N-(1R,3S)-1,2,2-trimethyl-3-(pyrrolidin-1-ylcarbonyl)cyclopentanecarboxyliminopyridinium ylide | 554411-13-1

• 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: N-(1R,3S)-1,2,2-trimethyl-3-(pyrrolidin-1-ylcarbonyl)cyclopentanecarboxyliminopyridinium ylide
• 英文别名: (1Z,1R,3S)-1,2,2-trimethyl-N-pyridin-1-ium-1-yl-3-(pyrrolidine-1-carbonyl)cyclopentane-1-carboximidate
• CAS: 554411-13-1
• 化学式: C₁₉H₂₇N₃O₂
• 分子量: 329.442
• InChiKey: HHLQIKMUXGZYCV-BEFAXECRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  59.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  丙基氯化镁 、 N-(1R,3S)-1,2,2-trimethyl-3-(pyrrolidin-1-ylcarbonyl)cyclopentanecarboxyliminopyridinium ylide 在 sodium tetrahydroborate 作用下， 以 乙醚 、 甲苯 、 甲醇 为溶剂， 反应 23.25h， 生成 (1R,3S)-1,2,2-trimethyl-N-[(6R)-6-propyl-3,6-dihydropyridin-1(2H)-yl]-3-(pyrrolidin-1-ylcarbonyl)cyclopentanecarboxamide 、 (1R,3S)-1,2,2-trimethyl-N-[(6S)-6-propyl-3,6-dihydropyridin-1(2H)-yl]-3-(pyrrolidin-1-ylcarbonyl)cyclopentanecarboxamide
  参考文献：
  名称：

  Complexation Promoted Additions to N-Benzoyliminopyridinium Ylides. A Novel and Highly Regioselective Approach to Polysubstituted Piperidines

  摘要：

  Unprecedented regioselectivities were observed for the addition of different organometallic nucleophiles to N-benzoyliminopyridinium ylides. Even benzylic and branched aliphatic Grignard reagents, which usually give substantial amounts of 1,4-adducts, showed excellent 1,2-regioselectivities. The electronic nature of the pyridinium ylide is taken into account to explain these results.

  DOI：

  10.1021/ja0348647
• 作为产物：
  描述：

  (1R,3S)-(+)-樟脑酐 在 草酰氯 、 potassium carbonate 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 17.0h， 生成 N-(1R,3S)-1,2,2-trimethyl-3-(pyrrolidin-1-ylcarbonyl)cyclopentanecarboxyliminopyridinium ylide
  参考文献：
  名称：

  Complexation Promoted Additions to N-Benzoyliminopyridinium Ylides. A Novel and Highly Regioselective Approach to Polysubstituted Piperidines

  摘要：

  Unprecedented regioselectivities were observed for the addition of different organometallic nucleophiles to N-benzoyliminopyridinium ylides. Even benzylic and branched aliphatic Grignard reagents, which usually give substantial amounts of 1,4-adducts, showed excellent 1,2-regioselectivities. The electronic nature of the pyridinium ylide is taken into account to explain these results.

  DOI：

  10.1021/ja0348647

文献信息

• Complexation Promoted Additions to <i>N</i>-Benzoyliminopyridinium Ylides. A Novel and Highly Regioselective Approach to Polysubstituted Piperidines
  作者：Claude Legault、André B. Charette

  DOI：10.1021/ja0348647

  日期：2003.5.1

  Unprecedented regioselectivities were observed for the addition of different organometallic nucleophiles to N-benzoyliminopyridinium ylides. Even benzylic and branched aliphatic Grignard reagents, which usually give substantial amounts of 1,4-adducts, showed excellent 1,2-regioselectivities. The electronic nature of the pyridinium ylide is taken into account to explain these results.