1-[(1-naphthalen-1-ylethylamino)phenylmethyl]naphthalen-2-ol | 1228146-08-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-[(1-naphthalen-1-ylethylamino)phenylmethyl]naphthalen-2-ol
• 英文别名: 1-[(S)-[[(1S)-1-naphthalen-1-ylethyl]amino]-phenylmethyl]naphthalen-2-ol
• CAS: 1228146-08-4
• 化学式: C₂₉H₂₅NO
• 分子量: 403.524
• InChiKey: SLFWOGAADNHCCI-WRONEBCDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  31
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  32.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-[(1-naphthalen-1-ylethylamino)phenylmethyl]naphthalen-2-ol 、 氯甲基膦酸二氯化物 在 吡啶 作用下， 以 甲苯 为溶剂， 以73%的产率得到(1S,3S)-3-(chloromethyl)-2-[(1S)-1-naphthalen-1-ylethyl]-1-phenyl-1H-benzo[f][1,3,2]benzoxazaphosphinine 3-oxide
  参考文献：
  名称：

  Stacked Naphthyls and Weak Hydrogen-Bond Interactions Govern the Conformational Behavior of P-Resolved Cyclic Phosphonamides: A Combined Experimental and Computational Study

  摘要：

  P-Enantiomerically pure cyclic phosphonamides have been synthesized via a cyclization reaction of (S,S)-aminobenzylnaphthols with chloromethylphosphonic dichloride. The reaction is highly stereoselective and gives almost exclusively (S,S,SP)-cyclic phosphonamides in good yields. Analysis of the X-ray crystal structures shows clearly that the cyclization reaction forces the two naphthyl rings into a stable parallel displaced stacking assembly and indicates also the existence of intramolecular CH···π interactions and weak forms of intermolecular hydrogen bondings, involving the oxygen and the chlorine atoms. QM computations and NMR spectra in solution confirm the stacked molecular assembly as the preferred arrangement of the two naphthyl groups.

  DOI：

  10.1021/jo502094g
• 作为产物：
  描述：

  (S)-(-)-1-(1-萘基)乙胺 、 苯甲醛 、 2-萘酚 反应 72.0h， 以20%的产率得到1-[(1-naphthalen-1-ylethylamino)phenylmethyl]naphthalen-2-ol
  参考文献：
  名称：

  光学活性aminonaphthols作为NMR的溶剂化剂为扁桃酸的手性识别应用

  摘要：

  一系列光学活性氨基萘酚衍生物的制备和筛选作为手性溶解剂以鉴别与c α由外消旋扁桃酸为h 1点H NMR分析。努力是为了建立在该非共价相互作用氨基萘酚衍生物的结构和选择性的相关性。通过指示系统可能用于确定未知对映体纯度的扁桃酸样品的ee，建立了实验对映体和计算对映体纯度之间的线性关系。

  DOI：

  10.1016/j.tetasy.2014.04.003

文献信息

• Bioactivity of a Family of Chiral Nonracemic Aminobenzylnaphthols towards Candida albicans
  作者：Maria Capozzi、Cosimo Cardellicchio、Angela Magaletti、Antonio Bevilacqua、Marianne Perricone、Maria Corbo

  DOI：10.3390/molecules19045219

  日期：——

  Chiral nonracemic aminobenzylnaphthols were obtained by a Betti multi-component reaction between 2-naphthol, aryl aldehydes and enantiopure arylethylamine. Moreover, some new aminobenzylnaphthols were synthesized by a similar reaction between 2-naphthol, aryl aldehydes and prolinol. These aminobenzylnaphthols, synthesized from different components and thus having different structural features, were

  手性非外消旋氨基苄基萘酚是通过 2-萘酚、芳基醛和对映纯芳乙胺之间的 Betti 多组分反应获得的。此外，通过2-萘酚、芳醛和脯氨醇之间的类似反应合成了一些新的氨基苄基萘酚。这些氨基苄基萘酚由不同的成分合成并因此具有不同的结构特征，被测试为抑制白色念珠菌的抗酵母剂。使用微量稀释方法研究了对测试菌株的影响，并测试了三种不同的浓度（150、300 和 450 µg/mL）。发现从 1-萘基乙胺和天然脯氨醇获得的氨基苄基萘酚的最佳结果。双向方差分析的使用突出了脯氨醇衍生物在筛选的不同结构的氨基苄基萘酚中的更好性能。这种脯氨醇衍生物对白色念珠菌的活性令人感兴趣，并且可以代表克服菌株对传统抗真菌剂具有抗性问题的有希望的替代方案。
• Stacked aryl groups in <i>P</i>-resolved cyclic phosphonamides as a new conformational constraint
  作者：Maria Annunziata M. Capozzi、Claudia Pigliacelli、Giancarlo Terraneo、Cosimo Cardellicchio

  DOI：10.1039/c9ce01382b

  日期：——

  constraints promoted by weak interactions, the aryl-stacked structures of some chiral cyclic phosphonamides synthesised with the aid of Betti bases as chirality inducers were investigated by X-ray diffraction analysis and NMR spectroscopy. The synthesised systems showed the stacked conformation between two of their aryl groups, leading to pre-organized structures. The π–π stacking motif between the aromatic

  沿着系统研究弱相互作用促进的构象约束的路线，通过X射线衍射分析和NMR光谱研究了以Betti碱为手性诱导剂合成的一些手性环状膦酰胺的芳基堆积结构。合成的系统显示出其两个芳基之间的堆叠构象，从而导致预组织的结构。在固态和溶液中都观察到了芳香环之间的π-π堆积基序，这表明这种超分子合成子可以用作构象约束工具，用于开发基于手性环磷酰胺的候选药物分子。通过在一个芳香环上添加邻位取代基来实现π-π堆积图案的失效。
• Investigation on the weak interactions assembling the crystal structures of Betti bases
  作者：Cosimo Cardellicchio、Maria Annunziata M. Capozzi、Angel Alvarez-Larena、Joan F. Piniella、Francesco Capitelli

  DOI：10.1039/c2ce06295j

  日期：——

  The crystal structures of (S, S)-aminobenzylnaphthols, easily produced by a chromatography-free highly stereoselective Betti reaction, were investigated by means of single crystal X-ray diffraction analysis, and the main intra- and intermolecular interactions were described. The presence of a strong intramolecular hydrogen bond was confirmed, whereas the whole crystal building was found to be due mainly to other bondings, such as CH⋯O and CH⋯π interactions. As far as the last interactions were concerned, we observed many short distances from one hydrogen atom to an aryl plane, together with the appropriate geometric requirements for the assemblies. The observations suggest that these interactions can play a relevant role in the crystal building. The absence of similar short distance CH⋯π interactions in the crystal of a diastereomeric (R, S)-aminobenzylnaphthol could be a suggestion of the preferential crystallisation of the (S, S)-stereoisomer and, consequently, its prevalence as a product of the Betti reaction.

  通过单晶 X 射线衍射分析，研究了通过无色谱法高立体选择性贝蒂反应轻松制备的 (S, S) - 氨基苄基萘酚的晶体结构，并描述了主要的分子内和分子间相互作用。证实了分子内氢键的存在，同时发现整个晶体结构主要是由于其他键，如 CH⋯O 和 CH⋯π 相互作用造成的。就最后一种相互作用而言，我们观察到从一个氢原子到一个芳基平面之间的许多短距离，以及组装的适当几何要求。这些观察结果表明，这些相互作用在晶体结构中起着重要作用。非对映异构体（R，S）-氨基苄基萘酚的晶体中没有类似的 CH⋯π 短距离相互作用，这表明（S，S）-非对映异构体优先结晶，因此，它是贝蒂反应的主要产物。