3-(furan-2-yl)pentane-2,4-dione | 74897-15-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(furan-2-yl)pentane-2,4-dione
• 英文别名: ethyl 2-(2-furoyl)acetoacetate；3-(2-Furyl)pentane-2,4-dione
• CAS: 74897-15-7
• 化学式: C₉H₁₀O₃
• 分子量: 166.177
• InChiKey: YLHHGNLPMSROAJ-UHFFFAOYSA-N

物化性质

• 熔点：
  49 °C
• 沸点：
  202.9±25.0 °C(Predicted)
• 密度：
  1.111±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  47.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(furan-2-yl)pentane-2,4-dione 在 C₆H₅CH₂N⁽¹⁺⁾(CH₃)3*3Br^(1-) on Amberlyst A-26 、 potassium carbonate 作用下， 以 二氯甲烷 为溶剂， 反应 4.08h， 生成 3-furan-2-yl-6-methyl-pyridazine-4,5-dicarboxylic acid 4-ethyl ester 5-methyl ester
  参考文献：
  名称：

  Reaction of Some 1,2-Diaza-1,3-butadienes with Activated Methine Compounds. A Straightforward Entry to 1,4-Dihydropyridazine, Pyridazine, and 4,5(4H,5H)-Cyclopropylpyrazole Derivatives

  摘要：

  1-Aminocarbonyl-1,2-diaza-1,3-butadienes with beta-tri- or beta-dicarbonyl compounds containing at least two keto functions give 1,4-dihydropyridazines, while hydrazone 1,4-adducts are obtained in the case of compounds containing one or no keto function. 1,4-Dihydropyridazines are transformed into pyridazines. The same substrates with 3-phenoxypentane-2,4-dione afford pyridazines. Surprisingly, 1-alkoxycarbonyl-1,2-diaza-1,3-butadiene with methyl 2-acetylacetoacetate produce 1-alkoxycarbonyl-4,5(4H,5H)-(alkoxycarbonylcyclopropyl)pyrazoles deriving from 1-alkoxycarbonyl-1,2-dihydropyridazine intermediates by ring contraction. These pyrazole derivatives with acetic acid show ring expansion to 1-alkoxycarbonyl-1,4-dihydropyridazines that can be converted into 1,4-dihydropyridazines with sodium hydroxide. 1-Alkoxycarbonyl-4,5(4H, 5H)-(alkoxycarbonylcyclopropyl)pyrazoles or 1-alkoxycarbonyl-1,4-dihydropyridazines with trifluoroacetic acid provide 1-aminopyrroles via 1-alkoxycarbonyl-1,4-dihydropyridazine intermediates in the case of pyrazoles. The X-ray crystal structure of 1-tert-butoxycarbonyl-3,5-dimethyl-4-methoxycarbonyl-4,5(4H,5H)-(methoxycarbonylcyclopropyl)-1H-pyrazole was determined.

  DOI：

  10.1021/jo9816515
• 作为产物：
  描述：

  2,5-二甲氧基-2,5-二氢呋喃 、 乙酰丙酮 在 zinc(II) chloride 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 以58%的产率得到3-(furan-2-yl)pentane-2,4-dione
  参考文献：
  名称：

  呋喃基β-二酮基杂配铱(III)配合物的合成及其光致发光性能研究

  摘要：

  合成并表征了四种含有呋喃部分的铱配合物。呋喃单元的定位对配合物的光学性质有很大影响。开发的合成方法为将低聚呋喃化合物引入用于 OLED 应用的 IrIII 杂配配合物铺平了道路。

  DOI：

  10.1002/zaac.201500293

文献信息

• Lewis acid induced .alpha.-alkoxyalkylation of 1,3-dicarbonyl compounds
  作者：R. Antonioletti、F. Bonadies、Arrigo Scettri

  DOI：10.1021/jo00258a028

  日期：1988.11
• DASSOLI R.; DAURIA M.; PIANCATELLI G.; SSETTRI A., TETRAHEDRON, 1979, 35, NO 24, 2905-2907
  作者：DASSOLI R.、 DAURIA M.、 PIANCATELLI G.、 SSETTRI A.

  DOI：——

  日期：——
• ANTONIOLETTI, R.;BONADIES, F.;SCETTRI, A., J. ORG. CHEM., 53,(1988) N 23, C. 5540-5542
  作者：ANTONIOLETTI, R.、BONADIES, F.、SCETTRI, A.

  DOI：——

  日期：——
• US6187911B1
  申请人：——

  公开号：US6187911B1

  公开（公告）日：2001-02-13
• Reaction of Some 1,2-Diaza-1,3-butadienes with Activated Methine Compounds. A Straightforward Entry to 1,4-Dihydropyridazine, Pyridazine, and 4,5(4<i>H</i>,5<i>H</i>)-Cyclopropylpyrazole Derivatives
  作者：Orazio A. Attanasi、Paolino Filippone、Chiara Fiorucci、Elisabetta Foresti、Fabio Mantellini

  DOI：10.1021/jo9816515

  日期：1998.12.1

  1-Aminocarbonyl-1,2-diaza-1,3-butadienes with beta-tri- or beta-dicarbonyl compounds containing at least two keto functions give 1,4-dihydropyridazines, while hydrazone 1,4-adducts are obtained in the case of compounds containing one or no keto function. 1,4-Dihydropyridazines are transformed into pyridazines. The same substrates with 3-phenoxypentane-2,4-dione afford pyridazines. Surprisingly, 1-alkoxycarbonyl-1,2-diaza-1,3-butadiene with methyl 2-acetylacetoacetate produce 1-alkoxycarbonyl-4,5(4H,5H)-(alkoxycarbonylcyclopropyl)pyrazoles deriving from 1-alkoxycarbonyl-1,2-dihydropyridazine intermediates by ring contraction. These pyrazole derivatives with acetic acid show ring expansion to 1-alkoxycarbonyl-1,4-dihydropyridazines that can be converted into 1,4-dihydropyridazines with sodium hydroxide. 1-Alkoxycarbonyl-4,5(4H, 5H)-(alkoxycarbonylcyclopropyl)pyrazoles or 1-alkoxycarbonyl-1,4-dihydropyridazines with trifluoroacetic acid provide 1-aminopyrroles via 1-alkoxycarbonyl-1,4-dihydropyridazine intermediates in the case of pyrazoles. The X-ray crystal structure of 1-tert-butoxycarbonyl-3,5-dimethyl-4-methoxycarbonyl-4,5(4H,5H)-(methoxycarbonylcyclopropyl)-1H-pyrazole was determined.