3,6,7-trimethylquinoxalin-2(1H)-one | 28082-86-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 3,6,7-trimethylquinoxalin-2(1H)-one
• 英文别名: 3,6,7-trimethyl-1H-quinoxalin-2-one
• CAS: 28082-86-2
• 化学式: C₁₁H₁₂N₂O
• mdl: MFCD00135489
• 分子量: 188.229
• InChiKey: RYSAKTAGNQULLG-UHFFFAOYSA-N

物化性质

• 熔点：
  278-279 °C
• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.272
• 拓扑面积：
  41.5
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  3,6,7-trimethylquinoxalin-2(1H)-one 在 sodium methylate 作用下， 以 苯 为溶剂， 反应 16.0h， 生成 3,4-(2-methoxycarbonyl-2-methyl)-ethano-1,3,6,7-tetramethy L-3,4-dihydro-quinoxalin-2-one
  参考文献：
  名称：

  Nishio, Takehiko, Journal of the Chemical Society. Perkin transactions I, 1990, p. 565 - 570

  摘要：

  DOI：
• 作为产物：
  描述：

  3,4-dihydro-3,6,7-trimethyl-1H-quinoxalin-2-one 在 sodium hydroxide 、 双氧水 作用下， 以 水 为溶剂， 生成 3,6,7-trimethylquinoxalin-2(1H)-one
  参考文献：
  名称：

  Novel Approach to 3‐Methyl‐1H‐quinoxalin‐2‐ones

  摘要：

  A novel approach to the synthesis of 3-methyl-1H-quinoxalin-2-ones has been described. These compounds were regioselectively prepared by starting from substituted phenylamines and alpha-chloropropionyl chloride through the efficient procedures of acylation, nitration, reduction, intramolecular alkylation, and oxidation.

  DOI：

  10.1080/00397910500213880

文献信息

• Enantioselective, Visible Light Mediated Aza Paternò–Büchi Reactions of Quinoxalinones
  作者：Xinyao Li、Johannes Großkopf、Christian Jandl、Thorsten Bach

  DOI：10.1002/anie.202013276

  日期：2021.2

  3‐Substituted quinoxalin‐2(1H)‐ones and various aryl‐substituted or tethered olefins underwent an enantioselective, inter‐ or intramolecular aza Paternò–Büchi reaction upon irradiation at λ=420 nm in the presence of a chiral sensitizer (10 mol %). For the intermolecular reaction with 1‐arylethenes as olefin components, the scope of the reaction was studied (14 examples, 50–99 % yield, 86–98 % ee).

  3-取代喹喔啉-2（1 H ^） -酮和各种芳基取代或束缚烯烃进行对映选择性，分子间或分子内照射时在氮杂帕特诺-比希反应λ = 420nm的在手性敏化剂的存在下（10摩尔％）。对于以1-炔烃为烯烃组分的分子间反应，研究了反应范围（14个实例，收率50-99％，ee 86-98％）。通过单晶X射线晶体学阐明了产品的绝对和相对构型。该反应建议通过三重态能量转移在亚胺底物与催化剂之间的氢键1：1配合物中发生。在初步实验中，研究了分子内环加成，产物氮杂环丁烷的连续反应以及喹喔啉酮的替代反应模式。
• [Ir(P−OP)]-Catalyzed Asymmetric Hydrogenation of Diversely Substituted C═N-Containing Heterocycles
  作者：José Luis Núñez-Rico、Anton Vidal-Ferran

  DOI：10.1021/ol400854a

  日期：2013.4.19

  Iridium(I) complexes of enantiomerically pure phosphine-phosphite ligands ([Ir(Cl)(cod)(P—OP)]) efficiently catalyze the enantioselective hydrogenation of diverse C═N-containing heterocyclic compounds (benzoxazines, benzoxazinones, benzothiazinones, and quinoxalinones; 25 examples, up to 99% ee). A substrate-to-catalyst ratio as high as 2000:1 was reached.

  对映体纯的膦亚磷酸酯配体（[Ir（Cl）（cod）（P-OP）]）的铱（I）络合物有效催化多种含C═N的杂环化合物（苯并恶嗪，苯并恶嗪酮，苯并噻嗪酮和喹喔啉酮； 25个实例，ee最高可达99％）。底物与催化剂的比例高达2000：1。
• A novel method for heterocyclic amide–thioamide transformations
  作者：Walid Fathalla、Ibrahim A I Ali、Pavel Pazdera

  DOI：10.3762/bjoc.13.20

  日期：——

  In this paper, we introduce a novel and convenient method for the transformation of heterocyclic amides into heteocyclic thioamides. A two-step approach was applied for this transformation: Firstly, we applied a chlorination of the heterocyclic amides to afford the corresponding chloroheterocycles. Secondly, the chloroherocycles and N-cyclohexyl dithiocarbamate cyclohexylammonium salt were heated in

  在本文中，我们介绍了一种将杂环酰胺转化为杂环硫代酰胺的新颖便捷的方法。该转化过程采用了两步法：首先，我们对杂环酰胺进行了氯化，从而得到了相应的氯杂环。其次，将氯代杂环和N-环己基二硫代氨基甲酸酯环己基铵盐在氯仿中于61°C加热12 h，以优异的收率得到杂环硫代酰胺。
• Quinoxalinone compounds useful for expanding the lumina or air passages
  申请人：The Upjohn Company

  公开号：US04181724A1

  公开（公告）日：1980-01-01

  Compounds of the formula below are useful for expanding the lumina or air passages in a mammal in need of said treatment. The compounds are also useful for treating atopic eczema and urticaria. ##STR1## wherein X and Y are the same or different and are hydrogen, fluoro, chloro, bromo, nitro, trifluoromethyl, alkyl of one to four carbon atoms, inclusive, alkoxy of one to four carbon atoms, inclusive, and cyano; R.sub.1 is hydrogen, methyl or ethyl; R.sub.2 is hydrogen, alkyl of one to six carbon atoms, inclusive, phenyl, benzyl, CH.sub.2 Z wherein Z is fluoro, chloro, or bromo, CO.sub.2 M, CH.sub.2 CO.sub.2 M, CH.sub.2 CH.sub.2 CO.sub.2 M and CHR.sub.3 CO.sub.2 M wherein M is hydrogen, alkyl of one to four carbon atoms, inclusive, or a physiologically acceptable metal or amine cation and R.sub.3 is alkyl of one to three carbon atoms, inclusive, with the proviso that M is not hydrogen when R.sub.2 is CH.sub.2 CO.sub.2 M or a CHR.sub.3 CO.sub.2 M.

  以下的化合物公式对于需要扩张哺乳动物的腔道或空气通道的治疗非常有用。这些化合物也用于治疗特应性湿疹和荨麻疹。其中X和Y相同或不同，可以是氢、氟、氯、溴、硝基、三氟甲基、含1至4个碳原子的烷基、含1至4个碳原子的烷氧基和氰基；R1是氢、甲基或乙基；R2是氢、含1至6个碳原子的烷基、苯基、苄基、CH2Z（其中Z是氟、氯或溴）、CO2M、CH2CO2M、CH2CH2CO2M和CHR3CO2M，其中M是氢、含1至4个碳原子的烷基或生理上可接受的金属或胺阳离子，R3是含1至3个碳原子的烷基，但当R2为CH2CO2M或CHR3CO2M时，M不能是氢。
• Quinoxalinones useful for treating atopic eczema and urticaria
  申请人：The Upjohn Company

  公开号：US04242342A1

  公开（公告）日：1980-12-30

  Compounds of the formula below are useful for expanding the lumina of air passages in a mammal in need of said treatment. The compounds are also useful for treating atopic eczema and urticaria. ##STR1## wherein X and Y are the same or different and are hydrogen, fluoro, chloro, bromo, nitro, trifluoromethyl, alkyl of one to four carbon atoms, inclusive, alkoxy of one to four carbon atoms, inclusive, and cyano; R.sub.1 is hydrogen, methyl or ethyl; R.sub.2 is hydrogen, alkyl of one to six carbon atoms, inclusive, phenyl, benzyl, CH.sub.2 Z wherein Z is fluoro, chloro, or bromo, CO.sub.2 M, CH.sub.2 CO.sub.2 M, CH.sub.2 CH.sub.2 CO.sub.2 M and CHR.sub.3 CO.sub.2 M wherein M is hydrogen, alkyl of one to four carbon atoms, inclusive, or a physiologically acceptable metal or amine cation and R.sub.3 is alkyl of one to three carbon atoms, inclusive, with the proviso that M is not hydrogen when R.sub.2 is CH.sub.2 CO.sub.2 M or CHR.sub.3 CO.sub.2 M.

  以下式子的化合物对于需要扩张哺乳动物空气通道的治疗非常有用。该化合物也对治疗特应性湿疹和荨麻疹有用。其中X和Y相同或不同，可以是氢、氟、氯、溴、硝基、三氟甲基、含有一到四个碳原子的烷基、含有一到四个碳原子的烷氧基和氰基；R.sub.1是氢、甲基或乙基；R.sub.2是氢、含有一到六个碳原子的烷基、苯基、苄基、CH.sub.2 Z，其中Z是氟、氯或溴、CO.sub.2 M、CH.sub.2 CO.sub.2 M、CH.sub.2 CH.sub.2 CO.sub.2 M和CHR.sub.3 CO.sub.2 M，其中M是氢、含有一到四个碳原子的烷基或生理上可接受的金属或胺阳离子，R.sub.3是含有一到三个碳原子的烷基，但当R.sub.2为CH.sub.2 CO.sub.2 M或CHR.sub.3 CO.sub.2 M时，M不是氢。