N-(3-nitrobenzalidene)-2,4-dimethylaniline | 200421-65-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(3-nitrobenzalidene)-2,4-dimethylaniline
• 英文别名: N-(3-Nitrobenzylidene)-2,4-xylidine；N-(2,4-dimethylphenyl)-1-(3-nitrophenyl)methanimine
• CAS: 200421-65-4
• 化学式: C₁₅H₁₄N₂O₂
• 分子量: 254.288
• InChiKey: DBDZIKXNGYFZNF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  58.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(3-nitrobenzalidene)-2,4-dimethylaniline 、 N-(2,4-dimethylphenyl)-1-(4-nitrophenyl)methanimine 、 丁酮 在 碘 作用下， 以 乙腈 为溶剂， 反应 24.0h， 生成 、 、
  参考文献：
  名称：

  Cross double Mannich reaction catalyzed by I2: Synthesis of highly substituted 4-piperidones

  摘要：

  Cross double Mannich reaction and tandem cyclization were achieved under iodine catalyzed conditions, yielding a series of highly substituted 4-piperidones. Among the possible diastereomers, only one diastereomer was isolated, which could be ascribed to the chair-like transition state in six-membered ring, in which all of the hindered groups are located in the pseudoequatorial orientation. (C) 2011 Xiao Dong Jia. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.

  DOI：

  10.1016/j.cclet.2011.12.008
• 作为产物：
  描述：

  间硝基苯甲醛 、 2,4-二甲基苯胺 以 乙醇 为溶剂， 以93%的产率得到N-(3-nitrobenzalidene)-2,4-dimethylaniline
  参考文献：
  名称：

  Third-order Nonlinear Optical Properties and Crystal Structures of N-(2-Nitrobenzalidene)-2,4-dimethylaniline and N-(3-Nitrobenzalidene)- 2,4-dimethylaniline

  摘要：

  N-(2-硝基苯甲醛基)-2,4-二甲基苯胺（1）和N-(3-硝基苯甲醛基)-2,4-二甲基苯胺（2）已经被合成并通过X射线衍射分析进行了表征。使用构型相互作用（CI）方法理论评估了线性光学特性。研究化合物的最大单光子吸收（OPA）波长小于450 nm，使其在可见光和近红外区域具有良好的光学透明性。为了提供关于标题分子的三阶非线性光学（NLO）行为的见解，使用时间相关Hartree-Fock（TDHF）方法计算了λ=825-1125 nm和1050-1600 nm波长范围内的无色散（静态）和频率依赖（动态）线性偏振率（α）和二阶超极化率（γ）。从第一性原理计算的（超）极化率结果表明，两种化合物都表现出具有非零值的二阶超极化率，暗示了微观的三阶NLO行为。

  DOI：

  10.1515/znb-2007-1113

文献信息

• Cross double Mannich reaction catalyzed by I2: Synthesis of highly substituted 4-piperidones
  作者：Xiao Dong Jia、Xiang Ning Chen、Cong De Huo、Fang Fang Peng、Chang Qing、Xi Cun Wang

  DOI：10.1016/j.cclet.2011.12.008

  日期：2012.3

  Cross double Mannich reaction and tandem cyclization were achieved under iodine catalyzed conditions, yielding a series of highly substituted 4-piperidones. Among the possible diastereomers, only one diastereomer was isolated, which could be ascribed to the chair-like transition state in six-membered ring, in which all of the hindered groups are located in the pseudoequatorial orientation. (C) 2011 Xiao Dong Jia. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.
• Third-order Nonlinear Optical Properties and Crystal Structures of N-(2-Nitrobenzalidene)-2,4-dimethylaniline and N-(3-Nitrobenzalidene)- 2,4-dimethylaniline
  作者：Aslı Karakaş、Hüseyin Ünverb、Ayhan Elmalı

  DOI：10.1515/znb-2007-1113

  日期：2007.11.1

  N-(2-nitrobenzalidene)-2,4-dimethylaniline (1) and N-(3-nitrobenzalidene)-2,4-dimethylaniline (2) have been synthesized and characterized by X-ray diffraction analysis. Linear optical characteristics have been evaluated theoretically using the configuration interaction (CI) method. The maximum one-photon absorption (OPA) wavelengths of the studied compounds are shorter than 450 nm, giving rise to good optical transparency in the visible and near IR regions. To provide an insight into the third-order nonlinear optical (NLO) behavior of the title molecules, both dispersion-free (static) and frequency-dependent (dynamic) linear polarizabilities (α) and second hyperpolarizabilities (γ) at λ = 825 - 1125 nm and 1050 - 1600 nm wavelength ranges have been computed using the time-dependent Hartree-Fock (TDHF) method. The ab initio computational results on (hyper)polarizabilities reveal that both compounds exhibit second hyperpolarizabilities with non-zero values, implying microscopic third-order NLO behavior.

  N-(2-硝基苯甲醛基)-2,4-二甲基苯胺（1）和N-(3-硝基苯甲醛基)-2,4-二甲基苯胺（2）已经被合成并通过X射线衍射分析进行了表征。使用构型相互作用（CI）方法理论评估了线性光学特性。研究化合物的最大单光子吸收（OPA）波长小于450 nm，使其在可见光和近红外区域具有良好的光学透明性。为了提供关于标题分子的三阶非线性光学（NLO）行为的见解，使用时间相关Hartree-Fock（TDHF）方法计算了λ=825-1125 nm和1050-1600 nm波长范围内的无色散（静态）和频率依赖（动态）线性偏振率（α）和二阶超极化率（γ）。从第一性原理计算的（超）极化率结果表明，两种化合物都表现出具有非零值的二阶超极化率，暗示了微观的三阶NLO行为。