3,4-dihydro-2-methyl-5-nitro-3-oxo-2H-1,4-benzoxazine

• 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: 3,4-dihydro-2-methyl-5-nitro-3-oxo-2H-1,4-benzoxazine
• 英文别名: 2-methyl-5-nitro-2H-1,4-benzoxazin-3(4H)-one；5-nitro-2-methyl-1,4-benzoxazin-3-one；2-methyl-5-nitro-4H-1,4-benzoxazin-3-one
• 化学式: C₉H₈N₂O₄
• 分子量: 208.174
• InChiKey: KJLTZKFWTJOQFY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  84.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-氨基-3-硝基苯酚 、 2-溴丙酸乙酯 在 N-甲基吡咯烷酮 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 反应 0.05h， 以60%的产率得到3,4-dihydro-2-methyl-5-nitro-3-oxo-2H-1,4-benzoxazine
  参考文献：
  名称：

  Microwave-assisted one-pot regioselective synthesis of 2-alkyl-3,4-dihydro-3-oxo-2H-1,4-benzoxazines

  摘要：

  A protocol for regioselective one-pot synthesis of 2-alkyl-3,4-dihydro-3-oxo-2H-1,4-benzoxazines under controlled microwave heating has been developed. Starting from commercially available 2-aminophenols, a base-mediated regioselective O-alkylation took place with 2-bromoalkanoates to give the acyclic intermediates, which underwent spontaneously an intramolecular amidation reaction to furnish 2-alkyl-3,4-dihydro-3-oxo-2H-1.4-benzoxazines in 44-82% yields. For the acyclic intermediate possessing an electron-withdrawing group, microwave heating was necessary for the annulation reaction. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.04.072

文献信息

• Herbicidal sulfonamides
  申请人：ICI AUSTRALIA LIMITED

  公开号：EP0385775A1

  公开（公告）日：1990-09-05

  Compounds of the formula and salts thereof, W and W₁ being independently O or S; A being a nitrogen-containing heterocyclic ring system, E being O, S(O)m or NR₄ where m is 0-2; E₁ being CH₂, CH₂CH₂, CH (C₁-C₄ alkyl), C(C₁-C₄ alkyl)₂ or CH (aryl); R₁ and R₂ are independently hydrogen, halogen or one of a variety of organic substituents. The compounds are effective herbicides.

  该公式化合物及其盐，其中W和W₁独立地为O或S；A为含氮杂环环系统，E为O，S(O)m或NR₄，其中m为0-2；E₁为CH₂，CH₂CH₂，CH（C₁-C₄烷基），C（C₁-C₄烷基）₂或CH（芳基）；R₁和R₂独立地为氢，卤素或多种有机取代基。这些化合物是有效的除草剂。
• [DE] BENZOXAZIN- UND BENZOTHIAZIN-DERIVATE UND DEREN VERWENDUNG IN ARZNEIMITTELN<br/>[EN] BENZOXAZINE AND BENZOTHIAZINE DERIVATIVES AND THEIR USE IN PHARMACEUTICALS<br/>[FR] DERIVES DE BENZOXAZINE ET DE BENZOTHIAZINE ET LEUR UTILISATION DANS DES MEDICAMENTS
  申请人：SCHERING AKTIENGESELLSCHAFT

  公开号：WO1999012915A1

  公开（公告）日：1999-03-18

  (DE) Es werden Verbindungen der Formel (I) beschrieben sowie deren Herstellung und Verwendung in Arzneimitteln.(EN) The invention relates to compounds of the formula formula (I) and to their production and their use in pharmaceuticals.(FR) La présente invention concerne des composés correspondant à la formule (I), ainsi que leur production et leur utilisation dans des médicaments.

  (德语)根据本发明，涉及具有表式(I)化合物及其制备方法及在药物中的应用。(英文)本发明涉及公式(I)的化合物及其制备和在药物中的应用。(法语)LLEGAL穿越者发明涉及对应化工业园区(Capteur de Traction)的目标部分… 把本发明结合到一个实际应用中，将有助于实现这一目标。
• BENZOXAZIN- UND BENZOTHIAZIN-DERIVATE UND DEREN VERWENDUNG IN ARZNEIMITTELN
  申请人：SCHERING AKTIENGESELLSCHAFT

  公开号：EP1015437B1

  公开（公告）日：2003-12-03
• US6365736B1
  申请人：——

  公开号：US6365736B1

  公开（公告）日：2002-04-02
• Microwave-assisted one-pot regioselective synthesis of 2-alkyl-3,4-dihydro-3-oxo-2H-1,4-benzoxazines
  作者：Wei-Min Dai、Xuan Wang、Chen Ma

  DOI：10.1016/j.tet.2005.04.072

  日期：2005.7

  A protocol for regioselective one-pot synthesis of 2-alkyl-3,4-dihydro-3-oxo-2H-1,4-benzoxazines under controlled microwave heating has been developed. Starting from commercially available 2-aminophenols, a base-mediated regioselective O-alkylation took place with 2-bromoalkanoates to give the acyclic intermediates, which underwent spontaneously an intramolecular amidation reaction to furnish 2-alkyl-3,4-dihydro-3-oxo-2H-1.4-benzoxazines in 44-82% yields. For the acyclic intermediate possessing an electron-withdrawing group, microwave heating was necessary for the annulation reaction. (c) 2005 Elsevier Ltd. All rights reserved.