(1R,2R)-N,N'-dibenzyl-bis[(R)-2-hydroxy(2-phenyl)ethyl]-1,2-diaminocyclohexane | 208037-05-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (1R,2R)-N,N'-dibenzyl-bis[(R)-2-hydroxy(2-phenyl)ethyl]-1,2-diaminocyclohexane
• 英文别名: (1R)-2-[benzyl-[(1R,2R)-2-[benzyl-[(2R)-2-hydroxy-2-phenylethyl]amino]cyclohexyl]amino]-1-phenylethanol
• CAS: 208037-05-2
• 化学式: C₃₆H₄₂N₂O₂
• 分子量: 534.742
• InChiKey: HGDDYLHBGUSGNQ-NWJWHWDBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  40
• 可旋转键数：
  12
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  46.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1R,2R)-N,N'-dibenzyl-bis[(R)-2-hydroxy(2-phenyl)ethyl]-1,2-diaminocyclohexane 在 20% palladium hydroxide-activated charcoal 、 氢气 作用下， 以 甲醇 为溶剂， 以71.7%的产率得到(1R,2R)-bis[(R)-2-hydroxy(2-phenyl)ethyl]-1,2-diaminocyclohexane
  参考文献：
  名称：

  Synthesis and application of amino alcohol imides as NMR solvating agents for chiral discrimination of carboxylic acids

  摘要：

  A series of amino alcohol imides 2-8 have been synthesized from commercially available starting materials by regioselective ring opening reaction of epoxides with chiral amines. Compounds 2-8 were tested as chiral solvating agents (CSAs) for enantiomeric discrimination of biological important carboxylic acids. C-2-Symmetric (S,R,R,S)-3 was found to be a satisfactory CSA for mandelic acid with Delta Delta delta of 24.8 Hz. CSA (S, S)-5 exhibited the best enantiomeric discrimination for alpha-phenyl-alpha-methoxyacetic acid with Delta Delta delta of 32 Hz. Enantiomeric differentiated values found for mandelic acid, o-chloro mandelic acid, ibuprofen and naproxen are 7.2, 4.4, 2 and 3 Hz respectively. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2016.05.009
• 作为产物：
  描述：

  苯甲醛 以 甲醇 为溶剂， 生成 (1R,2R)-N,N'-dibenzyl-bis[(R)-2-hydroxy(2-phenyl)ethyl]-1,2-diaminocyclohexane
  参考文献：
  名称：

  Synthesis and application of amino alcohol imides as NMR solvating agents for chiral discrimination of carboxylic acids

  摘要：

  A series of amino alcohol imides 2-8 have been synthesized from commercially available starting materials by regioselective ring opening reaction of epoxides with chiral amines. Compounds 2-8 were tested as chiral solvating agents (CSAs) for enantiomeric discrimination of biological important carboxylic acids. C-2-Symmetric (S,R,R,S)-3 was found to be a satisfactory CSA for mandelic acid with Delta Delta delta of 24.8 Hz. CSA (S, S)-5 exhibited the best enantiomeric discrimination for alpha-phenyl-alpha-methoxyacetic acid with Delta Delta delta of 32 Hz. Enantiomeric differentiated values found for mandelic acid, o-chloro mandelic acid, ibuprofen and naproxen are 7.2, 4.4, 2 and 3 Hz respectively. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2016.05.009

文献信息

• Synthesis of new diaza-18-crown-6 ethers derived from trans-(R,R)-1,2-diaminocyclohexane and investigation of their enantiomeric discrimination ability with amino acid ester salts
  作者：Mehmet Karakaplan、Devran Ak、Mehmet Çolak、Şafak Özhan Kocakaya、Halil Hoşgören、Necmettin Pirinççioğlu

  DOI：10.1016/j.tet.2012.10.020

  日期：2013.1

  achieved. Enantiomeric discrimination of these macrocycles against amino acid methyl ester salts was examined by 1H NMR titration method. They exhibit strong binding ability and some of them show a very high enantioselectivity towards amino acid esters, corresponding to 5.37 kJ/mol of binding energy difference in CDCl3 at 25 °C. Computational modelling showed parallel results with experimental calculations

  合成了四个C 2对称的diaza -18-crown-6醚，这些醚衍生自反式-（R，R）-1,2-二氨基环己烷，其甲基，苯基和苯氧甲基部分连接在冠环的立体中心上。通过1 H NMR滴定法检查了这些大环与氨基酸甲酯盐的对映体区别。它们具有很强的结合能力，其中一些对氨基酸酯具有很高的对映选择性，相当于CDCl 3中的结合能差为5.37 kJ / mol。在25°C下。计算模型显示出与实验计算结果平行的结果，从而提供了对分子识别模式和宿主与客人之间结合位点的详细了解。