(S)-(naphthalen-1-ylmethylene)-α-phenylethylamine | 101475-72-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (S)-(naphthalen-1-ylmethylene)-α-phenylethylamine
• 英文别名: [1]naphthylmethylene-((S)-1-phenyl-ethyl)-amine；[1]Naphthylmethylen-((S)-1-phenyl-aethyl)-amin；[1]Naphthylaldehyd-((S)-1-phenyl-aethylimin)；1-naphthalen-1-yl-N-[(1S)-1-phenylethyl]methanimine
• CAS: 101475-72-3
• 化学式: C₁₉H₁₇N
• 分子量: 259.351
• InChiKey: LGVAJFHALSBONP-HNNXBMFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  12.4
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  、 1-萘甲醛 以 neat (no solvent) 为溶剂， 反应 0.5h， 生成 (S)-(naphthalen-1-ylmethylene)-α-phenylethylamine
  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

• Synthesis of 1,3-aminonaphthols by diastereoselective Betti-type aminoalkylation of dihydroxy naphthalenes; diastereoselectivity, absolute configuration, and application
  作者：Maya Marinova、Kalina Kostova、Pavleta Tzvetkova、Maya Tavlinova-Kirilova、Angel Chimov、Rosica Nikolova、Boris Shivachev、Vladimir Dimitrov

  DOI：10.1016/j.tetasy.2013.09.023

  日期：2013.12

  Dihydroxy naphthalenes have been applied in Betti-type solventless condensation between aldehydes and (S)-phenylethylamine as a chiral auxiliary. A series of chiral 1,3-aminonaphthols has been synthesized and isolated in diastereoisomerically pure form. The absolute configurations of the aminonaphthols synthesized have been determined by means of advanced NMR experiments and confirmed by X-ray crystallography

  二羟基萘已用于醛与（S）-苯乙胺之间的Betti型无溶剂缩合，作为手性助剂。已经合成和分离了一系列非对映异构纯形式的手性1，3-氨基萘。合成的氨基萘的绝对构型已通过高级NMR实验确定，并通过X射线晶体学证实。新的手性氨基萘已被测试为将二乙基锌和炔基锌试剂加到醛中的对映体，其对映选择性高达98％ee。
• 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.
• One-pot solvent-free reductive amination with a solid ammonium carbamate salt from CO₂ and amine
  作者：Philjun Kang、Kyu Myung Lee、Won Koo Lee、Kyu Hyung Lee、Byeongno Lee、Jaeheung Cho、Nam Hwi Hur

  DOI：10.1039/c4ra07558g

  日期：——

  Many amines are liquid and their handling is inconvenient compared with the corresponding solids.

  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。