2-hydroxy-2-(trifluoromethyl)pentan-4-olide | 126953-87-5

• 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: 2-hydroxy-2-(trifluoromethyl)pentan-4-olide
• 英文别名: 2-Hydroxy-2-trifluoromethyl-4-methyl-4-butanolide；3-hydroxy-5-methyl-3-(trifluoromethyl)oxolan-2-one
• CAS: 126953-87-5
• 化学式: C₆H₇F₃O₃
• 分子量: 184.115
• InChiKey: MONOBJASYTUNNI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.62
• 重原子数：
  12.0
• 可旋转键数：
  0.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  46.53
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  2-羟基-4-氧代-2-(三氟甲基)戊酸甲酯 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 5.0h， 以1.43 g的产率得到2-hydroxy-2-(trifluoromethyl)pentan-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

文献信息

• The lactonization of esters of 2-hydroxy-2-trifluoromethyl-4-pentenoic acids
  作者：A. S. Golubev、I. V. Karelin、V. G. Andreev、A. F. Kolomiets、A. V. Fokin、N. P. Aktaev

  DOI：10.1007/bf00957819

  日期：1989.9
• GOLUBEV, A. S.;KARELIN, N. V.;ANDREEV, V. G.;KOLOMIETS, A. F.;FOKIN, A. V+, IZV. AN CCCP. CEP. XIM.,(1989) N, S. 2158
  作者：GOLUBEV, A. S.、KARELIN, N. V.、ANDREEV, V. G.、KOLOMIETS, A. F.、FOKIN, A. V+

  DOI：——

  日期：——