(R)-1-((tert-butyldimethylsilyl)oxy)-5-hydroxy-2-methylpentan-3-one | 1453868-04-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (R)-1-((tert-butyldimethylsilyl)oxy)-5-hydroxy-2-methylpentan-3-one
• CAS: 1453868-04-6
• 化学式: C₁₂H₂₆O₃Si
• 分子量: 246.422
• InChiKey: DSRUUBSDZCKAMU-SNVBAGLBSA-N

物化性质

• 沸点：
  299.1±20.0 °C(predicted)
• 密度：
  0.934±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  16.0
• 可旋转键数：
  6.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  46.53
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (R)-1-((tert-butyldimethylsilyl)oxy)-5-hydroxy-2-methylpentan-3-one 在 咪唑 、 四丁基氟化铵 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 16.0h， 生成 (3S,4R)-5-((tert-butyldimethylsilyl)oxy)-4-methylpentane-1,3-diol
  参考文献：
  名称：

  Stereocontrolled Synthesis of 1,3-Diols from Enones: Cooperative Lewis Base-Mediated Intramolecular Carbonyl Hydrosilylations

  摘要：

  A streamlined synthesis of beta-hydroxy ketone substrates has been developed to further investigate a recently discovered cooperative Lewis base-mediated intramolecular carbonyl hydrosilylation reaction. The synthesis features an enone beta-borylation/oxidation sequence that has proven to be quite general and high-yielding. This has allowed for additional investigations into the diastereoselectivity of the hydrosilylation reaction through the preparation of important polyketide fragments.

  DOI：

  10.1021/jo401293a
• 作为产物：
  描述：

  (R)-1-((tert-butyldimethylsilyl)oxy)-2-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pentan-3-one 在 sodium perborate monohydrate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 3.0h， 以100%的产率得到(R)-1-((tert-butyldimethylsilyl)oxy)-5-hydroxy-2-methylpentan-3-one
  参考文献：
  名称：

  Stereocontrolled Synthesis of 1,3-Diols from Enones: Cooperative Lewis Base-Mediated Intramolecular Carbonyl Hydrosilylations

  摘要：

  A streamlined synthesis of beta-hydroxy ketone substrates has been developed to further investigate a recently discovered cooperative Lewis base-mediated intramolecular carbonyl hydrosilylation reaction. The synthesis features an enone beta-borylation/oxidation sequence that has proven to be quite general and high-yielding. This has allowed for additional investigations into the diastereoselectivity of the hydrosilylation reaction through the preparation of important polyketide fragments.

  DOI：

  10.1021/jo401293a