methyl 1-(4-methylphenyl)-4,5-dioxo-3-(1-oxo-3-phenylprop-2-en-2-yl)-4,5-dihydro-1H-pyrrole-2-carboxylate | 1377181-80-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: methyl 1-(4-methylphenyl)-4,5-dioxo-3-(1-oxo-3-phenylprop-2-en-2-yl)-4,5-dihydro-1H-pyrrole-2-carboxylate
• CAS: 1377181-80-0
• 化学式: C₂₂H₁₇NO₅
• 分子量: 375.381
• InChiKey: UUNOVQVVWFFDGB-JLHYYAGUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.62
• 重原子数：
  28.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  80.75
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  methyl 1-(4-methylphenyl)-4,5-dioxo-3-(1-oxo-3-phenylprop-2-en-2-yl)-4,5-dihydro-1H-pyrrole-2-carboxylate 、 ethyl 3-(benzylamino)-3-phenylacrylate 以 甲苯 为溶剂， 反应 2.0h， 以68%的产率得到ethyl 7-benzyl-4-cinnamoyl-3-hydroxy-1-(4-methylphenyl)-2,6-dioxo-8-phenyl-1,7-diazaspiro[4.4]nona-3,8-diene-9-carboxylate
  参考文献：
  名称：

  Five-membered 2,3-dioxo heterocycles: C. Reaction of methyl 1-aryl-3-cinnamoyl-4,5-dioxo-4,5-dihydro-1H-pyrrole-2-carbocylates with acyclic enamines

  摘要：

  Methyl 1-aryl-3-cinnamoyl-4,5-dioxo-4,5-dihydro-1H-pyrrole-2-carbocylates react with N-substituted ethyl 3-amino-3-phenylprop-2-enoates, ethyl 3-aminobut-2-enoates, 3-amino-1,3-diphenylprop-2-en-1-ones, and dimethyl 2-arylaminofumarates to give 9-ethoxycarbonyl-, 9-benzoyl-, and 8,9-bis(methoxycarbonyl)-4-cinnamoyl-1,7-diazaspiro[4.4]nona-3,8-dienes.

  DOI：

  10.1134/s107042801403018x
• 作为产物：
  描述：

  methyl (2Z,5E)-2-hydroxy-4-oxo-6-phenylhexa-2,5-dienoate 以 甲苯 、 苯 为溶剂， 反应 6.17h， 生成 methyl 1-(4-methylphenyl)-4,5-dioxo-3-(1-oxo-3-phenylprop-2-en-2-yl)-4,5-dihydro-1H-pyrrole-2-carboxylate
  参考文献：
  名称：

  Five-membered 2,3-dioxo heterocycles: LXXXV. Synthesis of methyl 1-aryl-4,5-dioxo-3-(1-oxo-3-phenylprop-2-en-1-yl)-4,5-dihydro-1H-pyrrole-2-carboxylates and their reaction with 3-amino-5,5-dimethylcyclohex-2-en-1-ones. Molecular and crystalline structure of 4′-hydroxy-1′-(4-methoxyphenyl)-6,6-dimethyl-3′-(1-oxo-3-phenylprop-2-en-1-yl)-1-phenyl-6,7-dihydrospiro[indole-3,2′-pyrrole]-2,4,5′(1H,1′H,5H)-trione

  摘要：

  Treatment of methyl 2-arylamino-4-oxo-6-phenylhexa-2,5-dienoates with oxalyl chloride gave methyl 1-aryl-4,5-dioxo-3-(1-oxo-3-phenylprop-2-en-1-yl)-4,5-dihydro-1H-pyrrole-2-carboxylates which reacted with 3-benzylamino- and 3-arylamino-5,5-dimethylcyclohex-2-en-1-ones to produce 1'-aryl-1-benzyl- and 1,1'-diaryl-4'-hydroxy-6,6-dimethyl-3'-(1-oxo-3-phenylprop-2-en-1-yl)-6,7-dihydrospiro[indole-3,2'-pyrrole]-2,4,5'(1H,1'H,5H)-triones.

  DOI：

  10.1134/s1070428012040173

文献信息

• Five-membered 2,3-dioxo heterocycles: LXXXIX. Reaction of methyl 1-aryl-3-cinnamoyl-4,5-dioxo-4,5-dihydro-1H-pyrrole-2-carboxylates with (E)-4-arylaminopent-3-en-2-ones. Crystalline and molecular structure of 9-acetyl-4-cinnamoyl-3-hydroxy-1-(4-methoxyphenyl)-8-methyl-7-phenyl-1,7-diazaspiro[4.4]nona-3,8-diene-2,6-dione
  作者：P. S. Silaichev、V. O. Filimonov、P. A. Slepukhin、A. N. Maslivets

  DOI：10.1134/s1070428012100120

  日期：2012.10

  Methyl 1-aryl-3-cinnamoyl-4,5-dioxo-4,5-dihydro-1H-pyrrole-2-carboxylates reacted with 4-benzylamino- and 4-arylaminopent-3-en-2-ones to give 1-aryl-7-benzyl- and 1,7-diaryl-9-acetyl-4-cinnamoyl-3-hydroxy-8-methyl-1,7-diazaspiro[4.4]nona-3,8-diene-2,6-diones. The crystalline and molecular structures of 9-acetyl-4-cinnamoyl-3-hydroxy-1-(4-methoxyphenyl)-8-methyl-7-phenyl-1,7-diazaspiro[4.4]nona-3,8-diene-2,6-dione were studied by X-ray analysis.