1-(1-pyrrolidin-2-yl)-2-pyrrolidone | 7060-52-8

• 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-(1-pyrrolidin-2-yl)-2-pyrrolidone
• 英文别名: 1-(1-pyrrolin-2-yl)-2-pyrrolidinone；2-pyrrolinyl-2-pyrrolidinone；4,5,4',5'-tetrahydro-3H,3'H-[1,2']bipyrrolyl-2-one；1-<Δ¹-Pyrrolinyl-(2)>-pyrrolidon-(2)；1-(Δ^1'-Pyrrolin-2'-yl)-pyrrolidon-2；1-(1-Pyrrolin-2-yl)-2-pyrrolidinon；2-Pyrrolidinone, 1-(3,4-dihydro-2H-pyrrol-5-yl)-；1-(3,4-dihydro-2H-pyrrol-5-yl)pyrrolidin-2-one
• CAS: 7060-52-8
• 化学式: C₈H₁₂N₂O
• 分子量: 152.196
• InChiKey: CPYBTXZHLQTZNG-UHFFFAOYSA-N

物化性质

• 熔点：
  61 °C(Solv: ligroine (8032-32-4))
• 沸点：
  254.4±23.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  32.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-吡咯烷酮 以58%的产率得到
  参考文献：
  名称：

  MAZURKIEWICZ, R., ACTA CHIM. HUNG., 1984, 116, N 1, 95-102

  摘要：

  DOI：

文献信息

• 2-(Perfluoroalkyl)ethanols by Thermal Alkylation of Ambidentate Lactams with 2-(Perfluoroalkyl)-1-iodoalkanes, in the Presence of Added Water. A Change in Mechanism and Stoichiometry of the Reaction. Isolation of a Water Adduct of the Lactim Ether Intermediate
  作者：Neal O. Brace

  DOI：10.1021/jo960831g

  日期：1996.1.1

  Thermal alkylation of amides by an alkyl halide gives alcohols and esters, and the intriguing behavior of ambidentate lactams in this reaction with 2-(perfluoroalkyl)-1-iodoethanes and lactam 2 is summarized in Scheme 1. 2-(Perfluoroalkyl)ethanols (3) are the principal alkylation product, and there is obtained a range of coproducts in varying amounts. A lactim ether salt (6.HI) is the first reaction

  流程1中概述了酰胺与烷基卤的热烷基化反应生成醇和酯，歧化内酰胺在与2-（全氟烷基）-1-碘乙烷和内酰胺2的反应中表现出令人着迷的行为.2-（全氟烷基）乙醇（3 ）是主要的烷基化产物，并且获得了各种量的副产物。乳酸亚胺醚盐（6.HI）是一系列反应中的第一个反应中间体。对于δ-戊内酰胺（8）或ε-己内酰胺（11），转化为3的幅度急剧下降，R（F）CH = CH（2）（4）成为主要产品。然而，当引入水时，碘代烷1的2的烷基化速率增加，向3和4的转化率降低，并形成了新的内酰胺醚盐7.HI（6.HI的水加合物）。由于副产物2弱碱性且平衡位于碱性胺盐（7.HI）一侧，抑制了向3的转化。2-羟基-2-[[[（（（2-（全氟己基）乙基]氧基]吡咯烷）的质谱图包括母体离子和带有羟基的完整吡咯烷环的片段（m / z = 131） 。在质子溶剂中含有7.HI的产物混合物的碱性水解可得到3和2的高产率。较高的内酰
• A process to produce N-ethenyl-N-alkyl-alkylamides
  申请人：S.P.C.M. SA

  公开号：EP2835365A1

  公开（公告）日：2015-02-11

  A process to produce N-ethenyl-N-alkyl-alkylamide including the steps of reacting at least a N-monoalkyl-alkylamide with a reactant including 1,3-dioxolan-2-one in the presence of at least a catalyst to form an intermediate, and of decarboxylating said intermediate to synthesize N-ethenyl-N-alkyl-alkylamide.

  一种制备N-乙烯基-N-烷基-烷基酰胺的方法，包括以下步骤：在至少一个催化剂的存在下，将至少一个N-单烷基-烷基酰胺与包含1,3-二氧杂环戊酮的反应物反应，形成中间体，并且脱羧化该中间体以合成N-乙烯基-N-烷基-烷基酰胺。
• Phosphorylation ofN-trimethylsilyllactams
  作者：A. B. Uryupin、I. A. Rakhov、V. A. Kolesova、P. V. Petrovskii、T. A. Mastryukova、M. I. Kabachnik

  DOI：10.1007/bf00697149

  日期：1994.9

  Treatment of N-trimethylsilyllactams with phosphoryl chlorides results in mixtures of products, whose formation can be explained by competition between N- and O-phosphorylation.
• Thermal Alkylation of Ambidentate Lactams with 2-(Perfluoroalkyl)-1-iodoalkanes. The Effect of Reaction Conditions and Ring Size on the Synthesis of 2-(Perfluoroalkyl)ethanols and the Mechanism of Reaction
  作者：Neal O. Brace

  DOI：10.1021/jo00112a029

  日期：1995.4

  The perfluoroalkylated long chain alcohol and their derivatives exhibit strong surface activity in solution and novel surface modification properties as adsorbed layers or films. A new, little known synthesis of 2-(perfluoroalkyl)ethanols (R(F)CH(2)CH(2)OH) employs a lactam, e.g., 2-pyrrolidinone (2), with an iodoalkane, e.g., C6F13CH2CH2I (1) Alkylation of 2 by heating with 1 gives C6F13CH2CH2OH (3) in 83% distilled yield, and treating the residual lactim ether salt (6 HI) with K2CO3 gives additional 3, up to 94% yield. Rate of alcohol formation (k(alc)) is unaffected by molar ratio of 2:1, yet rate of 1 reaction (k(iodo)) increases 2.44 times with doubling of 2:1 and side product C6F13CH=CH2 (4) decreases from 4 to 2%. For homologous lactams [(CH2)(n)NHC=O] (n = 3-5), selectivities (mel 3:4) are as follows: 5-membered ring, 18.4; 6-membered ring, 0.73; 7-membered ring, 0.13. Conversions to 3 are as follows: 6-membered ring, 19.4%; and 7-membered ring, 1.75%, Table 13. A three-step mechanism is proposed: (1) O-alkylation of the lactam by 1 gives lactim salt I; (2) N-substitution of salt I by another molecule of lactam forms a tetrahedral adduct (II); (3) breakdown of salt II gives 3 and iminolactam salt III. In model experiments, heating of 2 and lactim 6 yields 99% of 3 and iminolactam 5 and 1% of 4. By contrast, 7-membered 14 with 2 gives 45% of 3 and iminolactam 12, besides 4 and epsilon-caprolactam 10 (20%). For higher lactams, two competitive reactions can be discerned: (1) the S(N)2 displacement of alcohol by N-attack on salt II and a unimolecular, concerted fragmentation of the lactim, to lactam and alkene.
• Urjupin A. B., Rakhow I. A., Kolesowa W. A., Petrowskiii P. W., Mastrjuko+, Isw. AN. Ser. khim, (1994) N 9, S 1644-1648
  作者：Urjupin A. B., Rakhow I. A., Kolesowa W. A., Petrowskiii P. W., Mastrjuko+

  DOI：——

  日期：——