N-phenyl-4-methyl-3-pyrrolin-2-one | 85692-13-3

• 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: N-phenyl-4-methyl-3-pyrrolin-2-one
• 英文别名: 4-methyl-1-phenyl-1,5-dihydro-pyrrol-2-one；N-phenyl-4-phenyl-3-pyrrolin-2-one；4-methyl-N-phenyl-Δ³-pyrroline-2-one；4-Methyl-1-phenyl-1,5-dihydro-pyrrol-2-on；3-methyl-1-phenyl-2H-pyrrol-5-one
• CAS: 85692-13-3
• 化学式: C₁₁H₁₁NO
• 分子量: 173.214
• InChiKey: XFMPUYARLXTYRY-UHFFFAOYSA-N

物化性质

• 熔点：
  87-88 °C
• 沸点：
  262.9±10.0 °C(Predicted)
• 密度：
  1.141±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2-bromo-N-allyl-N-phenylacetamide 在 palladium diacetate 、 三乙胺 、 三苯基膦 作用下， 以 乙腈 为溶剂， 以16%的产率得到N-phenyl-4-methyl-3-pyrrolin-2-one
  参考文献：
  名称：

  Yang, Shyh-Chyun; Shea, Fang-Rong, Journal of the Chinese Chemical Society, 1995, vol. 42, # 6, p. 969 - 972

  摘要：

  DOI：

文献信息

• One-pot synthesis of α,β-unsaturated butyralactams from allyl amines
  作者：José Barluenga、Francisco J. Fañanás、Francisco Foubelo、Miguel Yus

  DOI：10.1016/s0040-4039(00)80627-9

  日期：1988.1

  The successive reaction of different allylamines with -butyl -lithium, -butyl-lithium, and diethyl carbonate at temperatures ranging between -50 and 20°C leads after hydrolysis to the corresponding α,β-unsaturated butyrolactams in an one-pot process.

  在一锅法中水解成相应的α，β-不饱和丁内酰胺后，不同的烯丙胺与-丁基-锂，-丁基-锂和碳酸二乙酯在-50至20°C的温度下连续反应。
• Barluenga, Jose; Foubelo, Francisco; Fananas, Francisco J., Journal of Chemical Research, Miniprint, 1989, # 7, p. 1524 - 1552
  作者：Barluenga, Jose、Foubelo, Francisco、Fananas, Francisco J.、Yus, Miguel

  DOI：——

  日期：——
• MgI₂-Mediated Ring Expansions of Secondary Methylenecyclopropyl Amides
  作者：Mark Lautens、Wooseok Han、Jack Hung-Chang Liu

  DOI：10.1021/ja028967l

  日期：2003.4.1

  Ring expansion of secondary methylenecyclopropyl amides in the presence of MgI2 was investigated. Various isomeric five-membered unsaturated lactams were obtained, depending on the character of the substituent Q. The amide group served as a nucleophile in ring closing as well as an activator for ring opening. In the presence of a variety of aryl aldimines or aldehydes, alkylative ring expansion occurred in a single step under mild and neutral conditions leading to gamma'-amino- or -hydroxy-alkylated pyrrol-2-ones. Also, it was shown that a 4-methylpyrrol-2-one could be transformed to a gamma-hydroxy-alkylated product by the use of a direct vinylogous aldol reaction.
• BARLUENGA, JOSE;FOUBELO, FRANCISCO;FANANAS, FRANCISCO J.;YUS, MIGUEL, J. CHEM. RES. (S),(1989) N, C. 200-201
  作者：BARLUENGA, JOSE、FOUBELO, FRANCISCO、FANANAS, FRANCISCO J.、YUS, MIGUEL

  DOI：——

  日期：——
• CHALCHAT, J. -C.;GARRY, R. -P.;MICHET, A., C. R. ACAD. SCI., 1982, 295, N 10, 871-873
  作者：CHALCHAT, J. -C.、GARRY, R. -P.、MICHET, A.

  DOI：——

  日期：——