1-(1,3-二氢苯并咪唑-2-亚基)萘-2-酮 | 402929-36-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 1-(1,3-二氢苯并咪唑-2-亚基)萘-2-酮
• 英文名称: 1-(1H-benzo[d]imidazol-2-yl)naphthalen-2-ol
• 英文别名: 2-Naphthalenol, 1-(1H-benzimidazol-2-yl)-；1-(1H-benzimidazol-2-yl)naphthalen-2-ol
• CAS: 402929-36-6
• 化学式: C₁₇H₁₂N₂O
• 分子量: 260.295
• InChiKey: KHBKKJOTFZKPLZ-UHFFFAOYSA-N

物化性质

• 熔点：
  260 °C(Solv: chloroform (67-66-3); methanol (67-56-1))
• 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)：
  4
• 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

• 作为反应物：
  描述：

  对氰基氯苄 、 1-(1,3-二氢苯并咪唑-2-亚基)萘-2-酮 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以99 %的产率得到4-(((1-(1-(4-cyanobenzyl)-1H-benzo[d]imidazol-2-yl)naphthalen-2-yl)oxy)methyl)benzonitrile
  参考文献：
  名称：

  新型1,2,5-三取代苯并咪唑化合物的便捷绿色合成及其抗菌活性评价

  摘要：

  在微波辐射下探索了 1,2,5-三取代苯并咪唑的有效合成。以 2-取代苯并咪唑和 4-取代苄基氯为起始原料，使用 K 2 CO 3作为酸结合剂制备了 20 种新型 1,2,5-三取代苯并咪唑。该方法显示出广泛的底物适应性，并在 15 分钟内以中等到优异的收率提供了目标产物。在获得的最佳反应条件下考察了不同取代基对产率的影响。此外，给出了正交空间群P 2ac 2ab中化合物4c的晶体结构。此外，合成化合物对耻垢分枝杆菌的抗菌活性使用利福平作为阳性对照评估体外细胞水平。产物4s在合成的化合物中抗菌活性最好，优于利福平。

  DOI：

  10.1007/s13738-022-02736-z
• 作为产物：
  描述：

  1-((苯基亚胺)甲基)萘-2-酚 生成 1-(1,3-二氢苯并咪唑-2-亚基)萘-2-酮
  参考文献：
  名称：

  Excited-State Intramolecular Proton Transfer of Naphthalene-Fused 2-(2′-Hydroxyaryl)benzazole Family

  摘要：

  Intramolecularly hydrogen-bonded organic compounds often exhibit fluorescence emission at considerably longer wavelengths than typical fluorescence as a result of excited-state intramolecular proton transfer (ESIPT). The structure-property relationship of such ESIPT molecules, however, remains obscure. The present article reports the excited-state dynamics of a new family of ESIPT Molecules, 2-(2'-hydroxynaphthyl)benzazoles 1-3, based on steady-state and time-resolved spectroscopy measurements. In comparison with the parent compound HBO, all three compounds 1-3 exhibited absorption bands at longer wavelengths and emitted fluorescence front the excited keto-tautomer K* at shorter wavelengths, indicating that the introduction of a naphthalene ring increases the energy gap between the ground and excited states for the keto-tautomer despite the expansion of the aromatic ring. Time-resolved fluorescence spectra revealed dual emission for compounds 1 and 3, consisting of two distinct fluorescence bands originating from K* and the excited rotamer E'*, whereas 2 exhibited fluorescence only from the K* state, In the transient absorption spectra, both the T-T absorption band and the ground state absorption band of the Z-keto tautomer were observed for 1. whereas only the T-T absorption band was observed for 2 and only the Z-keto tautomer hand was observed for 3.

  DOI：

  10.1021/jp904370t

文献信息

• Rapid One Pot Synthesis of Benzoimidazoles Using MnO<sub>2</sub> Nanoparticles Supported on Silica as Efficient Oxidant Agent under Solvent-Free Conditions
  作者：Hossein Naeimi、Zahra Babaei

  DOI：10.2174/1570178612666150306002100

  日期：2015.5.9

  A novel one-pot and mild synthesis of benzoimidazole derivatives through the reaction of o-Phenylenediamine with aromatic aldehydes in the presence of MnO2 nanoparticles supported on silica as oxidizing agent under grinding conditions. The significant features of the present protocol are; simplicity of procedure, high products yields, purity of products, solvent-free condition, and easily work-up procedure.

  通过在研磨条件下，以二氧化锰纳米颗粒负载于硅胶作为氧化剂，利用邻苯二胺与芳香醛反应，实现了一种新颖的、温和的一锅法苯并咪唑衍生物合成。当前方案的显著特点包括：操作简便、产物产率高、纯度优良、无溶剂条件以及简单易行的后处理过程。
• A Mild and Simple One-pot Synthesis of 2-Substituted Benzimidazole Derivatives Using DDQ as an Efficient Oxidant at Room Temperature
  作者：Hossein Naeimi、Zahra Babaei

  DOI：10.1002/jccs.201400293

  日期：2015.1

  A series of 2‐substituted benzimidazoles were prepared through one‐pot reaction of o‐phenylenediamine with various aryl aldehydes in the presence of 2,3‐dichloro‐5,6‐dicyano‐1,4‐benzoquinone (DDQ) in acetonitrile as solvent at room temperature. The reactions were smoothly preceded in excellent yields and short reaction times with an easy work‐up. The pure benzimidazoles as products were confirmed and

  在2,3-二氯-5,6-二氰基-1,4-苯醌（DDQ）在乙腈中作为溶剂存在下，通过邻苯二胺与各种芳基醛的单锅反应制备了一系列2-取代的苯并咪唑在室温下。反应容易进行，收率高，反应时间短，易于操作。证实了纯苯并咪唑为产物，并通过物理和光谱数据表征。
• Highly efficient AgNO₃ -catalyzed approach to 2-(benzo[<i>d</i> ]azol-2-yl)phenols from salicylaldehydes with 2-aminothiophenol, 2-aminophenol and benzene-1,2-diamine
  作者：Xinwei He、Yuhao Wu、Wenjing Jin、Xiaoshun Wang、Cong Wu、Yongjia Shang

  DOI：10.1002/aoc.4284

  日期：2018.4

  derivatives in good to excellent yields (63–98%) is described. The reaction proceeds via condensation/intramolecular nucleophilic addition/oxidation process between substituted salicylaldehydes and 2‐aminothiophenol, 2‐aminophenol or benzene‐1,2‐diamine under mild reaction conditions. Notably, this reaction utilizes cheap AgNO3 as a readily available and low‐cost benign oxidant at low catalyst loadings with

  描述了一种新的，便捷有效的AgNO 3催化策略，用于制备2-（苯并[ d ] azol-2-基）苯酚衍生物，产率高至优异（63-98％）。反应在温和的反应条件下通过取代的水杨醛与2-氨基硫酚，2-氨基酚或苯1,2-二胺之间的缩合/分子内亲核加成/氧化过程进行。值得注意的是，该反应利用廉价的AgNO 3作为易于获得的低成本良性氧化剂，催化剂负载低，具有出色的官能团耐受性。
• One‐pot synthesis of novel benzimidazoles with a naphthalene moiety as antimicrobial agents and molecular docking studies
  作者：Ronak Haj Ersan、Ahmet Yuksel、Tugba Ertan‐Bolelli、Aylin Dogen、Serdar Burmaoglu、Oztekin Algul

  DOI：10.1002/jccs.202000125

  日期：2021.2

  design a greener approach for the synthesis of a potent class of antimicrobials, 1,2‐phenylenediamine derivatives were reacted with various 1/2‐carboxylic acid‐substituted naphthalene derivatives to generate a series of naphthyl‐substituted benzimidazole derivatives (11–19) using polyphosphoric acid as catalyst under microwave irradiation and conventional synthesis method. This is an eco‐friendly and

  为了设计一种更绿色的方法来合成强大的抗菌剂，将1,2-苯二胺衍生物与各种1 / 2-羧酸取代的萘衍生物反应，生成了一系列萘基取代的苯并咪唑衍生物（11 – 19）在微波辐射和常规合成方法下，使用多磷酸作为催化剂。这是一种环保，快速的反应方法，适用于多种苯并咪唑的合成方法。根据光谱数据确定合成化合物的结构，并筛选其抗菌活性。化合物18在所有革兰氏阳性和革兰氏阴性细菌菌株中显示最大效价，最小抑菌浓度（MIC）值在7.81–62.50μg/ ml范围内。发现仅化合物17对所有真菌菌株最具活性，其MIC值为15.62μg/ ml。在这项研究中，我们进行了分子对接实验，以了解化合物17和18与大肠杆菌拓扑异构酶I之间的相互作用，并将我们获得的结果与2-（3,4-二甲氧基苯基）-5- [5-（ 4-甲基哌嗪-1-基）-1H-苯并咪唑-2-基] -1H-苯并咪唑（DMA）。化合物17和18与重要的活性位
• Molecular half-subtractor based on 3,3′-bis(1H-benzimidazolyl-2-yl)[1,1′]binaphthalenyl-2,2′-diol
  作者：Vijay Luxami、Subodh Kumar

  DOI：10.1039/b805558k

  日期：——

  Title fluorophore (1) possessing 2,2′-binaphthol and benzimidazole moieties has been investigated for elaboration of half-subtractor logic operation. For comparison differently substituted systems have been studied. Fluorophore 1 showed strong fluorescence at 585 nm due to ESIPT phenomena which was completely quenched on addition of HClO4 with concomitant appearance of a new emission band at 435 nm with hypsochromic shift of 150 nm. The addition of TBAOH to the solution of 1 gave a new hypsochromically shifted emission band at 515 nm (Δλ = 70 nm) with concomitant quenching at 585 nm. Thus, fluorophore 1 with large differentials of emission maxima under neutral, acidic and basic conditions provides four opportunities for arithmetic operation half-subtractor. i.e. with 435/515 nm (INHIBIT) and 475 nm (XOR) gates and with 435/515 nm (INHIBIT) and 585 nm (XNOR) gates which have been elaborated as combinatorial logic circuits for a molecular half-subtractor with acid and base as input variables. The elaboration of half-subtractor with only XOR logic in the case of fluorophore 2 possessing a molecular structure half that of fluorophore 1 and complete lack of logic gates in fluorophore 5 with change in position of benzimidazole moiety further signify the importance of the structural architecture in fluorophore 1.

  我们研究了具有 2,2â²-萘酚和苯并咪唑分子的标题荧光团 (1)，以阐述半减逻辑运算。为了进行比较，还研究了不同的取代系统。由于 ESIPT 现象，荧光团 1 在 585 纳米波长处显示出强烈的荧光，加入 HClO4 后荧光完全熄灭，同时在 435 纳米波长处出现一条新的发射带，其次色偏移为 150 纳米波长。在 1 的溶液中加入 TBAOH 后，在 515 纳米（δ" = 70 纳米）处出现了新的低色移发射带，同时在 585 纳米处出现淬灭。因此，在中性、酸性和碱性条件下发射最大值相差很大的荧光团 1 为半减法器的算术运算提供了四种机会，即 435/515 nm（INHIBIT）和 475 nm（XOR）门，以及 435/515 nm（INHIBIT）和 585 nm（XNOR）门。荧光团 2 的分子结构仅为荧光团 1 的一半，而荧光团 5 中随着苯并咪唑分子位置的变化完全没有逻辑门，这两种情况下仅用 XOR 逻辑电路就能制作出半分断器，进一步说明了荧光团 1 结构架构的重要性。