4-phenyl-2-trifluoromethylbutane-1,2,4-triol | 404576-87-0

• 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: 4-phenyl-2-trifluoromethylbutane-1,2,4-triol
• 英文别名: 4-Phenyl-2-(trifluoromethyl)butane-1,2,4-triol；4-phenyl-2-(trifluoromethyl)butane-1,2,4-triol
• CAS: 404576-87-0
• 化学式: C₁₁H₁₃F₃O₃
• 分子量: 250.218
• InChiKey: JHPDTILHUDNGTE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  60.7
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  methyl 4-phenyl-2-hydroxy-4-oxo-2-(trifluoromethyl)butanoate 在 sodium tetrahydroborate 作用下， 以 甲醇 、 乙醚 为溶剂， 生成 4-phenyl-2-trifluoromethylbutane-1,2,4-triol 、 methyl 4-phenyl-2,4-dihydroxy-2-(trifluoromethyl)butanoate
  参考文献：
  名称：

  Fluorinated butanolides and butenolides

  摘要：

  2-Hydroxy-2-trifluoromethylbutan-4-olides (8-10) were prepared by a four step synthesis starting from a ketone and methyl 3,3,3-trifluoropyruvate (1) as a building block. Uncatalyzed chemospecific aldolization of ketones with 1 afforded 2 hydroxy-4-oxoesters 2-4 that were selectively reduced at the oxo group by sodium borohydride to the corresponding 2,4-dihydroxyesters 5-7. Acid-catalyzed cyclization of dihydroxysters 5-7 to lactones 8-10 was strongly dependent on their structure. The lactone-ring closure with the hydroxy group at the hydroxylated cyclopentane ring afforded bicyclic lactone (10) with cyclopentane cis-annulation. 2-Hydroxy-2 trifluoromethylbutanolides appeared to be highly resistent to dehydration or eliminations of the corresponding mesylates or triflates. (C) 2001 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s0022-1139(01)00450-x

文献信息

• Fluorinated butanolides and butenolides
  作者：Oldřich Paleta、Jiřı́ Paleček、Bohumil Dolenský

  DOI：10.1016/s0022-1139(01)00450-x

  日期：2001.10

  2-Hydroxy-2-trifluoromethylbutan-4-olides (8-10) were prepared by a four step synthesis starting from a ketone and methyl 3,3,3-trifluoropyruvate (1) as a building block. Uncatalyzed chemospecific aldolization of ketones with 1 afforded 2 hydroxy-4-oxoesters 2-4 that were selectively reduced at the oxo group by sodium borohydride to the corresponding 2,4-dihydroxyesters 5-7. Acid-catalyzed cyclization of dihydroxysters 5-7 to lactones 8-10 was strongly dependent on their structure. The lactone-ring closure with the hydroxy group at the hydroxylated cyclopentane ring afforded bicyclic lactone (10) with cyclopentane cis-annulation. 2-Hydroxy-2 trifluoromethylbutanolides appeared to be highly resistent to dehydration or eliminations of the corresponding mesylates or triflates. (C) 2001 Elsevier Science B.V. All rights reserved.