[6-Methyl-2-oxo-4H-benzo[1,4]oxazin-(3Z)-ylidene]-acetic acid methyl ester | 70917-48-5

• 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: [6-Methyl-2-oxo-4H-benzo[1,4]oxazin-(3Z)-ylidene]-acetic acid methyl ester
• 英文别名: methyl 2-(6-methyl-2-oxo-4H-1,4-benzoxazin-3-ylidene)acetate
• CAS: 70917-48-5
• 化学式: C₁₂H₁₁NO₄
• mdl: MFCD04028579
• 分子量: 233.224
• InChiKey: BQNDINDPXYNXTK-UHFFFAOYSA-N

物化性质

• 熔点：
  211-212 °C(Solv: ethanol (64-17-5))
• 沸点：
  379.2±42.0 °C(Predicted)
• 密度：
  1.345±0.06 g/cm3(Predicted)

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：

  [6-Methyl-2-oxo-4H-benzo[1,4]oxazin-(3Z)-ylidene]-acetic acid methyl ester 以 正己烷 为溶剂， 反应 24.0h， 生成 rac-methyl (7aR,8R,10aS)-15-methyl-6,7,11-trioxo-8,9-diphenyl-6,7,8,9-tetrahydro-7aH,11H-[1,2]oxazolo[5′,4′:2,3]pyrrolo[2,1-c][1,4]benzoxazine-7a-carboxylate
  参考文献：
  名称：

  Dipolar [3+2]-Cycloaddition of Nitrones to 3-Alkoxycarbonyl- and 3-Pivaloyl-Substituted Hetareno[e]pyrrole-2,3-diones

  摘要：

  DOI：

  10.1134/s1070428022030058
• 作为产物：
  描述：

  邻氨基对甲苯酚 、 丁炔二酸二甲酯 以 甲醇 为溶剂， 反应 0.08h， 以96%的产率得到[6-Methyl-2-oxo-4H-benzo[1,4]oxazin-(3Z)-ylidene]-acetic acid methyl ester
  参考文献：
  名称：

  An Efficient Synthesis of Functionalized 6,10-Dioxo-6,10-dihydro-5H-pyrido[1,2-a]quinoxalines and 6,10-Dioxo-6,10-dihydropyrido[2,1-c][1,4]benz­oxazines

  摘要：

  介绍了一种 8-羟基-6,10-二氧代-6,10-二氢-5H-吡啶并[1,2-a]喹喔啉-7-羧酸烷基酯和 8-羟基-6,10-二氧代-6,10-二氢吡啶并[2,1-c][1,4]苯并恶嗪-7-羧酸烷基酯的高效合成方法。这涉及丙二酰氯与 2-[3,4-二氢-3-氧代喹喔啉-2(1H)-亚基]乙酸烷基酯或 2-(2-氧代-2H-苯并[b][1,4]恶嗪-3(4H)-亚基)乙酸烷基酯在 CH2Cl2 中于室温下的反应。

  DOI：

  10.1055/s-0029-1217542

文献信息

• Trifluoroacetic acid-promoted Michael addition–cyclization reactions of vinylogous carbamates
  作者：Ram Tilak Naganaboina、Amrita Nayak、Rama Krishna Peddinti

  DOI：10.1039/c4ob00437j

  日期：——

  A simple and efficient methodology has been developed for the synthesis of pyrrolobenzoxazine and 3-arylamino coumarin derivatives promoted by trifluoroacetic acid. The initial step in the current protocol involves a Michael addition of the 1,4-benzoxazinone derivatives to the Michael acceptors and subsequent cyclization.

  已开发出一种简单高效的方法，通过三氟乙酸促进合成吡咯苯并噁嗪和3-芳基氨基香豆素衍生物。当前方案的初始步骤涉及1,4-苯并噁嗪衍生物与Michael受体的Michael加成，然后进行环化反应。
• FeCl₃-Mediated Domino Reaction of Benzoxazinones with Aroylmethylidene Malonates: Synthesis to Functionalized Pyrrolobenzoxazines
  作者：Shweta Bisht、Rama Krishna Peddinti

  DOI：10.1021/acs.joc.7b02207

  日期：2017.12.15

  efficient domino approach for the synthesis of pyrrolobenzoxazine derivatives is described. The FeCl3-promoted domino reaction between aroylmethylidene malonates and benzoxazinones has been successfully established to afford the title compounds in good to excellent yield under mild reaction conditions. The domino protocol provides a concise and straightforward access to highly substituted pyrrolobenzoxazines

  描述了一种用于合成吡咯并苯并恶嗪衍生物的有效多米诺方法。已经成功地建立了芳基亚甲基丙二酸酯和苯并恶嗪酮之间的FeCl 3促进的多米诺反应，以在温和的反应条件下以良好或优异的收率提供标题化合物。多米诺协议提供了简洁，直接的途径，可以高效，出色的官能团耐受性来直接访问高度取代的吡咯并苯并恶嗪。
• Iodine-Catalyzed Regioselective Synthesis of Multisubstiuted Pyrrole Polyheterocycles Free from Rotamers and Keto–Enol Tautomers
  作者：Nitika Sharma、Rama Krishna Peddinti

  DOI：10.1021/acs.joc.7b01538

  日期：2017.9.15

  A highly regioselective iodine-mediated cascade reaction for the synthesis of multifunctional polyheterocyclic systems is developed by employing 3-(2-oxo-2-arylethylidene)oxindoles and 1,4-benzoxazinone as starting materials. The polyheterocycles are skillfully embraced with oxindole, pyrrole, and coumarin scaffolds, which are well-known for their enriched biological activity. The current approach

  以3-（2-氧代-2-芳基亚乙基）氧吲哚和1,4-苯并恶嗪酮为原料，开发了一种高区域选择性碘介导的级联反应，用于合成多功能多杂环系统。多杂环被羟吲哚，吡咯和香豆素支架巧妙地包裹在一起，它们以其丰富的生物活性而闻名。当前的方法在温和的反应条件下起作用。反应得到单一产物，并且没有形成旋转异构体和酮-烯醇异构体产物。该方法对环境无害且在原子上经济，该反应的唯一副产物是水。该方案消除了纯化技术，例如用于分离产物的柱色谱法。通过倾析溶剂或通过重结晶分离产物。
• Kawahara, Norio; Katsuyama, Michiko; Itoh, Tsuneo, Heterocycles, 1980, vol. 14, # 1, p. 15 - 18
  作者：Kawahara, Norio、Katsuyama, Michiko、Itoh, Tsuneo、Ogura, Haruo

  DOI：——

  日期：——
• Synthesis and Biological Assessment of Pyrrolobenzoxazine Scaffold as a Potent Antioxidant
  作者：Tania Kundu、Bharati Bhattacharjee、Subhenjit Hazra、Arnab K. Ghosh、Debasish Bandyopadhyay、Animesh Pramanik

  DOI：10.1021/acs.jmedchem.9b00717

  日期：2019.7.11

  Reduction of mitochondrial oxidative stress-mediated diseases is an important pharmaceutical objective in recent biomedical research. In this context, a series of novel pyrrolobenzoxazines (PyBs) framework with enormous diversity (compounds 5a-w) was synthesized by employing a low-temperature greener pathway, and antioxidant property of the synthesized compounds was successfully demonstrated on preclinical model goat heart mitochondria, in vitro. Copper ascorbate (Cu-As) was utilized as an oxidative stress generator. Out of screened PyBs, the compound possessing -OH and -OMe groups on benzene nucleus along with pyrrolobenzoxazine core moiety (compound 5w) displayed magnificent antioxidant property with a minimum effective dose of 66 mu M during the biochemical assessment. The ameliorative effect of synthesized pyrrolobenzoxazine moiety on levels of biomarkers of oxidative stress, antioxidant enzyme, activities of Krebs cycle and respiratory chain enzymes, mitochondrial morphology, and Ca2+ permeability of mitochondrial membrane was investigated in the presence of Cu-As. Furthermore, the binding mode of Cu-As by compound 5w was explored successfully using isothermal titration calorimetry (ITC) analysis.