Dimethyl(7-oxabicyclo[4.1.0]heptan-1-yl)silane | 562077-68-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧杂环己烷
• 英文名称: Dimethyl(7-oxabicyclo[4.1.0]heptan-1-yl)silane
• 英文别名: dimethyl(7-oxabicyclo[4.1.0]heptan-1-yl)silane
• CAS: 562077-68-3
• 化学式: C₈H₁₆OSi
• 分子量: 156.3
• InChiKey: JITCKHKWRRKGSH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.72
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 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：

  Dimethyl(7-oxabicyclo[4.1.0]heptan-1-yl)silane 在 dihydrogen hexachloroplatinate 、 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 生成 (1S,2R)-2-[dimethyl(propan-2-yloxy)silyl]cyclohexan-1-ol
  参考文献：
  名称：

  Desilylation versus elimination reactions of β-hydroxysilanes: effect of substituents on silicon

  摘要：

  beta-Hydroxy(trimethyl)silanes undergo stereospecific desilylation reactions to give alcohols using KOt-Bu in DMSO:H2O, but the reactions are very slow. In this work, desilylation reactions are facilitated using beta-hydroxysilanes with (i-PrO)Me2Si, HMe2Si, or HOMe2Si groups (e.g. 9-->11). The (HO)Me2Si compound (10) (or alkoxide) was shown to be an intermediate, and undergoes beta elimination less readily than the Me3Si compound (7). (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)00540-9
• 作为产物：
  描述：

  1-碘环己烯 在 disodium hydrogenphosphate 、 叔丁基锂 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 、 二氯甲烷 为溶剂， 反应 6.75h， 生成 Dimethyl(7-oxabicyclo[4.1.0]heptan-1-yl)silane
  参考文献：
  名称：

  Desilylation versus elimination reactions of β-hydroxysilanes: effect of substituents on silicon

  摘要：

  beta-Hydroxy(trimethyl)silanes undergo stereospecific desilylation reactions to give alcohols using KOt-Bu in DMSO:H2O, but the reactions are very slow. In this work, desilylation reactions are facilitated using beta-hydroxysilanes with (i-PrO)Me2Si, HMe2Si, or HOMe2Si groups (e.g. 9-->11). The (HO)Me2Si compound (10) (or alkoxide) was shown to be an intermediate, and undergoes beta elimination less readily than the Me3Si compound (7). (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)00540-9

文献信息

• Desilylation versus elimination reactions of β-hydroxysilanes: effect of substituents on silicon
  作者：Paul F. Hudrlik、Petros Gebreselassie、Laykea Tafesse、Anne M. Hudrlik

  DOI：10.1016/s0040-4039(03)00540-9

  日期：2003.4

  beta-Hydroxy(trimethyl)silanes undergo stereospecific desilylation reactions to give alcohols using KOt-Bu in DMSO:H2O, but the reactions are very slow. In this work, desilylation reactions are facilitated using beta-hydroxysilanes with (i-PrO)Me2Si, HMe2Si, or HOMe2Si groups (e.g. 9-->11). The (HO)Me2Si compound (10) (or alkoxide) was shown to be an intermediate, and undergoes beta elimination less readily than the Me3Si compound (7). (C) 2003 Elsevier Science Ltd. All rights reserved.