2-naphthimidamide hydrochloride | 14948-94-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-naphthimidamide hydrochloride
• 英文别名: naphthalene-2-carboximidamide;hydrochloride
• CAS: 14948-94-8
• 化学式: C₁₁H₁₀N₂*ClH
• 分子量: 206.675
• InChiKey: IGXALCCFUFBKQT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.55
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  49.9
• 氢给体数：
  3
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-naphthimidamide hydrochloride 在 氢氧化钾 作用下， 生成 5-benzylidene-2-[2]naphthyl-3,5-dihydro-imidazol-4-one
  参考文献：
  名称：

  The Action of Aromatic Aldehydes upon the Addition Products Obtained from Aromatic Amidines and Glyoxal

  摘要：

  DOI：

  10.1021/ja01310a054
• 作为产物：
  描述：

  ethyl 2-naphthylimidate hydrochloride 在 氨 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 24.0h， 以86%的产率得到2-naphthimidamide hydrochloride
  参考文献：
  名称：

  Facile synthesis of 3,5-diaryl-1,2,4-triazoles via copper-catalyzed domino nucleophilic substitution/oxidative cyclization using amidines or imidates as substrates

  摘要：

  Two methods for the synthesis of 3,5-diaryl-1,2,4-triazoles, both domino reactions, are reported. The first procedure, the Cu(OTf)(2)-catalyzed reaction between two amidines using NaHCO3 as a base, 1,10-phenanthroline as an additive and K-3[Fe(CN)(6)]/atmospheric oxygen as the oxidant, delivers 3,5-diaryl-1,2,4-triazoles with yields up to 68%. The second procedure for the synthesis of 3,5-diaryl-1,2,4-triazoles with yields up to 64% rests on the Cu(OTf)(2)-catalyzed reaction between two imidates and ammonium carbonate. This method features the formation of three bonds in a single synthetic step. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.01.019

文献信息

• Base-Mediated Syntheses of Di- and Trisubstituted Imidazoles from Amidine Hydrochlorides and Bromoacetylenes
  作者：Xiao Yun Chen、Ulli Englert、Carsten Bolm

  DOI：10.1002/chem.201502707

  日期：2015.9.14

  A new transition metal‐free method for the preparation of substituted imidazoles from easy‐to‐handle amidine hydrochlorides and bromoacetylenes has been developed. The reactions proceed in air and use inexpensive K2CO3 as base. Additions of 2,2′‐bipyridine and water have beneficial effects on the product yields. Various di‐ and trisubstituted imidazoles have been prepared in good yields (up to 88 %)

  已开发出一种新的无过渡金属的方法，该方法由易于处理的am盐酸盐和溴乙炔制备取代的咪唑。反应在空气中进行，并使用廉价的K 2 CO 3作为碱。添加2,2'-联吡啶和水对产品收率有有利影响。各种二，三取代的咪唑均以高收率（高达88％）制备。
• 一种以三联咔唑为核心的化合物及其在有机 电致发光器件上的应用
  申请人：中节能万润股份有限公司

  公开号：CN108239070B

  公开（公告）日：2021-06-15

  本发明公开了一种以三联咔唑为核心的化合物及其在有机电致发光器件上的应用，所述化合物以三联咔唑为核心，具有分子间不易结晶、不易聚集、具有良好成膜性的特点。本发明化合物作为有机电致发光器件的发光层材料使用时，器件的电流效率、功率效率和外量子效率均得到很大改善；同时，对于器件寿命提升非常明显，化合物结构如通式(1)所示,
• Traceless solid phase synthesis of 2-substituted pyrimidines using an ‘off-the-shelf’ chlorogermane-functionalised resin
  作者：Alan C. Spivey、Ratnasothy Srikaran、Christopher M. Diaper、David J. Turner

  DOI：10.1039/b303064d

  日期：——

  The parallel solid phase synthesis of an 18-member library of 2-substituted pyrimidines is described using a chlorogermane-functionalised resin. The success of the key Pinner-type condensations between a resin-bound enaminone and an array of amidine hydrochlorides highlights the stability of arylgermane linkers (cf. arylsilanes) towards strongly basic/nucleophilic conditions.

  本文描述了使用含氯锗功能化树脂进行的18种2-取代嘧啶的平行固相合成。树脂结合的烯胺酮与一系列氨基脲盐酸盐之间关键的Pinner型缩合反应的成功，突显了芳基锗连接子（相对于芳基硅烷）在强碱性/亲核性条件下的稳定性。
• Identification of <i>C</i>-β-<scp>d</scp>-Glucopyranosyl Azole-Type Inhibitors of Glycogen Phosphorylase That Reduce Glycogenolysis in Hepatocytes: <i>In Silico</i> Design, Synthesis, <i>in Vitro</i> Kinetics, and <i>ex Vivo</i> Studies
  作者：Daniel Barr、Eszter Szennyes、Éva Bokor、Ziad H. Al-Oanzi、Colin Moffatt、Sándor Kun、Tibor Docsa、Ádám Sipos、Matthew P. Davies、Rachel T. Mathomes、Timothy J. Snape、Loranne Agius、László Somsák、Joseph M. Hayes

  DOI：10.1021/acschembio.9b00172

  日期：2019.7.19

  glycogenolysis (IC50 = 30-60 μM). Structural and predicted physicochemical properties associated with their effectiveness were analyzed with permeability related parameters identified as crucial factors. The most effective ligand series 5 contained an imidazole ring, and the calculated pKa (Epik: 6.2; Jaguar 5.5) for protonated imidazole suggests that cellular permeation through the neutral state is favored

  最近发现了几种C-β-d-吡喃葡萄糖基唑类化合物，是迄今为止发现的最有效的糖原磷酸化酶（GP）催化部位抑制剂。为了进一步探索它们的翻译潜力，已经进行了离体实验以降低肝细胞糖原分解的有效性。在计算机上预测了用于这些实验的新化合物，其中首次证明了使用分子力学通用化的伯恩表面积（MM-GBSA）方法对GP催化位点抑制剂效能进行有效排名。对于27种配体的同类训练，在Pearson（RP）和Spearman（RS）相关性（均为0.98），预测指数（PI = 0.99）和接收器工作特征曲线下面积（AU-ROC = 0。99）获得了预测的与实验的结合亲和力，另外还使用密度泛函理论（DFT）考虑了配体互变异构/电离状态。随后合成了7种2-芳基4（5）-（β-d-吡喃葡萄糖基）-咪唑和2-芳基-4-（β-d-吡喃葡萄糖基）-噻唑，并且针对兔肌肉GPb的动力学实验揭示了新的有效抑制剂在低微摩尔范围内（5c =
• Matrix isolation and photochemistry of 1- and 2-naphthylchlorocarbene
  作者：Pawel Rempala、Robert S. Sheridan

  DOI：10.1039/a905042f

  日期：——

  We have for the first time characterized the 1- and 2-naphthylchlorocarbenes by IR and UV/vis spectroscopy in N2 matrices at 10 K. Although evidence suggests the presence of predominantly only one geometric isomer in the case of the 1-naphthylchlorocarbene, the IR and UV/vis spectra of the 2-naphthylchlorocarbene indicate two distinct conformations. With selective irradiation, the longer-wavelength absorbing s-Z-isomer of 2-naphthylchlorocarbene can be photochemically driven to the alternate s-E conformation. Irradiation of the 1- and 2-naphthylchlorocarbenes induces cyclization to 7-chloro-4,5-benzobicyclo[4.1.0]hepta-2,4,6-triene and 7-chloro-2,3-benzobicyclo[4.1.0]hepta-2,4,6-triene, respectively. The cyclization can be reversed by irradiation at shorter wavelengths.Our results on the singlet naphthylchlorocarbenes photochemical ring-closures parallel observations of Chapman, McMahon, and co-workers on the parent triplet 1- and 2-naphthylcarbenes (P. R. West, A. M. Mooring, R. J. McMahon and O. L. Chapman, J. Org. Chem., 1986, 51, 1316; S. W. Albrecht and R. J. McMahon, J. Am. Chem. Soc., 1993, 115, 855). In particular, under matrix isolation conditions, the naphthylcarbenes appear to photochemically only cyclize to the corresponding cyclopropenes, which in turn only photochemically ring-open back to the carbenes. Ring-expansion in these systems to benzocycloheptatetraenes is not detected.

  尽管有证据表明 1-萘基-1-氯代碳主要只存在一种几何异构体，但 2-萘基-1-氯代碳的红外和紫外/可见光谱却显示出两种不同的构象。在选择性辐照下，2-萘基二氯甲烷吸收波长较长的 s-Z 异构体可通过光化学作用转变为另一种 s-E 构象。辐照 1-萘基和 2-萘基氯化羰烯可分别诱导环化成 7-氯-4,5-苯并双环[4.1.0]庚-2,4,6-三烯和 7-氯-2,3-苯并双环[4.1.0]庚-2,4,6-三烯。我们对单色萘基氯化萘光化学环闭的研究结果与 Chapman、McMahon 及合作者对母体三色 1-和 2-萘基萘的观察结果相同（P. R. West、A. M. Mooring、R. J. McMahon 和 O. L. Chapman，J. Org.Chem.，1986，51，1316；S. W. Albrecht 和 R. J. McMahon，J. Am.Chem.Soc.，1993，115，855）。特别是，在基质分离条件下，萘羧似乎只能光化学环化成相应的环丙烯，而环丙烯又只能光化学环开回到萘。在这些体系中，没有检测到环向苯并环庚四烯的扩展。