1-(3,4,5,6-四氢-2H-氮杂-7-基)吡咯烷-2-酮 | 90683-34-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吖庚因类
• 中文名称: 1-(3,4,5,6-四氢-2H-氮杂-7-基)吡咯烷-2-酮
• 英文名称: 1-(4,5,6,7-tetrahydro-3H-azepin-2-yl)-2-pyrrolidinone
• 英文别名: 1-(3,4,5,6-Tetrahydro-2H-azepin-7-yl)pyrrolidin-2-one
• CAS: 90683-34-4
• 化学式: C₁₀H₁₆N₂O
• 分子量: 180.25
• InChiKey: CZJDAWDQJNAGGU-UHFFFAOYSA-N

物化性质

• 熔点：
  56.5-58.5 °C(Solv: ligroine (8032-32-4))
• 沸点：
  78-81 °C(Press: 0.1 Torr)
• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 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 、 1-氮杂-2-甲氧基-1-环庚烯 以34%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

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

  DOI：——

  日期：——