2-methyl-2,3-dihydro-4H-1,3-benzoxazin-4-one | 20602-57-7

• 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-methyl-2,3-dihydro-4H-1,3-benzoxazin-4-one
• 英文别名: 2-methyl-2,3-dihydro-benzo[e][1,3]oxazin-4-one；2-methyl-2,3-dihydro-benz[e][1,3]oxazin-4-one；2-Methyl-2,3-dihydro-benz[e][1,3]oxazin-4-on；2-Methyl-3,4-dihydro-1,3-benzoxazine-4-one；4-Oxo-2-methyl-5,6-benzo-1,3-oxazin；2-Methyl-2H-1,3-benzoxazin-4(3H)-one；2-methyl-2,3-dihydro-1,3-benzoxazin-4-one
• CAS: 20602-57-7
• 化学式: C₉H₉NO₂
• 分子量: 163.176
• InChiKey: MOFJSTXFUSYCDO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  12
• 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：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-methyl-2,3-dihydro-4H-1,3-benzoxazin-4-one 、 N,N-二甲基甲酰胺 在 三氯氧磷 作用下， 反应 1.0h， 以90%的产率得到2-methyl-4-oxo-2H-1,3-benzoxazine-3(4H)-carbaldehyde
  参考文献：
  名称：

  The Vilsmeier–Haack formylation of 2,3-dihydro-4H-1,3-benzoxazin-4-ones and isomeric 1,2-dihydro-4H-3,1-benzoxazin-4-ones: an effective approach to functionalized 2H-/4H-chromenes and tetrahydroacridines

  摘要：

  We found that 1,3- and isomeric 3,1-benzoxazin-4-ones react with the Vilsmeier reagent in vastly different ways. Thus, either 2H- or 4H-chromenes were obtained in good yields when 1,3-benzoxazin-4-ones were reacted at 75-80 degrees C, while the formylation of 3,1-benzoxazines at ambient temperature leads to acridine-9-one or 9-chloroacridine derivatives, depending on the amount of Vilsmeier reagent and the nature of substrate. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.06.069
• 作为产物：
  描述：

  2-甲基-1,3-苯并恶嗪-4-酮,高氯酸 在 sodium tetrahydroborate 作用下， 以 乙腈 为溶剂， 反应 20.0h， 以68%的产率得到2-methyl-2,3-dihydro-4H-1,3-benzoxazin-4-one
  参考文献：
  名称：

  Reactions of 4-oxo-1,3-benzoxazinium perchlorates with sodium borohydride

  摘要：

  Reduction of 4-oxo-1,3-benzoxazinium perchlorates with sodium borohydride depending on the structure of starting salt and the reaction conditions leads to different products. 2-Alkyl- and 2-phenylsubstituted salts react with sodium borohydride to give 2,3-dihydro-4-oxo-1,3-benzoxazines. 2-Arylvinyl- and 2-heterylvinyl-substituted perchlorates either form 4-oxo-1,3-benzoxazines or undergo hydrogenation to aryl- or heterylethyldihydrobenzoxazinones.

  DOI：

  10.1134/s1070363209070184

文献信息

• Novel compounds and their use as positive AMPA receptor modulators
  申请人：Neurosearch A/S.

  公开号：US20040043987A1

  公开（公告）日：2004-03-04

  The invention provides novel compounds represented by the general formula 5 compound represented by the formula: 1 wherein the bond represented by the broken line may be a single, a double bond or absent; and if the bond is absent, then the nitrogen is substituted with a hydrogen and R 2 ; X represents SO 2 or C═O or CH 2 ; Y represents —CH(R 4 )—, —N(R 4 )— or —N(R 4 )—CH 2 —, O; and the meaning of R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , and R 8 are as defined in the application The compounds are useful as positive modulators of the AMPA-receptor.

  该发明提供了一种新型化合物，其通式5的化合物如下所示：其中由虚线表示的键可以是单键、双键或不存在；如果键不存在，则氮原子用氢和R2取代；X代表SO2或C═O或CH2；Y代表—CH(R4)—、—N(R4)—或—N(R4)—CH2—、O；R2、R3、R4、R5、R6、R7和R8的含义如申请中所定义。这些化合物可用作AMPA受体的阳性调节剂。
• Compounds and their use as positive AMPA receptor modulators
  申请人：NeuroSearch A/S

  公开号：US07235548B2

  公开（公告）日：2007-06-26

  The invention provides novel compounds represented by the general formula compound represented by the formula: wherein the bond represented by the broken line may be a single, a double bond or absent; and if the bond is absent, then the nitrogen is substituted with a hydrogen and R2; X represents SO2 or C═O or CH2; Y represents —CH(R4)—, —N(R4)— or —N(R4)—CH2—, O; and the meaning of R2, R3, R4, R5, R6, R7, and R8 are as defined in the application The compounds are useful as positive modulators of the AMPA-receptor.

  本发明提供了由一般式化合物表示的新化合物，该一般式化合物由以下式子表示：其中，由断线表示的键可以是单键、双键或不存在；如果键不存在，则氮被氢和R2取代；X代表SO2、C═O或CH2；Y代表—CH(R4)—、—N(R4)—或—N(R4)—CH2—、O；而R2、R3、R4、R5、R6、R7和R8的含义如申请书中所定义。这些化合物可用作AMPA受体的正向调节剂。
• 2-Methyl-4-keto-1,3-benzodioxanes from Salicylic Acids and Vinyl Acetate
  作者：David T. Mowry、William H. Yanko、Eugene L. Ringwald

  DOI：10.1021/ja01202a032

  日期：1947.10
• Reaction of salicylic acid derivatives with acetylene
  作者：G. G. Skvortsova、L. V. Andriyankova、Z. V. Stepanova

  DOI：10.1007/bf00955793

  日期：1983.10
• Hicks, Journal of the Chemical Society, 1910, vol. 97, p. 1033
  作者：Hicks

  DOI：——

  日期：——