N,N"-(1R)-[1,1'-binaphthalene]-2,2'-diylbis(N'-phenyl)-urea

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N,N"-(1R)-[1,1'-binaphthalene]-2,2'-diylbis(N'-phenyl)-urea
• 英文别名: N-[1-[2-[(C-hydroxy-N-phenylcarbonimidoyl)amino]naphthalen-1-yl]naphthalen-2-yl]-N'-phenylcarbamimidic acid
• 化学式: C₃₄H₂₆N₄O₂
• 分子量: 522.606
• InChiKey: JLXWOYYGUMLOBE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.2
• 重原子数：
  40
• 可旋转键数：
  7
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  89.2
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  异氰酸苯酯 、 [1,1’-联萘]-2,2’-二胺 以 二氯甲烷 为溶剂， 生成 N,N"-(1R)-[1,1'-binaphthalene]-2,2'-diylbis(N'-phenyl)-urea
  参考文献：
  名称：

  Yb（III）/手性双脲复合物催化的Danishefsky型二烯和缺电子烯烃的高度对映选择性Diels-Alder反应

  摘要：

  描述了新型的轴向手性双脲配体BINUREA的合成和实用性。这种尿素配体与三氟甲基磺酸late和DBU的复合物可用于Danishefsky型二烯和缺电子烯烃的催化对映选择性Diels-Alder反应，使加合物具有优异的收率和对映体过量（ee）。

  DOI：

  10.1016/j.tetlet.2009.07.110

文献信息

• Highly enantioselective Diels–Alder reaction of Danishefsky-type diene and electron-deficient olefins catalyzed by an Yb(III)/chiral bis-urea complex
  作者：Shinji Harada、Nozomi Toudou、Shiharu Hiraoka、Atsushi Nishida

  DOI：10.1016/j.tetlet.2009.07.110

  日期：2009.10

  The synthesis and utility of the novel axially chiral bis-urea ligand BINUREA are described. A complex of this urea ligand with ytterbium triflate and DBU can be used in the catalytic enantioselective Diels–Alder reaction of Danishefsky-type diene and electron-deficient olefins to give the adducts in good to excellent yield and enantiomeric excess (ee).

  描述了新型的轴向手性双脲配体BINUREA的合成和实用性。这种尿素配体与三氟甲基磺酸late和DBU的复合物可用于Danishefsky型二烯和缺电子烯烃的催化对映选择性Diels-Alder反应，使加合物具有优异的收率和对映体过量（ee）。
• Urea derivatives based on a 1,1′-binaphthalene skeleton as chiral solvating agents for sulfoxides
  作者：Roman Holakovský、Michal März、Radek Cibulka

  DOI：10.1016/j.tetasy.2015.10.011

  日期：2015.12

  Five optically active urea derivatives 1-5 were synthesized via reaction of (R)-1,1'-binaphthalene-2,2'-diamine with the corresponding isocyanates. Analysis by H-1 nuclear magnetic resonance spectroscopy demonstrated that 1 was the best chiral solvating agent for the determination of the enantiomeric excesses of various sulfoxides (13 examples). This compound was more efficient in terms of discriminating between enantiomers than the commercially available chiral solvating agent ((R)-(3,5-dinitro-benzoyl)-alpha-phenethylamine). Large non-equivalent chemical shifts (0.1 ppm) can be achieved, especially with aliphatic sulfoxides. (C) 2015 Elsevier Ltd. All rights reserved.