trans-dimethyl(3-phenethyloxiran-2-yl)(phenyl)silane

• 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: trans-dimethyl(3-phenethyloxiran-2-yl)(phenyl)silane
• 英文别名: dimethyl-phenyl-[(2S,3S)-3-(2-phenylethyl)oxiran-2-yl]silane
• 化学式: C₁₈H₂₂OSi
• 分子量: 282.458
• InChiKey: MKOWLYKGSLHYGM-ROUUACIJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.54
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-溴丙烯 、 trans-dimethyl(3-phenethyloxiran-2-yl)(phenyl)silane 在 叔丁基锂 、 copper(l) cyanide 作用下， 以 乙醚 、 正己烷 为溶剂， 反应 4.0h， 以48%的产率得到syn-4-(dimethyl(phenyl)silyl)-5-methyl-1-phenylhex-5-en-3-ol
  参考文献：
  名称：

  syn-β-Hydroxyallylic Silanes from Terminal Epoxide α-Lithiation–Silylation and Alkenylation: Application to the Tetrahydrofuran Portion of the Lytophilippines

  摘要：

  Lithiation-in situ silylation of terminal epoxides using lithium 2,2,6,6-tetramethylpiperidide in combination with phenyldimethyl(or diethyl)silyl chloride provides a direct process for the synthesis of trans-alpha,beta-epoxysilanes, which undergo alpha-ring opening with alkenylcoppers to give syn-beta-hydroxyallylic silanes. The chemistry is applied in an annulation approach to the C-10-C-19 tetrahydrofuran-containing portion of the lytophilippines.

  DOI：

  10.1021/ol3018853
• 作为产物：
  描述：

  1,2-Epoxy-4-phenylbutane 、 苯基二甲基氯硅烷 在 2,2,6,6-四甲基哌啶 、 正丁基锂 作用下， 以 正己烷 、 甲基叔丁基醚 为溶剂， 反应 16.0h， 以63%的产率得到trans-dimethyl(3-phenethyloxiran-2-yl)(phenyl)silane
  参考文献：
  名称：

  syn-β-Hydroxyallylic Silanes from Terminal Epoxide α-Lithiation–Silylation and Alkenylation: Application to the Tetrahydrofuran Portion of the Lytophilippines

  摘要：

  Lithiation-in situ silylation of terminal epoxides using lithium 2,2,6,6-tetramethylpiperidide in combination with phenyldimethyl(or diethyl)silyl chloride provides a direct process for the synthesis of trans-alpha,beta-epoxysilanes, which undergo alpha-ring opening with alkenylcoppers to give syn-beta-hydroxyallylic silanes. The chemistry is applied in an annulation approach to the C-10-C-19 tetrahydrofuran-containing portion of the lytophilippines.

  DOI：

  10.1021/ol3018853

文献信息

• <i>syn</i>-β-Hydroxyallylic Silanes from Terminal Epoxide α-Lithiation–Silylation and Alkenylation: Application to the Tetrahydrofuran Portion of the Lytophilippines
  作者：David M. Hodgson、Saifullah Salik

  DOI：10.1021/ol3018853

  日期：2012.9.7

  Lithiation-in situ silylation of terminal epoxides using lithium 2,2,6,6-tetramethylpiperidide in combination with phenyldimethyl(or diethyl)silyl chloride provides a direct process for the synthesis of trans-alpha,beta-epoxysilanes, which undergo alpha-ring opening with alkenylcoppers to give syn-beta-hydroxyallylic silanes. The chemistry is applied in an annulation approach to the C-10-C-19 tetrahydrofuran-containing portion of the lytophilippines.