((1S,2S)-2-(2-(benzyloxy)ethyl)cyclopropyl)di-tert-butoxysilanol

• 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: ((1S,2S)-2-(2-(benzyloxy)ethyl)cyclopropyl)di-tert-butoxysilanol
• 英文别名: hydroxy-bis[(2-methylpropan-2-yl)oxy]-[(1R,2R)-2-(2-phenylmethoxyethyl)cyclopropyl]silane
• 化学式: C₂₀H₃₄O₄Si
• 分子量: 366.573
• InChiKey: HGFNICPTKZDABT-QZTJIDSGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.54
• 重原子数：
  25
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  间氯溴苯 、 ((1S,2S)-2-(2-(benzyloxy)ethyl)cyclopropyl)di-tert-butoxysilanol 在 三氟化硼乙醚 、 四(三苯基膦)钯 、 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 16.25h， 以80%的产率得到1-((1S,2R)-2-(2-(benzyloxy)ethyl)cyclopropyl)-3-chlorobenzene
  参考文献：
  名称：

  Dual Role of Silanol Groups in Cyclopropanation and Hiyama−Denmark Cross-Coupling Reactions

  摘要：

  Di-tert-butoxy(alkenyl)silanols serve as substrates in the Simmons-Smith cyclopropanation reaction furnishing the corresponding di-tert-butoxy(cyclopropyl)silanols, which may be included in a Hiyama-Denmark cross-coupling reaction. The silanol group bears two distinct roles as it provides a directing group during the cyclopropanation and mediates the transmetalation event in the cross-coupling. The nature of the ligands on the silicon atom had a profound effect on reactivity in the cross-coupling, whereby substituting the alkoxide groups for fluorides allowed for efficient cross-coupling.

  DOI：

  10.1021/ol1002863
• 作为产物：
  描述：

  二碘甲烷 、 (E)-(4-(benzyloxy)but-1-enyl)di-tert-butoxysilanol 在 diethylzinc 作用下， 以 乙二醇二甲醚 、 二氯甲烷 为溶剂， 反应 0.17h， 以98%的产率得到((1S,2S)-2-(2-(benzyloxy)ethyl)cyclopropyl)di-tert-butoxysilanol
  参考文献：
  名称：

  Dual Role of Silanol Groups in Cyclopropanation and Hiyama−Denmark Cross-Coupling Reactions

  摘要：

  Di-tert-butoxy(alkenyl)silanols serve as substrates in the Simmons-Smith cyclopropanation reaction furnishing the corresponding di-tert-butoxy(cyclopropyl)silanols, which may be included in a Hiyama-Denmark cross-coupling reaction. The silanol group bears two distinct roles as it provides a directing group during the cyclopropanation and mediates the transmetalation event in the cross-coupling. The nature of the ligands on the silicon atom had a profound effect on reactivity in the cross-coupling, whereby substituting the alkoxide groups for fluorides allowed for efficient cross-coupling.

  DOI：

  10.1021/ol1002863

文献信息

• Dual Role of Silanol Groups in Cyclopropanation and Hiyama−Denmark Cross-Coupling Reactions
  作者：Louis-Philippe B. Beaulieu、Lukas B. Delvos、André B. Charette

  DOI：10.1021/ol1002863

  日期：2010.3.19

  Di-tert-butoxy(alkenyl)silanols serve as substrates in the Simmons-Smith cyclopropanation reaction furnishing the corresponding di-tert-butoxy(cyclopropyl)silanols, which may be included in a Hiyama-Denmark cross-coupling reaction. The silanol group bears two distinct roles as it provides a directing group during the cyclopropanation and mediates the transmetalation event in the cross-coupling. The nature of the ligands on the silicon atom had a profound effect on reactivity in the cross-coupling, whereby substituting the alkoxide groups for fluorides allowed for efficient cross-coupling.