4,5-di(4-toluoyl)-1-(4-tolyl)-1H-pyrrole-2,3-dione | 1210884-32-4

• 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-di(4-toluoyl)-1-(4-tolyl)-1H-pyrrole-2,3-dione
• 英文别名: 4,5-bis(4-methylbenzoyl)-1-(4-methylphenyl)pyrrole-2,3-dione
• CAS: 1210884-32-4
• 化学式: C₂₇H₂₁NO₄
• 分子量: 423.468
• InChiKey: KKTHXEIVLBNQGU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  32
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  71.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-amino-4,6-dimethylpyrazolo[3,4-b]pyridine 、 4,5-di(4-toluoyl)-1-(4-tolyl)-1H-pyrrole-2,3-dione 以 甲苯 为溶剂， 以83%的产率得到8,10-dimethyl-N-(4-tolyl)-2,3-di(4-toluoyl)-pyrido[2',3':3,4]pyrazolo[1,5-a]pyrimidine-4-carboxamide
  参考文献：
  名称：

  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

  摘要：

  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.

  DOI：

  10.1134/s1070428013080186
• 作为产物：
  描述：

  乙烷,三氯氟- 以 苯 为溶剂， 反应 1.41h， 生成 4,5-di(4-toluoyl)-1-(4-tolyl)-1H-pyrrole-2,3-dione
  参考文献：
  名称：

  Five-membered 2,3-dioxoheterocycles: LXXXIV. [4+2]-Cycloaddition of styrene to 4,5-diaroyl-1H-pyrrole-2,3-diones. Crystal and molecular structures of 7a-(2,5-dimethylbenzoyl)-4-(2,5-dimethylphenyl)-1-(4-methoxyphenyl)-6-phenyl-7,7a-dihydropyrano[4,3-b]-pyrrole-2,3(1H,6H)-dione

  摘要：

  1-Aryl-4,5-diaroyl-1H-pyrrole-2,3-diones react with styrene to form substituted 7,7a-dihydropyrano[4,3-b] pyrrole-2,3(1H,6H)-diones whose structure was confirmed by XRD analysis. The crystal and molecular structure of 7a-(2,5-dimethylbenzoyl)-4-(2,5-dimethyl-phenyl)-1-(4-methoxyphenyl)-6-phenyl-7,7a-dihydropyrano[4,3-b] pyrrole-2,3(1H,6H)dione was examined.

  DOI：

  10.1134/s1070428012020157

文献信息

• 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。
• Reaction of 4,5-Diaroyl-1H-pyrrole-2,3-diones with Thiosemicarbazide. Synthesis of 1H-Pyrazole-5-carboxamides
  作者：D. I. Antonov、M. V. Dmitriev、O. A. Kourova、A. N. Maslivets

  DOI：10.1134/s1070428021120241

  日期：2021.12

  Abstract The reactions of 4,5-diaroyl-1H-pyrrole-2,3-diones with thiosemicarbazide and semicarbazide in­volved elimination of carbothioamide or carboxamide group and afforded substituted 3,4-diaroyl-1H-pyrazole-5-carboxamides. This reaction provides a convenient preparative route to 1H-pyrazole-5-carboxamides that attract interest for medicinal chemistry.

  摘要 4,5-diaroyl-1 H -pyrrole- 2,3-diones 与氨基硫脲和氨基脲的反应涉及消除硫代氨基甲酸酯或羧酰胺基团，并得到取代的 3,4-diaroyl-1 H -pyrazole -5-carboxamides。该反应提供了一种方便的制备 1 H-吡唑-5-甲酰胺的途径，吸引了药物化学的兴趣。
• 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: LXXXVII. [4+2]-cycloaddition of alkyl vinyl ethers and 3,4-dihydro-2H-pyran to 4,5-diaroyl-1 H-pyrrole-2,3-diones
  作者：P. S. Silaichev、N. V. Kudrevatykh、A. N. Maslivets

  DOI：10.1134/s1070428012080118

  日期：2012.8

  1-Aryl-4,5-diaroyl-1H-pyrrole-2,3-diones react with alkyl vinyl ethers and 3,4-dihydro-2H-pyran affording 1,4-diaryl-7a-aroyl-6-ethoxy-7,7a-dihydropyrano[4,3-b]pyrrole-2,3(1H,6H)-diones and 1,4-diaryl-9baroyl-1,7,8,9,9a-hexahydro-5aH-pyrano[3',2':5,6]pyrano[4,3-b]-pyrrole-2,3-diones respectively.