3-(4-fluorobenzoyl)-1H-benzo[b]pyrrolo[1,2-d][1,4]oxazine-1,2,4-trione | 1408243-51-5

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 3-(4-fluorobenzoyl)-1H-benzo[b]pyrrolo[1,2-d][1,4]oxazine-1,2,4-trione
• 英文别名: 3-(4-fluorobenzoyl)-1H-pyrrolo[2,1-c][1,4]benzoxazine-1,2,4-trione
• CAS: 1408243-51-5
• 化学式: C₁₈H₈FNO₅
• 分子量: 337.264
• InChiKey: IYSRYAFUAMOFGD-UHFFFAOYSA-N

物化性质

• 沸点：
  480.9±55.0 °C(predicted)
• 密度：
  1.61±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  25.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  80.75
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  3-(4-fluorobenzoyl)-1H-benzo[b]pyrrolo[1,2-d][1,4]oxazine-1,2,4-trione 反应 0.58h， 以91%的产率得到7-(4-fluorobenzoyl)-6,10-dioxo-9-(2-oxo-2H-1,4-benzoxazin-3-yl)-6,10-dihydrobenzo[b]pyrido[1,2-d][1,4]oxazin-8-yl 4-fluorobenzoate
  参考文献：
  名称：

  Five-membered 2,3-dioxo heterocycles: LXXXVIII. Reaction of 3-aroylpyrrolo[1,2-d][1,4]benzoxazine-1,2,4(4H)-triones with N,N′-dicyclohexylcarbodiimide under thermolysis conditions

  摘要：

  Thermolysis of 3-aroylpyrrolo[1,2-d][1,4]benzoxazine-1,2,4(4H)-triones generates aroyl(2-oxo-1,4-benzoxazin-3-yl)ketenes which react as dienes at the aroylketene fragment in [4 + 2]-cycloaddition at the C=N bond of N,N'-dicyclohexylcarbodiimide with formation of 3-[6-aryl-4-oxo-3-cyclohexyl-2-cyclohexylimino-3,4-dihydro-2H-1,3-oxazin-5-yl]-2H-1,4-benzoxazin-2-ones. Thermolysis of the latter is accompanied by elimination of N,N'-dicyclohexylcarbodiimide, and aroyl(2-oxo-1,4-benzoxazin-3-yl)ketenes thus generated undergo cyclodimerization to produce 7-aroyl-6,10-dioxo-9-(2-oxo-2H-1,4-benzoxazin-3-yl)-6,10-dihydrobenzo[b]pyrido[1,2-d][1,4]oxazin-8-yl benzoates.

  DOI：

  10.1134/s1070428012090151
• 作为产物：
  描述：

  4-(4-氟苯基)-2,4-二氧代丁酸甲酯 以 乙醇 、 苯 为溶剂， 反应 0.08h， 生成 3-(4-fluorobenzoyl)-1H-benzo[b]pyrrolo[1,2-d][1,4]oxazine-1,2,4-trione
  参考文献：
  名称：

  1,4-苯并恶嗪-2-酮衍生物的合成、体外对结核分枝杆菌的抗菌活性和基于反向对接的靶向捕捞

  摘要：

  测试了 17 种带有烯胺酮部分的 1,4-苯并恶嗪-2-酮及其三种类似物对结核分枝杆菌(H37Rv)的抗菌活性。BACTEC 在培养 41 天后测定最低杀菌浓度 (MBC)。带有未取代苯并部分的 1,4-Benzoxazin-2-ones 显示出最有希望的活性 (MBC = 5.00 µg/ml)。对于大多数活性化合物，在 41 天内每天测定抗菌活性。最有希望的化合物在孵育第 4 天的浓度为 0.31 µg/ml、第 6 天的浓度为 0.62 µg/ml、第 9 天的浓度为 2.50 µg/ml 和第 41 天的浓度为 5.00 µg/ml 时显示出抑菌效果。所有研究的化合物，连同他们报道的一些类似物，与结核分枝杆菌的35 种蛋白质对接在这些生物体中找到它们的有效目标。作为反向对接的结果，天冬氨酸 1-脱羧酶panD被选为最合适的目标。将最具活性的化合物与来自结核分枝杆菌的吡嗪酰胺抗性菌株

  DOI：

  10.1002/ardp.202000199

文献信息

• Facile regiodivergent synthesis of spiro pyrrole-substituted pseudothiohydantoins and thiohydantoins via reaction of [<i>e</i>]-fused 1<i>H</i>-pyrrole-2,3-diones with thiourea
  作者：Aleksandr I Kobelev、Nikita A Tretyakov、Ekaterina E Stepanova、Maksim V Dmitriev、Michael Rubin、Andrey N Maslivets

  DOI：10.3762/bjoc.15.280

  日期：——

  A highly divergent synthesis of regioisomeric thiohydantoins and pseudothiohydantoins spiro-fused to a pharmacologically valuable pyrrole-2-one fragment involving the reaction of [e]-fused 1H-pyrrole-2,3-diones with thioureas was developed. The obtained spiro pseudothiohydantoin derivatives were found to undergo a pseudothiohydantoin-thiohydantoin rearrangement. The reactions were shown to proceed

  研发了一种高度分散的合成，其是将与[e]-融合的1H-吡咯-2,3-二酮与硫脲反应的药理学上有价值的吡咯-2-酮片段螺合稠合的区域异构硫代乙内酰脲和假硫代乙内酰脲。发现所获得的螺假硫代乙内酰脲衍生物进行了假硫代乙内酰脲-硫代乙内酰脲重排。显示反应在无催化剂条件下以良好的产率进行，并且无需应用制备色谱法就可以分离出产物。
• Facile approach to alkaloid-like 6/6/5/5-tetracyclic spiroheterocycles via 1,3-dipolar cycloaddition reaction of fused 1H-pyrrole-2,3-diones with nitrones
  作者：Ekaterina E. Stepanova、Maksim V. Dmitriev、Andrey N. Maslivets

  DOI：10.1016/j.tetlet.2020.151595

  日期：2020.3

  A facile synthetic approach towards 6/6/5/5-tetracyclic spiroheterocycles has been developed from the highly diastereoselective 1,3-dipolar cycloaddition reaction of [e]-fused 1H-pyrrole-2,3-diones with nitrones. The described novel heterocyclic systems are heteroanalogs of cytotoxic alkaloids, kibalaurifoline and gitingensine. The developed reaction represents the first example of involvement of 1H-pyrrole-2

  从[ e ]稠合的1 H-吡咯-2,3-二酮与硝酮的高度非对映选择性1,3-偶极环加成反应，已经开发出一种简便的合成方法，用于合成6/6/5 / 5-四环螺杂环。所描述的新型杂环系统是细胞毒性生物碱，奇巴拉妥林和gitingensine的杂类似物。发达的反应代表了1 H-吡咯-2，3-二酮在[ e ]侧融合在1，3-偶极环加成反应中的第一个例子。
• Reaction of Pyrrolobenzoxazinetriones with N,N′-Disubstituted Ureas. Synthesis of Substituted Spiro[imidazole-2,2′-pyrroles]
  作者：N. V. Babikova、A. I. Kobelev、A. I. Belozerova、M. V. Dmitriev、A. N. Maslivets

  DOI：10.1134/s107042802109013x

  日期：2021.9

  N,N′-disubstituted ureas to give 1,3-disubstituted 9-aroyl-8-hydroxy-6-(2-hydroxyphenyl)-1,3,6-triazaspiro[4.4]non-8-ene-2,4,7-triones whose structure was confirmed by X-ray analysis. The resulting spiro heterocyclic systems contain a hydantoin fragment and are therefore interesting from the viewpoint of pharmaceutical chemistry.

  摘要 3-Aroylpyrrolo[2,1- c ][1,4] benzoxazine -1,2,4-triones 与对称的N , N '-二取代脲反应得到 1,3-二取代 9-aroyl-8-hydroxy-6 -(2-hydroxyphenyl)-1,3,6-triazaspiro[4.4]non-8-ene-2,4,7-triones，其结构经 X 射线分析证实。所得螺杂环系统包含乙内酰脲片段，因此从药物化学的角度来看是有趣的。
• Synthesis of Spiro[pyrrole-2,5′-pyrrolo[2,3-d]pyrimidines] by Reaction of Pyrrolobenzoxazinetriones with 6-Amino-1,3-dimethyluracil
  作者：A. I. Kobelev、M. V. Dmitriev、A. N. Maslivets

  DOI：10.1134/s1070428024040109

  日期：2024.4

  to give 3-aroyl-4-hydroxy-1-(2-hydroxyaryl)-1′,3′-dimethylspiro[pyrrole-2,5′-pyrrolo­[2,3-d]pyrimidine]-2′,4′,5,6′(1H,1′H,3′H,7′H)-tetraones. The product structure was confirmed by X-ray analysis. The described reaction provides a simple route to the difficultly accessible spiro[pyrrole-2,5′-pyrrolo[2,3-d]­pyrimidine] heterocyclic system.

  抽象的 3-芳酰基吡咯并[2,1-c][1,4]苯并恶嗪-1,2,4-三酮与6-氨基-1,3-二甲基嘧啶-2,4(1H,3H)-二酮反应得到3-芳酰基-4-羟基-1-(2-羟基芳基)-1',3'-二甲基螺[吡咯-2,5'-吡咯并[2,3-d]嘧啶]-2',4',5,6' (1H,1'H,3'H,7'H)-四酮。通过X射线分析确认了产物结构。所述反应为难以获得的螺[吡咯-2,5'-吡咯并[2,3-d]嘧啶]杂环​​体系提供了一条简单的途径。
• Five-membered 2,3-dioxo heterocycles: XCI. Reaction of 3-aroyl-1H-pyrrolo[2,1-c][1,4]benzoxazine-1,2,4-triones with dimedone. Crystalline and molecular structure of 3′-benzoyl-4′-hydroxy-1′-(2-hydroxyphenyl)-6,6-dimethyl-6,7-dihydrospiro[1-benzofuran-3,2′-pyrrole]-2,4,5′(1′H,5H)-trione
  作者：N. M. Tutynina、N. L. Racheva、V. A. Maslivets、Z. G. Aliev、A. N. Maslivets

  DOI：10.1134/s1070428013010168

  日期：2013.1

  3-Aroyl-1H-pyrrolo[2,1-c][1,4]benzoxazine-1,2,4-triones reacted with 5,5-dimethylcyclohexane-1,3-dione to give 3'-aroyl-4'-hydroxy-1'-(2-hydroxyphenyl)-6,6-dimethyl-6,7-dihydrospiro[1-benzofuran-3,2'-pyrrole]-2,4,5'(1'H,5H)-triones. The crystalline and molecular structures of 3'-benzoyl-4'-hydroxy-1'-(2-hydroxyphenyl)-6,6-dimethyl-6,7-dihydrospiro[1-benzofuran-3,2'-pyrrole]-2,4,5'(1'H,5H)-trione were determined by X-ray analysis. DOI: 10.1134/S1070428013010168