2-furfurylidenemalonaldehyde | 82700-55-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: 2-furfurylidenemalonaldehyde
• 英文别名: [(Furan-2-yl)methylidene]propanedial；2-(furan-2-ylmethylidene)propanedial
• CAS: 82700-55-8
• 化学式: C₈H₆O₃
• 分子量: 150.134
• InChiKey: RWQCVFYLZQZNMP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  对三氟甲基苯胺 、 2-furfurylidenemalonaldehyde 以 乙腈 为溶剂， 反应 0.25h， 以92%的产率得到1,3-di-(N-4-trifluormethyl-phenylamino)-3-(2-furyl)-2-formyl-1-propenes
  参考文献：
  名称：

  Safar, Peter; Kovac, Jaroslav, Collection of Czechoslovak Chemical Communications, 1989, vol. 54, # 9, p. 2433 - 2442

  摘要：

  DOI：
• 作为产物：
  描述：

  2-(2-furylmethylene)propane-1,3-diol 在 4-(benzyloxycarbonyl)-2,2,6,6-tetramethylpiperidine-1-oxyl 、 碘苯二乙酸 、 对甲苯磺酸 作用下， 以 四氢吡喃 为溶剂， 反应 4.0h， 以58%的产率得到(E)-2-hydroxymethyl-3-(2-furyl)-2-propenal
  参考文献：
  名称：

  Regioselective TEMPO oxidation of 2-alkylidene-1,3-propanediols to (E)-2-hydroxymethyl-2-alkenals and application to 4-alkylidene-2-penten-5-olide synthesis

  摘要：

  The oxidation system comprised of TEMPO and (diacetoxyiodo)benzene (stoichiometric) is enhanced during the conversion of primary alcohols to aldehydes by adding a catalytic amount of acids, p-TsOH and PPTS. 2-Alkylidene-1,3-propanediols, available from 1,3-dihydroxyacetone, are oxidized under the stated conditions to the corresponding (E)-2-hydroxymethyl-2-alkenals, which are utilized as an intermediate for the expeditious synthesis of 4-alkylidene-2-penten-5-olides. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.10.034

文献信息

• Arylmethylenemalonaldehydes and their heterocyclic analogues: A novel group of organic lewis acids
  作者：Z. Arnold、V. Král、D. Dvořák

  DOI：10.1016/s0040-4039(00)87200-7

  日期：1982.1
• Arnold, Zdenek; Dvorak, Dalimil; Kral, Vladimir, Collection of Czechoslovak Chemical Communications, 1984, vol. 49, # 11, p. 2613 - 2619
  作者：Arnold, Zdenek、Dvorak, Dalimil、Kral, Vladimir

  DOI：——

  日期：——
• SAFAR, PETER;KOVAC, JAROSLAV, COLLECT. CZECHOSL. CHEM. COMMUN., 54,(1989) N, C. 2433-2442
  作者：SAFAR, PETER、KOVAC, JAROSLAV

  DOI：——

  日期：——
• ARNOLD, Z.;DVORAK, D.;KRAL, V., COLLECT. CZECHOSL. CHEM. COMMUN., 1984, 49, N 11, 2613-2619
  作者：ARNOLD, Z.、DVORAK, D.、KRAL, V.

  DOI：——

  日期：——
• Regioselective TEMPO oxidation of 2-alkylidene-1,3-propanediols to (E)-2-hydroxymethyl-2-alkenals and application to 4-alkylidene-2-penten-5-olide synthesis
  作者：Wei Peng、Kazumi Ashida、Toshiaki Hirabaru、Li-Jian Ma、Tsutomu Inokuchi

  DOI：10.1016/j.tet.2010.10.034

  日期：2010.12

  The oxidation system comprised of TEMPO and (diacetoxyiodo)benzene (stoichiometric) is enhanced during the conversion of primary alcohols to aldehydes by adding a catalytic amount of acids, p-TsOH and PPTS. 2-Alkylidene-1,3-propanediols, available from 1,3-dihydroxyacetone, are oxidized under the stated conditions to the corresponding (E)-2-hydroxymethyl-2-alkenals, which are utilized as an intermediate for the expeditious synthesis of 4-alkylidene-2-penten-5-olides. (C) 2010 Elsevier Ltd. All rights reserved.