2(3H)-呋喃酮,二氢-5-羟基-5-(三氟甲基)- | 117192-54-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 中文名称: 2(3H)-呋喃酮,二氢-5-羟基-5-(三氟甲基)-
• 英文名称: 5-hydroxy-5-(trifluoromethyl)dihydrofuran-2(3H)-one
• 英文别名: 5-hydroxy-5-trifluoromethyltetrahydrofuran-2-one；5-hydroxy-5-trifluoromethyltetrahydro-2-furanone；5-Hydroxy-5-(trifluoromethyl)oxolan-2-one
• CAS: 117192-54-8
• 化学式: C₅H₅F₃O₃
• 分子量: 170.088
• InChiKey: QYWWZFJVMSFHSP-UHFFFAOYSA-N

物化性质

• 沸点：
  250.3±40.0 °C(Predicted)
• 密度：
  1.623±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  苯基氯化镁 、 2(3H)-呋喃酮,二氢-5-羟基-5-(三氟甲基)- 在 盐酸 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 16.67h， 以67%的产率得到5-phenyl-5-(trifluoromethyl)dihydrofuran-2(3H)-one
  参考文献：
  名称：

  Nucleophilic trifluoromethylation of anhydrides employing (trifluoromethyl)trimethylsilane: Synthesis of γ-trifluoromethylated γ-butyrolactones

  摘要：

  Fluoride-catalyzed nucleophilic trifluoromethylation of acid anhydrides using CF3SiMe3 provided the corresponding gamma-hydroxy-gamma-trifluoromethyl-gamma-butyrolactones. The utility of these adducts was further demonstrated by treatment with Grignard reagents, leading to gamma-trifluoromethylated gamma-butyrolactones. (C) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2013.06.006
• 作为产物：
  描述：

  丁二酸酐 、 (三氟甲基)三甲基硅烷 在 四丁基二氟三苯硅酸铵 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以67%的产率得到2(3H)-呋喃酮,二氢-5-羟基-5-(三氟甲基)-
  参考文献：
  名称：

  Nucleophilic trifluoromethylation of anhydrides employing (trifluoromethyl)trimethylsilane: Synthesis of γ-trifluoromethylated γ-butyrolactones

  摘要：

  Fluoride-catalyzed nucleophilic trifluoromethylation of acid anhydrides using CF3SiMe3 provided the corresponding gamma-hydroxy-gamma-trifluoromethyl-gamma-butyrolactones. The utility of these adducts was further demonstrated by treatment with Grignard reagents, leading to gamma-trifluoromethylated gamma-butyrolactones. (C) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2013.06.006

文献信息

• Reactions of bromotrifluoromethane with acid derivatives in the presence of zinc
  作者：C. Francèse、M. Tordeux、C. Wakselman

  DOI：10.1016/0040-4039(88)85326-7

  日期：1988.1

  Reaction of zinc with bromotrifluoromethane in pyridine gives poorly reactive trifluoromethyl zinc derivatives in the presence of ethyl benzoate whereas the Barbier condensation occurs with activated esters, like ethyl trifluoroacetate or ethyl oxalate, and cyclic anhydrides.

  锌与溴三氟甲烷在吡啶中的反应在苯甲酸乙酯存在下反应性差的三氟甲基锌衍生物，而Barbier缩合反应发生在活化的酯（如三氟乙酸乙酯或草酸乙酯）和环状酸酐上。
• Tordeux, Marc; Francese, Catherine; Wakselman, Claude, Journal of the Chemical Society. Perkin transactions I, 1990, # 7, p. 1951 - 1957
  作者：Tordeux, Marc、Francese, Catherine、Wakselman, Claude

  DOI：——

  日期：——
• TORDEUX, MARC;FRANCESE, CATHERINE;WAKSELMAN, CLAUDE, J. CHEM. SOC. PERKIN TRANS. PT 1,(1990) N, C. 1951-1957
  作者：TORDEUX, MARC、FRANCESE, CATHERINE、WAKSELMAN, CLAUDE

  DOI：——

  日期：——
• FRANCESE, C.;TORDEUX, M.;WAKSELMAN, C., TETRAHEDRON LETT., 29,(1988) N 9, 1029-1030
  作者：FRANCESE, C.、TORDEUX, M.、WAKSELMAN, C.

  DOI：——

  日期：——
• Nucleophilic trifluoromethylation of anhydrides employing (trifluoromethyl)trimethylsilane: Synthesis of γ-trifluoromethylated γ-butyrolactones
  作者：Chonticha Masusai、Darunee Soorukram、Chutima Kuhakarn、Patoomratana Tuchinda、Vichai Reutrakul、Manat Pohmakotr

  DOI：10.1016/j.jfluchem.2013.06.006

  日期：2013.10

  Fluoride-catalyzed nucleophilic trifluoromethylation of acid anhydrides using CF3SiMe3 provided the corresponding gamma-hydroxy-gamma-trifluoromethyl-gamma-butyrolactones. The utility of these adducts was further demonstrated by treatment with Grignard reagents, leading to gamma-trifluoromethylated gamma-butyrolactones. (C) 2013 Elsevier B.V. All rights reserved.