(S)-1-<(2,2-Dimethylpropanoyl)amino>-1-naphthylethane | 74687-25-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (S)-1-<(2,2-Dimethylpropanoyl)amino>-1-naphthylethane
• 英文别名: N-((S)-1-(naphthalen-1-yl)ethyl)pivalamide；2,2-dimethyl-N-[(1S)-1-naphthalen-1-ylethyl]propanamide
• CAS: 74687-25-5
• 化学式: C₁₇H₂₁NO
• 分子量: 255.36
• InChiKey: BCOGNHXSESTSPI-LBPRGKRZSA-N

物化性质

• 沸点：
  445.4±24.0 °C(Predicted)
• 密度：
  1.039±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  (S)-(-)-1-(1-萘基)乙胺 、 三甲基乙酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 9.0h， 以87%的产率得到(S)-1-<(2,2-Dimethylpropanoyl)amino>-1-naphthylethane
  参考文献：
  名称：

  Chiral Recognition Studies: Intra- and Intermolecular 1H{1H}-Nuclear Overhauser Effects as Effective Tools in the Study of Bimolecular Complexes

  摘要：

  DOI：

  10.1021/jo00115a048

文献信息

• Kinetic resolution of primary amines via enantioselective N-acylation with acyl chlorides in the presence of supramolecular cyclodextrin nanocapsules
  作者：Haruyasu Asahara、Toshiyuki Kida、Takuya Iwamoto、Tomoaki Hinoue、Mitsuru Akashi

  DOI：10.1016/j.tet.2013.11.097

  日期：2014.1

  non-enzymatic kinetic resolution of primary amines via enantioselective N-acylation with acyl chlorides was accomplished for the first time by using the selective sequestration of one enantiomer within a supramolecular cyclodextrin (CD) nanocapsule in nonpolar solvents. In addition, the first example of a crystalline structure for an inclusion complex between an acyl chloride and a CD derivative is reported

  通过使用超分子环糊精（CD）纳米胶囊在非极性溶剂中的选择性螯合，首次实现了通过酰氯与对映体选择性N-酰化伯胺的非酶动力学拆分。另外，报道了酰氯和CD衍生物之间的包合配合物的晶体结构的第一个例子。
• Chiral Recognition Studies: Intra- and Intermolecular 1H{1H}-Nuclear Overhauser Effects as Effective Tools in the Study of Bimolecular Complexes
  作者：William H. Pirkle、Shaun R. Selness

  DOI：10.1021/jo00115a048

  日期：1995.5
• A Versatile and Practical Solvating Agent for Enantioselective Recognition and NMR Analysis of Protected Amines
  作者：Daniel P. Iwaniuk、Christian Wolf

  DOI：10.1021/jo101426a

  日期：2010.10.1

  The 3,5-dinitrobenzoyl-derived 1-naphthylethyl amide 3 is an attractive CSA for NMR analysis of protected amines. It is readily prepared in a single step and combines practical resolution of diastereomeric complexes due to signal sharpness and effective signal separation. Crystallographic analysis shows that 3 forms a chiral cleft that can selectively bind one enantiomer of a substrate through hydrogen bonding, pi-pi stacking, and CH/pi interactions. The enantioselective complex formation causes strong upfield shifts in the H-1 NMR spectrum even in the presence of only 5 mol % of 3.