4-Oxo-2,3-dimethyl-Δ²-pyrrolin | 19983-85-8

• 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-Oxo-2,3-dimethyl-Δ²-pyrrolin
• 英文别名: 4,5-Dimethyl-1h-pyrrol-3(2h)-one；4,5-dimethyl-1,2-dihydropyrrol-3-one
• CAS: 19983-85-8
• 化学式: C₆H₉NO
• 分子量: 111.144
• InChiKey: LJPOILTUULDXIV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  8
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-Oxo-2,3-dimethyl-Δ²-pyrrolin 以 乙腈 为溶剂， 25.0~600.0 ℃ 、1.33 Pa 条件下， 反应 0.92h， 生成 2,3-dimethylpyrano<3,2-b>pyrrol-5(1H)-one
  参考文献：
  名称：

  3-Hydroxypyrroles and 1H-pyrrol-3(2H)-ones. Part 13. Reactions of methoxymethylene Meldrum's acid with 3-hydroxypyrroles, with 3-methoxypyrroles and with other active substrates, and pyrolytic heterocyclisations of the products

  摘要：

  Methoxymethylene Meldrum's acid 2 in acetonitrile solution acts as a useful C-electrophile for active substrates such as pyrrole, indole or tertiary enaminones to give substitution products (e.g. 5, 6 or 12, respectively). Primary enaminones react exclusively at the nitrogen atom under these conditions. The effect of ring substituents on the regiochemistry of electrophilic substitution of 3-hydroxypyrroles and 3-methoxypyrroles was studied using methoxymethylene Meldrum's acid as the electrophile. Flash vacuum pyrolysis of the Meldrum's acid derivatives obtained in many of these reactions gave access to a range of heterocyclic systems, including the pyridone 48, quinolinedione 43, benzazepinedione 41 and fused pyrones 50, 52 and 54.

  DOI：

  10.1039/p19930002017
• 作为产物：
  描述：

  2-Ethoxycarbonyl-3-hydroxy-4,5-dimethylpyrrol 、 盐酸 以92%的产率得到
  参考文献：
  名称：

  PFEIFFER G.; BAUER H., J. LIEBIGS ANN. CHEM. , 1976, NO 2, 383-386

  摘要：

  DOI：

文献信息

• Synthese und Eigenschaften von 2-Amino-3-oxo-3<i>H</i>-azepinen
  作者：Theophil Eicher、Alfred Kruse

  DOI：10.1055/s-1985-34137

  日期：——

  Synthesis and Properties of 2-Amino-3-oxo-3H-azepines The attempted syntheses of 2-amino-3-oxo-3H-azepines 3 as well as their mono- and dibenzoannellated derivatives 4-6 are reported. The spectroscopic and chemical behaviour of the compounds 4-6 are discussed and compared with those of the five-membered ring analogues 1 and 2.

  2-氨基-3-氧代-3H-氮杂七环的合成与性质 报告了2-氨基-3-氧代-3H-氮杂七环3的合成尝试，以及它们的单苯并和二苯并衍生物4-6。讨论了化合物4-6的光谱和化学行为，并与五元环类似物1和2进行了比较。
• Photochemical Synthesis of 2-Alkylidene-4-pyrrolin-3-ones
  作者：Ramin Ghaffari-Tabrizi、Paul Margaretha

  DOI：10.1002/hlca.19820650334

  日期：1982.5.5

  Irradiation (λ =313 nm) of the 4-pyrrolin-3-ones 1a–1c in acetone-, 3-pentanone-and cyclopentanone solution affords the title compounds 2, formally via H-abstrac-tion by the excited ketone and recombination of the radical pair formed.

  在丙酮-，3-戊酮-和环戊酮溶液中辐照4-吡咯啉-3-酮1a-1c（λ= 313 nm），得到标题化合物2，其形式是通过被激发的酮进行的H吸收和自由基的重组对形成。
• GHAFFARI-TABRIZI, R.;MARGARETHA, P., HELV. CHIM. ACTA, 1982, 65, N 3, 1029-1031
  作者：GHAFFARI-TABRIZI, R.、MARGARETHA, P.

  DOI：——

  日期：——
• EICHER, TH.;KRUSE, A., SYNTHESIS, BRD, 1985, N 6-7, 612-619
  作者：EICHER, TH.、KRUSE, A.

  DOI：——

  日期：——
• 3-Hydroxypyrroles and 1H-pyrrol-3(2H)-ones. Part 13. Reactions of methoxymethylene Meldrum's acid with 3-hydroxypyrroles, with 3-methoxypyrroles and with other active substrates, and pyrolytic heterocyclisations of the products
  作者：Paul A. Derbyshire、Gordon A. Hunter、Hamish McNab、Lilian C. Monahan

  DOI：10.1039/p19930002017

  日期：——

  Methoxymethylene Meldrum's acid 2 in acetonitrile solution acts as a useful C-electrophile for active substrates such as pyrrole, indole or tertiary enaminones to give substitution products (e.g. 5, 6 or 12, respectively). Primary enaminones react exclusively at the nitrogen atom under these conditions. The effect of ring substituents on the regiochemistry of electrophilic substitution of 3-hydroxypyrroles and 3-methoxypyrroles was studied using methoxymethylene Meldrum's acid as the electrophile. Flash vacuum pyrolysis of the Meldrum's acid derivatives obtained in many of these reactions gave access to a range of heterocyclic systems, including the pyridone 48, quinolinedione 43, benzazepinedione 41 and fused pyrones 50, 52 and 54.