6-benzylideneamino-2H-chromen-2-one | 24922-39-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 6-benzylideneamino-2H-chromen-2-one
• 英文别名: 6-benzylideneaminocoumarin；(E)-6-(benzylideneamino)-2H-chromen-2-one；6-Benzylidenamino-cumarin；6-benzylidenamino-coumarin
• CAS: 24922-39-2
• 化学式: C₁₆H₁₁NO₂
• 分子量: 249.269
• InChiKey: JGGXMRCFUJMMJT-GZTJUZNOSA-N

物化性质

• 熔点：
  151-152 °C(Solv: N,N-dimethylformamide (68-12-2))
• 沸点：
  469.4±40.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.54
• 重原子数：
  19.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  42.57
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  6-benzylideneamino-2H-chromen-2-one 在 sodium acetate 、 溶剂黄146 作用下， 以 苯 为溶剂， 反应 6.17h， 生成 (Z)-4-benzylidene-1-(coumarin-6-yl)-2-phenyl-5-imidazolone
  参考文献：
  名称：

  Rao, Laxmi; Sanjayan, Gangadhar J.; Mukerjee, Arya K., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1995, vol. 34, # 4, p. 351 - 353

  摘要：

  DOI：
• 作为产物：
  描述：

  香豆素 在 硫酸 、 硝酸 、 铁粉 、 氯化铵 作用下， 以 乙醇 为溶剂， 反应 2.0h， 生成 6-benzylideneamino-2H-chromen-2-one
  参考文献：
  名称：

  Intramolecular charge transfer in coumarin based donor-acceptor systems: Formation of a new product through planar intermediate

  摘要：

  Fluorescence behavior and intramolecular charge transfer (ICT) property of N,N '-dimethylamino substituted anil derivative of coumarinyl amine was studied by steady state and time-resolved fluorescence spectroscopy in combination with density functional theory calculation. Quantitative analysis of the effect of solvent hydrogen bonding on several spectral parameters was done using multiple regression analysis based on Kamlet-Taft model. The present system shows an additional long wavelength fluorescence band almost instantaneously in presence of methanol in sharp contrast to the model unsubstituted analogue. This new fluorescence band is believed to be due to the formation of a new isomer (cis-type) through a planar intermediate. While there is a substantial barrier (similar to 50 kJ mol(-1)) in the ground state, the isomerization process in the excited state in polar-protic environment proceeds very fast and believed to be catalyzed by hydrogen bond formation at the imine nitrogen atom in combination with stabilization of the resulting species through ICT. (C) 2015 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jphotochem.2015.02.007

文献信息

• Schiff Bases Derived from 6-Amino-2H-chromen-2-one. Synthesis and 1H NMR Spectra
  作者：N. I. Ganushchak、L. O. Kobrin、E. E. Bilaya、V. L. Mizyuk

  DOI：10.1007/s11178-005-0294-8

  日期：2005.7

  A number of 6-arylmethylideneamino-2H-chromen-2-ones were synthesized by reaction of 6-amino-2H-chromen-2-one with aromatic and heterocyclic aldehydes. A linear relation was revealed between the chemical shifts of the azomethine CH=N proton and protons in the chromene ring, on the one hand, and Hammett constants σ of the para substituents, on the other. Formation of intramolecular hydrogen bond in ortho-hydroxy derivatives induces a downfield shift of signals from protons in positions 3–5, 7, and 8 and CH=N proton (9-H) and upfield shift of the o-H signal (14-H).

  通过6-氨基-2H-色烯-2-酮与芳香醛和杂环醛的反应，合成了一系列6-芳甲亚氨基-2H-色烯-2-酮。一方面，氮甲亚胺CH=N质子和色烯环上质子的化学位移与另一方面取代基的Hammett常数σ之间存在线性关系。邻羟基衍生物中的分子内氢键导致3-5、7和8位以及CH=N质子（9-H）的信号向低场移动，而o-H信号（14-H）向高场移动。
• Morgan; Micklethwait, Journal of the Chemical Society, 1904, vol. 85, p. 1233
  作者：Morgan、Micklethwait

  DOI：——

  日期：——