1-phenyl-5-(diacetylmethyl)-2-pyrrolidinone | 88460-85-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: 1-phenyl-5-(diacetylmethyl)-2-pyrrolidinone
• 英文别名: 3-(5-Oxo-1-phenylpyrrolidin-2-yl)pentane-2,4-dione
• CAS: 88460-85-9
• 化学式: C₁₅H₁₇NO₃
• 分子量: 259.305
• InChiKey: MALFTMXQMMJZMX-UHFFFAOYSA-N

物化性质

• 熔点：
  99-102 °C
• 沸点：
  475.7±15.0 °C(Predicted)
• 密度：
  1.179±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  54.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-phenyl-5-(diacetylmethyl)-2-pyrrolidinone 在 四磷十氧化物 作用下， 反应 1.5h， 生成 4-acetyl-5-methyl-3,3a-dihydro-2H-pyrrolo[1,2-a]quinolin-1-one
  参考文献：
  名称：

  One-Pot Synthesis of Pyrrolo[1,2-a]quinolin-1-ones by the Cyclocondensation of 5-Hydroxy-1-arylpyrrolidin-2-ones with Dicarbonyls

  摘要：

  A one-pot synthesis of pyrrolo[1,2-a]quinolin-1-ones has been developed from the reactions of 5-hydroxy-1-arylpyrrolidin-2-ones with 1,3-dicarbonyl compounds under the promotion of H3PO4/P2O5 or HOAc/H2SO4. The pyrrolo[1,2-a]quinolin-1-ones are formed by two-step reactions, that is, the coupling of N-acyliminium ion intermediates produced from 5-hydroxy-1-arylpyrrolidin-2-ones with 1,3-dicarbonyls and subsequent Friedel-Crafts reactions of the resulting ketone with the aryl ring.

  DOI：

  10.1002/jhet.1508
• 作为产物：
  描述：

  N-苯基马来酰亚胺 在 cerium(III) chloride heptahydrate 、 磷酸 作用下， 以 甲醇 为溶剂， 反应 0.25h， 生成 1-phenyl-5-(diacetylmethyl)-2-pyrrolidinone
  参考文献：
  名称：

  One-Pot Synthesis of Pyrrolo[1,2-a]quinolin-1-ones by the Cyclocondensation of 5-Hydroxy-1-arylpyrrolidin-2-ones with Dicarbonyls

  摘要：

  A one-pot synthesis of pyrrolo[1,2-a]quinolin-1-ones has been developed from the reactions of 5-hydroxy-1-arylpyrrolidin-2-ones with 1,3-dicarbonyl compounds under the promotion of H3PO4/P2O5 or HOAc/H2SO4. The pyrrolo[1,2-a]quinolin-1-ones are formed by two-step reactions, that is, the coupling of N-acyliminium ion intermediates produced from 5-hydroxy-1-arylpyrrolidin-2-ones with 1,3-dicarbonyls and subsequent Friedel-Crafts reactions of the resulting ketone with the aryl ring.

  DOI：

  10.1002/jhet.1508

文献信息

• Speckamp, W. N.; Boer, J. J. J. de, Recueil des Travaux Chimiques des Pays-Bas, 1983, vol. 102, # 9, p. 405 - 409
  作者：Speckamp, W. N.、Boer, J. J. J. de

  DOI：——

  日期：——
• Speckamp, W. N.; Boer, J. J. J. de, Recueil des Travaux Chimiques des Pays-Bas, 1983, vol. 102, # 9, p. 410 - 414
  作者：Speckamp, W. N.、Boer, J. J. J. de

  DOI：——

  日期：——
• SPECKAMP, W. N.;DE, BOER, J. J. J., REC. TRAV. CHIM. PAYS-BAS, 1983, 102, N 9, 410-414
  作者：SPECKAMP, W. N.、DE, BOER, J. J. J.

  DOI：——

  日期：——
• SPECKAMP, W. N.;DE, BOER, J. J. J., REC. TRAV. CHIM. PAYS-BAS, 1983, 102, N 9, 405-409
  作者：SPECKAMP, W. N.、DE, BOER, J. J. J.

  DOI：——

  日期：——
• One-Pot Synthesis of Pyrrolo[1,2-<i>a</i>]quinolin-1-ones by the Cyclocondensation of 5-Hydroxy-1-arylpyrrolidin-2-ones with Dicarbonyls
  作者：Xuerui Wang、Wenxue Zhang、Hongjuan Shen、Wei Zhang

  DOI：10.1002/jhet.1508

  日期：2013.5

  A one-pot synthesis of pyrrolo[1,2-a]quinolin-1-ones has been developed from the reactions of 5-hydroxy-1-arylpyrrolidin-2-ones with 1,3-dicarbonyl compounds under the promotion of H3PO4/P2O5 or HOAc/H2SO4. The pyrrolo[1,2-a]quinolin-1-ones are formed by two-step reactions, that is, the coupling of N-acyliminium ion intermediates produced from 5-hydroxy-1-arylpyrrolidin-2-ones with 1,3-dicarbonyls and subsequent Friedel-Crafts reactions of the resulting ketone with the aryl ring.