1-[(R)-phenyl{[(1'R)-1'-(1-naphthyl)ethyl]amino}methyl]-2-naphthol

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-[(R)-phenyl{[(1'R)-1'-(1-naphthyl)ethyl]amino}methyl]-2-naphthol
• 英文别名: 1-[(R)-phenyl-(1'R)-(1-naphthyl)ethylaminomethyl]-2-naphthol；1-[(R)-[[(1R)-1-naphthalen-1-ylethyl]amino]-phenylmethyl]naphthalen-2-ol
• 化学式: C₂₉H₂₅NO
• 分子量: 403.524
• InChiKey: SLFWOGAADNHCCI-ACSYHNTCSA-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：

  5,11,17,23-tetra-t-butyl-25,27-di(2-bromopropyl)-26,28-dihydroxycalix[4]arene 、 1-[(R)-phenyl{[(1'R)-1'-(1-naphthyl)ethyl]amino}methyl]-2-naphthol 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以73%的产率得到25,27-bis[(1-((R)-phenyl{[(1'R)-1'-naphthylethyl]amino}methyl)naphthalen-2-yloxy)propoxy]-26,28-dihydroxy-5,11,17,23-tetra(tert-butyl)calix[4]arene
  参考文献：
  名称：

  带有氨基萘部分的手性杯[4]芳烃的合成及其在羧酸的对映体识别中的应用†

  摘要：

  制备了两个在下部边缘用手性氨基萘酚官能化的武装手性杯[4]芳烃8-16，并通过FTIR，1 H和13 C，DEPT和COZY NMR光谱学和元素分析对这些受体的结构进行了表征。通过1 H NMR和UV / Vis光谱研究了这些受体与各种羧酸的对映选择性识别。受体对外消旋物质的对映异构体表现出不同的手性识别能力，并在宿主和客体之间形成2：1或1：1的复合物。还证明手性杯[4]芳烃9和16 可以用作手性NMR溶剂来确定对映体的纯度 扁桃酸。

  DOI：

  10.1039/c0ob00399a
• 作为产物：
  描述：

  (R)-1-(1-萘基)乙胺 、 苯甲醛 、 2-萘酚 反应 72.0h， 以82%的产率得到1-[(R)-phenyl{[(1'R)-1'-(1-naphthyl)ethyl]amino}methyl]-2-naphthol
  参考文献：
  名称：

  Microwave-assisted, highly enantioselective addition of diethylzinc to aromatic aldehydes catalyzed by chiral aminonaphthols

  摘要：

  New optically active aminonaphthols were obtained by condensation of 2-naphthol, benzaldehyde and (R)-(+)-1-(1-naphthyl)ethylamine or (R)-(+)-1-(2-naphthyl)ethylamine. Their N-methylated derivatives were also synthesized. The new aminonaphthols 2, 4, 5 and 7 were found to catalyze the enantioselective ethylation of aryl aldehydes to 1-aryl-1-propanots (up to 92% ee). The reactions were accelerated greatly by microwave irradiation. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.01.025

文献信息

• A facile synthesis of 3,4-dialkyl-3,4-dihydro-2<i>H</i>-1,3-benzoxazin-2-ones and naphthoxazin-2-ones and their reactions with organolithium and Grignard reagents – Preparation of <i>N</i>-[1-(2′-hydroxyphenyl)alkyl]amides
  作者：Cristina Cimarelli、Gianni Palmieri、Emanuela Volpini

  DOI：10.1139/v04-100

  日期：2004.8.1

  A facile and simple method for the preparation of 3,4-dialkyl-3,4-dihydro-2H-1,3-benzoxazin-2-ones or naphthoxazin-2-ones in high yields from aminoalkylphenols and aminoalkylnaphthols is described. The reactions of the products obtained with organolithium and Grignard reagents were studied, and a method for the preparation of N-[1-(2-hydroxyphenyl)alkyl]-N-alkylamides, which are of pharmaceutical interest, from benzoxazinones was developed. A possible reaction mechanism is also proposed. The relative configuration of chiral products was determined from conformational analysis of ¹H NMR spectra.Key words: benzoxazinones, naphthoxazinones, organometallic reagents, amide preparation, aminoalkylphenols.

  一种简便易行的方法，通过氨基烷基苯酚和氨基烷基萘酚的反应，高产率制备3,4-二烷基-3,4-二氢-2H-1,3-苯并噁嗪-2-酮或萘噁嗪-2-酮。研究了产物与有机锂和格氏试剂的反应，并开发了一种从苯并噁嗪酮制备具有药物兴趣的N-[1-(2-羟基苯基)烷基]-N-烷基酰胺的方法。同时提出了可能的反应机理。通过构象分析的1H NMR光谱确定了手性产物的相对构型。关键词：苯并噁嗪酮，萘噁嗪酮，有机金属试剂，酰胺制备，氨基烷基苯酚。
• A practical stereoselective synthesis of secondary and tertiary aminonaphthols: chiral ligands for enantioselective catalysts in the addition of diethylzinc to benzaldehyde
  作者：Cristina Cimarelli、Gianni Palmieri、Emanuela Volpini

  DOI：10.1016/s0957-4166(02)00651-1

  日期：2002.11

  A practical procedure for the stereoselective synthesis of a wide group of functionalized aminoalkylnaphthols, using inexpensive starting materials, is reported. Selective N-alkylation was carried out by cyclization of secondary aminoalkylnaphthols with formaldehyde, followed by reduction or alkylation with organometallic reagents. The catalytic activity of this class of compounds was tested in the addition of diethylzine to benzaldehyde, resulting in moderate to good enantio selectivities. It is noteworthy that the aminonaphthols obtained as the major diastereomer in the solvent free synthesis, have the best asymmetric induction properties in the alkylation reaction. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Chiral calix[4]arenes bearing aminonaphthol moieties as membrane carriers for amino acid methyl esters and mandelic acid
  作者：Mustafa Durmaz、Selahattin Bozkurt、Hayriye Nevin Naziroglu、Mustafa Yilmaz、Abdulkadir Sirit

  DOI：10.1016/j.tetasy.2011.04.019

  日期：2011.4

  Chiral calix[4]arene derivatives functionalized at the lower rim with chiral aminonaphthol units have been prepared. The structures of these receptors were characterized by a combination of (1)H NMR, (13)C NMR, FTIR and elemental analysis. The transport of amino acid derivatives (phenylglycine, phenylalanine and tryptophan methyl ester hydrochlorides) and mandelic acid were studied through a bulk liquid membrane in the presence of chiral calix[4]arene derivatives. The transport rate and enantioselectivity of the amino acid esters studied depended mainly upon the structure of the chiral receptors. The influence of calixarene and amino acid ester structures upon transport through a liquid membrane is discussed. The receptors with hydrogen bonding sites and aromatic groups showed considerable higher transport rates and stereoselectivities. (C) 2011 Elsevier Ltd. All rights reserved.
• Microwave-assisted, highly enantioselective addition of diethylzinc to aromatic aldehydes catalyzed by chiral aminonaphthols
  作者：István Szatmári、Reijo Sillanpää、Ferenc Fülöp

  DOI：10.1016/j.tetasy.2008.01.025

  日期：2008.3

  New optically active aminonaphthols were obtained by condensation of 2-naphthol, benzaldehyde and (R)-(+)-1-(1-naphthyl)ethylamine or (R)-(+)-1-(2-naphthyl)ethylamine. Their N-methylated derivatives were also synthesized. The new aminonaphthols 2, 4, 5 and 7 were found to catalyze the enantioselective ethylation of aryl aldehydes to 1-aryl-1-propanots (up to 92% ee). The reactions were accelerated greatly by microwave irradiation. (C) 2008 Elsevier Ltd. All rights reserved.
• Synthesis of chiral calix[4]arenes bearing aminonaphthol moieties and their use in the enantiomeric recognition of carboxylic acids
  作者：Mustafa Durmaz、Mustafa Yilmaz、Abdulkadir Sirit

  DOI：10.1039/c0ob00399a

  日期：——

  exhibited different chiral recognition abilities towards the enantiomers of racemic materials and formed 2 : 1 or 1 : 1 complexes between host and guest. It was also demonstrated that chiral calix[4]arenes 9 and 16 could be used as chiral NMR solvating agents to determine the enantiomeric purity of mandelic acid.

  制备了两个在下部边缘用手性氨基萘酚官能化的武装手性杯[4]芳烃8-16，并通过FTIR，1 H和13 C，DEPT和COZY NMR光谱学和元素分析对这些受体的结构进行了表征。通过1 H NMR和UV / Vis光谱研究了这些受体与各种羧酸的对映选择性识别。受体对外消旋物质的对映异构体表现出不同的手性识别能力，并在宿主和客体之间形成2：1或1：1的复合物。还证明手性杯[4]芳烃9和16 可以用作手性NMR溶剂来确定对映体的纯度 扁桃酸。