(S)-(naphthalen-1-ylmethyl)-α-phenethylamine | 24652-82-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (S)-(naphthalen-1-ylmethyl)-α-phenethylamine
• 英文别名: S-(-)-N-(1-naphthylmethyl)-α-methylbenzylamine；1-Phenyl-N-(β-methylennaphthalin)-aethylamin；(1S)-N-(naphthalen-1-ylmethyl)-1-phenylethanamine
• CAS: 24652-82-2
• 化学式: C₁₉H₁₉N
• 分子量: 261.367
• InChiKey: ZHBRSTZUNUZOJO-HNNXBMFYSA-N

物化性质

• 沸点：
  402.4±14.0 °C(Predicted)
• 密度：
  1.074±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (S)-(naphthalen-1-ylmethyl)-α-phenethylamine 、 2-硝基苯甲酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以86%的产率得到(S)-N-(naphthalen-1-ylmethyl)-2-nitro-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
• 作为产物：
  描述：

  (S)-(naphthalen-1-ylmethylene)-α-phenylethylamine 在 platinum(IV) oxide 、 氢气 作用下， 以 neat (no solvent) 为溶剂， 反应 26.0h， 生成 (S)-(naphthalen-1-ylmethyl)-α-phenethylamine
  参考文献：
  名称：

  One-pot solvent-free reductive amination with a solid ammonium carbamate salt from CO₂ and amine

  摘要：

  许多胺类化合物是液体，与相应的固体相比，它们的处理不太方便。

  DOI：

  10.1039/c4ra07558g

文献信息

• Efficient, Selective, and Green:  Catalyst Tuning for Highly Enantioselective Reactions of Ethylene
  作者：Craig R. Smith、T. V. RajanBabu

  DOI：10.1021/ol800395m

  日期：2008.4.1

  Fine tuning of the biaryl and amino moieties of Feringa's phosphoramidite ligands yields structurally simpler, yet more efficient and selective, ligands for asymmetric hydrovinylation of vinylarenes and acylic 1,3-dienes. The enantioselectivities and yields observed in the formation of the 3-arylbutenes are among the highest for all asymmetric catalytic processes reported to date for the synthesis of intermediates for the widely used antiinflammatory 2-arylpropionic acids including naproxen, ibuprofen, fenoprofen, and flurbiprofen.
• (R)-2,2'-BINAPHTHOYL-(S,S)-DI(1-PHENYLETHYL) AMINOPHOSPHINE. SCALABLE PROTOCOLS FOR THE SYNTHESES OF PHOSPHORAMIDITE (FERINGA) LIGANDS
  作者：Smith, Craig R.、Mans, Daniel J.、RajanBabu、Denmark, Scott E.、Nguyen, T.

  DOI：10.15227/orgsyn.085.0238

  日期：——
• US5001251A
  申请人：——

  公开号：US5001251A

  公开（公告）日：1991-03-19
• US5097043A
  申请人：——

  公开号：US5097043A

  公开（公告）日：1992-03-17
• 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.