(S)-N-(naphthalen-1-ylmethyl)-2-(4-tert-butylphenylsulfonylamino)-N-(α-phenylethyl)benzamide

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (S)-N-(naphthalen-1-ylmethyl)-2-(4-tert-butylphenylsulfonylamino)-N-(α-phenylethyl)benzamide
• 英文别名: 2-[(4-tert-butylphenyl)sulfonylamino]-N-(naphthalen-1-ylmethyl)-N-[(1S)-1-phenylethyl]benzamide
• 化学式: C₃₆H₃₆N₂O₃S
• 分子量: 576.759
• InChiKey: JEHVPDLWSQVSFL-SANMLTNESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.8
• 重原子数：
  42
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  74.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  对叔丁基苯磺酰氯 、 (S)-N-(naphthalen-1-ylmethyl)-2-amino-N-(α-phenylethyl)benzamide 在 吡啶 作用下， 反应 12.0h， 以89%的产率得到(S)-N-(naphthalen-1-ylmethyl)-2-(4-tert-butylphenylsulfonylamino)-N-(α-phenylethyl)benzamide
  参考文献：
  名称：

  Synthesis and dynamics of atropisomeric (S)-N-(α-phenylethyl)benzamides

  摘要：

  The synthesis of atropisomeric 2-substituted benzamides 2a-e, 3a-e, and 4a-e, and characterization by X-ray structure analysis of 2d, 2e, 3c, 3e, 4c, and 4e are reported. Dynamic H-1 NMR spectroscopic studies of benzamides 2b-d, 3b-d, and 4b-d indicate that only two of the four possible rotamers are present in solution, with population ratios ranging between 1.5:1 and 4. 1:1. The measured free energy of activation to interconversion of the rotamers ranged from 12.4 to 18.9 kcal mol(-1). Benzamides ArCON[(S)-phenethyl]2 (2e, 3e, and 4e), exhibited atropisomer ratios between 1.7:1 and 1: 1, and free energies of interconversion of the rotamers ranged from 11.5 to 17.6 kcal mol(-1). The highest rotation barriers were observed for the ortho-nitro derivatives 2a-e. Molecular calculations at the semiempirical level (PM3MM) gave free energies of activation for benzamides 2e and 3e of 23.6 and 12.4 kcal mol(-1), respectively, which are comparable to the experimental values. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.10.010

文献信息

• Synthesis and dynamics of atropisomeric (S)-N-(α-phenylethyl)benzamides
  作者：Gabriela Huelgas、Sylvain Bernès、Mario Sánchez、Leticia Quintero、Eusebio Juaristi、Cecilia Anaya de Parrodi、Patrick J. Walsh

  DOI：10.1016/j.tet.2007.10.010

  日期：2007.12

  The synthesis of atropisomeric 2-substituted benzamides 2a-e, 3a-e, and 4a-e, and characterization by X-ray structure analysis of 2d, 2e, 3c, 3e, 4c, and 4e are reported. Dynamic H-1 NMR spectroscopic studies of benzamides 2b-d, 3b-d, and 4b-d indicate that only two of the four possible rotamers are present in solution, with population ratios ranging between 1.5:1 and 4. 1:1. The measured free energy of activation to interconversion of the rotamers ranged from 12.4 to 18.9 kcal mol(-1). Benzamides ArCON[(S)-phenethyl]2 (2e, 3e, and 4e), exhibited atropisomer ratios between 1.7:1 and 1: 1, and free energies of interconversion of the rotamers ranged from 11.5 to 17.6 kcal mol(-1). The highest rotation barriers were observed for the ortho-nitro derivatives 2a-e. Molecular calculations at the semiempirical level (PM3MM) gave free energies of activation for benzamides 2e and 3e of 23.6 and 12.4 kcal mol(-1), respectively, which are comparable to the experimental values. (c) 2007 Elsevier Ltd. All rights reserved.