(E)-4-phenyl-2-(dimethyl-(4-methylthien-2-yl)silyl)but-3-enol | 189275-32-9

• 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: (E)-4-phenyl-2-(dimethyl-(4-methylthien-2-yl)silyl)but-3-enol
• 英文别名: (E)-2-[dimethyl-(5-methylthiophen-2-yl)silyl]-4-phenylbut-3-en-1-ol
• CAS: 189275-32-9
• 化学式: C₁₇H₂₂OSSi
• 分子量: 302.513
• InChiKey: ZTRGKDZYECYKKF-ZHACJKMWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.05
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  48.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-4-phenyl-2-(dimethyl-(4-methylthien-2-yl)silyl)but-3-enol 在 偶氮二异丁腈 、 三正丁基氢锡 、 potassium carbonate 作用下， 以 乙醚 、 苯 为溶剂， 反应 170.0h， 生成 Dimethyl-(5-methyl-thiophen-2-yl)-((3S,5S)-5-phenyl-tetrahydro-furan-3-yl)-silane
  参考文献：
  名称：

  Electrophilic 5-endo-trig cyclisations of 2-silyl-3-alkenols. A stereoselective route to polysubstituted tetrahydrofurans

  摘要：

  Electrophilic 5-endo-trig cyclisations of allylsilanes have been carried out leading to tri- and tetrasubstituted tetrahydrofurans with reasonable fields and excellent diastereoselectivities. A rationalization of both the regio- and the stereoselectivity has been proposed. A silicon group having a thienyl fragment attached to the silicon has also been devised was shown to be oxidized under both electrophilic and nucleophilic conditions. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00109-9
• 作为产物：
  描述：

  ethyl (E)-2-(dimethyl(5-methylthien-2-yl)silyl)-4-phenylbut-3-enoate 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 0.5h， 以92%的产率得到(E)-4-phenyl-2-(dimethyl-(4-methylthien-2-yl)silyl)but-3-enol
  参考文献：
  名称：

  Electrophilic 5-endo-trig cyclisations of 2-silyl-3-alkenols. A stereoselective route to polysubstituted tetrahydrofurans

  摘要：

  Electrophilic 5-endo-trig cyclisations of allylsilanes have been carried out leading to tri- and tetrasubstituted tetrahydrofurans with reasonable fields and excellent diastereoselectivities. A rationalization of both the regio- and the stereoselectivity has been proposed. A silicon group having a thienyl fragment attached to the silicon has also been devised was shown to be oxidized under both electrophilic and nucleophilic conditions. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00109-9

文献信息

• Stereoselective synthesis of substituted tetrahydrofurans via selenoetherification of 2-silyl-3-alkenols. A study of allylic stereocontrol
  作者：Yannick Landais、Denis Planchenault、Valéry Weber

  DOI：10.1016/0040-4039(95)00410-e

  日期：1995.4

  5-endo-trig selenoetherifications of substituted 2-silyl-3-alkenols gave tri- or tetrasubstituted 2,4-cis tetrahydrofurans in moderate to good yields with excellent diastereoselectivities. Opposite stereoselectivities were found with an analogous allylic diol. A transition state model has been proposed to rationalize this stereochemical outcome.

  5 -内trig的取代的2-甲硅烷基-3-烯醇的selenoetherifications得到三-或四取代的2,4-顺式的四氢呋喃在中度至良好的产率具有优良的非对映选择性。发现与类似的烯丙基二醇相反的立体选择性。已经提出了过渡状态模型来合理化这种立体化学结果。
• Electrophilic 5-endo-trig cyclisations of 2-silyl-3-alkenols. A stereoselective route to polysubstituted tetrahydrofurans
  作者：Olivier Andrey、Laurent Ducry、Yannick Landais、Denis Planchenault、Valéry Weber

  DOI：10.1016/s0040-4020(97)00109-9

  日期：1997.3

  Electrophilic 5-endo-trig cyclisations of allylsilanes have been carried out leading to tri- and tetrasubstituted tetrahydrofurans with reasonable fields and excellent diastereoselectivities. A rationalization of both the regio- and the stereoselectivity has been proposed. A silicon group having a thienyl fragment attached to the silicon has also been devised was shown to be oxidized under both electrophilic and nucleophilic conditions. (C) 1997 Elsevier Science Ltd.