5-(diethylamino)-2-(((4-nitrophenyl)imino)methyl)phenol | 23764-68-3

• 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: 5-(diethylamino)-2-(((4-nitrophenyl)imino)methyl)phenol
• 英文别名: 4-nitroaniline-4-diethylaminosalicylaldehyde schiff base；N-4-Diethylaminosalicyliden-p-nitroanilin；(diethylaminosalicylaldiminato)nitrobenzene；5-(Diethylamino)-2-[(E)-[(4-nitrophenyl)imino]methyl]phenol；5-(diethylamino)-2-[(4-nitrophenyl)iminomethyl]phenol
• CAS: 23764-68-3
• 化学式: C₁₇H₁₉N₃O₃
• 分子量: 313.356
• InChiKey: YWJKGDSRRVCFNC-UHFFFAOYSA-N

物化性质

• 熔点：
  167 °C(Solv: acetonitrile (75-05-8))
• 沸点：
  520.3±50.0 °C(Predicted)
• 密度：
  1.17±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  81.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-(diethylamino)-2-(((4-nitrophenyl)imino)methyl)phenol 在 三氟化硼乙醚 、 N,N-二异丙基乙胺 作用下， 以 1,1-二氯乙烷 为溶剂， 以72%的产率得到
  参考文献：
  名称：

  Facile Synthesis of Highly Fluorescent Boranil Complexes

  摘要：

  Complexation of a large variety of Anils (aniline-imines) with boron(III) precursors provides stable Boranils, some of which have been structurally characterized. Analysis of their optical properties reveals that the fluorescence stems from an intraligand charge transfer (ILCT) state with the best quantum yields reaching 90%. Chemistry on the Boranils allows grafting of photoactive modules acting as energy antennae for borondipyrromethene (Bodipy) and subphtalocyanine (SubPc) fluorophores.

  DOI：

  10.1021/ol2011665
• 作为产物：
  描述：

  4-(二乙氨基)水杨醛 、 4-硝基苯胺 以 甲醇 为溶剂， 反应 24.0h， 以89%的产率得到5-(diethylamino)-2-(((4-nitrophenyl)imino)methyl)phenol
  参考文献：
  名称：

  使用荧光传感器检测细胞中的硼酸衍生物†

  摘要：

  含硼化合物的检测需要非常昂贵的设备和/或繁琐的样品预处理。为了开发一种方便的硼酸衍生物检测方法，合成了硼螯合配体以用作荧光传感器。本文报道了硼酸衍生物荧光传感器的合成及性能。

  DOI：

  10.1039/c5ob00753d

文献信息

• Synthesis and optical properties of aggregation-induced emission (AIE) molecules based on the ESIPT mechanism as pH- and Zn²⁺-responsive fluorescent sensors
  作者：Liqiang Yan、Tingting Qing、Renjie Li、Zhongwei Wang、Zhengjian Qi

  DOI：10.1039/c6ra09920c

  日期：——

  A series salicylaldehyde derives with AIE properties were designed and synthesized, which can be used as potential pH and Zn²⁺ sensing.

  设计并合成了一系列具有AIE特性的水杨醛衍生物，可用作潜在的pH和Zn2+传感器。
• Identification of fatty liver disease at diverse stages using two-photon absorption of triphenylamine-based BODIPY analogues
  作者：Tao Shao、Tianyan Liu、Hui Liu、Mingzhu Zhang、Yu Shen、Awei Gao、Xiaohe Tian、Qiong Zhang、Jieying Wu、Yupeng Tian

  DOI：10.1039/c9tb00421a

  日期：——

  03B can target 3T3-L1 model cells at different fatty liver disease (FLD)-induced stages and clearly distinguish FLD tissue and display a lesion in situ.

  “03B”可以针对不同脂肪肝疾病（FLD）诱导阶段的3T3-L1模型细胞，并清晰地区分FLD组织并显示原位病变。
• Synthesis, crystal structures, and molecular hyperpolarizabilities of a new Schiff base ligand, and its copper(II), nickel(II), and cobalt(II) metal complexes
  作者：Pascal G. Lacroix、Frédéric Averseng、Isabelle Malfant、Keitaro Nakatani

  DOI：10.1016/j.ica.2004.03.004

  日期：2004.11

  condensation of 4-(diethylamino)salicylaldehyde with 4-nitroaniline is reported, with its nickel(II), copper(II), and cobalt(II) complexes. The crystal structures are reported for the four derivatives. While, Ni I I L 2 and Cu I I L 2 are centrosymmetric molecules, Co I I L 2 exhibits a pseudo-tetrahedral molecular structure. The quadratic hyperpolarizabilities (β) of HL and Co I I L 2 , measured by electric

  据报道从4-（二乙氨基）水杨醛与4-硝基苯胺的席夫碱缩合获得的新配体（HL）及其镍（II），铜（II）和钴（II）配合物。报告了四种衍生物的晶体结构。Ni IIL 2和Cu IIL 2是中心对称分子，而Co IIL 2表现出伪四面体分子结构。通过电场感应二次谐波（EFISH）技术测得的HL和Co IIL 2的二次超极化率（β）分别等于66和110 x 10-3 0 cm 5 esu-1。除了几何效应（伪T d对称性）之外，金属中心的配位还提供了NLO响应的内在增强。另外，在金属络合后发现热稳定性提高了约60°。
• Synthesis, X-ray diffraction analysis, and chemical–optical characterizations of boron complexes from bidentate ligands
  作者：Mario Rodríguez、José Luis Maldonado、Gabriel Ramos-Ortíz、Oscar Domínguez、Ma. Eugenia Ochoa、Rosa Santillan、Norberto Farfán、Marco-Antonio Meneses-Nava、Oracio Barbosa-García

  DOI：10.1016/j.poly.2012.06.043

  日期：2012.8

  Herein is reported the synthesis and X-ray diffraction analysis for three boron complexes (2a-2c) prepared from the reaction of bidentate ligands (1a-1c) and diphenylborinic acid. Chemical characterization for the borinates is completed with IR. UV-Vis and NMR techniques, particularly B-11 NMR spectra confirmed the formation of boron complexes. X-ray diffraction analysis showed that for compounds 2a and 2c a non-planar conformation for the main pi-backbone is acquired after boron complexation; for compound 2b the planar conformation is preserved. Additionally, cubic nonlinear optical (NLO) properties were evaluated, through the optical susceptibility chi((3)) (-3 omega, omega, omega, omega), using the THG Maker-Fringes technique. Results showed that chi((3)) response decreases from ligands to boron complexes: this behavior could be attributed to a structural conformation or deformation of the electronic pi-system after boron complexation. The demonstrated electronic and structural features of these borinates could be useful for new strategies in the design of novel NLO dyes. (C) 2012 Elsevier Ltd. All rights reserved.