3-amino-6-methyl-4-phenylpyridin-2(1H)-one | 1607833-75-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 3-amino-6-methyl-4-phenylpyridin-2(1H)-one
• 英文别名: 3-amino-6-methyl-4-phenylpyridine-2(1H)-one；3-amino-6-methyl-4-phenyl-1H-pyridin-2-one
• CAS: 1607833-75-9
• 化学式: C₁₂H₁₂N₂O
• 分子量: 200.24
• InChiKey: MSPRHYGMOLDPDT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  55.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-amino-6-methyl-4-phenylpyridin-2(1H)-one 在 aluminum (III) chloride 、 sodium tetrahydroborate 、 p-toluenesulfonic acid 作用下， 以 氯苯 、 甲苯 为溶剂， 生成
  参考文献：
  名称：

  5-Ethyl-5,6-dihydrobenzo[c] [1,7]naphthyridin-4(3H)-ones – A new class of fluorescent dyes

  摘要：

  Reduction of benzo[c] [1,7]naphthyridin-4(3H)-ones with sodium borohydride in acetic acid led to a series of 5-ethyl-5,6-dihydrobenzo[c] [1,7]naphthyridin-4(3H)-ones. The latter are photostable fluorophores emitting in the green region of the visible spectrum with a fluorescence quantum yield of up to 0.43 and a Stokes shift of up to 133 nm, containing an “embedded” amino acid motif. The localization

  DOI：

  10.1016/j.dyepig.2022.110388
• 作为产物：
  描述：

  3-amino-1-phenylbut-2-en-1-one 在 吡啶 、 hydrazine hydrate 作用下， 以 氯仿 、 正丁醇 为溶剂， 反应 3.0h， 生成 3-amino-6-methyl-4-phenylpyridin-2(1H)-one
  参考文献：
  名称：

  Synthesis of 3-Aminopyridin-2(1H)-Ones and 1H-Pyrido[2,3-b][1,4]Oxazin-2(3H)-Ones

  摘要：

  The interaction of 1,3-diketones with chloroacetamide produced N-(3-oxoalkenyl)chloroacetamides. Heating of N-(3-oxoalkenyl)chloroacetamides with an excess of pyridine in ethanol or butanol led to the formation of pyridin-2(1De)-ones, substituted with a pyridine ring at position 3. The reactions of these compounds with hydrazine hydrate produced 3-aminopyridin-2(1De)-ones. The synthesis of 1H-pyrido[2,3-b][1, 4]oxazin-2(3H)-ones was accomplished by a reaction of 3-aminopyridin-2(1De)-ones with chloroacetyl chloride.

  DOI：

  10.1007/s10593-014-1464-9

文献信息

• Synthesis of N-substituted 2-aminomethyl-5-methyl-7-phenyloxazolo[5,4-b]pyridines
  作者：Irina V. Palamarchuk、Mariya V. Matsukevich、Ivan V. Kulakov、Tulegen М. Seilkhanov、Aleksander S. Fisyuk

  DOI：10.1007/s10593-019-02537-y

  日期：2019.8

  4-b]pyridine was obtained by intramolecular cyclization based on the previously synthesized 2-chloro-N-(6-methyl-2-oxo-4-phenyl-1,2-dihydropyridin-3-yl)acetamide. The possibility of its use in the synthesis of previously unknown 2-aminomethyloxazolo[5,4-b]pyridine derivatives by nucleophilic substitution with various amines and a cyclic amide has been shown.

  根据先前合成的2-氯-N-（6-甲基-2-氧代-4-苯基-），通过分子内环化获得2-（氯甲基）-5-甲基-7-苯基恶唑并[5,4- b ]吡啶。1,2-二氢吡啶-3-基）乙酰胺。通过各种胺和环状酰胺的亲核取代，已经显示出其在合成先前未知的2-氨基甲基恶唑并[5,4- b ]吡啶衍生物中的用途。
• Synthesis and Photophysical Properties of 3-Amino-4-arylpyridin-2(1Н)-ones
  作者：Anton L. Shatsauskas、Anton A. Abramov、Sergey A. Chernenko、Anastasia S. Kostyuchenko、Alexander S. Fisyuk

  DOI：10.1055/s-0039-1690231

  日期：2020.1

  method has been developed for the preparation of oxazolo-[5,4-b]pyridin-2(1H)-ones based on the Hoffmann reaction of 2-oxo-1,2-dihydropyridine-3-carboxamides. Hydrolysis of oxazolo[5,4-b]pyridin-2(1H)-ones and the Hoffmann reaction of 2-oxo-1,2-dihydropyridine-3-carboxamides yielded 3-aminopyridin-2(1H)-ones, including 4-aryl substituted derivatives in the series, for which effective phosphors with a

  基于2-氧-1,2-二氢吡啶-3-羧酰胺的霍夫曼反应，已经开发了一种制备恶唑-[5,4 - b ]吡啶-2-2 （1 H）-的方法。恶唑并[5,4 - b ]吡啶-2（1 H）-one的水解和2-氧-1,2-二氢吡啶-3-羧酰胺的霍夫曼反应产生3-氨基吡啶-2（1 H）-one，包括该系列中的4-芳基取代衍生物，其有效荧光粉的量子产率高达0.78。通过紫外和发光光谱法研究了3-氨基吡啶-2（1 H）-1的光物理性质，揭示了其结构与光物理性质之间的关系。
• Synthesis and photophysical properties of the products of the reaction of 5-methyl-7-phenyl[1,3]oxazolo[5,4-b]pyridin-2(1H)-one with amino acids
  作者：Anton L. Shatsauskas、Yurii А. Zablotskii、Sergei А. Chernenko、Tatyana Yu. Zheleznova、Vladislav Yu. Shuvalov、Anastasiya S. Kostyuchenko、Alexander S. Fisyuk

  DOI：10.1007/s10593-021-03045-8

  日期：2021.12

  The reaction of amino acid esters with 7-phenyl[1,3]oxazolo[5,4-b]pyridin-2(1H)-one led to the derivatives of 3-(2-oxo-4-phenyl-1,2-dihydropyridin-3-yl)imidazolidine-2,4-diones and ethyl 2-[3-(2-oxo-4-phenyl-1,2-dihydropyridin-3-yl)ureido]acetates, as well as several of their structural analogs. The photophysical properties of the synthesized compounds were investigated.

  氨基酸酯与 7-phenyl[1,3]oxazolo[5,4 - b ]pyridin-2(1 H )-one 反应生成 3-(2-oxo-4-phenyl-1) 的衍生物， 2-dihydropyridin-3-yl)imidazolidine-2,4-diones 和 2-[3-(2-oxo-4-phenyl-1,2-dihydropyridin-3-yl)ureido] 乙酸乙酯，以及几种它们的结构类似物。研究了合成化合物的光物理性质。
• Synthesis of N-Derivatives of Cytisine, Anabasine, and Salsoline Alkaloids with Pharmacophore 3-Aminopyridine-2(1H)-one and 5-Methyl-7-phenyloxazole[5,4-b]pyridine Cycles
  作者：I. V. Palamarchuk、D. N. Ogurtsova、T. M. Seilkhanov、I. V. Kulakov

  DOI：10.1134/s1070363219120259

  日期：2019.12

  reaction of nucleophilic substitution of 2-chloro-N-(6-methyl-2-oxo-4-phenyl-1,2-dihydropyridin-3-yl)acetamide and 2-(chloromethyl)-5-methyl-7-phenyloxazolo[5,4-b]pyridine with cytisine, anabasine, and salsoline alkaloids has afforded the corresponding derivatives. Structure of the obtained compounds has been confirmed by means of 1H and 13C NMR spectroscopy.

  2-氯-N-（6-甲基-2-氧代-4-苯基-1,2-二氢吡啶-3-基）乙酰胺与2-（氯甲基）-5-甲基-7-苯基恶唑的亲核取代反应[5,4- b ]吡啶与胞嘧啶碱，金刚烷胺和索索林生物碱已提供相应的衍生物。所获得的化合物的结构已经通过1 H和13 C NMR光谱法确认。
• Synthesis, structure and biological activity 3- (arylmethyl) aminopyridine-2 (1 H ) -ones and 1 H -pyrido[2,3-b][1,4]oxazin-2(3 H )-ones
  作者：Ivan V. Kulakov、Irina V. Palamarchuk、Zarina T. Shulgau、Tulegen M. Seilkhanov、Yuriy V. Gatilov、Alexander S. Fisyuk

  DOI：10.1016/j.molstruc.2018.04.036

  日期：2018.8

  borohydride led to the formation of 3-(arylmethyl)-6-methyl-4-phenylpyridin-2(1H)-ones. Acylation of 3-amino-6-methyl-4-phenylpyridin-2(1H)-one with chloroacetyl chloride resulted either in the corresponding chloroacetamides or in 1H-pyrido[2,3-b][1,4]oxazin-2(3H)-ones. A possibility to form octahedral complex with calcium chloride was demonstrated by the example of 3-(benzylamino)-6-methyl-4-phenylpyridin-2(1H)-one

  摘要 3-氨基-6-甲基-4-苯基吡啶-2(1H)-one 与芳香醛反应得到相应的席夫碱，用硼氢化钠还原形成 3-(芳甲基)-6-甲基-4-苯基吡啶-2(1H)-ones。3-氨基-6-甲基-4-苯基吡啶-2(1H)-one 与氯乙酰氯酰化产生相应的氯乙酰胺或 1H-吡啶并[2,3-b][1,4]恶嗪-2( 3H)-个。通过 3-(苄基氨基)-6-甲基-4-苯基吡啶-2(1H)-one 的例子证明了与氯化钙形成八面体络合物的可能性。所有制备的化合物的结构均通过 1H 和 13C NMR 光谱以及单晶 X 射线衍射法证实。在一系列新化合物中，