3-(4-bromobenzoyl)pyrrolo[1,2-a]quinoxaline-1,2,4(5H)-trione | 403608-97-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 3-(4-bromobenzoyl)pyrrolo[1,2-a]quinoxaline-1,2,4(5H)-trione
• 英文别名: 3-(4-bromobenzoyl)-5H-pyrrolo[1,2-a]quinoxaline-1,2,4-trione
• CAS: 403608-97-9
• 化学式: C₁₈H₉BrN₂O₄
• 分子量: 397.184
• InChiKey: YDPKBBZQUIBTPX-UHFFFAOYSA-N

物化性质

• 熔点：
  255-257 °C
• 密度：
  1.82±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  83.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(4-bromobenzoyl)pyrrolo[1,2-a]quinoxaline-1,2,4(5H)-trione 以 diphenyl ether-biphenyl eutectic 为溶剂， 以90%的产率得到3-(4-bromobenzoyl)furo[3,2-b]quinoxalin-2(4H)-one
  参考文献：
  名称：

  Five-membered 2,3-dioxoheterocycles: LXXIII. Synthesis and thermolysis of 3-acylpyrrolo[1,2-a]quinoxaline-1,2,4(5H)-triones

  摘要：

  Reactions of (Z)-3-(phenacylidene-2-oxo)-3,4-dihydroquinoxalin-2(1H)-ones and (Z)-3-(3,3-dimethyl-2-oxobutylidene)-3,4-dihydroquinoxalin-2(1H)-one with oxalyl chloride led to the formation of 3-acyl-1H-pyrrolo[1,2-a]quinoxaline-1,2,4(5H)-triones that at the thermal decarbonylation generated acyl(3-oxoquinoxalin-2-yl)ketenes which underwent the intramolecular stabilization giving 3-acylfuro[3,2-b]quinoxalin-2(4H)-ones.

  DOI：

  10.1134/s1070428011020151
• 作为产物：
  描述：

  4-(4-溴苯基)-2,4-二氧代丁酸甲酯 以 1,4-二氧六环 、 氯仿 为溶剂， 生成 3-(4-bromobenzoyl)pyrrolo[1,2-a]quinoxaline-1,2,4(5H)-trione
  参考文献：
  名称：

  Five-membered 2,3-dioxoheterocycles: LXXIII. Synthesis and thermolysis of 3-acylpyrrolo[1,2-a]quinoxaline-1,2,4(5H)-triones

  摘要：

  Reactions of (Z)-3-(phenacylidene-2-oxo)-3,4-dihydroquinoxalin-2(1H)-ones and (Z)-3-(3,3-dimethyl-2-oxobutylidene)-3,4-dihydroquinoxalin-2(1H)-one with oxalyl chloride led to the formation of 3-acyl-1H-pyrrolo[1,2-a]quinoxaline-1,2,4(5H)-triones that at the thermal decarbonylation generated acyl(3-oxoquinoxalin-2-yl)ketenes which underwent the intramolecular stabilization giving 3-acylfuro[3,2-b]quinoxalin-2(4H)-ones.

  DOI：

  10.1134/s1070428011020151

文献信息

• ——
  作者：I. V. Mashevskaya、R. R. Makhmudov、G. A. Aleksandrova、O. V. Golovnina、A. V. Duvalov、A. N. Maslivets

  DOI：10.1023/a:1010475811489

  日期：——
• ——
  作者：I. V. Mashevskaya、R. R. Makhmudov、G. A. Aleksandrova、O. S. Kudinova、S. V. Kol'tsova、A. F. Goleneva、A. N. Maslivets

  DOI：10.1023/a:1010443516455

  日期：——
• Reaction of 3-aroylpyrrolo[1,2-a]quinoxaline-1,2,4(5H)-triones with quinaldine and substituted quinoxalines
  作者：V. V. Konovalova、Yu. V. Shklyaev、A. N. Maslivets

  DOI：10.1134/s1070428015050176

  日期：2015.5

  3-Aroylpyrrolo[1,2-a]quinoxaline-1,2,4(5H)-triones react with quinaldine and substituted 2-methylquinoxalines affording 3-aroyl-2-hydroxy-3a-(quinolin-2-ylmethyl)pyrrolo[1,2-a]quinoxaline-1,4-(3aH,5H)-diones and 3-aroyl-2-hydroxy-3a-(quinoxalin-2-ylmethyl)pyrrolo[1,2-a]quinoxaline-1,4-(3aH,5H)-diones respectively.
• Reactions of 3-Aroylpyrrolo[1,2-a]quinoxaline-1,2,4(5H)-triones with 2,3-Dihydrofuran and 3,4-Dihydro-2H-pyran
  作者：S. O. Kasatkina、E. E. Stepanova、M. V. Dmitriev、A. N. Maslivets

  DOI：10.1134/s107042801807014x

  日期：2018.7

  3-Aroylpyrrolo[1,2-a]quinoxaline-1,2,4(5H)-triones reacted with 2,3-dihydrofuran and 3,4-dihydro-2H-pyran to give mixtures of the corresponding hetero-Diels-Alder (furo- and pyrano[3,2: 5,6]pyrano- [4,3: 2,3]pyrrolo[1,2-a]quinoxalines) and Michael adducts (furyl- and pyranylpyrrolo[1,2-a]quinoxalines).
• Five-membered 2,3-dioxoheterocycles: XCVI. Reactions of 3-aroylpyrrolo[1,2-a]quinoxaline-1,2,4(5h)-triones with substituted 1,3,3-trimethyl-2-azaspiro[4.5]dec-1-enes
  作者：V. V. Konovalova、K. A. Galata、Yu. V. Shklyaev、A. N. Maslivets

  DOI：10.1134/s1070428013110171

  日期：2013.11

  3-Aroylpyrrolo[1,2-a]quinoxaline-1,2,4(5H)-triones react with 1,3,3,7,9-pentamethyl-2-azaspiro-[4.5] deca-1,6,9-trien-8-one and 2',5',5'-trimethyl-4',5'-dihydro-4H-spiro[naphthalene-1,3'-pyrrol]-4-one providing 3-aroyl-2-hydroxy-3a-(3,3,7,9-tetramethyl-8-oxo-2-azaspiro[4.5]deca-1,6,9-trien-1-yl)methyl}pyrrolo[1,2-a-quinoxaline-1,4(3a H,5H)-diones and 3-aroyl-2-hydroxy-3a-(5',5'-dimethyl-4-oxo-4',5'-dihydro-4H-spiro[naphthalene-1,3'-pyrrol]-2'-yl)methyl}pyrrolo[1,2-a]-quinoxaline-1,4(3aH,5H)-diones.