N-(4-dimethylaminobenzylide)-benzene-1,2-diamine | 61022-73-9

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N-(4-dimethylaminobenzylide)-benzene-1,2-diamine
• 英文别名: N-(4-(N,N-dimethylaminobezylidene)benzene)-1,2-diamine；1,2-Benzenediamine, N-[[4-(dimethylamino)phenyl]methylene]-；2-[[4-(dimethylamino)phenyl]methylideneamino]aniline
• CAS: 61022-73-9
• 化学式: C₁₅H₁₇N₃
• 分子量: 239.32
• InChiKey: ZAZVSQQJRHVEKB-UHFFFAOYSA-N

物化性质

• 熔点：
  148 °C(Solv: ethanol (64-17-5))
• 沸点：
  441.9±30.0 °C(Predicted)
• 密度：
  1.05±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  41.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(4-dimethylaminobenzylide)-benzene-1,2-diamine 在 sodium hydrogensulfite 作用下， 以 乙醇 为溶剂， 反应 4.0h， 生成 2-(p-N,N-二甲基氨基苯基)-1H-苯并咪唑
  参考文献：
  名称：

  2-芳基-1H-苯并[d]咪唑衍生物作为潜在微管靶向剂的合成与评价

  摘要：

  微管靶向剂（MTA）是抗癌药物发现的潜在候选药物。通过合成分子破坏微管形成或抑制解聚过程可以产生出色的抗癌候选药物。在这里，我们将 2,5-取代-1 H-苯并[d]咪唑衍生物作为潜在的秋水仙碱、诺考达唑结合位点靶向剂。使用温和的反应条件合成了大约 20 种苯并咪唑衍生物，收率 82.0%–94.0%。合成的化合物在三种细胞系中显示出中等至优异的抗癌活性，包括 Hela 细胞、A549 细胞、MRC-5 细胞。化合物B15、B16、B19和B20是三种不同细胞系中IC 50 <15 μM 的潜在候选者。在 MTT 测定中，化合物B15、B16、B19和B20显示出优异的抗增殖活性，使用 HeLa 和 A549 细胞系的 IC 50值在 5.3 ± 0.21 至 18.1 ± 0.32 μM 范围内。B15、B16、B19和B20的预测吸收、分布、代谢和排泄 (ADME) 特性和药物相似特性表

  DOI：

  10.1002/ddr.21909
• 作为产物：
  描述：

  2,2’-[(4-dimethylaminophenyl)methylene]bis(3-hydroxy-5,5-dimethyl-2-cyclohexene-1-one) 、 邻苯二胺 以 异丙醇 为溶剂， 以45%的产率得到N-(4-dimethylaminobenzylide)-benzene-1,2-diamine
  参考文献：
  名称：

  Investigation of the products of interaction of cyclic diketones with nitrogen-containing 1,4-binucleophiles

  摘要：

  DOI：

  10.1007/s10593-005-0098-3

文献信息

• Synthesis and Antibacterial Activities of Some Schiff Bases
  作者：Mohamed N. Ibrahim、Salaheddin A. I. Sharif、Ahmad N. EL-Tajory、Asma A. Elamari

  DOI：10.1155/2011/258340

  日期：——

  Schiff basesp-hydroxybenzylidene-2-carboxyaniline,p-nitrobenz-ylidene-2-carboxyaniline,p-(N, N-dimethyl)aminobenzylidene-2-carboxyaniline,N-(4-hydroxybezylidene)-benzene-1,2-diamine,N--(4-nitrobezylidene)benzene-1,2-diamine,N-(4-(N, N-dimethylaminobezylidene)benzene-1,2-diamine,N-(4-(N,N-dimethylamino)benzylidene)naphthalen-1-amine,N-(4-nitrobenzylidene)naphthalen-1-amine,N--(4-chlorobenzylidene)naphthalen-1-amine,sodium-4-(4-(N,N-dimethyl amino)benzylideneamino)naphthalene-1-sulfonate,sodium -4-(4-nitrobenzylidene-amino)naphthalene-1-sulfonate and sodium-4-(4-chlorobenzylideneamino) naphthalene-1-sulfonate obtained by condensation of aniline and naphthyl-amine derivatives with some aromatic aldehydes were characterized by physical and spectral methods. The biological activity of these products were as antibacterial agents against three species of human pathogenic bacteria such asEscherichia coli, Staphylococcus aureusandKlebsiella sp. Nearly 50% of these compounds showed reasonable activity against the bacterial species investigated and we found that the antibacterial activity is dependent on the molecular structure of the compounds.

  希夫碱p-羟基苯甲醛基-2-羧基苯胺，p-硝基苯甲醛基-2-羧基苯胺，p-(N, N-二甲基)氨基苯甲醛基-2-羧基苯胺，N-(4-羟基苯甲醛基)苯-1,2-二胺，N-(4-硝基苯甲醛基)苯-1,2-二胺，N-(4-(N, N-二甲基氨基苯甲醛基)苯-1,2-二胺，N-(4-(N, N-二甲基氨基)苯甲醛基)萘-1-胺，N-(4-硝基苯甲醛基)萘-1-胺，N-(4-氯苯甲醛基)萘-1-胺，钠-4-(4-(N, N-二甲基氨基)苯甲醛基氨基)萘-1-磺酸盐，钠-4-(4-硝基苯甲醛基氨基)萘-1-磺酸盐和钠-4-(4-氯苯甲醛基氨基)萘-1-磺酸盐，通过苯胺和萘胺衍生物与一些芳香醛缩合而得，通过物理和光谱方法进行了表征。这些产物的生物活性作为抗菌剂针对三种人类致病细菌如大肠杆菌、金黄色葡萄球菌和克雷伯氏菌。近50%的这些化合物对所研究的细菌种类显示了合理的活性，我们发现抗菌活性取决于化合物的分子结构。
• Synthesis, Characterization and Use of Schiff Bases as Fluorimetric Analytical Reagents (Part II)
  作者：Mohamed N. Ibrahim、Salaheddin A. I. Sharif

  DOI：10.1155/2011/821616

  日期：——

  Many Schiff bases were prepared by condensation reaction of certain aromatic amines with aromatic aldehydes derivatives and then the fluorescence properties of these Schiff bases were examined in acidic and basic media. It is shown that these compounds can be used for fluorimetric monitoring of small pH changes.

  许多席夫碱是通过某些芳香胺与芳香醛衍生物的缩合反应制备的，然后检查了这些席夫碱在酸性和碱性介质中的荧光特性。结果表明，这些化合物可用于荧光测定监测小pH变化。
• Naphthalimide-based probe as an in situ indicator of photochemical reaction for self-reporting imidazole ring formation
  作者：Bin Yang、Xia Yan、Haichuang Lan、Peng Geng、Yanfen Fang、Shuzhang Xiao

  DOI：10.1016/j.dyepig.2023.111592

  日期：2023.11

  bearing an active photochemical reactive site based on naphthalimide was designed and synthesized. Under UV irradiation, the photocyclization reaction to form imidazole occurred through the intramolecular addition reaction between α-amine and imine. This photochemical reaction was dynamically monitored in real time by significant fluorescence and UV spectrum changes. The reaction mechanism was further

  荧光探针是传感领域有前途的超灵敏候选者。在此，设计并合成了一种基于萘二甲酰亚胺的带有活性光化学反应位点的荧光指示剂。在紫外光照射下，α-胺与亚胺发生分子内加成反应，发生光环化反应生成咪唑。通过显着的荧光和紫外光谱变化实时动态监测这种光化学反应。通过NMR、MS、IR和自由基猝灭反应进一步验证了反应机理。基于该机制的类似底物的光环化反应也通过自报告光谱变化进行监测。
• Three-Way Chemoselectivity Switching through Coupled Equilibria
  作者：Thamon Puangsamlee、Ognjen Š. Miljanić

  DOI：10.1021/acs.orglett.0c02003

  日期：2020.8.7

  Controlling the chemoselectivity of reactions operating on complex mixtures, including those found in biological and petrochemical feedstocks or in the primordial soup from which life emerged, is generally challenging. The selectivity of imine oxidation can be controlled in dynamic combinatorial libraries, wherein coupled equilibria of imine exchange and the diaza-Cope rearrangement determine whether and when the oxidizable precursor is made available to the oxidant. Adjusting the rate of oxidant addition allows the isolation of three dominant products.
• Investigation of the products of interaction of cyclic diketones with nitrogen-containing 1,4-binucleophiles
  作者：N. N. Kolos、E. N. Yurchenko、V. D. Orlov、S. V. Shishkina、O. V. Shishkin

  DOI：10.1007/s10593-005-0098-3

  日期：2004.12