3-<(3,4-Dimethoxyphenyl)methylene>-2,4(3H,5H)-furandione | 87191-98-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-<(3,4-Dimethoxyphenyl)methylene>-2,4(3H,5H)-furandione
• 英文别名: 3-(3,4-Dimethoxybenzyliden)-2,4-tetrahydrofurandion；3-(3,4-dimethoxy-benzylidene)-furan-2,4-dione；3-[(3,4-Dimethoxyphenyl)methylidene]oxolane-2,4-dione
• CAS: 87191-98-8
• 化学式: C₁₃H₁₂O₅
• 分子量: 248.235
• InChiKey: CLVLYYLLGBWQAE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-<(3,4-Dimethoxyphenyl)methylene>-2,4(3H,5H)-furandione 在 sodium cyanoborohydride 作用下， 以 四氢呋喃 、 盐酸 、 水 为溶剂， 反应 12.0h， 以60%的产率得到3-(3,4-dimethoxybenzyl)tetrahydrofuran-2,4-dione
  参考文献：
  名称：

  Chemoselective reduction of 3-arylmethylidenetetrahydrofuran-2,4-diones with triethylsilane and sodium cyanotrihydridoborate in acid media

  摘要：

  3-Arylmethylidenetetrahydrofuran-2,4-diones were smoothly reduced to the corresponding 3-benzyl derivatives in 50-98% yield with triethylsilane in trifluoroacetic acid or with sodium cyanotrihydridoborate in the system tetrahydrofuran-2 N hydrochloric acid. The reduction of 3-(3-arylprop-2-en-1-ylidene)-tetrahydrofuran-2,4-diones with sodium cyanotrihydridoborate gave 3-cinnamyltetrahydrofuran-2,4-diones as the only products.

  DOI：

  10.1134/s1070428009060098
• 作为产物：
  描述：

  4-羟乙酰乙酸内酯 、 3,4-二甲氧基苯甲醛 以 乙醇 为溶剂， 生成 3-<(3,4-Dimethoxyphenyl)methylene>-2,4(3H,5H)-furandione
  参考文献：
  名称：

  Tetronic acid in reaction with aromatic aldehydes and 2-naphthylamine. Investigation of fluorescent and nonlinear-optical characteristics of compounds obtained

  摘要：

  By Knoevenagel condensation and by three-component condensation 3-arylmethylenetetrahydrofuran-2,4-diones and previously unknown 8,11-dihydro-11-arylbenzo[f]furo[3,4-b]quinolin-10(7H)-ones were respectively synthesized. The luminescent spectra and nonlinear-optical characteristics of compounds obtained were investigated.

  DOI：

  10.1134/s1070428008070142

文献信息

• Substituted .gamma.-lactones. 28. 3-(Phenylmethylene)-2,4-(3H,5H)furandiones
  作者：Hans Zimmer、W. W. Hillstrom、James C. Schmidt、Paul D. Seemuth、R. Vogeli

  DOI：10.1021/jo00402a012

  日期：1978.4
• Substituted .gamma.-butyrolactones. Part 32. Ring construction using 3-(arylmethylene)-2,4(3H,5H)-furandione: synthesis of pyrazolones and furo[3,4-c][1,5]benzothiazepinones
  作者：Diane Grob Schmidt、Hans Zimmer

  DOI：10.1021/jo00171a041

  日期：1983.11
• Tetronic acid in reaction with aromatic aldehydes and 2-naphthylamine. Investigation of fluorescent and nonlinear-optical characteristics of compounds obtained
  作者：N. G. Kozlov、S. L. Bondarev、A. P. Kadutskii、L. I. Basalaeva、F. S. Pashkovskii

  DOI：10.1134/s1070428008070142

  日期：2008.7

  By Knoevenagel condensation and by three-component condensation 3-arylmethylenetetrahydrofuran-2,4-diones and previously unknown 8,11-dihydro-11-arylbenzo[f]furo[3,4-b]quinolin-10(7H)-ones were respectively synthesized. The luminescent spectra and nonlinear-optical characteristics of compounds obtained were investigated.
• Chemoselective reduction of 3-arylmethylidenetetrahydrofuran-2,4-diones with triethylsilane and sodium cyanotrihydridoborate in acid media
  作者：F. S. Pashkovskii、E. M. Shchukina、F. A. Lakhvich

  DOI：10.1134/s1070428009060098

  日期：2009.6

  3-Arylmethylidenetetrahydrofuran-2,4-diones were smoothly reduced to the corresponding 3-benzyl derivatives in 50-98% yield with triethylsilane in trifluoroacetic acid or with sodium cyanotrihydridoborate in the system tetrahydrofuran-2 N hydrochloric acid. The reduction of 3-(3-arylprop-2-en-1-ylidene)-tetrahydrofuran-2,4-diones with sodium cyanotrihydridoborate gave 3-cinnamyltetrahydrofuran-2,4-diones as the only products.