tert-butyl 3-hydroxy-5-oxo-3-(trifluoromethyl)pentanoate | 956398-51-9

• 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: tert-butyl 3-hydroxy-5-oxo-3-(trifluoromethyl)pentanoate
• CAS: 956398-51-9
• 化学式: C₁₀H₁₅F₃O₄
• 分子量: 256.222
• InChiKey: PLOYUJUZLPJOTM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  tert-butyl 3-hydroxy-5-oxo-3-(trifluoromethyl)pentanoate 在 盐酸 、 三乙酰氧基硼氢化钠 、 三氟乙酸 作用下， 以 二氯甲烷 、 乙腈 、 苯 为溶剂， 反应 52.5h， 生成 (4S)-4-hydroxy-4-(trifluoromethyl)tetrahydro-2H-pyran-2-one
  参考文献：
  名称：

  New synthetic approach to mevalonate and mevaldate fluoroanalogues

  摘要：

  6,6,6-Tri- and 6,6-difluoromevalonate were synthesized by new method starting from the corresponding beta-alkoxyvinyl polyfluromethyl ketones. Enantiomers of fluoromevalonates were obtained by column chromatography separation of diastereomeric (S)-(-)-1-phenylethylamides of fluoromevalonates with the following hydrolysis. Racemic 6,6,6-tri- and 6,6-difluoromevaldates were also prepared. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.08.015
• 作为产物：
  描述：

  tert-butyl (E)-5-ethoxy-3-hydroxy-3-(trifluoromethyl)-4-pentenoate 在 盐酸 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以56%的产率得到tert-butyl 3-hydroxy-5-oxo-3-(trifluoromethyl)pentanoate
  参考文献：
  名称：

  New synthetic approach to mevalonate and mevaldate fluoroanalogues

  摘要：

  6,6,6-Tri- and 6,6-difluoromevalonate were synthesized by new method starting from the corresponding beta-alkoxyvinyl polyfluromethyl ketones. Enantiomers of fluoromevalonates were obtained by column chromatography separation of diastereomeric (S)-(-)-1-phenylethylamides of fluoromevalonates with the following hydrolysis. Racemic 6,6,6-tri- and 6,6-difluoromevaldates were also prepared. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.08.015

文献信息

• New synthetic approach to mevalonate and mevaldate fluoroanalogues
  作者：Ivan S. Kondratov、Igor I. Gerus、Valery P. Kukhar、Olga V. Manoilenko

  DOI：10.1016/j.tetasy.2007.08.015

  日期：2007.8

  6,6,6-Tri- and 6,6-difluoromevalonate were synthesized by new method starting from the corresponding beta-alkoxyvinyl polyfluromethyl ketones. Enantiomers of fluoromevalonates were obtained by column chromatography separation of diastereomeric (S)-(-)-1-phenylethylamides of fluoromevalonates with the following hydrolysis. Racemic 6,6,6-tri- and 6,6-difluoromevaldates were also prepared. (c) 2007 Elsevier Ltd. All rights reserved.