3-methoxy-1-methylquinoxalin-2(1H)-one | 90915-50-7

• 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-methoxy-1-methylquinoxalin-2(1H)-one
• 英文别名: 3-methoxy-1-methyl-1H-quinoxalin-2-one；3-Methoxy-1-methyl-1H-chinoxalin-2-on；1-Methyl-3-methoxy-2-oxo-1,2-dihydro-chinoxalin；3-Methoxy-1-methyl-2-oxochinoxalin；3-methoxy-1-methylquinoxalin-2-one
• CAS: 90915-50-7
• 化学式: C₁₀H₁₀N₂O₂
• 分子量: 190.202
• InChiKey: VSQQTRPFBUTQPT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  41.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  N-甲基-2-硝基苯胺 在 palladium on activated charcoal 、 乙醚 、 乙醇 作用下， 生成 3-methoxy-1-methylquinoxalin-2(1H)-one
  参考文献：
  名称：

  Cheeseman, Journal of the Chemical Society, 1955, p. 1804,1806

  摘要：

  DOI：

文献信息

• C(sp2)–H/O–H cross-dehydrogenative coupling of quinoxalin-2(1H)-ones with alcohols under visible-light photoredox catalysis
  作者：Long-Yong Xie、Yi-Shu Liu、Hong-Ru Ding、Shao-Feng Gong、Jia-Xi Tan、Jun-Yi He、Zhong Cao、Wei-Min He

  DOI：10.1016/s1872-2067(19)63526-6

  日期：2020.8

  Abstract An efficient and practical route to various 3-alkoxylquinoxalin-2(1H)-ones through visible-light photocatalytic C(sp2)−H/O−H cross-dehydrogenation coupling of quinoxalin-2(1H)-ones and alcohols, employing ambient air as an oxidant at room temperature under metal-free conditions, was developed.

  摘要 通过可见光光催化 C(sp2)-H/O-H 交叉脱氢偶联喹喔啉-2(1H)-酮和醇，制备各种 3-烷氧基喹喔啉-2(1H)-酮的高效实用途径，采用开发了室温下无金属条件下的环境空气作为氧化剂。
• Electrosynthesis of C3 Alkoxylated Quinoxalin-2(1<i>H</i> )-ones through Dehydrogenative C-H/O-H Cross-Coupling
  作者：Xinpeng Jiang、Liechao Yang、Zenghui Ye、Xiaofan Du、Liyun Fang、Yu Zhu、Keda Chen、Jianjun Li、Chuanming Yu

  DOI：10.1002/ejoc.201901928

  日期：2020.3.22

  Various 3‐alkoxylated quinoxalin‐2(1H)‐ones were synthesized in a simple undivided cell via electrochemically dehydrogenative C–H/O–H cross‐coupling between quinoxalin‐2(1H)‐ones and alcohols under mild conditions.

  在温和的条件下，通过喹喔啉-2（1 H）-酮与醇之间的电化学脱氢C–H / O–H交叉偶联，在一个简单的未分隔电池中合成了各种3-烷氧基化的喹喔啉-2（1 H）-酮。
• Visible‐Light‐Induced Alkoxylation of Quinoxalin‐2(1 <i>H</i> )‐ones with Alcohols for the Synthesis of Heteroaryl Ethers
  作者：Lulu Zhao、Lei Wang、Yanhui Gao、Zhiming Wang、Pinhua Li

  DOI：10.1002/adsc.201900732

  日期：2019.12.3

  A direct and simple strategy to heteroaryl ethers via a visible‐light‐induced alkoxylation of quinoxalin‐2(1H)‐ones with alcohols under ambient conditions was developed. The commercially available, low cost alcohols served as alkoxylation reagents and solvents. This reaction has advantages of novel protocol, mild conditions, good functional‐group tolerance, and high yields of products.

  在环境条件下，通过可见光诱导的喹喔啉-2（1 H）-酮与醇的烷氧基化反应，开发了一种直接，简单的杂芳基醚化策略。市售的低成本醇用作烷氧基化试剂和溶剂。该反应的优点是方案新颖，条件温和，官能团耐受性好，产品收率高。
• 78. Quinoxaline derivatives. Part III. Cyclisation of 3 : 4-dihydro-3-oxoquinoxaline-2-carboxyureides to 1 : 2 : 3 : 4-tetrahydro-3-oxoquinoxaline-spiro-5′-hydantoins
  作者：J. W. Clark-Lewis

  DOI：10.1039/jr9570000422

  日期：——
• Convergent Paired Electrolysis for [3+2] Cycloaddition of Azidotrimethylsilane with N‐Heterocycles
  作者：Abhijit Bankura、Subhadeep Ghosh、Sumit Biswas、Indrajit Das

  DOI：10.1002/cssc.202400381

  日期：2024.11.11

  A widely used method to obtain tetrazoles is through the azide and nitrile [3+2] cycloaddition. However, this process often involves using non‐recyclable transition metals or Lewis acid catalysts and stoichiometric amounts of oxidants and additives, which reduces atom efficiency. We have discovered a convergent paired electrochemical reaction to perform this cycloaddition reaction, without the need for metal catalysts or oxidants. This tetrazolation strategy uses azidotrimethylsilane (TMSN3) and N‐heterocycles in an undivided cell at a constant current. We use a mixture of CH3CN and equivalent amounts of H2O as co‐solvent at room temperature. It is crucial to produce a stoichiometric amount of active hydroxyl ions through the cathodic reduction of water. Cyclic voltammetry (CV) studies and control experiments confirm that the cycloaddition reaction is specific to the electrode electron transfer process, eliminating the need for a mediator to shuttle electrons. This metal‐ and oxidant‐free strategy is highly compatible with different functional groups and produces products with moderate to good yields. We have successfully tetrazolated bioactive compounds at a late stage, scaled up batches efficiently, and synthesized free amino‐containing N‐heterocycles via denitrogenation of tetrazoles.