(-)-(S)-2-N-methylamino-2,3-dimethylbutanamide | 1016562-12-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (-)-(S)-2-N-methylamino-2,3-dimethylbutanamide
• 英文别名: (S)-2-N-methylamino-2,3-dimethylbutanamide；(2S)-2,3-dimethyl-2-(methylamino)butanamide
• CAS: 1016562-12-1
• 化学式: C₇H₁₆N₂O
• 分子量: 144.217
• InChiKey: DRXHRWNPGGCPER-ZETCQYMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  55.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-吡啶甲酸 、 (-)-(S)-2-N-methylamino-2,3-dimethylbutanamide 在 4-二甲氨基吡啶 、 达卡巴嗪 、 sodium hydroxide 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以62%的产率得到(-)-(S)-(5-isopropyl-1,5-dimethyl-4,5-dihydro-1H-imidazol-4-on-2-yl)pyridine
  参考文献：
  名称：

  Synthesis of (R)- and (S)-2-N-methylamino-2,3-dimethylbutanamides and (R)- and (S)-(5-isopropyl-1,5-dimethyl-4,5-dihydro-1H-imidazol-4-on-2-yl)pyridines

  摘要：

  Both (R)- and (S)-2-N-methylamino-2,3-dimethylbutanamides have been prepared by the reductive benzylation of (R)- and (S)-2-amino-2,3-dimethylbutanamides, followed by reductive methylation and hydrogenolytic removal of the benzyl group. The reductive benzylation is chemoselective, and not accompanied by dibenzylation even with the application of excess benzaldehyde. Acylation of the (R)- and (S)-2-N-methylamino-2,3-dimethylbutanamides with picolinic acid and subsequent ring closure gave the respective (R)- and (S)-(5-isopropyl-1,5-dimethyl-4,5-dihydro-1H-imidazol-4-on-2-yl)pyridines. Their complexes with Cu(I) catalyze the Kharash-Sosnovsky allylic oxidation with overall yields as high as 99% but with low enantioselectivity. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.01.016
• 作为产物：
  描述：

  (+)-(S)-2-N-benzyl-N-methylamino-2,3-dimethylbutanamide 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 以90%的产率得到(-)-(S)-2-N-methylamino-2,3-dimethylbutanamide
  参考文献：
  名称：

  Synthesis of (R)- and (S)-2-N-methylamino-2,3-dimethylbutanamides and (R)- and (S)-(5-isopropyl-1,5-dimethyl-4,5-dihydro-1H-imidazol-4-on-2-yl)pyridines

  摘要：

  Both (R)- and (S)-2-N-methylamino-2,3-dimethylbutanamides have been prepared by the reductive benzylation of (R)- and (S)-2-amino-2,3-dimethylbutanamides, followed by reductive methylation and hydrogenolytic removal of the benzyl group. The reductive benzylation is chemoselective, and not accompanied by dibenzylation even with the application of excess benzaldehyde. Acylation of the (R)- and (S)-2-N-methylamino-2,3-dimethylbutanamides with picolinic acid and subsequent ring closure gave the respective (R)- and (S)-(5-isopropyl-1,5-dimethyl-4,5-dihydro-1H-imidazol-4-on-2-yl)pyridines. Their complexes with Cu(I) catalyze the Kharash-Sosnovsky allylic oxidation with overall yields as high as 99% but with low enantioselectivity. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.01.016

文献信息

• Highly Enantioselective Nitroaldol Reactions Catalyzed by Copper(II) Complexes Derived from Substituted 2-(Pyridin-2-yl)imidazolidin-4-one Ligands
  作者：Illia Panov、Pavel Drabina、Zdeňka Padělková、Petr Šimůnek、Miloš Sedlák

  DOI：10.1021/jo200703j

  日期：2011.6.3

  prepared and characterized. The absolute configurations of individual ligands were determined by X-ray analysis or NOESY experiments. The Cu(II) complexes of the respective ligands were studied as enantioselective catalysts of the nitroaldol (Henry) reaction of aldehydes with nitromethane, giving the corresponding substituted 2-nitroalkanols. In the case of an anti arrangement of the imidazolidin-4-one

  十光学纯取代的2-（吡啶-2-基）咪唑烷-4-酮，1A - d，2A -图4a和图2b - 4 b，制备和表征。各个配体的绝对构型通过X射线分析或NOESY实验确定。研究了各个配体的Cu（II）配合物，作为醛与硝基甲烷的硝基羟醛（Henry）反应的对映选择性催化剂，得到了相应的取代的2-硝基链烷醇。在咪唑烷丁-4-酮环的反排列情况下，获得的结果为91–96％ee，而在顺式排列的情况下，观察到显着下降至25–27％ee。