tert-butyl N-[(2S)-1-(3,5-dimethylanilino)-1-oxopropan-2-yl]carbamate | 126787-24-4

• 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: tert-butyl N-[(2S)-1-(3,5-dimethylanilino)-1-oxopropan-2-yl]carbamate
• CAS: 126787-24-4
• 化学式: C₁₆H₂₄N₂O₃
• 分子量: 292.378
• InChiKey: GRHJKWHWEXLLBF-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  67.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  tert-butyl N-[(2S)-1-(3,5-dimethylanilino)-1-oxopropan-2-yl]carbamate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 (2S)-2-amino-N-(3,5-dimethylphenyl)propanamide
  参考文献：
  名称：

  Enhanced gelation property due to intra-molecular hydrogen bonding in a new series of bis(amino acid)-functionalized pyridine-2,6-dicarboxamide organogelators

  摘要：

  A series of pyridine-2,6-dicarboxamide derivatives containing two alpha-amino acid pendant groups was prepared and characterized. Three of the synthesized compounds obtained from this series, all having aromatic amino acid side chains, were found to be excellent organo-gelators toward aromatic solvents (mgc similar to 10-20 mg/mL), alcoholic solvents (mgc similar to 4-15 mg/mL), and CCl4 ( mgc similar to 4-10 mg/mL). It was found that the intra-molecular hydrogen bonds between the pyridine dicarboxamide N-Hs and the pyridine N atom were the key structural elements for gel formation. This series of compounds represented one of the rare examples where both inter- and intra-molecular hydrogen bonds were needed for effective gel formation. FTIR, H-1 NMR, and CD spectroscopy revealed that both hydrogen bonding and pi-pi aromatic stacking were the driving forces for gelation. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.02.037
• 作为产物：
  描述：

  N-叔丁氧羰基-L-丙氨酸 、 1-氨基-3,5-二甲苯 在 2-乙氧基-1-乙氧碳酰基-1,2-二氢喹啉 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 tert-butyl N-[(2S)-1-(3,5-dimethylanilino)-1-oxopropan-2-yl]carbamate
  参考文献：
  名称：

  Tertiary Amine Appended Derivatives of N-(3,5-Dinitrobenzoyl)leucine as Chiral Selectors for Enantiomer Assays by Electrospray Ionization Mass Spectrometry

  摘要：

  合成了手性选择剂N-(3,5-二硝基苯甲酰)亮氨酸的衍生物，并将其用于单阶段电喷雾电离质谱实验中的对映体歧视。设计这些手性选择剂是为了将离子化位点与有效的手性识别所需的位点分离。将一种手性分析物加入到含有两个伪对映体手性选择剂的溶液中，这两个选择剂在绝对立体化学和连接用于通过质子化进行离子化的三级胺位点与其余手性选择剂的绳索长度上有所不同，形成了在电喷雾电离质谱中观察到的选择剂-分析物复合物，其中这些复合物的比例取决于分析物的对映体组成。选择剂-分析物复合物在电喷雾电离质谱中的比例与分析物的对映体组成之间的关系可以用来关联所观察到的对映选择性程度，并进行定量对映体组成的测定。本文还探讨了该方法的适用范围和局限性，并与使用N-(3,5-二硝基苯甲酰)亮氨酸衍生的手性固定相的手性高效液相色谱法观察到的对映选择性进行了比较。

  DOI：

  10.1021/ac050438n

文献信息

• Tertiary Amine Appended Derivatives of <i>N</i>-(3,5-Dinitrobenzoyl)leucine as Chiral Selectors for Enantiomer Assays by Electrospray Ionization Mass Spectrometry
  作者：ChengLi Zu、Bobby N. Brewer、Beibei Wang、Michael E. Koscho

  DOI：10.1021/ac050438n

  日期：2005.8.1

  Derivatives of the chiral selector N-(3,5-dinitrobenzoyl)leucine were prepared and used as chiral selectors for enantiomer discrimination in single-stage electrospray ionization mass spectrometric experiments. The chiral selectors were designed to remove the ionization site from the sites required for effective chiral recognition. Addition of a chiral analyte to a solution of the two pseudoenantiomeric chiral selectors, which differ in absolute stereochemistry and the length of the tether connecting the tertiary amine site used for ionization via protonation and the rest of the chiral selector, affords selector−analyte complexes in the electrospray ionization mass spectrum where the ratio of these complexes is dependent on the enantiomeric composition of the analyte. The relationship between the ratio of the selector−analyte complexes in the electrospray ionization mass spectrum and the enantiomeric composition of the analyte can be used to relate the extent of enantioselectivity that is being observed and for quantitative enantiomeric composition determinations. Investigations into the scope and limitations of this method, plus a comparison to the enantioselectivities observed by chiral HPLC using a N-(3,5-dinitrobenzoyl)leucine-derived chiral stationary phase, is presented.

  合成了手性选择剂N-(3,5-二硝基苯甲酰)亮氨酸的衍生物，并将其用于单阶段电喷雾电离质谱实验中的对映体歧视。设计这些手性选择剂是为了将离子化位点与有效的手性识别所需的位点分离。将一种手性分析物加入到含有两个伪对映体手性选择剂的溶液中，这两个选择剂在绝对立体化学和连接用于通过质子化进行离子化的三级胺位点与其余手性选择剂的绳索长度上有所不同，形成了在电喷雾电离质谱中观察到的选择剂-分析物复合物，其中这些复合物的比例取决于分析物的对映体组成。选择剂-分析物复合物在电喷雾电离质谱中的比例与分析物的对映体组成之间的关系可以用来关联所观察到的对映选择性程度，并进行定量对映体组成的测定。本文还探讨了该方法的适用范围和局限性，并与使用N-(3,5-二硝基苯甲酰)亮氨酸衍生的手性固定相的手性高效液相色谱法观察到的对映选择性进行了比较。
• Enhanced gelation property due to intra-molecular hydrogen bonding in a new series of bis(amino acid)-functionalized pyridine-2,6-dicarboxamide organogelators
  作者：Hak-Fun Chow、Guo-Xin Wang

  DOI：10.1016/j.tet.2007.02.037

  日期：2007.7

  A series of pyridine-2,6-dicarboxamide derivatives containing two alpha-amino acid pendant groups was prepared and characterized. Three of the synthesized compounds obtained from this series, all having aromatic amino acid side chains, were found to be excellent organo-gelators toward aromatic solvents (mgc similar to 10-20 mg/mL), alcoholic solvents (mgc similar to 4-15 mg/mL), and CCl4 ( mgc similar to 4-10 mg/mL). It was found that the intra-molecular hydrogen bonds between the pyridine dicarboxamide N-Hs and the pyridine N atom were the key structural elements for gel formation. This series of compounds represented one of the rare examples where both inter- and intra-molecular hydrogen bonds were needed for effective gel formation. FTIR, H-1 NMR, and CD spectroscopy revealed that both hydrogen bonding and pi-pi aromatic stacking were the driving forces for gelation. (c) 2007 Elsevier Ltd. All rights reserved.