4,5-dimethoxycarbonyl-1-(4'-methylphenyl)-1H-pyrrole-2,3-dione | 251986-56-8

• 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-dimethoxycarbonyl-1-(4'-methylphenyl)-1H-pyrrole-2,3-dione
• 英文别名: 1-(4-methylphenyl)-4,5-bis(methoxycarbonyl)-1H-pyrrole-2,3-dione；dimethyl 1-(4-methylphenyl)-4,5-dioxo-4,5-dihydro-1H-pyrrole-2,3-dicarboxylate；dimethyl 1-(4-methylphenyl)-4,5-dioxopyrrole-2,3-dicarboxylate
• CAS: 251986-56-8
• 化学式: C₁₅H₁₃NO₆
• 分子量: 303.271
• InChiKey: XYUQDWBECYNMBH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  90
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4,5-dimethoxycarbonyl-1-(4'-methylphenyl)-1H-pyrrole-2,3-dione 以 二苯醚 为溶剂， 反应 0.5h， 以90%的产率得到dimethyl 6-methyl-4-oxo-1,4-dihydroquinoline-2,3-dicarboxylate
  参考文献：
  名称：

  A Synthesis of 4-Quinolone-3-carboxylic Acids via Pyrolysis of N-Aryldioxopyrrolines

  摘要：

  A synthesis of 4-quinolone-3-carboxylic acids (8) was achieved by pyrolysis of 4,5-dimethoxycarbonyl-1-aryl-1H-pyrrole-2,3-diones (3) followed by selective demethoxycarbonylation of the resulting 2,3-dimethoxycarbonyl-4-quinolones (4) in excellent overall yields.

  DOI：

  10.3987/com-99-8629
• 作为产物：
  描述：

  乙烷,三氯氟- 、 alkaline earth salt of/the/ methylsulfuric acid 以 四氢呋喃 、 甲醇 、 乙醚 为溶剂， 生成 4,5-dimethoxycarbonyl-1-(4'-methylphenyl)-1H-pyrrole-2,3-dione
  参考文献：
  名称：

  A Synthesis of 4-Quinolone-3-carboxylic Acids via Pyrolysis of N-Aryldioxopyrrolines

  摘要：

  A synthesis of 4-quinolone-3-carboxylic acids (8) was achieved by pyrolysis of 4,5-dimethoxycarbonyl-1-aryl-1H-pyrrole-2,3-diones (3) followed by selective demethoxycarbonylation of the resulting 2,3-dimethoxycarbonyl-4-quinolones (4) in excellent overall yields.

  DOI：

  10.3987/com-99-8629

文献信息

• Spiro-condensation of 5-methoxycarbonyl-1H-pyrrole-2,3-diones with cyclic enoles to form spiro substituted furo[3,2-c]-coumarins and quinolines
  作者：Alexey Yu. Dubovtsev、Pavel S. Silaichev、Mikhail A. Nazarov、Maksim V. Dmitriev、Andrey N. Maslivets、Michael Rubin

  DOI：10.1039/c6ra16889b

  日期：——

  Highly efficient spiro-cyclization enabling cyclic enoles to act as 1,3-bis-nucleophiles in reaction with pyrrole-2,3-diones acting as 1,2-bis-electrophiles was developed.

  高效的螺环闭合反应使得环状烯醇能够作为1,3-双亲核试剂与作为1,2-双电亲试剂的吡咯-2,3-二酮发生反应。
• Cycloaddition of Huisgen 1,4-dipoles: synthesis and rapid epimerization of functionalized spiropyrido[2,1-<i>b</i>][1,3]oxazine-pyrroles and related products
  作者：Andrew R. Galeev、Anna A. Moroz、Maksim V. Dmitriev、Andrey N. Maslivets

  DOI：10.1039/d1ra08384h

  日期：——

  cycloaddition has emerged as a powerful tool for the synthesis of various cyclic compounds. In the present work, 1H-pyrrole-2,3-diones are proposed as new dipolarophiles for 1,4-dipolar cycloaddition. Their [4 + 2] cycloaddition with dipoles generated from dimethyl acetylenedicarboxylate and pyridine was found to proceed regioselectively affording spiro[pyrido[2,1-b][1,3]oxazine-2,3'-pyrroles] as diastereomeric

  1,4-偶极环加成已成为合成各种环状化合物的有力工具。在目前的工作中，1H-吡咯-2,3-二酮被提议作为1,4-偶极环加成反应的新亲偶极试剂。发现它们与乙炔二甲酸二甲酯和吡啶产生的偶极子发生[4 + 2]环加成，区域选择性地进行，得到螺[吡啶并[2,1-b][1,3]恶嗪-2,3'-吡咯]作为非对映异构体混合物，其存在在溶液中快速平衡。经证实，这种快速差向异构化现象是其他类似螺吡啶并[2,1-b][1,3]恶嗪甚至相关螺喹嗪的特征，这一点通过对先前报道的相关产品的研究得到证实，并在这项工作，1,4-偶极环加成反应。
• Diastereoselective 1,3-Dipolar Cycloaddition of Nitrones to 1H-Pyrrole-2,3-diones. Synthesis of pyrrolo[3,2-d]isoxazoles
  作者：A. A. Moroz、V. E. Zhulanov、M. V. Dmitriev、D. N. Babentsev、A. N. Maslivets

  DOI：10.1134/s1070428018050184

  日期：2018.5

  1H-pyrrol-2,3-diones react with nitrones affording substituted pyrrolо[3,2-d]isoxazoles. The structures of ethyl (3R*,3aR*,6aR*)-6-benzyl-3-(4-bromophenyl)-4,5-dioxo-2,6a-diphenylhexahydro-3aHpyrrolo[ 3,2-d]isoxazole-3a-carboxylate and dimethyl (3R*,3aR*,6aS*)-3-(4-bromophenyl)-4,5-dioxo-2,6-diphenyltetrahydro-3aH-pyrrolo[3,2-d]isoxazole-3a,6a(4H)-dicarboxylate were proved by single-crystal X-ray analysis

  1 H-吡咯-2,3-二酮与硝基反应，得到取代的吡咯[3,2- d ]异恶唑。乙基（3 R *，3a R *，6a R *）-6-苄基-3-（4-溴苯基）-4,5-二氧代-2,6a-二苯基六氢-3a H吡咯并[3,2- d]异恶唑-3a-羧酸盐和二甲基（3 R *，3a R *，6a S *）-3-（4-溴苯基）-4,5-二氧代-2,6-二苯基四氢-3a H-吡咯[3，通过单晶X射线分析证明了2-d]异恶唑-3a，6a（4 H）-二羧酸盐。
• Five-membred 2,3-dioxoheterocycles: LXXXI. Reactions of 4,5-bis(methoxycarbonyl)-1H-pyrrole-2,3-diones with N-substituted 3-amino-5,5-dimethyl-2-cyclohex-2-en-1-ones. crystal and molecular structure of methyl 4′-hydroxy-6,6-dimethyl-1,1′-bis(4-methylphenyl)-2,4,5′-trioxo-1,1′,2,4,5,5′,6,7-octahydrospiro[indole-3,2′-pyrrole]-3′-carboxylate
  作者：P. S. Silaichev、M. A. Chudinova、P. A. Slepukhin、A. N. Maslivets

  DOI：10.1134/s107042801111011x

  日期：2011.11

  1-Aryl-4,5-bis(methoxycarbonyl)-1H-pyrrole-2,3-diones react with N-substituted 3-amino-5,5-dimethylcyclohex-2-en-1-ones affording methyl 1,1'-diaryl-4'-hydroxy-6,6-dimethyl-2,4,5'-trioxo-1,1',2,4,5,5',6,7-octahydrospiro[indole-3,2'-pyrrole]-3'-carboxylates whose structure was proved by XRD analysis.
• Spiro heterocyclization of dimethyl 1-(4-methylphenyl)-4,5-dioxo-4,5-dihydro-1H-pyrrole-2,3-dicarboxylate by the action of 3-arylamino-5,5-dimethylcyclohex-2-en-1-ones
  作者：P. S. Silaichev、M. A. Chudinova、A. N. Maslivets

  DOI：10.1134/s1070428011100289

  日期：2011.10