave THF at room temperature by sonication, to generate a strong base, 4-lithiobutoxide. This feature was successfully exploited to the straightforward synthesis of bis-silanes in one pot. Examples are provided for maximizing both the chemical yield and the regioselectivity of the reductive silylation through the tuning of the reaction conditions. By changing these conditions, several allylsilanes can be selectively synthesized from one thioether.