(S)-3-amino-4,4-dimethyl-1-phenylpyrrolidin-2-one | 1007129-51-2

• 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: (S)-3-amino-4,4-dimethyl-1-phenylpyrrolidin-2-one
• 英文别名: (3S)-3-amino-4,4-dimethyl-1-phenylpyrrolidin-2-one
• CAS: 1007129-51-2
• 化学式: C₁₂H₁₆N₂O
• 分子量: 204.272
• InChiKey: SXOMSEQNFPJPJN-SNVBAGLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  46.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  吡啶-2,6-二甲醛 、 (S)-3-amino-4,4-dimethyl-1-phenylpyrrolidin-2-one 在 sodium cyanoborohydride 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以100%的产率得到(S,S)-2,6-bis[(4,4-dimethyl-2-oxo-1-phenylpyrrolidin-3-yl)aminomethyl]pyridine
  参考文献：
  名称：

  Enantiodivergent synthesis of 3-amino-4,4-dimethyl-1-phenylpyrrolidin-2-one and derivatives: amino analogues of pantolactone

  摘要：

  An enantiodivergent preparation of (+)-(R)- and (-)-(S)-3-amino-4,4-dimethyl-1-phenylpyrrolidin-2-one, (R)- and (S)-9, and several derivatives, from 4,4-dimethyl-1-phenylpyrrolidin-2,3-dione, 4, and (R)- or (S)-1-phenylethylamine, (R)- or (S)-5, as the chirality transfer agents, is described. Amine (S)-9 has also been used as a chiral auxiliary in a diastereoselective Michael reaction. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.11.013
• 作为产物：
  描述：

  (3S,1'R)-4,4-dimethyl-1-phenyl-3-[(1-phenylethyl)amino]pyrrolidin-2-one 在 palladium on activated charcoal 盐酸 、 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 138.0h， 以87%的产率得到(S)-3-amino-4,4-dimethyl-1-phenylpyrrolidin-2-one
  参考文献：
  名称：

  Enantiodivergent synthesis of 3-amino-4,4-dimethyl-1-phenylpyrrolidin-2-one and derivatives: amino analogues of pantolactone

  摘要：

  An enantiodivergent preparation of (+)-(R)- and (-)-(S)-3-amino-4,4-dimethyl-1-phenylpyrrolidin-2-one, (R)- and (S)-9, and several derivatives, from 4,4-dimethyl-1-phenylpyrrolidin-2,3-dione, 4, and (R)- or (S)-1-phenylethylamine, (R)- or (S)-5, as the chirality transfer agents, is described. Amine (S)-9 has also been used as a chiral auxiliary in a diastereoselective Michael reaction. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.11.013

文献信息

• Enantiodivergent synthesis of 3-amino-4,4-dimethyl-1-phenylpyrrolidin-2-one and derivatives: amino analogues of pantolactone
  作者：Pelayo Camps、Diego Muñoz-Torrero、Jordi Rull、Mercè Font-Bardia、Xavier Solans

  DOI：10.1016/j.tetasy.2007.11.013

  日期：2007.12

  An enantiodivergent preparation of (+)-(R)- and (-)-(S)-3-amino-4,4-dimethyl-1-phenylpyrrolidin-2-one, (R)- and (S)-9, and several derivatives, from 4,4-dimethyl-1-phenylpyrrolidin-2,3-dione, 4, and (R)- or (S)-1-phenylethylamine, (R)- or (S)-5, as the chirality transfer agents, is described. Amine (S)-9 has also been used as a chiral auxiliary in a diastereoselective Michael reaction. (c) 2007 Elsevier Ltd. All rights reserved.