(1α,2β,6β)-1-(trimethylsilyl)-7-oxabicyclo<4.1.0.>heptan-2-ol | 143100-78-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1α,2β,6β)-1-(trimethylsilyl)-7-oxabicyclo<4.1.0.>heptan-2-ol
• 英文别名: 2,3-epoxy-2-trimethylsilylcyclohexanol；(1S,2R,6S)-1-trimethylsilyl-7-oxabicyclo[4.1.0]heptan-2-ol
• CAS: 143100-78-1
• 化学式: C₉H₁₈O₂Si
• 分子量: 186.326
• InChiKey: ZJOKQTXKEXTISL-VGMNWLOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.55
• 重原子数：
  12
• 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：
  32.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1α,2β,6β)-1-(trimethylsilyl)-7-oxabicyclo<4.1.0.>heptan-2-ol 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 生成 (1R*,2R*,3S*)-2,3-epoxycyclohexanol
  参考文献：
  名称：

  Highly regio - and diastereoselective synthesis of epoxy alcohols directly from vinyl silanes by photo-oxygenation and titanium-catalyzed oxygen transfer

  摘要：

  The photooxygenation of vinyl silanes 1 in the presence of Ti(OiPr)4 afforded

  DOI：

  10.1016/s0040-4039(00)92663-7
• 作为产物：
  描述：

  2-(三甲基甲硅烷基)环己-2-烯-1-醇 在 碳酸氢钠 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 生成 (1α,2β,6β)-1-(trimethylsilyl)-7-oxabicyclo<4.1.0.>heptan-2-ol 、 (1α,2α,6β)-1-(trimethylsilyl)-7-oxabicyclo<4.1.0.>heptan-2-ol
  参考文献：
  名称：

  Highly Regio- and Diastereoselective One-Pot Synthesis of Silyl Epoxy Alcohols and Vinylsilanes by Direct Hydroxy-Epoxidation

  摘要：

  A direct synthesis of silyl epoxy alcohols from vinyl silanes is described. It consists of the regioselective ene reaction of the vinylsilanes with singlet oxygen, which proceeds with predominant hydrogen abstraction at the position geminal to the silyl group. The resulting silyl allylic hydroperoxides were treated, without isolation, subsequently with Ti(O-i-Pr)(4) to afford the silyl epoxy alcohols in good yields and very high diastereomeric ratios, which ranged from 93:7 to greater than 97:3. Alternatively, the vinylsilanes were photooxygenated directly in the presence of the titanium catalyst and the silyl epoxy alcohols obtained in good yields. The method was applied to di- and trisubstituted acyclic vinylsilanes with a methyl group geminal to silicon and cyclic derivatives all give consistently good results. In this novel hydroxy-epoxidation, the regioselectivity of the singlet oxygen ene reaction as well as the diastereoselectivity of the oxygen transfer can be controlled by the steering effects of the silyl group.

  DOI：

  10.1021/jo00091a021

文献信息

• Stereochemically defined cyclohexanediois through the regioselective ring-opening of silylated epoxy alcohols
  作者：Waldemar Adam、Michael Prein、Markus J. Richter

  DOI：10.1016/0040-4020(95)00977-9

  日期：1996.1

  The nucleophilic ring-opening of the silylated epoxy alcohol 2 leads to highly functionalized building blocks of defined stereochemistry, whereby the regioselectivity may be controlled through the proper choice of the nucleophile and the reaction conditions.

  甲硅烷基化的环氧醇的亲核开环2所导致高度官能化构建限定立体化学，由此所述区域选择性可通过亲核试剂的适当选择和反应条件来控制的块。