6H-cyclohepta(c)furannedicarboxaldehyde-5,7 | 121726-16-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 环七呋喃
• 英文名称: 6H-cyclohepta(c)furannedicarboxaldehyde-5,7
• 英文别名: 6H-cyclohepta[c]furan-5,7-dicarbaldehyde
• CAS: 121726-16-7
• 化学式: C₁₁H₈O₃
• 分子量: 188.183
• InChiKey: ZZITVHGBQMFYEK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 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：

  6H-cyclohepta(c)furannedicarboxaldehyde-5,7 在 三氟甲磺酸 、 sodium methylate 作用下， 以 甲醇 、 1,2-二氯乙烷 、 甲苯 为溶剂， 反应 44.5h， 生成 7-Cyclohexyl-17-ethyl-7,17-diazapentacyclo[11.7.1.03,11.05,9.015,19]henicosa-1,3,5(9),10,12,14,19-heptaene-6,8,16,18-tetrone
  参考文献：
  名称：

  Methanobenzo[10]annulene-2,3:8,9-bis(dicarboximide)衍生物的合成及光物理性质

  摘要：

  Bis(dicarboximide) derivatives possessing methanobenzo[10]annulene skeleton were synthesized. The annulation of another dicarboximide on mono(dicarboximide), namely 1,6-methanobenzo [10] annulene-3,4-dicarboximide, provided the improvement of their molar extinction coefficients and fluorescence quantum yields. The change in photophysical behavior between mono(dicarboximide) and bis(dicarboximide) was explained by collaboration with theoretical calculations.

  DOI：

  10.3987/com-17-13692
• 作为产物：
  描述：

  3,4-呋喃二羧醛 、 戊二醛 在 哌啶 作用下， 以 溶剂黄146 为溶剂， 反应 4.0h， 以68%的产率得到6H-cyclohepta(c)furannedicarboxaldehyde-5,7
  参考文献：
  名称：

  Facile Construction of Furan-Fused Methano[11]annulenone Skeleton by Successive Aldol Condensations from 3,4-Furandicarbaldehydes

  摘要：

  Aldol condensation of furan-3,4-dicarbaldehyde with pentanedial in acetic acid gave 6H-cyclohepta[c]furan-5,7-dicarbaldehyde in a good yield. Then, successive condensation of 6H-cyclohepta[c]furan-5,7-dicarbaldehyde with dimethyl 1,3 -acetonedicarboxylate under azeotropic conditions gave a diester derivative of furan-fused methano[11]annulenone also in a good yield. The hydrolysis of the diester groups and subsequent decarboxylation provided a non-substituted furan-fused methano[11]annulenone. A similar sequence starting from 2,5-dimethylfuran-3,4-dicarbaldehyde gave its dimethyl derivative. Cycloaddition and protonation of these furan-fused methano[11]annulenones were also studied.

  DOI：

  10.3987/com-08-s(f)52

文献信息

• Lepage, Lucette; Lepage, Yves, Bulletin de la Societe Chimique de France, 1988, # 3, p. 591 - 594
  作者：Lepage, Lucette、Lepage, Yves

  DOI：——

  日期：——
• Facile Construction of Furan-Fused Methano[11]annulenone Skeleton by Successive Aldol Condensations from 3,4-Furandicarbaldehydes
  作者：Shigeyasu Kuroda、Yanmei Zhang、Nobuhiko Takezawa、Yosikazu Horino、Ayumi Takai、Yasutomo Tsuji、Ryuta Miyatake、Mitsunori Oda

  DOI：10.3987/com-08-s(f)52

  日期：——

  Aldol condensation of furan-3,4-dicarbaldehyde with pentanedial in acetic acid gave 6H-cyclohepta[c]furan-5,7-dicarbaldehyde in a good yield. Then, successive condensation of 6H-cyclohepta[c]furan-5,7-dicarbaldehyde with dimethyl 1,3 -acetonedicarboxylate under azeotropic conditions gave a diester derivative of furan-fused methano[11]annulenone also in a good yield. The hydrolysis of the diester groups and subsequent decarboxylation provided a non-substituted furan-fused methano[11]annulenone. A similar sequence starting from 2,5-dimethylfuran-3,4-dicarbaldehyde gave its dimethyl derivative. Cycloaddition and protonation of these furan-fused methano[11]annulenones were also studied.
• Synthesis and Photophysical Property of Methanobenzo[10]annulene-2,3:8,9-bis(dicarboximide) Derivatives
  作者：Tatsuya Yanagisawa、Mitsunori Oda、Naoki Kobayashi、Ryuta Miyatake

  DOI：10.3987/com-17-13692

  日期：——

  Bis(dicarboximide) derivatives possessing methanobenzo[10]annulene skeleton were synthesized. The annulation of another dicarboximide on mono(dicarboximide), namely 1,6-methanobenzo [10] annulene-3,4-dicarboximide, provided the improvement of their molar extinction coefficients and fluorescence quantum yields. The change in photophysical behavior between mono(dicarboximide) and bis(dicarboximide) was explained by collaboration with theoretical calculations.