Z-(tert-butyl)(dimethyl)(2-methylidene-1-phenethyl-oct-3-enyloxy)silane | 845508-88-5

• 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: Z-(tert-butyl)(dimethyl)(2-methylidene-1-phenethyl-oct-3-enyloxy)silane
• 英文别名: tert-butyl-dimethyl-[(Z)-4-methylidene-1-phenyldec-5-en-3-yl]oxysilane
• CAS: 845508-88-5
• 化学式: C₂₃H₃₈OSi
• 分子量: 358.64
• InChiKey: QGTHXOPPNKVOPQ-QINSGFPZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.31
• 重原子数：
  25
• 可旋转键数：
  11
• 环数：
  1.0
• 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

• 作为反应物：
  描述：

  Z-(tert-butyl)(dimethyl)(2-methylidene-1-phenethyl-oct-3-enyloxy)silane 在 Grubbs catalyst first generation 作用下， 以 氘代苯 为溶剂， 生成 E-(tert-butyl)(dimethyl)(2-methylidene-1-phenethyl-oct-3-enyloxy)silane
  参考文献：
  名称：

  Equilibrium Control in Enyne Metathesis:  Crossover Studies and the Kinetic Reactivity of (E,Z)-1,3-Disubstituted-1,3-Dienes

  摘要：

  The stereoselectivity of diene bond formation in the ruthenium-carbene mediated intermolecular enyne metathesis was studied. Initial reaction between an alkyne and 1-hexene gave mixtures of E- and Z-isomers in the newly formed 1,3-diene. However, over time the mixtures equilibrated to form mostly the diene of the E-configuration. To evaluate individual reactivity of the E- and Z-dienes, they were independently synthesized. The E-diene was found to be kinetically-stable under nominal metathesis conditions while the Z-diene isomerized to the E-isomer. The Z-isomeric dienes were found to react with other alkenes to produce a new diene of E-configuration. A secondary metathesis mechanism involving ruthenium alkylidene intermediates was invoked to explain the dynamic stereochemistry observed in this study.

  DOI：

  10.1021/jo0482209
• 作为产物：
  描述：

  3-[(tert-butyl)(dimethyl)silanyloxy]-2-methylidene-5-phenylpentanol 在 草酰氯 、 双(三甲基硅烷基)氨基钾 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 Z-(tert-butyl)(dimethyl)(2-methylidene-1-phenethyl-oct-3-enyloxy)silane
  参考文献：
  名称：

  Equilibrium Control in Enyne Metathesis:  Crossover Studies and the Kinetic Reactivity of (E,Z)-1,3-Disubstituted-1,3-Dienes

  摘要：

  The stereoselectivity of diene bond formation in the ruthenium-carbene mediated intermolecular enyne metathesis was studied. Initial reaction between an alkyne and 1-hexene gave mixtures of E- and Z-isomers in the newly formed 1,3-diene. However, over time the mixtures equilibrated to form mostly the diene of the E-configuration. To evaluate individual reactivity of the E- and Z-dienes, they were independently synthesized. The E-diene was found to be kinetically-stable under nominal metathesis conditions while the Z-diene isomerized to the E-isomer. The Z-isomeric dienes were found to react with other alkenes to produce a new diene of E-configuration. A secondary metathesis mechanism involving ruthenium alkylidene intermediates was invoked to explain the dynamic stereochemistry observed in this study.

  DOI：

  10.1021/jo0482209