benzyl 3-methylquinoxaline-2-carboxylate | 389121-59-9

• 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: benzyl 3-methylquinoxaline-2-carboxylate
• 英文别名: benzyl 3-methylquinoxalin-2-carboxylate；benzyl 3-methylquinoxaline-2carboxylate；2-Quinoxalinecarboxylic acid, 3-methyl-, phenylmethyl ester
• CAS: 389121-59-9
• 化学式: C₁₇H₁₄N₂O₂
• 分子量: 278.31
• InChiKey: BGEFIJNJKJDLID-UHFFFAOYSA-N

物化性质

• 熔点：
  74 °C
• 沸点：
  416.7±40.0 °C(Predicted)
• 密度：
  1.237±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  52.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  乙酰丙酮苄酯 在 iron(III) trifluoromethanesulfonate 、 三乙胺 、 甲烷磺酰基叠氮化物 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 7.0h， 生成 benzyl 3-methylquinoxaline-2-carboxylate
  参考文献：
  名称：

  铁催化的1,2-二胺和重氮二羰基环化反应用于水中的多种和多官能化喹喔啉，吡嗪和苯并喹喔啉

  摘要：

  已经开发了一种新颖，简便的铁催化水中邻苯二胺和重氮羰基串联的方法，用于构造多官能化喹喔啉。关键策略包括一锅多米诺骨牌NH插入，环化和氧化反应。该方案提供了一种安全，温和的合成方法，可以高产率获得各种喹喔啉衍生物。这种方法还可以形成生物学上有趣的吡嗪和苯并喹喔啉。

  DOI：

  10.1002/adsc.201600503

文献信息

• A New Convenient Liquid- and Solid-Phase Synthesis of Quinoxalines from (E)-3-Diazenylbut-2-enes
  作者：Orazio A. Attanasi、Lucia De Crescentini、Paolino Filippone、Fabio Mantellini、Stefania Santeusanio

  DOI：10.1002/1522-2675(20010815)84:8<2379::aid-hlca2379>3.0.co;2-5

  日期：2001.8.15

  3-[(tert-Butoxy)carbonyl]diazenyl}but-2-enoates react in tetrahydrofuran at room temperature with aromatic 1,2-diamines to give 3-methylquinoxaline-2-carboxylates. These products were also obtained in solid-phase synthesis, by using polymer-bound 3-diazenylbut-2-enes.

  3-[(叔丁氧基)羰基]二烯基}丁-2-烯酸酯在室温下在四氢呋喃中与芳族1,2-二胺反应生​​成3-甲基喹喔啉-2-羧酸酯。这些产品也通过使用聚合物结合的 3-二氮烯基丁-2-烯在固相合成中获得。
• Improved Synthesis of SubstitutedQuinoxalines from New N=N-Polymer-bound 1,2-Diaza-1,3-butadienes
  作者：Paolino Filippone、Fabio Mantellini、Orazio A. Attanasi、Lucia De Crescentini、Stefania Santeusanio

  DOI：10.1055/s-2003-39886

  日期：——

  The first general protocol for the preparation of different N=N-polymer-bound 1,2-diaza-1,3-butadienes is reported. The utility of these supported reagents in the solid-phase in the preparation of 3-methyl quinoxaline-2-carboxylates by reaction with aromatic 1,2-diamines is presented.

  报告首次提出了制备不同 N=N 聚合物结合型 1,2-二氮杂-1,3-丁二烯的通用方案。介绍了这些固相支持试剂与芳香族 1,2-二胺反应制备 3-甲基喹喔啉-2-羧酸盐的实用性。
• Quinoxaline synthesis in novel tandem one-pot protocol
  作者：B.S.P. Anil Kumar、B. Madhav、K. Harsha Vardhan Reddy、Y.V.D. Nageswar

  DOI：10.1016/j.tetlet.2011.03.110

  日期：2011.6

  A variety of quinoxalines were synthesized via tandem one-pot procedure for the first time in water medium. The key strategy was the in situ preparation of alpha-halo-beta-keto esters by the reaction of N-bromo succinimide with beta-keto esters and further condensation with phenylene diamines. This novel eco-friendly approach offers an easy, efficient, and mild synthesis of highly substituted quinoxalines in good yields. (C) 2011 Elsevier Ltd. All rights reserved.
• One-pot synthesis of quinoxaline-2-carboxylate derivatives using ionic liquid as reusable reaction media
  作者：H.M. Meshram、P. Ramesh、G. Santosh Kumar、B. Chennakesava Reddy

  DOI：10.1016/j.tetlet.2010.05.099

  日期：2010.8

  The catalyst-free one-pot synthesis of quinoxaline-2-carboxylate is reported by the reaction of alpha-halo-beta-ketoesters with 1,2-diamines using an ionic liquid as an environmentally benign solvent The recovered ionic liquid was reused for four to five cycles Moreover, the method is applicable for a variety of 1,2-diamines and alpha-halo-beta-ketoesters (c) 2010 Elsevier Ltd All rights reserved
• Iron-Catalyzed Annulation of 1,2-Diamines and Diazodicarbonyls for Diverse and Polyfunctionalized Quinoxalines, Pyrazines, and Benzoquinoxalines in Water
  作者：Rameshwar Prasad Pandit、Sung Hong Kim、Yong Rok Lee

  DOI：10.1002/adsc.201600503

  日期：2016.11.17

  construction of polyfunctionalized quinoxalines has been developed. The key strategy includes the one‐pot domino N−H insertion, cyclization, and oxidation reactions. This protocol offers a safe and mild synthetic approach to access a variety of quinoxaline derivatives in high yields. This methodology also allows the formation of biologically interesting pyrazines and benzoquinoxalines.

  已经开发了一种新颖，简便的铁催化水中邻苯二胺和重氮羰基串联的方法，用于构造多官能化喹喔啉。关键策略包括一锅多米诺骨牌NH插入，环化和氧化反应。该方案提供了一种安全，温和的合成方法，可以高产率获得各种喹喔啉衍生物。这种方法还可以形成生物学上有趣的吡嗪和苯并喹喔啉。