4-甲基-3-吡咯啉-2-酮 | 53598-99-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯啉
• 中文名称: 4-甲基-3-吡咯啉-2-酮
• 英文名称: 4-methyl-3-pyrrolin-2-one
• 英文别名: 3-methyl-1,2-dihydropyrrol-5-one
• CAS: 53598-99-5
• 化学式: C₅H₇NO
• mdl: MFCD10699599
• 分子量: 97.1167
• InChiKey: VYLNLZWPJSQGRC-UHFFFAOYSA-N

物化性质

• 熔点：
  112-113℃ (ligroine )
• 沸点：
  274.0±23.0 °C(Predicted)
• 密度：
  1.049±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  7
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-甲基-3-吡咯啉-2-酮 在 sodium hydroxide 作用下， 生成 5-(4-acetyl-3-methyl-5-phenylazo-pyrrol-2-ylmethylene)-4-methyl-1,5-dihydro-pyrrol-2-one
  参考文献：
  名称：

  Plieninger; Lichtenwald, Hoppe-Seyler's Zeitschrift fur Physiologische Chemie, 1942, vol. 273, p. 206,219

  摘要：

  DOI：
• 作为产物：
  描述：

  3-甲基吡咯-2,5-二酮 在 palladium on activated charcoal sodium tetrahydroborate 、 amberlyst resin 、 氢气 作用下， 以 甲醇 、 乙醇 、 乙腈 为溶剂， 反应 4.83h， 生成 4-甲基-3-吡咯啉-2-酮
  参考文献：
  名称：

  A Facile Synthesis of CD45 Protein Tyrosine Phosphatase Inhibitor Marine Natural Product Pulchellalactam

  摘要：

  已经展示了一条简便的五步路线，从柠檬酸酰胺（5）出发，通过区域选择性NaBH4还原、催化氢化、树脂催化脱水、N-BOC保护和立体选择性缩合路径，合成自然界存在的CD45蛋白酪氨酸磷酸酶抑制剂(Z)-pulchellalactam，整体产率为64%。

  DOI：

  10.1055/s-2004-822407

文献信息

• A facile approach to α,β-unsaturated lactams by ring-closing metathesis
  作者：Humaira Yasmeen Gondal、Didier Buisson

  DOI：10.1007/s10593-016-1858-y

  日期：2016.3

  A facile and efficient strategy for the synthesis of α,β-unsaturated lactams through ring-closing metathesis of easily prepared diene amides is being reported here. Reaction conditions were optimized for metathetic cyclization of diene amides to obtain five- to sevenmembered unsubstituted and β-substituted α,β-unsaturated lactams in good to excellent yield.

  在此报道了通过容易制备的二烯酰胺的闭环易位合成α，β-不饱和内酰胺的简便有效的策略。优化了反应条件以使二烯酰胺进行易位环化，以良好至极好的收率获得五元至七元的未取代和β-取代的α，β-不饱和内酰胺。
• Easy approach to 3-benzylimino-2-pyrrolidinones from 3-chloro-4-chloromethyl-2-pyrrolidinones
  作者：Franco Ghelfi、Gianluca Ghirardini、Emanuela Libertini、Luca Forti、Ugo M. Pagnoni

  DOI：10.1016/s0040-4039(99)01798-0

  日期：1999.12

  3-chloro-4-chloromethyl-2-pyrrolidinones, benzylamine and NaI in THF at 80°C. An endo-dehydrohalogenation followed by a SN2′ substitution on the intermediate allyl chloride, and finally a shift of the exo-double bond to Δ3 with attendant tautomerization, appears to be the most probable reaction mechanism.

  通过在80℃下将3-氯-4-氯甲基-2-吡咯烷酮，苄胺和NaI在THF中加热，可以高收率制备3-苄基氨基-2-吡咯烷酮。一内切-dehydrohalogenation后跟一个SN 2 '在中间烯丙基氯取代，最后的移位外型-双键来Δ 3与伴随的互变异构化，似乎是最有可能的反应机理。
• Plieninger; Decker, Justus Liebigs Annalen der Chemie, 1956, vol. 598, p. 198,205
  作者：Plieninger、Decker

  DOI：——

  日期：——
• New synthesis of nitrogen heterocycles through amide-directed hydrocarbonylation of alkenamides catalyzed by rhodium complexes
  作者：Iwao Ojima、Anna Korda、William R. Shay

  DOI：10.1021/jo00006a013

  日期：1991.3

  Amide-directed hydrocarbonylation of 3-butenamide (1) catalyzed by rhodium complexes such as RhCl(PPh3)3, RhCl(CO)(PPh3)2, HRh(CO)(PPh3)3, and Rh4(CO)12 gives a mixture of 3,4-dihydro-2-pyridone (2), 4-methyl-3-pyrrolin-2-one (3), and a unique heterodimer, 6-(4-methyl-2-oxo-3-pyrrolin-1-yl)-2-piperidone (4). Dihydropyridone (2) is obtained in 88% yield with 98% selectivity by using HRh(CO)(PPh)3-dppb (2 equiv) catalyst system while 4 is yielded in 90% yield with 94% selectivity with the use of RhCl(PPh3)3-P(OPh)3 (10 equiv) as the catalyst. Control experiments revealed that this crossed coupling only proceeds in the copresence of rhodium catalyst, carbon monoxide, and hydrogen. The reactions of N-benzyl-3-butenamide (1a) gives a mixture of 1-benzyldihydropyridone (2a), 1-benzyl-4-methylpyrrolinone (3a), and 1-benzyl-6-formyl-3,4-dihydropyridone (5) and its 5-formyl isomer (6). The formation of 5 and 6 is suppressed by the addition of PPh3, and 2a is selectively isolated (72%) in the reaction using RhCl(CO)(PPh3)2-PPh3 (20 equiv) as the catalyst. The hydroformylation of 2a catalyzed by RhCl(PPh3)3 gives 5 in 80% isolated yield. The reaction of N-tert-butyl-3-butenamide (1b) gives a nearly 1:1 mixture of 1-tert-butyl-4-methylpyrrolinone (3b) and uncyclized N-tert-butyl-4-formylbutanamide (7) accompanied by a small amount of 1-tert-butyldihydropyridone (2b). In the reaction of N-trityl-3-butenamide (1c), no dihydropyridone (2c) was formed, and a mixture of 1-trityl-4-methylpyrrolinone (3c) (major) and N-trityl-4-formylbutanamide (8) (minor) is yielded. The reaction of 4-pentenamide gives 4-methyl-3,4-dihydro-2-pyridone (9) exclusively regardless of the structure of the rhodium catalysts used. Possible mechanisms for these reactions are discussed.
• New routes to nitrogen heterocycles through intramolecular amidocarbonylation of alkenamides catalyzed by rhodium complexes
  作者：Iwao Ojima、Anna Korda

  DOI：10.1016/s0040-4039(01)93873-0

  日期：——