5,7-dimethoxy-3-cyano-2-iminocoumarin | 794517-56-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 5,7-dimethoxy-3-cyano-2-iminocoumarin
• 英文别名: 2-Imino-5,7-dimethoxychromene-3-carbonitrile
• CAS: 794517-56-9
• 化学式: C₁₂H₁₀N₂O₃
• 分子量: 230.223
• InChiKey: JMGHWKGBFQLNGZ-UHFFFAOYSA-N

物化性质

• 熔点：
  191 °C(Solvent: Acetonitrile)
• 沸点：
  375.0±52.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  75.3
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5,7-dimethoxy-3-cyano-2-iminocoumarin 在 盐酸 作用下， 反应 2.0h， 生成 3-cyano-5,7-dimethoxycoumarin
  参考文献：
  名称：

  One-Pot Synthesis of 3-Carboxycoumarins via Consecutive Knoevenagel and Pinner Reactions in Water

  摘要：

  通过一步法，将适当取代的水杨醛与丙二腈在水中反应，成功制备了氯代、羟基、甲氧基和叔丁基取代的3-羧基香豆素。总体产率较高，且该方法无需使用有机溶剂。

  DOI：

  10.1055/s-2003-41061
• 作为产物：
  描述：

  4,6-二甲氧基水杨醛 、 丙二腈 在 sodium hydroxide 作用下， 反应 4.0h， 生成 5,7-dimethoxy-3-cyano-2-iminocoumarin
  参考文献：
  名称：

  One-Pot Synthesis of 3-Carboxycoumarins via Consecutive Knoevenagel and Pinner Reactions in Water

  摘要：

  通过一步法，将适当取代的水杨醛与丙二腈在水中反应，成功制备了氯代、羟基、甲氧基和叔丁基取代的3-羧基香豆素。总体产率较高，且该方法无需使用有机溶剂。

  DOI：

  10.1055/s-2003-41061

文献信息

• Novel Synthesis of 2‐Oxo‐2H‐Benzopyrano[2,3‐d]Pyrimidines
  作者：H. Turki、S. Abid、Y. Le Bigot、S. Fery‐Forgues、R. El Gharbi

  DOI：10.1081/scc-200031013

  日期：2004.1.1

  Abstract The synthesis of novel substituted 3‐cyanoiminocoumarins and corresponding N‐ethoxycarbonyl iminocoumarins is described. The condensation of N‐ethoxycarbonyl‐3‐cyano‐7‐diethylamino iminocoumarin with amines as N‐nucleophiles yields substituted 2‐oxo‐2H‐benzopyrano‐[2,3‐d]pyrimidines having promising optical properties.

  摘要 描述了新型取代的 3-氰基亚氨基香豆素和相应的 N-乙氧基羰基亚氨基香豆素的合成。N-乙氧基羰基-3-氰基-7-二乙氨基亚氨基香豆素与作为N-亲核试剂的胺缩合得到具有良好光学性质的取代的2-氧代-2H-苯并吡喃-[2,3-d]嘧啶。
• Seema; Kumar, Surender; Makrandi, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2005, vol. 44, # 6, p. 1307 - 1308
  作者：Seema、Kumar, Surender、Makrandi

  DOI：——

  日期：——
• Investigations in the methoxy-iminocoumarin series: Highly efficient photoluminescent dyes and easy preparation of green-emitting crystalline microfibers
  作者：Nihel Abid-Jarraya、Hamida Turki-Guermazi、Kacem Khemakhem、Souhir Abid、Nathalie Saffon、Suzanne Fery-Forgues

  DOI：10.1016/j.dyepig.2013.09.043

  日期：2014.2

  The fluorescence properties of four methoxy derivatives of 3-cyano-2-(N-ethoxycarbonyl)iminocoumarin, differing by the position and number of the methoxy substituents, were investigated. The 8-methoxy-iminocoumarin derivative was virtually non-fluorescent. The 7-methoxy-iminocoumarin derivative was only weakly fluorescent both in solution and in the solid state. The 6-methoxy-iminocoumarin derivative was poorly fluorescent in every solvent investigated, but it showed high photoluminescence in the solid state. To our knowledge, this is the first example of crystallization-enhanced emission (CEE) in the iminocoumarin series. The mechanism probably encompasses restricted rotation and favorable molecular packing. Moreover, this compound spontaneously crystallized as long microfibers. The 5,7-dimethoxy-iminocoumarin derivative exhibited good fluorescence in very polar solvents and was intensely luminescent in the crystalline state. The last two substitution patterns, 6-methoxy and 5,7-dimethoxy, could be of high interest for the design of new fluorescent materials. (C) 2013 Elsevier Ltd. All rights reserved.