5-(三氟甲基)呋喃-2(5H)-酮 | 2253-15-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢呋喃
• 中文名称: 5-(三氟甲基)呋喃-2(5H)-酮
• 中文别名: 5-(三氟甲基)-2(5H)-呋喃酮
• 英文名称: 4-trifluoromethylbut-2-en-4-olide
• 英文别名: 5-(trifluoromethyl)-2(5H)-furanone；5-(trifluoromethyl)furan-2(5H)-one；5-Trifluormethyl-2.5-dihydro-furan-2-on；5-trifluoromethyl-5H-furan-2-one；5-Trifluormethyl-5H-furan-2-on；2-(trifluoromethyl)-2H-furan-5-one
• CAS: 2253-15-8
• 化学式: C₅H₃F₃O₂
• 分子量: 152.073
• InChiKey: YMIVQORRFGTHJR-UHFFFAOYSA-N

物化性质

• 沸点：
  83 °C(Press: 12-13 Torr)
• 密度：
  1.444 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-(三氟甲基)呋喃-2(5H)-酮 在 potassium carbonate 、 甲基丙烯酸甲酯 作用下， 以 乙腈 为溶剂， 反应 7.0h， 以82%的产率得到Methyl 6-methyl-3-oxo-1-(trifluoromethyl)-2-oxabicyclo[3.2.0]heptane-6-carboxylate
  参考文献：
  名称：

  Convenient preparations and Michael reactions of 4-fluoroalkylated but-2-en-4-olides

  摘要：

  Trifluoromethyl, heptafluoropropyl and chlorodifluoromethyl substituted but-2-en-4-olides have been prepared both from 2-trimethylsiloxyfuran by fluoroalkylation with the corresponding bis(fluoroalkanoyl) peroxide and from 2-fluoroalkylfuran by oxidation with m-nitrobenzenesulfonyl peroxide. 4-Difluoromethylbut-2-en-4-olide was also prepared by chlorodifluoromethylation of 2-methoxy-furan followed by reduction of the chlorine. The 4-trifluoromethylated butenolide, thus prepared, could be readily converted into the anion by treatment with weak base. The anion so formed then reacted with electron-deficient olefins to give 4,4-disubstituted butenolides.

  DOI：

  10.1039/p19930000501
• 作为产物：
  描述：

  (3RS,3aSR,4RS,7SR,7aRS)-3-(trifluoromethyl)-3a,4,7,7a-tetrahydro-4,7-methanoisobenzofuran-1(3H)-one 240.0 ℃ 、6.67 Pa 条件下， 以82%的产率得到5-(三氟甲基)呋喃-2(5H)-酮
  参考文献：
  名称：

  以CF 3 SiMe 3为三氟甲基化剂合成γ-三氟甲基α，β-不饱和γ-丁内酯†

  摘要：

  描述了γ-三氟甲基α，β-不饱和γ-丁内酯的一般合成。氟催化的三氟甲基（CF 3）基团的亲核加成反应（三氟甲基）三甲基硅烷（CF 3 SiMe 3，Ruppert–Prakash试剂）制成被掩盖的马来酸酐1（环戊二烯–马来酸酐加合物）为相应的加合物2提供了高的立体选择性。在用格氏试剂处理加合物2，然后进行快速真空热解后，获得γ-三氟甲基α，β-不饱和γ-丁内酯4。

  DOI：

  10.1039/c3ob41247d

文献信息

• Reaction of 5-(Trifluoromethyl)-2(5H)-furanone under Basic Conditions: Stereo-Controlled Michael Dimerization
  作者：Takashi Okano、Masayuki Chokai、Shoji Eguchi、Yoshio Hayakawa

  DOI：10.1016/s0040-4020(00)00581-0

  日期：2000.8

  Treatment of 5-trifluoromethyl-2(5H)-furanone under basic conditions gave a stereoisomeric mixture of two out of four possible stereoisomers of bis(trifluoromethyl)dihydro-2,4-bisfuranonyl depending on the reaction conditions. Butenolide anion generated with LDA is kinetically stable and reaction with 2-cyclohexenone stereoselectively gave a Michael adduct.

  在碱性条件下处理5-三氟甲基-2（5 H）-呋喃酮，根据反应条件，得到双（三氟甲基）二氢-2,4-双呋喃酮基的四种可能的立体异构体中的两种的立体异构体混合物。用LDA生成的丁烯内酯阴离子在动力学上是稳定的，与2-环己烯酮的立体反应选择性地产生了迈克尔加合物。
• Fluorinated Paraffins
  作者：R. H. GROTH

  DOI：10.1021/jo01093a022

  日期：1959.11
• A synthesis of γ-trifluoromethyl α,β-unsaturated γ-butyrolactones using CF3SiMe3 as a trifluoromethylating agent
  作者：Chonticha Masusai、Darunee Soorukram、Chutima Kuhakarn、Patoomratana Tuchinda、Chaveng Pakawatchai、Saowanit Saithong、Vichai Reutrakul、Manat Pohmakotr

  DOI：10.1039/c3ob41247d

  日期：——

  corresponding adducts 2 with high stereoselectivity. The γ-trifluoromethyl α,β-unsaturated γ-butyrolactones 4 were obtained after treatment of the adducts 2 with Grignard reagents, followed by flash-vacuum pyrolysis.

  描述了γ-三氟甲基α，β-不饱和γ-丁内酯的一般合成。氟催化的三氟甲基（CF 3）基团的亲核加成反应（三氟甲基）三甲基硅烷（CF 3 SiMe 3，Ruppert–Prakash试剂）制成被掩盖的马来酸酐1（环戊二烯–马来酸酐加合物）为相应的加合物2提供了高的立体选择性。在用格氏试剂处理加合物2，然后进行快速真空热解后，获得γ-三氟甲基α，β-不饱和γ-丁内酯4。
• Convenient preparations and Michael reactions of 4-fluoroalkylated but-2-en-4-olides
  作者：Masato Yoshida、Rihoko Imai、Yuji Komatsu、Yoshihiro Morinaga、Nobumasa Kamigata、Masahiko Iyoda

  DOI：10.1039/p19930000501

  日期：——

  Trifluoromethyl, heptafluoropropyl and chlorodifluoromethyl substituted but-2-en-4-olides have been prepared both from 2-trimethylsiloxyfuran by fluoroalkylation with the corresponding bis(fluoroalkanoyl) peroxide and from 2-fluoroalkylfuran by oxidation with m-nitrobenzenesulfonyl peroxide. 4-Difluoromethylbut-2-en-4-olide was also prepared by chlorodifluoromethylation of 2-methoxy-furan followed by reduction of the chlorine. The 4-trifluoromethylated butenolide, thus prepared, could be readily converted into the anion by treatment with weak base. The anion so formed then reacted with electron-deficient olefins to give 4,4-disubstituted butenolides.