N-苄基-4-甲基-3-吡咯啉-2-酮 | 42855-59-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: N-苄基-4-甲基-3-吡咯啉-2-酮
• 英文名称: N-benzyl-4-methyl-3-pyrrolin-2-one
• 英文别名: 1-benzyl-3-methyl-2H-pyrrol-5-one
• CAS: 42855-59-4
• 化学式: C₁₂H₁₃NO
• 分子量: 187.241
• InChiKey: XQBYLLVRMLPMCQ-UHFFFAOYSA-N

物化性质

• 沸点：
  372.0±22.0 °C(Predicted)
• 密度：
  1.128±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  溴乙烷 、 N-苄基-4-甲基-3-吡咯啉-2-酮 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 3.25h， 以57%的产率得到1-benzyl-3-ethyl-4-methyl-1,5-dihydro-2H-pyrrol-2-one
  参考文献：
  名称：

  Scalable Synthesis of 3-Ethyl-4-methyl-1,5-dihydro-2H-pyrrol-2-one: An Important Building Block of the Antidiabetic Drug Glimepiride

  摘要：

  已完成对抗糖尿病药物格列美脲的重要组成部分3-乙基-4-甲基-1,5-二氢-2H-吡咯-2-酮的四步实用且易扩展的合成。关键特点是在水中合成3-甲基-4-羟基-2-丁烯酮，并通过三氟甲磺酸介导的N-苄基内酰胺N-去保护。这一过程的主要优点是可扩展的合成路线和减少反应步骤的数量，为3-乙基-4-甲基-1,5-二氢-2H-吡咯-2-酮的工业规模合成铺平了道路。

  DOI：

  10.1055/s-0040-1707344
• 作为产物：
  描述：

  N-benzyl-N-bromoacetyl-2-propenylamine 在 三乙胺 、 三苯基膦 、 palladium dichloride 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以73%的产率得到N-苄基-4-甲基-3-吡咯啉-2-酮
  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

• New synthesis of heterocycles by use of palladium catalyzed cycli zation of α-haloamide with internal double bond
  作者：Miwako Mori、Nana Kanda、Izumi Oda、Yoshio Ban

  DOI：10.1016/s0040-4020(01)91346-8

  日期：1985.1
• 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.
• Cyclization of α-haloamide with internal double bond by use of the low-valent metal complex
  作者：Miwako Mori、Izumi Oda、Yoshio Ban

  DOI：10.1016/s0040-4039(00)85827-x

  日期：1982.1
• 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：——
• OJIMA, IWAO;KORDA, ANNA, TETRAHEDRON LETT., 30,(1989) N6, C. 6283-6286
  作者：OJIMA, IWAO、KORDA, ANNA

  DOI：——

  日期：——