2-[4-(allylamino)-6-{[(1S)-1-(1-naphthyl)ethyl]amino}-1,3,5-triazin-2-yloxy]ethylamine | 385366-63-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-[4-(allylamino)-6-{[(1S)-1-(1-naphthyl)ethyl]amino}-1,3,5-triazin-2-yloxy]ethylamine
• 英文别名: 2-{[4-allylamino-6-(S)-(1-(1-naphthyl)ethylamino)-1,3,5-triazin-2-yl]oxy}ethylamine；6-(2-aminoethoxy)-2-N-[(1S)-1-naphthalen-1-ylethyl]-4-N-prop-2-enyl-1,3,5-triazine-2,4-diamine
• CAS: 385366-63-2
• 化学式: C₂₀H₂₄N₆O
• 分子量: 364.45
• InChiKey: UVVIFYFNLPINJO-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  27
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  98
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-[4-(allylamino)-6-{[(1S)-1-(1-naphthyl)ethyl]amino}-1,3,5-triazin-2-yloxy]ethylamine 在 偶氮二异丁腈 、 2-乙氧基-1-乙氧碳酰基-1,2-二氢喹啉 作用下， 以 四氢呋喃 、 氯仿 为溶剂， 反应 66.0h， 生成 N-[(1S)-2-[2-[[4-[[(1S)-1-naphthalen-1-ylethyl]amino]-6-[3-(3-trimethoxysilylpropylsulfanyl)propylamino]-1,3,5-triazin-2-yl]oxy]ethylamino]-2-oxo-1-phenylethyl]-3,5-dinitrobenzamide
  参考文献：
  名称：

  Biselector enantioselective stationary phases for HPLC: dependence of the chiral discrimination properties on stereochemistry and chemical nature of each unit of the chiral auxiliary

  摘要：

  Optically active 1-(1-naphthyl)ethylamine, N-3,5-dinitrobenzoylphenylglycine and N-3,5-dinitrobenzoylleucine were used as chiral building blocks to prepare three new enantiomerically pure bifunctional chiral auxiliaries for enantioselective HPLC, belonging to a family of biselector systems, the first example of which (CSP1) has been described previously. These compounds were covalently linked to silica gel to produce three chiral stationary phases (CSPs 2-4), whose enantiodiscriminating capability towards the HPLC resolution of selected racemic compounds was assessed. The obtained results allowed us to establish the influence of the stereochemistry and/or the chemical structure of each chiral moiety of the biselector system on their enantiorecognition properties. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00402-0
• 作为产物：
  描述：

  tert-butyl 2-(4-chloro-6-{[(1S)-1-(1-naphthyl)ethyl]amino}-1,3,5-triazin-2-yloxy)ethylcarbamate 在 三氟乙酸 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 20.25h， 生成 2-[4-(allylamino)-6-{[(1S)-1-(1-naphthyl)ethyl]amino}-1,3,5-triazin-2-yloxy]ethylamine
  参考文献：
  名称：

  （S）-亮氨酸和[（S）-1-（1-萘基）乙基]胺作为双官能体系的手性构建基-新手性固定相的合成及其在外消旋化合物的HPLC拆分中的双选择器性能评估

  摘要：

  [[ S ] -1-（1-萘基）乙基]胺和（S）-亮氨酸衍生的两个选择剂已彼此化学键合，所得手性助剂与硅胶共价连接，从而产生新的手性固定相（CSP）用于对映异构体的HPLC拆分。CSP能够分离某些选定的外消旋化合物的对映异构体：由Oi's CSP拆分的对映异构体{衍生自[1-（1-萘基）乙基]胺}和由Pirkle's CSP拆分的对映异构体[源自N-（3,5 -二硝基苯甲酰基）亮氨酸]。获得的结果表明，CSP具有有效的双选择器系统的特性。

  DOI：

  10.1002/1099-0690(200109)2001:18<3523::aid-ejoc3523>3.0.co;2-#

文献信息

• ( <i>S</i> )‐Leucine and [( <i>S</i> )‐1‐(1‐Naphthyl)ethyl]amine as Chiral Building Blocks for a Bifunctional System − Synthesis of a New Chiral Stationary Phase and Evaluation of Its Biselector Properties in the HPLC Resolution of Racemic Compounds
  作者：Anna Iuliano、Emanuele Attolino、Piero Salvadori

  DOI：10.1002/1099-0690(200109)2001:18<3523::aid-ejoc3523>3.0.co;2-#

  日期：2001.9

  Two selectors derived from [(S)-1-(1-naphthyl)ethyl]amine and (S)-leucine have been chemically bonded to one another and the resulting chiral auxiliary linked covalently to silica gel, to produce a new chiral stationary phase (CSP) for the HPLC resolution of enantiomers. The CSP is able to separate the enantiomers of some selected racemic compounds: both those resolved by Oi’s CSP derived from [1

  [[ S ] -1-（1-萘基）乙基]胺和（S）-亮氨酸衍生的两个选择剂已彼此化学键合，所得手性助剂与硅胶共价连接，从而产生新的手性固定相（CSP）用于对映异构体的HPLC拆分。CSP能够分离某些选定的外消旋化合物的对映异构体：由Oi's CSP拆分的对映异构体衍生自[1-（1-萘基）乙基]胺}和由Pirkle's CSP拆分的对映异构体[源自N-（3,5 -二硝基苯甲酰基）亮氨酸]。获得的结果表明，CSP具有有效的双选择器系统的特性。
• Biselector enantioselective stationary phases for HPLC: dependence of the chiral discrimination properties on stereochemistry and chemical nature of each unit of the chiral auxiliary
  作者：Anna Iuliano、Emanuele Attolino、Piero Salvadori

  DOI：10.1016/s0957-4166(02)00402-0

  日期：2002.8

  Optically active 1-(1-naphthyl)ethylamine, N-3,5-dinitrobenzoylphenylglycine and N-3,5-dinitrobenzoylleucine were used as chiral building blocks to prepare three new enantiomerically pure bifunctional chiral auxiliaries for enantioselective HPLC, belonging to a family of biselector systems, the first example of which (CSP1) has been described previously. These compounds were covalently linked to silica gel to produce three chiral stationary phases (CSPs 2-4), whose enantiodiscriminating capability towards the HPLC resolution of selected racemic compounds was assessed. The obtained results allowed us to establish the influence of the stereochemistry and/or the chemical structure of each chiral moiety of the biselector system on their enantiorecognition properties. (C) 2002 Elsevier Science Ltd. All rights reserved.