(2R,4R)-1-hydroxy-5-((4-methoxybenzyl)oxy)-2,4-dimethylpentan-3-one | 1453868-14-8

• 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: (2R,4R)-1-hydroxy-5-((4-methoxybenzyl)oxy)-2,4-dimethylpentan-3-one
• CAS: 1453868-14-8
• 化学式: C₁₅H₂₂O₄
• 分子量: 266.337
• InChiKey: JQIDDCGPIHBSLY-VXGBXAGGSA-N

物化性质

• 沸点：
  404.8±30.0 °C(predicted)
• 密度：
  1.078±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.05
• 重原子数：
  19.0
• 可旋转键数：
  8.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  55.76
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (2R,4R)-1-hydroxy-5-((4-methoxybenzyl)oxy)-2,4-dimethylpentan-3-one 在 sodium hypochlorite 、 2,2,6,6-四甲基哌啶氧化物 、 三乙酰氧基硼氢化钠 、 碳酸氢钠 、 potassium bromide 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 0.33h， 生成 (2S,3R,4R)-3-hydroxy-5-((4-methoxybenzyl)oxy)-2,4-dimethylpentanal
  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：

  methyl (R)-N-methyl-N-methoxy-3-(4-methoxybenzyloxy)-2-methylpropanoate 在 titanium(IV) isopropylate 、 四氯化钛 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.86h， 生成 (2R,4R)-1-hydroxy-5-((4-methoxybenzyl)oxy)-2,4-dimethylpentan-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