(2S,3R)-3-Butyl-2-methyl-pyrrolidine | 141708-35-2

• 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: (2S,3R)-3-Butyl-2-methyl-pyrrolidine
• 英文别名: (2S,3R)-3-butyl-2-methylpyrrolidine
• CAS: 141708-35-2
• 化学式: C₉H₁₉N
• 分子量: 141.257
• InChiKey: OJBMWVGFVLZXQN-DTWKUNHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-硝基苯甲酰氯 、 (2S,3R)-3-Butyl-2-methyl-pyrrolidine 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 ((2S,3R)-3-Butyl-2-methyl-pyrrolidin-1-yl)-(4-nitro-phenyl)-methanone 、 ((2S,3S)-3-Butyl-2-methyl-pyrrolidin-1-yl)-(4-nitro-phenyl)-methanone
  参考文献：
  名称：

  Asymmetric conjugate additions to chiral bicyclic lactams. Synthesis of aracemic trans-2,3-disubstituted pyrrolidines

  摘要：

  The trans-2,3-disubstituted pyrrolidine moiety, found in the pyrrolizidine alkaloids as well as other natural products, has been accessed from the alpha,beta-unsaturated bicyclic lactams 1d and 10. Conjugate addition of lower order cyanocuprates to lactams 1d and 10 resulted in endo entry of the cuprate with high diastereoselectivity. Other cuprates were investigated and resulted in diminished or opposite stereoselectivities. Further transformation of the beta-substituted lactams provided the title compounds in good overall yield and high enantiomeric excess.

  DOI：

  10.1021/jo00040a018
• 作为产物：
  描述：

  (3S,7aR)-7a-Methyl-5-oxo-3-phenyl-2,3,5,7a-tetrahydro-pyrrolo[2,1-b]oxazole-6-carboxylic acid benzyl ester 在 palladium on activated charcoal aluminium hydride 、 甲酸铵 作用下， 以 四氢呋喃 、 甲醇 、 甲苯 为溶剂， 反应 28.83h， 生成 (2S,3R)-3-Butyl-2-methyl-pyrrolidine
  参考文献：
  名称：

  Asymmetric conjugate additions to chiral bicyclic lactams. Synthesis of aracemic trans-2,3-disubstituted pyrrolidines

  摘要：

  The trans-2,3-disubstituted pyrrolidine moiety, found in the pyrrolizidine alkaloids as well as other natural products, has been accessed from the alpha,beta-unsaturated bicyclic lactams 1d and 10. Conjugate addition of lower order cyanocuprates to lactams 1d and 10 resulted in endo entry of the cuprate with high diastereoselectivity. Other cuprates were investigated and resulted in diminished or opposite stereoselectivities. Further transformation of the beta-substituted lactams provided the title compounds in good overall yield and high enantiomeric excess.

  DOI：

  10.1021/jo00040a018

文献信息

• Asymmetric conjugate additions to chiral bicyclic lactams. Synthesis of aracemic trans-2,3-disubstituted pyrrolidines
  作者：A. I. Meyers、Lawrence Snyder

  DOI：10.1021/jo00040a018

  日期：1992.7

  The trans-2,3-disubstituted pyrrolidine moiety, found in the pyrrolizidine alkaloids as well as other natural products, has been accessed from the alpha,beta-unsaturated bicyclic lactams 1d and 10. Conjugate addition of lower order cyanocuprates to lactams 1d and 10 resulted in endo entry of the cuprate with high diastereoselectivity. Other cuprates were investigated and resulted in diminished or opposite stereoselectivities. Further transformation of the beta-substituted lactams provided the title compounds in good overall yield and high enantiomeric excess.