ethyl 2-butyl-3-hydroxy-3-methylnonanoate

• 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 2-butyl-3-hydroxy-3-methylnonanoate
• 化学式: C₁₆H₃₂O₃
• 分子量: 272.428
• InChiKey: ZDONNPCPRWTKPR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  19
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.94
• 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：

  DL-2-己酸乙酯 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 2-butyl-3-hydroxy-3-methylnonanoate
  参考文献：
  名称：

  Branched-chain carbohydrate lactones from a samarium(II) iodide-promoted serial deoxygenation-carbonyl addition reaction

  摘要：

  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).

  DOI：

  10.1021/jo00067a045

文献信息

• Flavour-release compositions
  申请人：PHILIP MORRIS INCORPORATED

  公开号：EP0064326A1

  公开（公告）日：1982-11-10

  This invention provides tobacco and foodstuff compositions which contain a hydroxy-substituted carboxylate compound as a flavorant additive. In one of its embodiments, this invention provides tobacco compositions which contain a hydroxy-substituted alkanoate flavorant additive such as ethyl 2-(2-butyl)-3-hydroxy-methyl-3-(3-phenyl)propionate: Under smoking conditions the above illustrated hydroxy-substituted alkanoate additive and its pyrolysis products flavor the mainstream and sidestream smoke.

  本发明提供了含有羟基取代的羧酸盐化合物作为香料添加剂的烟草和食品组合物。 在其中一个实施方案中，本发明提供了含有羟基取代的烷酸盐香料添加剂的烟草组合物，例如 2-(2-丁基)-3-羟基-甲基-3-(3-苯基)丙酸乙酯：在吸烟条件下，上述羟基取代的烷酸盐添加剂及其热解产物可为主流和侧流烟雾提供香味。
• The conversion of α- to β-hydroxy esters by a deoxygenation/condensation reaction promoted by samarium diiodide
  作者：Eric J. Enholm、Shujun Jiang

  DOI：10.1016/s0040-4039(00)74119-0

  日期：1992.1

  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.
• US4473085A
  申请人：——

  公开号：US4473085A

  公开（公告）日：1984-09-25
• US4607118A
  申请人：——

  公开号：US4607118A

  公开（公告）日：1986-08-19
• 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).