(E)-2-(1-hydroxy-3-phenylallylidene)-2H-indene-1,3-dione | 1246402-96-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: (E)-2-(1-hydroxy-3-phenylallylidene)-2H-indene-1,3-dione
• 英文别名: 2-(1-hydroxy-3-phenyl-allylidene)-2H-inden-1,3-dione；2-[1-hydroxy-3-phenyl-allylidene]indan-1,3-dione
• CAS: 1246402-96-9
• 化学式: C₁₈H₁₂O₃
• 分子量: 276.291
• InChiKey: NDNIOMBMWZXDGO-ZHACJKMWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.59
• 重原子数：
  21.0
• 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：
  54.37
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (E)-2-(1-hydroxy-3-phenylallylidene)-2H-indene-1,3-dione 、 硫酸二甲酯 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 4.0h， 以49%的产率得到(E)-2-(1-methoxy-3-phenylallylidene)-2H-indene-1,3-dione
  参考文献：
  名称：

  Synthesis, optical and electrochemical properties of substituted 2-cinnamoyl-1, 3-indandione O-methyl ethers

  摘要：

  Seven new 2-cinnamoyl-1,3-indandione (2CID) O-methyl ethers with different substituents (R = -H, -CH3, -OCH3, -N(C6H5)(2), -N(CH2CH2CN)(2), julolidyl, -N(CH3)(2)) in 4-position of the cinnamoyl moiety were synthesized. The methylation with dimethylsulfate occurred at the oxygen atom of the exocyclic enol group with high selectivity.The synthesized compounds were characterized by H-1, C-13 NMR, IR, UV-Vis and luminescence spectroscopy, their electrochemical properties were investigated by cyclic voltammetry. The obtained results indicates that introducing an electron donating substituents in the 4-position of cinnamoyl moiety facilitates electrochemical oxidation, remarkably shifts absorption and emission bands to longer wavelengths, simultaneously increases extinction coefficient (epsilon). O-methyl ethers with strong electron donating groups (R = -N(C6H5)(2), -N(CH2CH2CN)(2), julolidyl, -N(CH3)(2)) in molecule are characterized by luminescence with maximum in range from 547 to 647 nm and absolute photoluminescence quantum yields from 0.02 to 0.32. Quantum yield (QY) of chromophore containing julolidyl fragment is solvent dependent. It was 0.32 in chloroform and decreased in other polar (ethanol, acetone) solvents. (C) 2016 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2016.02.090
• 作为产物：
  描述：

  苯甲醛 、 2-乙基-1,3-氢化茚二酮 在 哌啶 作用下， 反应 1.0h， 以70%的产率得到(E)-2-(1-hydroxy-3-phenylallylidene)-2H-indene-1,3-dione
  参考文献：
  名称：

  Structure and properties of a series of 2-cinnamoyl-1,3-indandiones and their metal complexes

  摘要：

  通过光谱学（红外、核磁共振、电子吸收和发射光谱）和/或单晶X射线衍射方法，合成了七种2-肉桂酰-1,3-茚满二酮及其金属（II）络合物，并对其进行了表征。有机化合物的光谱显示，在可见光区域有很强的吸收，弱荧光，斯托克斯位移适中至强。还研究了浓度、加水以及金属离子络合对光学性质的影响。为了寻找潜在的实际应用，研究了2-肉桂酰-1,3-茚满二酮与金属（II）离子的络合。通过元素分析和红外光谱分离并分析了与Cu（II）、Cd（II）、Zn（II）、Co（II）和Ni（II）的一系列非带电络合物。大多数络合物都存在水分子，很可能与金属离子配位，从而形成八面体几何结构。对于顺磁Cu（II）络合物，根据EPR数据，提出了扭曲的扁平四面体结构。然而，金属络合物与游离配体的光学性质没有明显差异。

  DOI：

  10.1007/s13738-011-0024-9

文献信息

• Experimental and theoretical study on the structure and optical properties of 2-acyl-1,3-indandiones – Conformational effects
  作者：Anife Ahmedova、Gordana Pavlović、Diana Zhiryakova、Dubravka Šišak、Neyko Stoyanov、Michael Springborg、Mariana Mitewa

  DOI：10.1016/j.molstruc.2010.07.008

  日期：2010.9

  A series of six 2-acyl-1,3-indandione derivatives is studied by means of experimental (single crystal X-ray diffraction, NMR, electron absorption and emission spectroscopy) and theoretical methods (HF, DFT and TD-DFT) All possible tautomers and rotamers are described quantum-chemically on the basis of their structure, energy and optical properties. Although the heterocyclic substituent may easily rotate about a C-C bond, according to the calculated energies, the conformation in the most stable gas-phase optimized structures is the same as in the crystalline form. These results suggest that the intermolecular interactions are very weak compared to the intramolecular ones, like strong intramolecular hydrogen bonding and pi-electron delocalization. Therefore, a good account of the experimental results was obtained theoretically by considering only the conformational modes of the isolated molecules in ground and excited states. The experimentally observed spectra of the studied series of compounds are characterized by very strong absorption in the visible region and weak fluorescence showing moderate to strong Stokes shift (C) 2010 Elsevier B.V. All rights reserved.