1-acetyl-3,3-methylene-5,5-dimethyl-2-pyrrolidinone

• 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-acetyl-3,3-methylene-5,5-dimethyl-2-pyrrolidinone
• 英文别名: 2-Pyrrolidinone, 1-acetyl-5,5-dimethyl-3-methylene-(9CI)；1-acetyl-5,5-dimethyl-3-methylidenepyrrolidin-2-one
• 化学式: C₉H₁₃NO₂
• 分子量: 167.208
• InChiKey: AVYZBJIKOQJRRE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  phenyl-glyoxal-2-(N-phenyl oxime ) 、 1-acetyl-3,3-methylene-5,5-dimethyl-2-pyrrolidinone 以 苯 为溶剂， 以50%的产率得到(3R,5S)-7-Acetyl-3-benzoyl-8,8-dimethyl-2-phenyl-1-oxa-2,7-diaza-spiro[4.4]nonan-6-one
  参考文献：
  名称：

  Stereoselectivity in the 1,3-dipolar cycloaddition of nitrones to 1-substituted 3,3-methylene-5,5-dimethyl-2-pyrrolidinones

  摘要：

  The stereoselectivity of the nitrone cycloaddition with 1-substituted 3,3-methylene-5,5-dimethyl-2-pyrrolidinones 1 is discussed. C,N-Diarylnitrones give mixtures of diastereomeric spirocycloadducts 3 and 4, in which 3 always dominates. In contrast, N-methylnitrones react under the formation of 4 as major products. Cycloaddition of C-benzoyl nitrones 7 with 1 affords exclusively single isoxazolidines 8. Semi-empirical quantum mechanical methods (AM1) were used to rationalize the regio- and stereoselectivity of the reactions.

  DOI：

  10.1007/bf00811091

文献信息

• Use of some aryl and heteroaryl nitrilimines and nitrones in the synthesis of spiroheterocycles
  作者：Eva Jedlovská、Lubor Fišera

  DOI：10.1002/jhet.5570410504

  日期：2004.9

  1,3-Dipolar cycloadditions of C-(5-nitro-2-furyl)-N-methyl nitrilimine (2a), C-(5-nitro-2-furyl)-N-phenyl nitrilimine (2b), C-4-nitrophenyl-N-methyl nitrilimine (2c) and C,N-diphenyl nitrilimine (2d) with 1-R-substituted 3,3-methylene-5,5-dimethylpyrrolidin-2-ones (1a-d) where R is H, acetyl, 1,1-dimethylethoxycarbonyl and 1-methylethenyl proceed with complete regioselectivity in good yields to afford

  C-（5-硝基-2-呋喃基）-N-甲基亚硝胺（2a），C-（5-硝基-2-呋喃基）-N-苯基亚硝胺（2b），C -4的1,3-偶极环加成-硝基苯基-N-甲基亚硝胺（2c）和C，N-二苯基亚硝胺（2d）与1-R-取代的3,3-亚甲基-5,5-二甲基吡咯烷-2-酮（1a-d），其中R为H ，乙酰基，1,1-二甲基乙氧基羰基和1-甲基乙烯基以完全的区域选择性进行，并具有良好的收率，得到1,3,7-三取代-6-氧代-8,8-二甲基-1,2,7-三氮杂螺[4,4]单独的] non-2-enes （5a-g）。C的环加成-（5-硝基-2-呋喃基）-N-苯基硝酮（3b）与亲二氟体1a的环外双键进行，生成2-苯基-3-（5-硝基-2-呋喃基）-6-oxo-8，具有完全区域和立体选择性的8-二甲基-1-氧杂2，7-二氮杂螺[4,4]壬烷（7）。
• Stereoselectivity in the 1,3-dipolar cycloaddition of nitrones to 1-substituted 3,3-methylene-5,5-dimethyl-2-pyrrolidinones
  作者：L. Jaroškoá、L'. Fišera、I. Matejková、P. Ertl、N. Prónayová

  DOI：10.1007/bf00811091

  日期：1994.12

  The stereoselectivity of the nitrone cycloaddition with 1-substituted 3,3-methylene-5,5-dimethyl-2-pyrrolidinones 1 is discussed. C,N-Diarylnitrones give mixtures of diastereomeric spirocycloadducts 3 and 4, in which 3 always dominates. In contrast, N-methylnitrones react under the formation of 4 as major products. Cycloaddition of C-benzoyl nitrones 7 with 1 affords exclusively single isoxazolidines 8. Semi-empirical quantum mechanical methods (AM1) were used to rationalize the regio- and stereoselectivity of the reactions.