ethyl 3-hydroxy-2,3-dimethyl-5-phenylpentanoate | 889-65-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ethyl 3-hydroxy-2,3-dimethyl-5-phenylpentanoate
• 英文别名: Ethyl 3-hydroxy-2,3-dimethyl-5-phenylpentanoate
• CAS: 889-65-6
• 化学式: C₁₅H₂₂O₃
• 分子量: 250.338
• InChiKey: PGURRMJYBVLKGU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  乳酸乙酯 在 吡啶 、 六甲基磷酰三胺 、 samarium diiodide 作用下， 以 四氢呋喃 、 氯仿 为溶剂， 反应 1.0h， 生成 ethyl 3-hydroxy-2,3-dimethyl-5-phenylpentanoate
  参考文献：
  名称：

  The conversion of α- to β-hydroxy esters by a deoxygenation/condensation reaction promoted by samarium diiodide

  摘要：

  A mild reaction sequence begins by transforming an alpha-hydroxy ester to an alpha-benzoate ester. Next, the alpha-benzoate ester is both reductively deoxygenated with samarium diiodide and subsequently condensed with a ketone present in the reaction mixture to afford a beta-hydroxy ester with two new alkyl appendages.

  DOI：

  10.1016/s0040-4039(00)74119-0

文献信息

• Branched-chain carbohydrate lactones from a samarium(II) iodide-promoted serial deoxygenation-carbonyl addition reaction
  作者：Eric J. Enholm、Shujun Jiang、Khalil Abboud

  DOI：10.1021/jo00067a045

  日期：1993.7

  A new deoxygenation-carbonyl addition reaction mediated by samarium(II) iodide (SmI2) in THF/HMPA was examined with carbohydrate lactones and several substrates containing an alpha-alkoxy carboxylic ester. In a single reaction, these compounds were deoxygenated and subsequently coupled to several ketones by a carbonyl addition reaction. The first reactions studied simple ester and ketone adducts which were later elaborated to more complex optically active carbohydrate lactones appended to terpene ketones. Simple esters smoothly afforded beta-hydroxy carbonyl products. Fully benzoate-protected 3-deoxycarbohydrate lactones were reacted with simple ketones to produce C2-branched sugars. The attendant carbonyl addition to the least sterically hindered face of the aldonolactone provided the major products. Moderate diastereoselectivities (up to 5:1) were observed in the simple ketone products as determined by difference NOE studies. Finally, the terpene ketones, (-)-menthone or (+)-dihydrocarvone, were coupled to 3-deoxycarbohydrate lactones which gave C2-branched sugars with very high diastereoselectivities (up to 99:1).