2-(1H-naphtho[2,3-d]imidazol-2-yl)-phenol | 30384-72-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 2-(1H-naphtho[2,3-d]imidazol-2-yl)-phenol
• 英文别名: 2-(2'-hydroxyphenyl)-1H-naphth-[2,3-d]-imidazole；2-(2-Hydroxyphenyl)-1H-napht<2,3-d>imidazol；2-(1H-benzo[f]benzimidazol-2-yl)phenol
• CAS: 30384-72-6
• 化学式: C₁₇H₁₂N₂O
• 分子量: 260.295
• InChiKey: MDUDOPQCMMCITN-UHFFFAOYSA-N

物化性质

• 沸点：
  534.1±52.0 °C(Predicted)
• 密度：
  1.349±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  48.9
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  邻甲基苄醇 、 2,3-二氨基萘 在 manganese triacetate 、 溶剂黄146 作用下， 反应 36.0h， 以69%的产率得到2-(1H-naphtho[2,3-d]imidazol-2-yl)-phenol
  参考文献：
  名称：

  2-（1 H-苯并咪唑-2-基）-苯酚衍生物的合成及荧光性质

  摘要：

  在室温下，在乙酸锰（III）存在下，由2-羟基芳族醛与芳族1,2-二胺高产率合成了2-（2-羟基芳基）-1 H-苯并恶唑衍生物。九荧光粉2-（2-羟基芳基）-1 ħ -benzirrndazoles与取代基（S）X（X = H，CH 3，CH 3 O，Cl）的和两个荧光粉2-（2-羟基芳基）-1 ħ -naphth [ 2,3-天制备具有H或Cl取代基的咪唑类，收率为38-87％，并在甲醇中测量了所合成的11种化合物的紫外吸收和荧光光谱。在激发态分子内质子转移机理，斯托克斯位移，量子产率以及荧光强度与取代基之间的关系的基础上，研究了所制备的2-（2-羟基芳基）苯并咪唑衍生物的荧光特性。

  DOI：

  10.1002/jhet.5570410309

文献信息

• Microwave-assisted one step high-throughput synthesis of benzimidazoles
  作者：Shou-Yuan Lin、Yuko Isome、Ethan Stewart、Ji-Feng Liu、Daniel Yohannes、Libing Yu

  DOI：10.1016/j.tetlet.2006.02.127

  日期：2006.4

  One-pot synthesis of benzimidazoles from diamines and carboxylic acids was developed under microwave irradiation condition, which provided a practical and efficient method for high-throughput synthesis of this important class of heterocyclic compounds. (c) 2006 Elsevier Ltd. All rights reserved.
• Recognition‐Induced Enhanced Emission of Core‐Fluorescent ESIPT‐type Macrocycles
  作者：Paulina Jurek、Hanna Jędrzejewska、Michał F. Rode、Agnieszka Szumna

  DOI：10.1002/chem.202203116

  日期：2023.1.9

  AbstractCore‐fluorescent cavitands based on 2‐(2′‐resorcinol)benzimidazole fluorophores (RBIs) merged with the resorcin[4]arene skeleton were designed and synthesized. The cavitands, due to the presence of intramolecular hydrogen bonds and increased acidity, show excited state intramolecular proton transfer (ESIPT) and readily undergo deprotonation to form dianionic cavitands, capable of strong binding to organic cations. The changes in fluorescence are induced by deprotonation and binding events and involve huge Stokes shifts (due to emission from anionic double keto tautomers) and cation‐selective enhancement of emission originating from the restriction of intramolecular motion (RIR) upon recognition in the cavity. Ab initio calculations indicate that the macrocyclic scaffold stabilizes the ground state tautomeric forms of the fluorophores that are not observed for non‐macrocyclic analogs. In the excited state, the emitting forms for both macrocyclic scaffolds and non‐macrocyclic analogs are anionic double keto tautomers, which are the result of excited state intramolecular proton transfer (ESIPT) or excited state double proton transfer (ESDPT).
• Synthesis and fluorescent properties of 2-(1<i>H</i>-benzimidazol-2-yl)-phenol derivatives
  作者：Jie Ouyang、Chenguang Ouyang、Yuki Fujii、Yoshiharu Nakano、Takuji Shoda、Tetsuo Nagano

  DOI：10.1002/jhet.5570410309

  日期：2004.5

  and the ultraviolet absorption and fluorescent spectra of the eleven compounds synthesized were measured in methanol. The fluorescent characteristics of the 2-(2-hydroxyaryl)benzimidazole derivatives prepared were investigated on the basis of excited-state intramolecular proton transfer mechanism, Stokes' shift, quantum yield, and the relationship between fluorescent intensity and the substituents were

  在室温下，在乙酸锰（III）存在下，由2-羟基芳族醛与芳族1,2-二胺高产率合成了2-（2-羟基芳基）-1 H-苯并恶唑衍生物。九荧光粉2-（2-羟基芳基）-1 ħ -benzirrndazoles与取代基（S）X（X = H，CH 3，CH 3 O，Cl）的和两个荧光粉2-（2-羟基芳基）-1 ħ -naphth [ 2,3-天制备具有H或Cl取代基的咪唑类，收率为38-87％，并在甲醇中测量了所合成的11种化合物的紫外吸收和荧光光谱。在激发态分子内质子转移机理，斯托克斯位移，量子产率以及荧光强度与取代基之间的关系的基础上，研究了所制备的2-（2-羟基芳基）苯并咪唑衍生物的荧光特性。