4,5-dimethoxycarbonyl-1-phenyl-1H-pyrrole-2,3-dione | 251986-52-4

• 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-dimethoxycarbonyl-1-phenyl-1H-pyrrole-2,3-dione
• 英文别名: Dimethyl 4,5-dioxo-1-phenylpyrrole-2,3-dicarboxylate
• CAS: 251986-52-4
• 化学式: C₁₄H₁₁NO₆
• 分子量: 289.244
• InChiKey: DTDGAYDYOODVHD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 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-phenyl-1H-pyrrole-2,3-dione 以 二苯醚 为溶剂， 反应 0.5h， 以79%的产率得到dimethyl 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：

  丁炔二酸二甲酯 、 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-phenyl-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

• Regioselective [3+2] cycloaddition of nitrile oxides to 1Н-pyrrole-2,3-diones: synthesis of spiro[pyrroledioxazoles]
  作者：Anna А. Moroz、Maksim V. Dmitriev、Andrey N. Maslivets

  DOI：10.1007/s10593-021-03047-6

  日期：2021.12

  1,3-Dipolar cycloaddition of 1H-pyrrole-2,3-diones to nitrile oxides generated in situ from N-hydroxybenzimidoyl chlorides by the action of triethylamine proceeds regioselectively with the formation of 1,4,2-dioxazoles spiro-condensed with the pyrrol-2-one fragment.

  通过三乙胺的作用，1 H-吡咯-2,3-二酮与 N-羟基苯甲亚胺酰氯原位生成的腈氧化物发生1,3-偶极环加成反应，区域选择性地形成 1,4,2-二恶唑，与pyrrol-2-one 片段。
• 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。
• Synthesis of Imidazole Spiro Compounds From 5-Alkoxycarbonyl-1H-Pyrrole-2,3-Diones and Phenylurea
  作者：Aleksei Yu. Dubovtsev、Ekaterina S. Denislamova、Pavel S. Silaichev、Maksim V. Dmitriev、Andrey N. Maslivets

  DOI：10.1007/s10593-016-1913-8

  日期：2016.7

  arbamoyl)amino]-2,5-dihydro-1H-pyrrole-2-carboxylates, which cyclize in the presence of sodium methoxide, giving 8-hydroxy-3-phenyl-1,3,6-triazaspiro[4.4]-non-8-ene-2,4,7-triones. The crystal structures of 8-hydroxy-9-(4-methylbenzoyl)-3-phenyl-6-(p-tolyl)-1,3,6-triazaspiro[4.4]non-8-ene-2,4,7-trione and methyl 8-hydroxy-2,4,7-trioxo-3,6-diphenyl-1,3,6-triazaspiro[4.4]non-8-ene-9-carboxylate were studied

  5-烷氧基羰基取代的1 H-吡咯-2,3-二酮与苯基脲反应，形成烷基4-羟基-5-氧代-2-[（苯基氨基甲酰基）氨基] -2,5-二氢-1 H-吡咯-2 -羧酸盐，其在甲醇钠存在下环化，得到8-羟基-3-苯基-1,3,6-三氮杂螺[4.4]-非-8-烯-2,4,7-三酮。8-羟基-9-（4-甲基苯甲酰基）-3-苯基-6-（对甲苯基）-1,3,6-三氮杂螺[4.4] non-8-ene-2,4,7-的晶体结构研究了三酮和8-羟基-2,4,7-三氧代-3,6-二苯基-1,3,6-三氮杂螺[4.4]非-8-烯-9-羧酸甲酯。