1,4-Benzoxazinon-(2)-essigsaeure-(3)-ethylester | 22735-57-5

• 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: 1,4-Benzoxazinon-(2)-essigsaeure-(3)-ethylester
• 英文别名: 1,4-Benzoxazinon-(2)-yliden-(3)-essigsaeureethylester；2-Oxo-3-ethoxycarbonylmethylen-3,4-dihydro-2H-1,4-benzoxazin；(2-oxo-4H-benzo[1,4]oxazin-3-ylidene)-acetic acid ethyl ester；ethyl 2-(2-oxo-4H-1,4-benzoxazin-3-ylidene)acetate
• CAS: 22735-57-5
• 化学式: C₁₂H₁₁NO₄
• mdl: MFCD02130944
• 分子量: 233.224
• InChiKey: JXNWQTNYOLHESU-UHFFFAOYSA-N

物化性质

• 沸点：
  379.2±42.0 °C(predicted)
• 密度：
  1.343±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  17
• 可旋转键数：
  3
• 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：

  1,4-Benzoxazinon-(2)-essigsaeure-(3)-ethylester 在 platinum(IV) oxide 氢气 、 硝酸 、 sodium nitrite 作用下， 以 四氢呋喃 、 溶剂黄146 为溶剂， 生成 amino-(2-oxo-4H-benzo[1,4]oxazin-3-ylidene)-acetic acid ethyl ester
  参考文献：
  名称：

  Biekert,E.; Koessel,H., Justus Liebigs Annalen der Chemie, 1963, vol. 662, p. 93 - 104

  摘要：

  DOI：
• 作为产物：
  描述：

  2-氨基苯酚 、 丁炔二酸二乙酯 以 乙腈 为溶剂， 反应 0.5h， 生成 1,4-Benzoxazinon-(2)-essigsaeure-(3)-ethylester
  参考文献：
  名称：

  合成吡咯并[2,1-c] [1,4]苯并恶嗪和吡咯并[1,2-a]喹喔啉的新方法。

  摘要：

  有效合成烷基4,5-二氢-4-氧代-2-苯基吡咯并[2,1-c] [1,4]苯并恶嗪-3-羧酸酯和烷基4,5-二氢-4-氧代-2-苯基吡咯并描述了[1,2-a]喹喔啉-3-羧酸盐。这涉及使用对甲苯磺酸作为催化剂的邻氨基苯酚或邻苯二胺，炔属酯和β-硝基苯乙烯衍生物之间的三组分反应。

  DOI：

  10.2174/1386207316666131227150430

文献信息

• Novel Approach for the Synthesis of Pyrrolo[2,1-c][1,4]Benzoxazines and Pyrrolo[1,2-a]Quinoxalines
  作者：Tayebeh Sanaeishoar、Somayeh Adibi-Sedeh、Saghar Karimian

  DOI：10.2174/1386207316666131227150430

  日期：2014.1.31

  An efficient synthesis of alkyl 4,5-dihydro-4-oxo-2-phenylpyrrolo[2,1-c][1,4]benzoxazine-3-carboxylates and alkyl 4,5-dihydro-4-oxo-2-phenylpyrrolo[1,2-a]quinoxaline-3-carboxylates is described. This involves a three-component reaction between o-aminophenols or o-phenylenediamine, acetylenic esters and β-nitrostyrene derivatives using p-toluene sulfonic acid as a catalyst.

  有效合成烷基4,5-二氢-4-氧代-2-苯基吡咯并[2,1-c] [1,4]苯并恶嗪-3-羧酸酯和烷基4,5-二氢-4-氧代-2-苯基吡咯并描述了[1,2-a]喹喔啉-3-羧酸盐。这涉及使用对甲苯磺酸作为催化剂的邻氨基苯酚或邻苯二胺，炔属酯和β-硝基苯乙烯衍生物之间的三组分反应。
• 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。
• Zn(OTf)2-Catalyzed 1,6-Conjugate Addition of Benzoxazinones to p-Quinone Methides: Access to 3,3-Diaryl-2-(2-oxo-2H-1,4-benzoxazin-3-yl)propanoic Acid Esters
  作者：Rama Krishna Peddinti、Neha Dua、Sonali Ghosh

  DOI：10.1055/s-0040-1706600

  日期：2021.3

  An effective method for the synthesis of 3,3-diaryl-2-(2-oxo-2H-1,4-benzoxazin-3-yl)propanoic acid esters is reported. A novel zinc triflate-catalyzed regioselective 1,6-conjugate addition of vinylogous carbamates to p-quinone methides for accessing the title compounds has been developed. This protocol furnished the hybrid compounds in good to excellent yields. The reaction is rapid and has a broad

  报道了一种合成3,3-二芳基-2-（2-氧代-2 H -1,4-苯并恶嗪-3-基）丙酸酯的有效方法。已经开发了一种新的三氟甲磺酸锌催化的乙烯基氨基甲酸酯向对苯醌甲基化物的区域选择性的1,6-共轭加成，以得到标题化合物。该方案为杂种化合物提供了良好的优良收率。该反应是快速的并且具有广泛的底物范围。
• Biekert,E.; Koessel,H., Justus Liebigs Annalen der Chemie, 1963, vol. 662, p. 93 - 104
  作者：Biekert,E.、Koessel,H.

  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.