2-甲基-1,3-苯并恶嗪-4-酮,高氯酸 | 54789-70-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶嗪类
• 中文名称: 2-甲基-1,3-苯并恶嗪-4-酮,高氯酸
• 英文名称: 2-methyl-4-oxo-1,3-benzoxazinium perchlorate
• 英文别名: 4H-1,3-Benzoxazin-4-one, 2-methyl-, perchlorate；2-methyl-1,3-benzoxazin-4-one;perchloric acid
• CAS: 54789-70-7
• 化学式: C₉H₇NO₂*ClHO₄
• 分子量: 261.619
• InChiKey: PLSSPOPGLJZUIL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.84
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  115
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-甲基-1,3-苯并恶嗪-4-酮,高氯酸 在 肼 作用下， 以 溶剂黄146 为溶剂， 生成 6-(5-甲基-1,2-二氢-1,2,4-三唑-3-亚基)环己-2,4-二烯-1-酮
  参考文献：
  名称：

  Synthesis and properties of substituted [3-(2-hydroxyphenyl)-1H-1,2,4-triazol-1-yl]acetonitriles

  摘要：

  Alkylation of 3-substituted 5-(2-hydroxyphenyl)-1H-1,2,4-triazoles with chloroacetonitrile gave hitherto unknown N-cyanomethyl derivatives whose structure was determined by X-ray analysis and (1)H and (13)C NMR spectroscopy. Condensation of substituted [3-(2-hydroxyphenyl)-1H-1,2,4-triazol-1-yl]acetonitriles at the activated methylene group with acetone led to the formation of new 3-methyl-2-triazolylbut-2-enenitrile derivatives.

  DOI：

  10.1134/s1070428010070201
• 作为产物：
  描述：

  2-(氨基羰基)苯基乙酸酯 在 titanium(IV) isopropylate 、 盐酸 、 bis(1,5-cyclooctadiene)diiridium(I) dichloride 、 高氯酸 、 氢气 、 C₄₅H₃₆F₆FeN₂P₂S 作用下， 以 异丙醇 为溶剂， 25.0 ℃ 、6.08 MPa 条件下， 反应 24.0h， 生成 2-甲基-1,3-苯并恶嗪-4-酮,高氯酸
  参考文献：
  名称：

  阳离子中间体的不对称氢化，用于合成手性N，O-缩醛。

  摘要：

  半个多世纪以来，过渡金属催化的均相加氢主要集中在中性和易于制备的不饱和底物上。尽管将分子氢加到C = C，C = N和C = O键上代表了一个经过充分研究的范例，但阳离子物种的不对称氢化仍然是一个欠发达的领域。在这项研究中，我们寻求以阳离子中间体为目标的不对称氢化方面的突破，并因此有望将此强大工具应用于具有挑战性的手性分子的构建。在酸性条件下，N-或O-乙酰水杨酰胺都进行环化生成阳离子中间体，随后被铱或氢化铑配合物还原。结果N，O-乙缩醛的合成具有很高的对映选择性。这种催化策略显示出高效率（周转数高达4400）和高化学选择性。机理研究支持了阳离子中间体在原位形成并随后氢化的假说。已经提出了催化循环，其中氢化物从铱配合物转移到阳离子sp 2碳原子是决定速率的步骤。已经创建了催化剂的空间图以说明手性环境，并且定量结构-选择性关系分析显示了在此化学转化中如何实现对映异构体诱导。

  DOI：

  10.1002/chem.202002930

文献信息

• A short and efficient preparation of methyl-[1,2,4]oxadiazolium derivatives with plant-inducing activity
  作者：Markus R. Dobler

  DOI：10.1039/b316802f

  日期：——

  We have developed a concise and efficient synthetic method leading to a structurally diverse array of salicylic acid and oxadiazolium derivatives, starting from commercially available halogenated phenols.

  我们开发了一种简练高效的综合方法，从市售的卤代苯酚出发，合成了一系列结构多样性的水杨酸和恶二唑盐衍生物。
• Synthesis, structure, and spectral luminescent properties of novel 1,2,4-triazole derivatives containing benzthiazole group
  作者：A. D. Beldovskaya、G. A. Dushenko、N. I. Vikrishchuk、L. D. Popov、Yu. V. Revinskii、I. E. Mikhailov

  DOI：10.1134/s1070363213110200

  日期：2013.11

  Novel derivatives of 1,2,4-triazol with benzthiazole fragment have been prepared, including Cu(II) and Be complexes. Their structure and spectral luminescent properties have been investigated. With ohydroxyphenylbenzthiazolyl-1,2,4-triazole as an example, the density functional theory has been applied to find the stable conformers with different structures of coordination nodes, stabilized by intramolecular

  已经制备了具有苯并噻唑片段的1,2,4-三唑的新型衍生物，包括Cu（II）和Be配合物。已经研究了它们的结构和光谱发光性质。以邻羟基苯基苯并噻唑基-1，2，4-三唑为例，应用密度泛函理论寻找具有不同配位点结构的稳定构象体，并通过羟基氢与苯并噻唑氮的任一三唑之间的分子内氢键来稳定。
• Kinase and GPCR polypharmacological approach for the identification of efficient anticancer medicines
  作者：Hwangseo Park、Hoi-Yun Jung、Shinmee Mah、Kewon Kim、Sungwoo Hong

  DOI：10.1039/d0ob01917h

  日期：——

  Bifunctional molecules that inhibit casein kinase 1 delta and simultaneously antagonize muscarinic acetylcholine receptor M3 were identified.

  已识别出双功能分子，可以抑制酪蛋白激酶1 delta并同时拮抗肌动蛋白乙酰胆碱受体M3。
• Absorption and luminescence spectra of 5-aryl-3-methyl-1,2,4-oxadiazoles and their chelate complexes with Zinc(II) and copper(II)
  作者：I. E. Mikhailov、N. I. Vikrishchuk、L. D. Popov、G. A. Dushenko、A. D. Beldovskaya、Yu. V. Revinskii、V. I. Minkin

  DOI：10.1134/s1070363216050121

  日期：2016.5

  ethyl-1,2,4-oxadiazole and its O-methyl and O-acyl derivatives, as well as zinc(II) and copper(II) chelates, were synthesized. All these compounds showed luminescence with the emission maxima ranging from λ = 332 to 490 nm, but only 5-(2-methoxyphenyl)- and 5-(2-acetoxyphenyl)-3-methyl-1,2,4-oxadiazoles and zinc(II) complex of 5-(2-hydroxyphenyl)-3-methyl-1,2,4-oxadiazole were characterized by high

  合成了5-（2-羟基苯基）-3-甲基-1,2,4-恶二唑及其O-甲基和O-酰基衍生物，以及锌（II）和铜（II）螯合物。所有这些化合物均显示出最大发射波长在λ= 332至490 nm之间的发光，但只有5-（2-甲氧基苯基）-和5-（2-乙酰氧基苯基）-3-甲基-1,2,4-恶二唑和锌5-（2-羟基苯基）-3-甲基-1,2,4-恶二唑的（II）配合物具有高发光量子产率的特征（分别为φ= 0.308-0.452、0.089-0.153和0.115-0.334）。通过DFT量子化学计算确定了具有不同配位实体结构的5-（2-羟苯基）-3-甲基-1,2,4-恶二唑的稳定构象。
• Synthesis, structure, spectral and luminescence properties of the tetracoordinated diphenylboron and zinc complexes with 1,3,4-oxadiazole and 1,2,4-triazole ligands
  作者：Igor E. Mikhailov、Galina A. Dushenko、Mikhail E. Gurskii、Natalia I. Vikrischuk、Leonid D. Popov、Yurii V. Revinskii、Konstantin A. Lyssenko、Vladimir I. Minkin

  DOI：10.1016/j.poly.2019.03.044

  日期：2019.7

  The new diphenylboron 1c, 2c and zinc 1d, 2d complexes with 2-(2-hydroxyphenyl)-5-(3,4,5-trimethoxyphenyl)-1,3,4-oxadiazole 1a and 1-phenyl-3-methyl-1,2,4-triazole 2a as the chelating ligands and O-ethyl derivatives 1b, 2b of these ligands have been synthesized and their UV-Vis and photoluminescence studied. Molecular structures of the chelate diphenylboron complexes 1c and 2c were determined by X-ray single-crystal diffraction. Spectroscopic properties of all the compounds, including excited state intramolecular proton transfer (ESIPT) rearrangements observed in ligands 1a and 2a were analyzed using DFT and TD DFT calculations. The emission spectra of ligands 1a, 2a contain a moderate intensity band (phi 0.07, 0.19) in DMSO and two low intensity bands (phi 0.002-0.012) in other solvents. 2-(2-Ethoxyphenyl)-5-(3,4,5-trimethoxyphenyl)-1,3,4-oxadiazole 1b and all the complexes exhibit significant fluorescence both in polar and non-polar solvents in the blue region of the spectrum, 1b: phi 0.84-0.96, lambda(fl)(max) 363-406 nm: 1c,d, 2c,d: phi 0.43-0.65, lambda(fl)(max) 429-457 nm. The displayed spectral characteristics make these complexes promising for the use as blue emitters in the design of light-emitting organic diodes. (C) 2019 Elsevier Ltd. All rights reserved.