4-phenyl-2-hydroxy-2-(trifluoromethyl)butan-4-olide | 404576-89-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: 4-phenyl-2-hydroxy-2-(trifluoromethyl)butan-4-olide
• 英文别名: 3-hydroxy-5-phenyl-3-(trifluoromethyl)oxolan-2-one
• CAS: 404576-89-2
• 化学式: C₁₁H₉F₃O₃
• 分子量: 246.186
• InChiKey: STEMGBJJJCYXNR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.97
• 重原子数：
  17.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  46.53
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  4-phenyl-2-hydroxy-2-(trifluoromethyl)butan-4-olide 在 吡啶 、 氯化亚砜 作用下， 反应 720.0h， 以12%的产率得到2-chloro-4-phenyl-2-(trifluoromethyl)butan-4-olide
  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
• 作为产物：
  描述：

  methyl 4-phenyl-2-hydroxy-4-oxo-2-(trifluoromethyl)butanoate 在 sodium tetrahydroborate 、 对甲苯磺酸 作用下， 以 甲醇 、 乙醚 、 1,4-二氧六环 为溶剂， 反应 168.0h， 以3.27 g的产率得到4-phenyl-2-hydroxy-2-(trifluoromethyl)butan-4-olide
  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