(1S)-1-[(2S)-2-trimethylsilyloxiran-2-yl]pentan-1-ol | 143100-81-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S)-1-[(2S)-2-trimethylsilyloxiran-2-yl]pentan-1-ol
• CAS: 143100-81-6
• 化学式: C₁₀H₂₂O₂Si
• 分子量: 202.369
• InChiKey: OVMHHBBEDCLUPW-UWVGGRQHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.18
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  1.0
• 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

• 作为产物：
  描述：

  (Z)-2-trimethylsilyl-2-heptene 在 titanium(IV) isopropylate 、 4 A molecular sieve 氧气 、 tetraphenylporphyrin 作用下， 生成 (1S)-1-[(2S)-2-trimethylsilyloxiran-2-yl]pentan-1-ol
  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

文献信息

• Highly Regio- and Diastereoselective One-Pot Synthesis of Silyl Epoxy Alcohols and Vinylsilanes by Direct Hydroxy-Epoxidation
  作者：Waldemar Adam、Markus J. Richter

  DOI：10.1021/jo00091a021

  日期：1994.6

  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.
• The role of trimethylsilyl group in highly stereoselective eposidation of allylic alcohols
  作者：Hiroki Tomioka、Toshifumi Suzuki、Koichiro Oshima、Hitosi Nozaki

  DOI：10.1016/s0040-4039(00)87622-4

  日期：1982.1
• Highly regio - and diastereoselective synthesis of epoxy alcohols directly from vinyl silanes by photo-oxygenation and titanium-catalyzed oxygen transfer
  作者：Waldemar Adam、Markus Richter

  DOI：10.1016/s0040-4039(00)92663-7

  日期：1992.6

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