5-甲基四氢呋喃-2,4-二酮 | 5457-19-2

• 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: 5-甲基四氢呋喃-2,4-二酮
• 英文名称: 5-methyl-2,4-furandione
• 英文别名: 5-methyltetronic acid；5-methyl-furan-2,4-dione；(+/-)-4-hydroxy-3-oxo-valeric acid-lactone；(+/-)-4-Hydroxy-3-oxo-valeriansaeure-lacton；5-Methyl-furan-2,4-dion；5-methyl-2,4(3H,5H)-furandione；5-Methyloxolane-2,4-dione
• CAS: 5457-19-2
• 化学式: C₅H₆O₃
• 分子量: 114.101
• InChiKey: ZIQFRNVCLDSOAB-UHFFFAOYSA-N

物化性质

• 熔点：
  115 °C
• 沸点：
  291.1±33.0 °C(Predicted)
• 密度：
  1.230±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  8
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2932190090

反应信息

• 作为反应物：
  描述：

  5-甲基四氢呋喃-2,4-二酮 在 selenium(IV) oxide 作用下， 以 溶剂黄146 为溶剂， 反应 21.0h， 生成 2-(3,4-dimethoxy-2-phenylmethoxyphenyl)-3,7-dimethyl-5-oxo-7H-furo[3,4-b]pyridine-4-carbaldehyde
  参考文献：
  名称：

  吡啶合成过程中发生异常的重排。β-酮烯胺与tetronic酸的异常缩合。

  摘要：

  β-酮烯胺1与5-甲基tetronic酸的缩合过程反常。单晶X射线分析和化学证据确定了该缩合产物的重排吡啶结构15。

  DOI：

  10.1016/s0040-4039(01)81195-3
• 作为产物：
  描述：

  丙酰乙酸乙酯 在 palladium on activated charcoal 、 乙醚 、 水 、 溴 作用下， 130.0 ℃ 、4.0 kPa 条件下， 生成 5-甲基四氢呋喃-2,4-二酮
  参考文献：
  名称：

  Clutterbuck et al., Biochemical Journal, 1935, vol. 29, p. 1300,1306

  摘要：

  DOI：

文献信息

• Ring Closure in the Tetronic Acid Series¹
  作者：Evans B. Reid、George H. Denny

  DOI：10.1021/ja01526a046

  日期：1959.9
• Insecticidal heterolignans—Tubuline polymerization inhibitors with activity against chewing pests
  作者：Jens Frackenpohl、Isabelle Adelt、Horst Antonicek、Christian Arnold、Patricia Behrmann、Nicole Blaha、Jutta Böhmer、Oliver Gutbrod、Roman Hanke、Sabine Hohmann、Marc van Houtdreve、Peter Lösel、Olga Malsam、Martin Melchers、Valentina Neufert、Elisabeth Peschel、Udo Reckmann、Thomas Schenke、Hans-Peter Thiesen、Robert Velten、Kathrin Vogelsang、Hans-Christoph Weiss

  DOI：10.1016/j.bmc.2009.01.042

  日期：2009.6

  Starting from natural product podophyllotoxin 1 substituted heterolignans were identified with promising insecticidal in vivo activity. The impact of substitution in each segment of the core structure was investigated in a detailed SAR study, and variation of substituents in both aromatic moieties afforded derivatives 5 and 43 with broad insecticidal activity against lepidopteran and coleopteran species. In vitro measurements supported by modeling studies indicate that heterolignans 3-134 act as tubuline polymerization inhibitors interacting with the colchicine-binding site. Insect specific structure-activity effects were observed showing that the insecticidal SAR described herein differs from reported cytotoxicity studies. (C) 2009 Elsevier Ltd. All rights reserved.
• Benary, Chemische Berichte, 1911, vol. 44, p. 1765
  作者：Benary

  DOI：——

  日期：——
• 792. Tetronic acids and related compounds. Part I. Synthesis from α-hydroxy-esters
  作者：L. J. Haynes、A. H. Stanners

  DOI：10.1039/jr9560004103

  日期：——
• Heterocyclic Analogs of Prostaglandins: I. Synthesis of 3-Alkyl(Aralkyl)-2,5-dihydrofuran-2-ones as Synthons for 11-Deoxy-10-oxaprostanoids
  作者：F. S. Pashkovskii、Ya. M. Katok、T. S. Khlebnikova、E. V. Koroleva、F. A. Lakhvich

  DOI：10.1023/b:rujo.0000003193.75790.de

  日期：2003.7

  3-Acyl(arylmethyleneacyl)tetronic acids were synthesized. Selective hydrogenation of the carbonyl group in the acyl fragment and reduction of the conjugated double bond afforded in high yield the corresponding 3-alkyl(aralkyl) derivatives possessing either natural or modified prostaglandin alpha-chain. Reduction of the conjugated double bond in vinylogous 3-alkyl(aralkyl)tetronic acid amides with sodium cyanotrihydridoborate gave a mixture of stereoisomeric beta-amino lactones which underwent retro-Michael elimination of the amine residue, leading to 3-alkyl(aralkyl)-2,5-dihydrofuran-2-ones. The latter can be regarded as synthons for 11-deoxy-10-oxaprostanoids.