(E)-4-phenyl-2-(dimethylphenylsilyl)pent-3-enol | 175787-57-2

• 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-(dimethylphenylsilyl)pent-3-enol
• 英文别名: (E)-2-[dimethyl(phenyl)silyl]-4-phenylpent-3-en-1-ol
• CAS: 175787-57-2
• 化学式: C₁₉H₂₄OSi
• 分子量: 296.484
• InChiKey: QJMBZXBINANCMS-JQIJEIRASA-N

物化性质

• 沸点：
  426.9±45.0 °C(Predicted)
• 密度：
  1.01±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.07
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (E)-4-phenyl-2-(dimethylphenylsilyl)pent-3-enol 在 titanium(IV) isopropylate 、 叔丁基过氧化氢 、 溶剂黄146 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 28.0h， 生成 (E)-4-hydroxy-1-methyl-1-phenyl-2-butene-1-ol
  参考文献：
  名称：

  2-甲硅烷基-3-链烯醇的环氧化和环丙烷化。1,2-不对称感应的研究

  摘要：

  已经显示，通过底物可指导的反应，在高1,2-立体控制下，发生了2-甲硅烷基-3-链烯醇的环氧化和环丙烷化反应。无论SYN和抗氧化物，因此可从Ë和ž -allylsilanes。这与缺乏配位基团的烯丙基硅烷通常观察到的结果相反。

  DOI：

  10.1016/0040-4039(95)02386-0
• 作为产物：
  描述：

  (E)-2-(Dimethyl-phenyl-silanyl)-4-phenyl-pent-3-enoic acid ethyl ester 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 0.5h， 以85%的产率得到(E)-4-phenyl-2-(dimethylphenylsilyl)pent-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

• Studies on the Mercury-Desilylation of Chiral Cyclopropylmethylsilanes - A Stereocontrolled Access to Carba-Sugars
  作者：Yannick Landais、Liliana Parra-Rapado

  DOI：10.1002/(sici)1099-0690(200002)2000:3<401::aid-ejoc401>3.0.co;2-m

  日期：2000.2

  Mercury-desilylation of cyclopropylmethylsilanes affords a stereospecific access to homoallylic mercury intermediates, which can be elaborated further. This strategy is illustrated with a short access to carba-furanoses and carba-C-disaccharides.

  环丙基甲基硅烷的汞去甲硅烷基化提供了对均烯丙基汞中间体的立体有择访问，可以进一步详细说明。该策略通过对carba-呋喃糖和carba-C-二糖的短暂访问来说明。
• 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.
• Epoxidation and cyclopropanation of 2-silyl-3-alkenols. A study of 1,2-asymmetric induction
  作者：Yannick Landais、Liliana Parra-Rapado

  DOI：10.1016/0040-4039(95)02386-0

  日期：1996.2

  Epoxidation and cyclopropanation of 2-silyl-3-alkenols have been shown to occur with high 1,2-stereocontrol through substrate directable reactions. Both syn and anti epoxides are thus available from E and Z-allylsilanes. This contrasts with the results usually observed for allylsilanes lacking a coordinating group.

  已经显示，通过底物可指导的反应，在高1,2-立体控制下，发生了2-甲硅烷基-3-链烯醇的环氧化和环丙烷化反应。无论SYN和抗氧化物，因此可从Ë和ž -allylsilanes。这与缺乏配位基团的烯丙基硅烷通常观察到的结果相反。