Methyl-(7-nitro-2-oxo-2H-1,4-benzoxazin-3(4H)-ylidene)ethanoate | 1257269-06-9

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: Methyl-(7-nitro-2-oxo-2H-1,4-benzoxazin-3(4H)-ylidene)ethanoate
• 英文别名: methyl (2Z)-2-(7-nitro-2-oxo-4H-1,4-benzoxazin-3-ylidene)acetate
• CAS: 1257269-06-9
• 化学式: C₁₁H₈N₂O₆
• 分子量: 264.194
• InChiKey: GRGBLSNLDMZIBR-YVMONPNESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  110
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  Methyl-(7-nitro-2-oxo-2H-1,4-benzoxazin-3(4H)-ylidene)ethanoate 、 2-hydroxy-2-phenacyl-1,3-indanedione 在 三氟化硼乙醚 作用下， 以 乙腈 为溶剂， 以74 %的产率得到methyl 2-(1,3-dioxo-2,3-dihydro-1H-inden-2-yl)-7-nitro-4-oxo-1-phenyl-4H-benzo[b]pyrrolo[1,2-d]-[1,4]oxazine-3-carboxylate
  参考文献：
  名称：

  路易斯酸介导的分子内[3+2]环加成反应构建多杂环化合物

  摘要：

  已经证明了通过分子内[3+2]环加成从2-取代-2-羟基-茚满-1,3-二酮和1,4-苯并恶嗪酮实际有效地区域选择性合成吡咯稠合多杂环化合物。该方案避免了柱色谱法，并且通过简单的过滤即可以良好至优异的产率分离产物。释放电子基团和吸电子基团的电子效应都具有良好的耐受性。

  DOI：

  10.1002/ejoc.202300251
• 作为产物：
  描述：

  丁炔二酸二甲酯 、 2-氨基-5-硝基苯酚 以 甲醇 为溶剂， 反应 2.0h， 生成 Methyl-(7-nitro-2-oxo-2H-1,4-benzoxazin-3(4H)-ylidene)ethanoate
  参考文献：
  名称：

  Synthesis and SAR studies of 1,4-benzoxazine MenB inhibitors: Novel antibacterial agents against Mycobacterium tuberculosis

  摘要：

  Menaquinone is an essential component of the electron transport chain in many pathogens and consequently enzymes in the menaquinone biosynthesis pathway are potential drug targets for the development of novel antibacterial agents. In order to identify leads that target MenB, the 1,4-dihydroxy-2-naphthoyl-CoA synthase from Mycobacterium tuberculosis, a high-throughput screen was performed. Several 1,4-benzoxazines were identified in this screen and subsequent SAR studies resulted in the discovery of compounds with excellent antibacterial activity against M. tuberculosis H37Rv with MIC values as low as 0.6 mu g/ml. The 1,4-benzoxazine scaffold is thus a promising foundation for the development of antitubercular agents. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.08.076

文献信息

• KAWAHARA, NORIO;NAKAJIMA, TAKAKO;ITOH, TSUNEO;TAKAYANAGI, HIROAKI;OGURA, +, CHEM. AND PHARM. BULL., 1984, 32, N 3, 1163-1169
  作者：KAWAHARA, NORIO、NAKAJIMA, TAKAKO、ITOH, TSUNEO、TAKAYANAGI, HIROAKI、OGURA, +

  DOI：——

  日期：——