3-(4-ethoxybenzoyl)pyrrolo[1,2-a]quinoxaline-1,2,4(5H)-trione | 1289383-43-2

• 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-ethoxybenzoyl)pyrrolo[1,2-a]quinoxaline-1,2,4(5H)-trione
• 英文别名: 3-(4-ethoxybenzoyl)-5H-pyrrolo[1,2-a]quinoxaline-1,2,4-trione
• CAS: 1289383-43-2
• 化学式: C₂₀H₁₄N₂O₅
• 分子量: 362.342
• InChiKey: XOZDRGUBPULJIP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  92.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-(4-ethoxybenzoyl)pyrrolo[1,2-a]quinoxaline-1,2,4(5H)-trione 以 diphenyl ether-biphenyl eutectic 为溶剂， 以95%的产率得到3-(4-ethoxybenzoyl)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：

  邻苯二胺 以 1,4-二氧六环 、 氯仿 为溶剂， 生成 3-(4-ethoxybenzoyl)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

• Alkaloid-like annulated pyrano[4,3-b]pyrroles: antiviral activity and hydrolysis
  作者：Ekaterina E. Khramtsova、Maksim V. Dmitriev、Nikolay I. Bormotov、Olga А. Serova、Larisa N. Shishkina、Andrey N. Maslivets

  DOI：10.1007/s10593-021-02928-0

  日期：2021.4

  Alkaloid-like angular 6/6/5/6-annulated pyrano[4,3-b]pyrroles (pretazettine analogs) contain chemically labile groups that can react with water at room temperature. Their antiviral activity against Vaccinia virus and their tendency to hydrolysis were investigated. Compounds that were more resistant to hydrolysis exhibited the greatest antiviral activity.

  类生物碱的角6/6/5/6型环吡喃并[4,3- b ]吡咯（Pretazettine类似物）包含化学不稳定的基团，可在室温下与水反应。研究了它们对牛痘病毒的抗病毒活性及其水解趋势。更耐水解的化合物表现出最大的抗病毒活性。
• Synthesis of Pyrano[4′,3′:2,3]pyrrolo[1,2-a]quinoxalines by Reaction of Aroylpyrroloquinoxalines with Alkyl Vinyl Ethers
  作者：S. O. Kasatkina、M. S. Titov、E. E. Stepanova、M. V. Dmitriev、A. N. Maslivets

  DOI：10.1134/s1070428018040188

  日期：2018.4

  Thermally induced [4 + 2]-cycloaddition of 3-aroylpyrrolo[1,2-a]quinoxaline-1,2,4(5H)-triones with alkyl vinyl ethers afforded mixtures of diastereoisomeric (5S*,6aR*)- and (5R*,6aR*)-5-alkoxy-3-aryl-5,6-dihydropyrano[ 4′,3′: 2,3]pyrrolo[1,2-a]quinoxaline-1,2,7(8H)-triones.

  3-芳基吡咯并[1,2- a ]喹喔啉-1,2,4（5 H）-三酮与烷基乙烯基醚的热诱导[4 + 2]-环加成反应得到非对映异构体（5 S *，6a R *）的混合物-和（5 R *，6a R *）-5-烷氧基-3-芳基-5,6-二氢吡喃并[4'，3'：2,3]吡咯并[1,2- a ]喹喔啉-1,2， 7（8 H）-三酮。
• 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).
• Hetero-Diels–Alder Reaction of Aroylpyrrolo[1,2-a]quinoxalinetriones with Styrene
  作者：S. O. Kasatkina、E. E. Stepanova、M. V. Dmitriev、A. N. Maslivets

  DOI：10.1134/s1070428018100135

  日期：2018.10

  Hetero-Diels-Alder reaction of 3-aroylpyrrolo[1,2-a]quinoxaline-1,2,4(5H)-triones with styrene afforded diastereoisomeric (5R*,6aR*)- and (5S*,6aR*)-3,5-diaryl-5,6-dihydropyrano[4,3:2,3]pyrrolo[1,2-a]-quinoxaline-1,2,7(8H)-triones.