1-N-(anthracen-9-ylmethyl)benzene-1,2-diamine | 389826-84-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 1-N-(anthracen-9-ylmethyl)benzene-1,2-diamine
• 英文别名: N-(2-aminophenyl)-N-(9-anthrylmethyl)amine；9-(2-aminophenyl)aminomethylanthracene；N-(9-anthrylmethyl)benzene-1,2-diamine；N-(9-anthrylmethyl)-benzene-1,2-diamine；2-N-(anthracen-9-ylmethyl)benzene-1,2-diamine
• CAS: 389826-84-0
• 化学式: C₂₁H₁₈N₂
• 分子量: 298.387
• InChiKey: GNDZSKDYEMIOTP-UHFFFAOYSA-N

物化性质

• 沸点：
  537.9±33.0 °C(Predicted)
• 密度：
  1.242±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  38
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-N-(anthracen-9-ylmethyl)benzene-1,2-diamine 在 sodium tetrahydroborate 、 溶剂黄146 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 、 正丁醇 为溶剂， 反应 1.33h， 生成 anthracen-9-ylmethyl(1-anthracen-9-ylmethyl-1H-benzimidazol-2-yl)amin
  参考文献：
  名称：

  Effective pH sensors based on 1-(anthracen-9-ylmethyl)-1H-benzimidazol-2-amine

  摘要：

  1-(Anthracen-9-ylmethyl)-1H-benzimidazol-2-amine was synthesized by alkylation of benzimidazol-2-amine with 9-chloromethylanthracene, and a series of azomethines based on it was obtained. Spectral investigations of the 9-anthrylmethylbenzimidazole derivatives revealed their high chemosensor activity with respect to hydrogen cations. Quantum-chemical investigation of the structures obtained showed that they possess high proton affinity and can be regarded as analogs of "proton sponges".

  DOI：

  10.1007/s10593-012-0898-1
• 作为产物：
  描述：

  N¹-(anthracene-9-methylene)benzene-1,2-diamine 在 sodium tetrahydroborate 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 1-N-(anthracen-9-ylmethyl)benzene-1,2-diamine
  参考文献：
  名称：

  Chemosensors based on N-(2-aminophenyl)-N-(9-anthrylmethyl)amine: II

  摘要：

  A series of N-(9-anthrylmethyl)arylimines was prepared by condensation of N-(2-aminophenyl)-N-(9-anthrylmethyl)amine with aromatic aldehydes. The study of the luminescent and complexing properties of compounds obtained showed that 2-{[2-(9-anthrylmethylamino)phenylimino]methyl}-1-naphthol and 1-{[2-(9- anthrylmethylamino)phenylimino]methyl}-6-bromo-2-naphthol were efficient highly selective chemosensors of cations Hg(2+).

  DOI：

  10.1134/s1070428009020018

文献信息

• The synthesis and evaluation of o-phenylenediamine derivatives as fluorescent probes for nitric oxide detection
  作者：M. John Plater、Iain Greig、Miep H. Helfrich、Stuart H. Ralston

  DOI：10.1039/b105953j

  日期：2001.10.11

  A series of molecular probes for the determination of nitric oxide (NO) have been prepared. Each probe consists of an anthracene, coumarin or acridine fluorophore coupled to an electron rich o-phenylenediamine group. The o-phenylenediamine group can be substituted with methyl or methoxy groups to enhance its electron rich nature. The fluorophore fluorescence is quenched by photoelectron transfer (PET) from the aromatic amine to the lowest unoccupied orbital of the excited state fluorophore. Reaction with nitrosating species converts the o-phenylenediamine group into an electron deficient benzotriazole derivative. This group has a higher oxidation potential and does not quench the fluorophore fluorescence by photoelectron transfer so that these products are highly fluorescent. Some benzotriazole derivatives were made preparatively by alternative synthetic routes. The formation of fluorescent probes was evaluated by treatment of the precursors with nitrous fumes and S-nitroso-N-acetylpenicillamine (SNAP).

  制备了一系列用于测定一氧化氮（NO）的分子探针。每个探针由与富电子邻苯二胺基团偶联的蒽、香豆素或吖啶荧光团组成。邻苯二胺基团可以被甲基或甲氧基取代以增强其富电子性质。通过从芳香胺到激发态荧光团的最低未占据轨道的光电子转移（PET），荧光团荧光被淬灭。与亚硝化物质的反应将邻苯二胺基团转化为缺电子苯并三唑衍生物。该基团具有较高的氧化电位，并且不会通过光电子转移猝灭荧光团的荧光，因此这些产品具有高荧光性。一些苯并三唑衍生物是通过替代合成路线制备的。通过用亚硝酸处理前体来评估荧光探针的形成 烟雾和 S-亚硝基-N-乙酰青霉胺 (SNAP)。
• Chemosensors based on N-(9-anthrylmethyl)-benzene-1,2-diamine
  作者：I. E. Tolpygin、V. P. Rybalkin、E. N. Shepelenko、L. L. Popova、Yu. V. Revinskii、A. V. Tsukanov、O. I. Dmitrieva、A. D. Dubonosov、V. A. Bren’、V. I. Minkin

  DOI：10.1134/s1070428008040155

  日期：2008.4

  A number of N-(9-antrylmethyl)-N'-arylmethylidenebenzene-1,2-diamines and 1-(9-anthrylmethyl)-2-aryl-1H-benzimidazoles were synthesized by condensation of N-(9-anthrylmethyl)benzene-1,2-diamine with aromatic and heterocyclic aldehydes. Study on their luminescent properties and complexing ability showed that 2-[2-(9-anthrylmethylamino)phenylimino]methyl}-5-methylphenol, 2-[2-(9-anthryimethylamino)phenylimino]methyl}-4-methoxyphenol, and 2-[2-(9-anthrylmethylamino)phenylimino]methyl}-6-methoxy-4-nitrophenol are effective and highly selective chemosensors for H(+) and Hg(2+) ions.
• Chemosensors based on N-(2-aminophenyl)-N-(9-anthrylmethyl)amine: II
  作者：I. E. Tolpygin、E. N. Shepelenko、Yu. V. Revinskii、A. V. Tsukanov、A. D. Dubonosov、V. A. Bren’、V. I. Minkin

  DOI：10.1134/s1070428009020018

  日期：2009.2

  A series of N-(9-anthrylmethyl)arylimines was prepared by condensation of N-(2-aminophenyl)-N-(9-anthrylmethyl)amine with aromatic aldehydes. The study of the luminescent and complexing properties of compounds obtained showed that 2-[2-(9-anthrylmethylamino)phenylimino]methyl}-1-naphthol and 1-[2-(9- anthrylmethylamino)phenylimino]methyl}-6-bromo-2-naphthol were efficient highly selective chemosensors of cations Hg(2+).
• Effective pH sensors based on 1-(anthracen-9-ylmethyl)-1H-benzimidazol-2-amine
  作者：I. E. Tolpygin、Yu. V. Revinskii、A. G. Starikov、A. D. Dubonosov、V. A. Bren、V. I. Minkin

  DOI：10.1007/s10593-012-0898-1

  日期：2012.1

  1-(Anthracen-9-ylmethyl)-1H-benzimidazol-2-amine was synthesized by alkylation of benzimidazol-2-amine with 9-chloromethylanthracene, and a series of azomethines based on it was obtained. Spectral investigations of the 9-anthrylmethylbenzimidazole derivatives revealed their high chemosensor activity with respect to hydrogen cations. Quantum-chemical investigation of the structures obtained showed that they possess high proton affinity and can be regarded as analogs of "proton sponges".