(E)-2-((E)-3-(methyl(phenyl)amino)allylidene)-2,3-dihydro-1H-inden-1-one

• 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-((E)-3-(methyl(phenyl)amino)allylidene)-2,3-dihydro-1H-inden-1-one
• 英文别名: 2-[3-(N-methyl-N-phenyl amino)-2-propenylidene] indanone；DN2；(2E)-2-[(E)-3-(N-methylanilino)prop-2-enylidene]-3H-inden-1-one
• 化学式: C₁₉H₁₇NO
• 分子量: 275.35
• InChiKey: ZIACRBXJZUJVHP-HMFVYWHISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  β-环糊精 、 (E)-2-((E)-3-(methyl(phenyl)amino)allylidene)-2,3-dihydro-1H-inden-1-one 以 水 为溶剂， 反应 1.0h， 生成
  参考文献：
  名称：

  Spectroscopic study on encapsulation of two structurally similar donor–acceptor dyes in model cyclodextrin nanocavity

  摘要：

  Encapsulation of two structurally similar donor-acceptor dyes in beta-cyclodextrin (beta-CD) nanocavity has been studied by steady state and time resolved fluorescence spectroscopic procedures. In the dye, (E)-2-((E)-3-(methyl(phenyl)amino)allylidene)-2,3-dihydro-1H-inden-1-one, the rotation about C-N bond is possible, while such a rotation is strategically restricted in the dye (E)-2-((1-methyl-3a,7a-dihydro-1H-indol-3-yl)methylene)-2,3-dihydro-1H-inden-1-one. Results indicate that both the dyes form complexes with beta-CD but the stoichiometry and the nature of encapsulation are different. The dye in which the C-N bond rotation is permissible forms a 1:1 complex, with the acceptor centre (carbonyl group), rather than the donor centre (N atom) being encapsulated. The dye where the above mentioned rotation is restricted forms a 1:1 complex at a lower concentration of beta-CD, encapsulating the donor centre (indole N). However, at a higher concentration of beta-CD, 1:2 complex is formed involving both the acceptor and donor centres. Semi-empirical calculations at the PM3 level provide support to experimental findings. It is evidenced that the molecular structure of the guest is extremely important for encapsulation. (C) 2014 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2014.04.027
• 作为产物：
  描述：

  1,1,3,3-四甲氧基丙烷 、 1-茚酮 、 N-甲基苯胺 在 高氯酸 、 sodium methylate 作用下， 以 乙醇 为溶剂， 反应 2.5h， 生成 (E)-2-((E)-3-(methyl(phenyl)amino)allylidene)-2,3-dihydro-1H-inden-1-one
  参考文献：
  名称：

  Studies of solvation in homogeneous and heterogeneous media by electronic spectroscopic method

  摘要：

  Solvation characteristics in homogenous (pure and mixed binary solvents) and heterogeneous media (aqueous micelles, beta- and gamma-cyclodextrine solutions) have been studied by monitoring the emission characteristics of a newly synthesised dye. The longest wavelength absorption and emission band of the dye arise due to transition between S-0 and S-1 state. The maximum energy of electronic transition involving intramolecular charge transfer is found to be dependent on both the hydrogen-bond donating ability and the polarity-polarisability in pure solvent. The dipole moment in the S-1 state, as determined by solvatochromic procedure, agrees well with the value obtained by theoretical calculation at the AM1 level. Preferential solvation of the dye by alcohols has been found to occur in ethanol + water, propan-1-ol + water, propan-2-ol + water binary mixtures. In aqueous micellar media the dye molecule is located at the water-micelle interface. The binding constant for the dye-micelle interaction has also been determined. The results have been compared with those for a structurally related symmetrical ketocyanine dye. (C) 2003 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s1386-1425(03)00120-3

文献信息

• Studies of solvation in homogeneous and heterogeneous media by electronic spectroscopic method
  作者：Mrinmoy Shannigrahi、Ramkrishna Pramanik、Sanjib Bagchi

  DOI：10.1016/s1386-1425(03)00120-3

  日期：2003.11

  Solvation characteristics in homogenous (pure and mixed binary solvents) and heterogeneous media (aqueous micelles, beta- and gamma-cyclodextrine solutions) have been studied by monitoring the emission characteristics of a newly synthesised dye. The longest wavelength absorption and emission band of the dye arise due to transition between S-0 and S-1 state. The maximum energy of electronic transition involving intramolecular charge transfer is found to be dependent on both the hydrogen-bond donating ability and the polarity-polarisability in pure solvent. The dipole moment in the S-1 state, as determined by solvatochromic procedure, agrees well with the value obtained by theoretical calculation at the AM1 level. Preferential solvation of the dye by alcohols has been found to occur in ethanol + water, propan-1-ol + water, propan-2-ol + water binary mixtures. In aqueous micellar media the dye molecule is located at the water-micelle interface. The binding constant for the dye-micelle interaction has also been determined. The results have been compared with those for a structurally related symmetrical ketocyanine dye. (C) 2003 Elsevier Science B.V. All rights reserved.
• Spectroscopic study on encapsulation of two structurally similar donor–acceptor dyes in model cyclodextrin nanocavity
  作者：Amrita Sarkar、Niraja Kedia、Pradipta Purkayastha、Sanjib Bagchi

  DOI：10.1016/j.molstruc.2014.04.027

  日期：2014.6

  Encapsulation of two structurally similar donor-acceptor dyes in beta-cyclodextrin (beta-CD) nanocavity has been studied by steady state and time resolved fluorescence spectroscopic procedures. In the dye, (E)-2-((E)-3-(methyl(phenyl)amino)allylidene)-2,3-dihydro-1H-inden-1-one, the rotation about C-N bond is possible, while such a rotation is strategically restricted in the dye (E)-2-((1-methyl-3a,7a-dihydro-1H-indol-3-yl)methylene)-2,3-dihydro-1H-inden-1-one. Results indicate that both the dyes form complexes with beta-CD but the stoichiometry and the nature of encapsulation are different. The dye in which the C-N bond rotation is permissible forms a 1:1 complex, with the acceptor centre (carbonyl group), rather than the donor centre (N atom) being encapsulated. The dye where the above mentioned rotation is restricted forms a 1:1 complex at a lower concentration of beta-CD, encapsulating the donor centre (indole N). However, at a higher concentration of beta-CD, 1:2 complex is formed involving both the acceptor and donor centres. Semi-empirical calculations at the PM3 level provide support to experimental findings. It is evidenced that the molecular structure of the guest is extremely important for encapsulation. (C) 2014 Elsevier B.V. All rights reserved.