4,5-dibenzoyl-1-(4-methoxyphenyl)-1H-pyrrole-2,3-dione | 1198083-53-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯啉
• 英文名称: 4,5-dibenzoyl-1-(4-methoxyphenyl)-1H-pyrrole-2,3-dione
• 英文别名: 4,5-dibenzoyl-1-(4-methoxyphenyl)pyrrole-2,3-dione
• CAS: 1198083-53-2
• 化学式: C₂₅H₁₇NO₅
• 分子量: 411.414
• InChiKey: RWBHJUMUIIPYMJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  80.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4,5-dibenzoyl-1-(4-methoxyphenyl)-1H-pyrrole-2,3-dione 以 diphenyl ether-biphenyl eutectic 为溶剂， 反应 0.25h， 以89%的产率得到2,3-dibenzoyl-6-methoxyquinolin-4(1H)-one
  参考文献：
  名称：

  Five-membered 2,3-dioxoheterocycles: LXXXIII. Synthesis and thermolysis of 1-aryl-4,5-diaroyl-1H-pyrrole-2,3-diones

  摘要：

  The reaction of (Z)-2-amino-1,4-diarylbut-2-en-1,4-diones with oxalyl chloride led to the formation of 1-aryl-4,5-diaroyl-1H-pyrrole-2,3-diones that at the thermal decarbonylation gave aroyl(N-arylimidoyl)ketenes which underwent stabilization by molecular cyclization into 2,3-diaroylquinolin-4(1H)-ones.

  DOI：

  10.1134/s1070428012020145
• 作为产物：
  描述：

  草酰氯 、 (Z)-2-(4-methoxyphenylamino)-1,4-diphenylbut-2-ene-1,4-dione 以 苯 为溶剂， 反应 1.33h， 以67%的产率得到4,5-dibenzoyl-1-(4-methoxyphenyl)-1H-pyrrole-2,3-dione
  参考文献：
  名称：

  Five-membered 2,3-dioxoheterocycles: LXXXIII. Synthesis and thermolysis of 1-aryl-4,5-diaroyl-1H-pyrrole-2,3-diones

  摘要：

  The reaction of (Z)-2-amino-1,4-diarylbut-2-en-1,4-diones with oxalyl chloride led to the formation of 1-aryl-4,5-diaroyl-1H-pyrrole-2,3-diones that at the thermal decarbonylation gave aroyl(N-arylimidoyl)ketenes which underwent stabilization by molecular cyclization into 2,3-diaroylquinolin-4(1H)-ones.

  DOI：

  10.1134/s1070428012020145

文献信息

• [3+3]-Cyclocondensation of 4,5-Dibenzoyl-1H-pyrrole-2,3-diones with 5-Aminofuran. Synthesis of Furo[2,3-b]pyridines
  作者：D. I. Antonov、M. V. Dmitriev、A. N. Maslivets

  DOI：10.1134/s1070428021080182

  日期：2021.8

  4-benzoyl-5-(aminooxalyl)-6-phenylfuro[2,3-b]pyridine-2-carboxylates. 4,5-Diacyl-1H-pyrrole-2,3-diones react with N-unsubstituted five-membered cyclic enamines by a scheme different that characteristic of reactions with N-unsubstituted six-membered cyclic enamines. The studied reaction is a convenient preparative method for the synthesis of the furo[2,3-b]pyridines.

  摘要 4,5-二苯甲酰基-1 H-吡咯-2,3-二酮与 5-氨基呋喃-2-羧酸甲酯反应生成 4-苯甲酰基-5-(氨基草酰基)-6-苯基呋喃[2,3- b ]吡啶甲酯-2-羧酸盐。4,5-Diacyl-1 H -pyrrole- 2,3- diones与N-未取代的五元环烯胺反应的反应路线不同于与N-未取代的六元环烯胺反应的特征。所研究的反应是合成呋喃[2,3- b ]吡啶的一种方便的制备方法。
• Formal [3+3] Cyclocondensation of 4-Acyl-1H-pyrrole-2,3-diones with Five-Membered Cyclic Enamines To Form Substituted 1H-Py­razolo[3,4-b]pyridines and Isoxazolo[5,4-b]pyridines
  作者：Аndrey Maslivets、Alexey Dubovtsev、Maksim Dmitriev、Pavel Silaichev、Dmitriy Antonov

  DOI：10.1055/s-0036-1588407

  日期：——

  substituted 1H-pyrazolo[3,4-b]pyridines and isoxazolo[5,4-b]pyridines was developed through the formal [3+3] cascade cyclocondensation of 4-acyl-1H-pyrrole-2,3-diones as 1,3-bis-electrophiles with the five-membered cyclic enamines as 1,3-bis-nucleophiles. A highly efficient method for the preparation of multifunctional substituted 1H-pyrazolo[3,4-b]pyridines and isoxazolo[5,4-b]pyridines was developed through

  摘要 通过4-酰基-1的正式[3 + 3]级联环缩合反应，开发了一种高效的制备多功能取代的1 H-吡唑并[3,4- b ]吡啶和异恶唑并[5,4- b ]吡啶的方法。H-吡咯-2,3-二酮为1,3-双亲电子试剂，五元环烯胺为1,3-双亲核试剂。 通过4-酰基-1的正式[3 + 3]级联环缩合反应，开发了一种高效的制备多功能取代的1 H-吡唑并[3,4- b ]吡啶和异恶唑并[5,4- b ]吡啶的方法。H-吡咯-2,3-二酮为1,3-双亲电子试剂，五元环烯胺为1,3-双亲核试剂。
• Regio- and Diastereoselective [4+2]-Cycloaddition of 4,5-Diaroyl-1H-pyrrole-2,3-diones and Cyclopentadiene
  作者：A. A. Moroz、D. I. Antonov、M. V. Dmitriev、A. N. Maslivets

  DOI：10.1134/s1070428022030046

  日期：2022.3

  Abstract Thermally initiated [4+2]-cycloaddition of 4,5-diaroyl-1H-pyrrole-2,3-dione and cyclopentadiene as a dienophile afforded substituted 5a,8,8a,8b-tetrahydro-1H-cyclopenta[5,6]pyrano[4,3-b]pyrrole-2,3-diones whose structure was determined by X-ray analysis of one of the products. The reaction was regio- and diastereoselective, and only one endo-hetero-Diels–Alder adduct was formed. The described

  摘要 4,5-diaroyl-1 H -pyrrole -2,3-dione 和环戊二烯作为亲二烯体的热引发 [4+2]-环加成反应得到取代的 5a,8,8a,8b-tetrahydro-1 H -cyclopenta [5, 6]pyrano[4,3- b ]pyrrole-2,3-diones，其结构由其中一种产物的 X 射线分析确定。该反应具有区域选择性和非对映选择性，并且仅形成了一种内-杂-Diels-Alder 加合物。所描述的反应为难以获得的取代的环戊二烯[5,6]吡喃并[4,3- b ]吡咯衍生物提供了方便的制备途径。
• Five-membered 2,3-dioxo heterocycles: CIII. Spiro heterocyclization of 4,5-diaroyl-1H-pyrrole-2,3-diones with 3-aminobut-2-enenitrile
  作者：P. S. Silaichev、Yu. G. Stepanyan、N. V. Kudrevatykh、A. N. Maslivets

  DOI：10.1134/s1070428014060153

  日期：2014.6

  1-Aryl-4,5-diaroyl-1H-pyrrole-2,3-diones reacted with 3-aminobut-2-enenitrile to produce 1,6-diaryl-4-aroyl-3-hydroxy-8-methyl-2-oxo-1,7-diazaspiro[4.4]nona-3,6,8-triene-9-carbonitriles.
• Five-membered 2,3-dioxoheterocycles: XCIV. Recyclization of 4,5-diaroyl-1H-pyrrole-2,3-diones under the action of 3-aminopyrazolo[3,4-b]pyridine. Crystal and molecular structure of substituted pyrido[2′,3′:3,4]pyrazolo[1,5-a]pyrimidine
  作者：P. S. Silaichev、P. A. Slepukhin、A. N. Maslivets

  DOI：10.1134/s1070428013080186

  日期：2013.8

  1-Aryl-4,5-diaroyl-1H-pyrrole-2,3-diones react with 3-amino-4,6-dimethyl-2H-pyrazolo[3,4-b]-pyridine affording N-aryl-2,3-diaroyl-8,10-dimethylpyrido [2',3':3,4]pyrazolo[1,5-a]pyrimidine-4-carboxamides.