2-(2-hydroxyethyl)-5-propyl-2,4-dihydropyrazol-3-one | 895552-12-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑啉类
• 英文名称: 2-(2-hydroxyethyl)-5-propyl-2,4-dihydropyrazol-3-one
• 英文别名: 2-(2-hydroxyethyl)-5-propyl-4H-pyrazol-3-one
• CAS: 895552-12-2
• 化学式: C₈H₁₄N₂O₂
• mdl: MFCD10693283
• 分子量: 170.211
• InChiKey: OREMYQWVPYZGSP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  52.9
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(2-hydroxyethyl)-5-propyl-2,4-dihydropyrazol-3-one 在 哌啶 、 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 36.0h， 生成 2-[4-[2-(1-Methylpyridin-4-ylidene)ethylidene]-5-oxo-3-propylpyrazol-1-yl]ethyl benzoate
  参考文献：
  名称：

  Antiparallel-Aligned Neutral-Ground-State and Zwitterionic Chromophores as a Nonlinear Optical Material

  摘要：

  Efficient noncentrosymmetric arrangement of nonlinear optical (NLO) chromophores with high first-order hyperpolarizability (beta) for increased electro-optical (EO) efficiency has proven challenging as strong dipolar interactions between the chromophores encourage antiparallel alignment, attenuating the macroscopic EO effect. This work explores a novel approach to simultaneously achieve large beta values while providing an adjustable dipole moment by linking a strong neutral-ground-state (NGS) NLO chromophore with positive beta to a zwitterionic (ZWI) chromophore with negative beta in an antiparallel fashion. It is proposed that the overall beta of such a structure will be the sum of the absolute values of the two types of chromophores while the dipole moment will be the difference. Molecules 1-3 were synthesized to test the feasibility of this approach. Molecular dynamics calculations and NMR data supported that the NGS chromophore component and the ZWI chromophore component self-assemble to an antiparallel conformation in chloroform. Calculations showed that the dipole moment of 1 is close to the difference of the two component chromophores. Hyper-Rayleigh scattering (HRS) studies confirmed that the first hyperpolarizability of 1 is close to the sum of the two component chromophores. These results support the idea that an antiparallel-aligned neutral-ground-state chromophore and a zwitterionic chromophore can simultaneously achieve an increase in beta and a decrease of the dipole moment.

  DOI：

  10.1021/ja057903i
• 作为产物：
  描述：

  2-肼基乙醇 、 丁酰乙酸乙酯 反应 4.0h， 以60%的产率得到2-(2-hydroxyethyl)-5-propyl-2,4-dihydropyrazol-3-one
  参考文献：
  名称：

  Antiparallel-Aligned Neutral-Ground-State and Zwitterionic Chromophores as a Nonlinear Optical Material

  摘要：

  Efficient noncentrosymmetric arrangement of nonlinear optical (NLO) chromophores with high first-order hyperpolarizability (beta) for increased electro-optical (EO) efficiency has proven challenging as strong dipolar interactions between the chromophores encourage antiparallel alignment, attenuating the macroscopic EO effect. This work explores a novel approach to simultaneously achieve large beta values while providing an adjustable dipole moment by linking a strong neutral-ground-state (NGS) NLO chromophore with positive beta to a zwitterionic (ZWI) chromophore with negative beta in an antiparallel fashion. It is proposed that the overall beta of such a structure will be the sum of the absolute values of the two types of chromophores while the dipole moment will be the difference. Molecules 1-3 were synthesized to test the feasibility of this approach. Molecular dynamics calculations and NMR data supported that the NGS chromophore component and the ZWI chromophore component self-assemble to an antiparallel conformation in chloroform. Calculations showed that the dipole moment of 1 is close to the difference of the two component chromophores. Hyper-Rayleigh scattering (HRS) studies confirmed that the first hyperpolarizability of 1 is close to the sum of the two component chromophores. These results support the idea that an antiparallel-aligned neutral-ground-state chromophore and a zwitterionic chromophore can simultaneously achieve an increase in beta and a decrease of the dipole moment.

  DOI：

  10.1021/ja057903i

文献信息

• Antiparallel-Aligned Neutral-Ground-State and Zwitterionic Chromophores as a Nonlinear Optical Material
  作者：Yi Liao、Sanchali Bhattacharjee、Kimberly A. Firestone、Bruce E. Eichinger、Rajan Paranji、Cyrus A. Anderson、Bruce H. Robinson、Philip J. Reid、Larry R. Dalton

  DOI：10.1021/ja057903i

  日期：2006.5.1

  Efficient noncentrosymmetric arrangement of nonlinear optical (NLO) chromophores with high first-order hyperpolarizability (beta) for increased electro-optical (EO) efficiency has proven challenging as strong dipolar interactions between the chromophores encourage antiparallel alignment, attenuating the macroscopic EO effect. This work explores a novel approach to simultaneously achieve large beta values while providing an adjustable dipole moment by linking a strong neutral-ground-state (NGS) NLO chromophore with positive beta to a zwitterionic (ZWI) chromophore with negative beta in an antiparallel fashion. It is proposed that the overall beta of such a structure will be the sum of the absolute values of the two types of chromophores while the dipole moment will be the difference. Molecules 1-3 were synthesized to test the feasibility of this approach. Molecular dynamics calculations and NMR data supported that the NGS chromophore component and the ZWI chromophore component self-assemble to an antiparallel conformation in chloroform. Calculations showed that the dipole moment of 1 is close to the difference of the two component chromophores. Hyper-Rayleigh scattering (HRS) studies confirmed that the first hyperpolarizability of 1 is close to the sum of the two component chromophores. These results support the idea that an antiparallel-aligned neutral-ground-state chromophore and a zwitterionic chromophore can simultaneously achieve an increase in beta and a decrease of the dipole moment.