methyl 2,3-dihydro-7-methyl-2-oxo-4H-1,4-benzoxazine-3-methylenecarboxylate | 104827-36-3

• 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: methyl 2,3-dihydro-7-methyl-2-oxo-4H-1,4-benzoxazine-3-methylenecarboxylate
• 英文别名: (Z)-methyl 2-(7-methyl-2-oxo-2H-benzo[b][1,4]oxazin-3(4H)-ylidene)acetate；(Z)-3-methoxycarbonylmethylene-7-methyl-3,4-dihydro-2H-1,4-benzoxazin-2-one；(7-methyl-2-oxo-4H-benzo[1,4]oxazin-3-ylidene)-acetic acid methyl ester；Methyl-(7-methyl-2-oxo-2H-1,4-benzoxazin-3(4H)-ylidene)ethanoate；methyl (2Z)-2-(7-methyl-2-oxo-4H-1,4-benzoxazin-3-ylidene)acetate
• CAS: 104827-36-3
• 化学式: C₁₂H₁₁NO₄
• 分子量: 233.224
• InChiKey: JBPDUKBODBPEBG-TWGQIWQCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 2,3-dihydro-7-methyl-2-oxo-4H-1,4-benzoxazine-3-methylenecarboxylate 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 0.25h， 生成 methyl (Z)-2-(2-hydroxy-7-methyl-2H-benzo[b][1,4]oxazin-3(4H)-ylidene)acetate
  参考文献：
  名称：

  Expedient synthesis of novel 1,4-benzoxazine and butenolide derivatives

  摘要：

  已开发出一种快速高效的合成2-羟基-1,4-苯并噁嗪衍生物的方案。这些中间体作为合成一系列新型丁烯内酯衍生物和2-氨基-1,4-苯并噁嗪衍生物的前体。

  DOI：

  10.1039/c4ra01736f
• 作为产物：
  描述：

  丁炔二酸二甲酯 、 6-氨基间甲酚 反应 0.08h， 生成 methyl 2,3-dihydro-7-methyl-2-oxo-4H-1,4-benzoxazine-3-methylenecarboxylate
  参考文献：
  名称：

  球磨机中炔烃与邻位取代苯胺的加氢胺化反应：级联反应合成苯甲醚化的N-杂环

  摘要：

  结果表明，在行星式球磨机中，邻位取代的苯胺易于与乙炔二羧酸二乙酯发生加氢胺化反应。分子间加氢反应与分子内闭环的顺序偶联被用于由易得的结构单元即邻位具有OH，NH或SH基团的亲电炔烃和苯胺合成苯并恶嗪，喹喔啉和苯并噻嗪位置。对于杂环的形成，已表明几种应力条件能够以固态引发反应。就过程控制而言，在球磨机中进行处理似乎比用研钵和研杵粉碎更为有利。在后一种情况下，固态分析期间发生了显着的反应后修饰。低温研磨证明对试剂的分子转化有不利影响。

  DOI：

  10.1002/chem.201406306

文献信息

• Introduction of a clean and promising protocol for the synthesis of β-amino-acrylates and 1,4-benzoheterocycles: an emerging innovation
  作者：Garima Choudhary、Rama Krishna Peddinti

  DOI：10.1039/c1gc15701a

  日期：——

  A highly efficient, elegant and simple procedure with exceptionally mild conditions has been proposed for the synthesis of β-amino-acrylate derivatives and an array of biologically and pharmaceutically active benzoheterocycles. The protocol offers a valuable alternative to known methods and will find applications in the field of green synthesis. The regio- and stereo-chemistry of the products were established by IR, NMR and single crystal X-ray analysis.

  提出了一种高效、优雅且简单的过程，用于合成β-氨基丙烯酸酯衍生物和一系列具有生物学及药物活性的苯并杂环化合物，条件极为温和。该方案为已知方法提供了一种有价值的替代方案，并将应用于绿色合成领域。产品的区域和立体化学性质通过红外光谱、核磁共振和单晶X射线分析得以确定。
• Kawahara, Norio; Nakajima, Takako; Itoh, Tsuneo, Chemical and pharmaceutical bulletin, 1984, vol. 32, # 3, p. 1163 - 1169
  作者：Kawahara, Norio、Nakajima, Takako、Itoh, Tsuneo、Takayanagi, Hiroaki、Ogura, Haruo

  DOI：——

  日期：——
• Danswan, Geoff W.; Hairsine, Peter W.; Rowlands, David A., Journal of the Chemical Society. Perkin transactions I, 1982, p. 1049 - 1058
  作者：Danswan, Geoff W.、Hairsine, Peter W.、Rowlands, David A.、Taylor, John B.、Westwood, Robert

  DOI：——

  日期：——
• Synthesis and SAR studies of 1,4-benzoxazine MenB inhibitors: Novel antibacterial agents against Mycobacterium tuberculosis
  作者：Xiaokai Li、Nina Liu、Huaning Zhang、Susan E. Knudson、Richard A. Slayden、Peter J. Tonge

  DOI：10.1016/j.bmcl.2010.08.076

  日期：2010.11

  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.
• DANSWAN, G. W.;HAIRSINE, P. W.;ROWLANDS, D. A.;TAYLOR, J. B.;WESTWOOD, R., J. CHEM. SOC. PERKIN TRANS., 1982, N 4, 1049-1058
  作者：DANSWAN, G. W.、HAIRSINE, P. W.、ROWLANDS, D. A.、TAYLOR, J. B.、WESTWOOD, R.

  DOI：——

  日期：——