2-methoxy-4H-3,1-benzoxazin-4-one | 200354-53-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶嗪类
• 英文名称: 2-methoxy-4H-3,1-benzoxazin-4-one
• 英文别名: 2-Methoxy-3,1-benzoxazin-4-one
• CAS: 200354-53-6
• 化学式: C₉H₇NO₃
• 分子量: 177.159
• InChiKey: FBNDVODQCPMRJC-UHFFFAOYSA-N

物化性质

• 沸点：
  282.3±23.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  47.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-methoxy-4H-3,1-benzoxazin-4-one 生成 N-Carbomethoxyanthranilic acid
  参考文献：
  名称：

  A phosgene and peroxide-free one-pot tandem synthesis of isatoic anhydrides involving anthranilic acid, Boc anhydride, and 2-chloro-N-methyl pyridinium iodide

  摘要：

  A phosgene and peroxide-free approach for the synthesis of isatoic anhydrides has been described. The synthesis involves the carbamate formation with Boc anhydride followed by in situ cyclization to afford the isatoic anhydride. The importance of this synthetic strategy is in the ease of operation, scalability, and preparation from readily available raw materials. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.10.034
• 作为产物：
  描述：

  N-Carbomethoxyanthranilic acid 在 2-氯-1-甲基吡啶碘化物 作用下， 以 乙腈 为溶剂， 反应 0.17h， 以95%的产率得到2-methoxy-4H-3,1-benzoxazin-4-one
  参考文献：
  名称：

  A phosgene and peroxide-free one-pot tandem synthesis of isatoic anhydrides involving anthranilic acid, Boc anhydride, and 2-chloro-N-methyl pyridinium iodide

  摘要：

  A phosgene and peroxide-free approach for the synthesis of isatoic anhydrides has been described. The synthesis involves the carbamate formation with Boc anhydride followed by in situ cyclization to afford the isatoic anhydride. The importance of this synthetic strategy is in the ease of operation, scalability, and preparation from readily available raw materials. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.10.034

文献信息

• An Efficient Route to 3-Aryl-Substituted Quinolin-2-one and 1,8-Naphthyridin-2-one Derivatives of Pharmaceutical Interest
  作者：Christos A. Mitsos、Alexandros L. Zografos、Olga Igglessi-Markopoulou

  DOI：10.1021/jo0340051

  日期：2003.5.1

  Reaction of arylacetic ester enolates with 2-alkoxy-4H-3,1-benzoxazin-4-ones offers a short and versatile synthetic route to 3-aryl-4-hydroxyquinolin-2(1H)-ones, through the cyclization of the beta-ketoesters produced. Similar reactions of 4H-pyrido[2,3-d][1,3]oxazin-4-ones with ester enolates afford 1-acyl-4-hydroxy-1,8-naphthyridin-2(1H)-ones in a convenient two-step, one-pot procedure.

  芳酸酯烯酸酯与2-烷氧基-4H-3,1-苯并恶嗪-4-酮的反应通过β的环化为3-芳基-4-羟基喹啉-2（1H）-酮提供了一种短而通用的合成途径-酮酸酯生产。4H-吡啶并[2,3-d] [1,3]恶嗪-4-酮与烯醇酯的相似反应可在方便的情况下得到1-酰基-4-羟基-1,8-萘啶-2（1H）-酮。两步一锅法。
• Nickel-catalyzed Cycloadditions of Benzoxazinones with Alkynes: Synthesis of Quinolines and Quinolones
  作者：Nobuyoshi Maizuru、Tasuku Inami、Takuya Kurahashi、Seijiro Matsubara

  DOI：10.1246/cl.2011.375

  日期：2011.4.5

  A nickel-catalyzed cycloaddition has been developed where readily available benzoxazinones react with alkynes to afford substituted quinolines or quinolones. The specific cycloaddition can be achie...

  已经开发了镍催化的环加成反应，其中容易获得的苯并嗪酮与炔烃反应得到取代的喹啉或喹诺酮。具体的环加成可以实现...
• 2-Oxy-4H-3,1-benzoxazin-4-one derivatives and related compounds
  申请人：SYNTEX (U.S.A.) INC.

  公开号：EP0206323A1

  公开（公告）日：1986-12-30

  2-Oxy-4H-3,1-benzoxazin-4-ones represented by the formula: and the pharmaceutically acceptable acid addition salts thereof, pharmaceutical compositions with serine protease inhibiting effects, therapeutic uses of such compounds and methods for their manufacture are disclosed.

  本发明公开了由式： 的 2-氧基-4H-3,1-苯并恶嗪-4-酮及其药学上可接受的酸加成盐、具有丝氨酸蛋白酶抑制作用的药物组合物、这类化合物的治疗用途及其制造方法均已公开。
• Inhibition of cathepsin G by 4H-3,1-benzoxazin-4-ones
  作者：Michael Gütschow、Ulf Neumann

  DOI：10.1016/s0968-0896(97)00128-4

  日期：1997.10

  A series of 4H-3,1-benzoxazin-4-ones is reported that inhibit the serine proteases human cathepsin G and bovine chymotrypsin. The synthesis and kinetic parameters of the alkaline hydrolysis is described. These compounds act as acyl-enzyme inhibitors of both enzymes. The reaction of cathepsin G with 2-benzylamino-4H-3,1-benzoxazin-4-one (20) was studied in detail. A partition in deacylation of the initially formed acyl-enzyme was observed, leading to the formation of 2-(3-benzylureido)benzoic acid (26) and 3-benzylquinazoline-2,4-(1H,3H)-dione (27). A 6-methyl substitution strongly increased the acylation rate of both proteases. Introduction of an aryl moiety into the 2-substituent led to compounds with K-i values towards cathepsin G in the nanomolar range. Their inhibitory potency is stronger than that of other synthetic inhibitors of cathepsin G. (C) 1997 Elsevier Science Ltd.
• US4665070A
  申请人：——

  公开号：US4665070A

  公开（公告）日：1987-05-12