N,N'-(1,1'-binaphthyl-2,2'-diyl)dibenzamide | 18741-86-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N,N'-(1,1'-binaphthyl-2,2'-diyl)dibenzamide
• 英文别名: N,N'-[1,1]binaphthyl-2,2'-diyl-bis-benzamide；2.2'-Bis-benzamino-[1.1']binaphthyl；N,N'-[1,1]Binaphthyl-2,2'-diyl-bis-benzamid；N-[1-[2-[[hydroxy(phenyl)methylidene]amino]naphthalen-1-yl]naphthalen-2-yl]benzenecarboximidic acid
• CAS: 18741-86-1
• 化学式: C₃₄H₂₄N₂O₂
• 分子量: 492.577
• InChiKey: RPDMHDBMYVVJOP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 重原子数：
  38
• 可旋转键数：
  5
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  58.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N,N'-(1,1'-binaphthyl-2,2'-diyl)dibenzamide 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 以1.32 g的产率得到R-N,N'-二苄基联萘胺
  参考文献：
  名称：

  New axially chiral atropos and tropos secondary diamines as ligands for enantioselective intramolecular hydroamination

  摘要：

  The highly constrained, axially chiral atropos diamines (R',S,S)-1, (R',R,R)-1 and (R',S,R)-1 and their tropos analogue (R')-2 have been prepared via bis-N,N-dialkylation of (R)-2,2'-diamino-1,1'-binaphthyl, using either (R)- or (S)-2,2'-bis(bromomethyl)-1,1'-binaphthyl and 2,2'-bis(bromomethyl)-1,1'-biphenyl as alkylating agents, followed by selective nickel chloride-catalysed bis(monohydrogenolysis) of the tertiary amino groups of the so-obtained (R',R,R)-4, (R',S,S)4, (R',R,)-4 and (R')-6, respectively, by lithium aluminium hydride in refluxing THF or THF/diglyme. The diamines (R',S,S)-1, (R',R,R)-1, (R',S,R)-1 and (R')-2 have been evaluated as ligands for ytterbium-catalysed intramolecular hydroamination and compared to the ligand 1,1'-binaphthyl-2,2'-bis(benzylamine) (R')-3. They afforded highly active catalysts for the cyclisation of aminopentenes and ammohexenes with up to 58% ee. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.11.029
• 作为产物：
  描述：

  2,2'-Dinitro-binaphthyl-1,1' 在 溶剂黄146 、 锌 作用下， 生成 N,N'-(1,1'-binaphthyl-2,2'-diyl)dibenzamide
  参考文献：
  名称：

  65.一些二萘基。第一部分：合成和性质

  摘要：

  DOI：

  10.1039/jr9320000528

文献信息

• New Ligands for Enantioselective Recognition of Chiral Carboxylates Based on 1,1'-Binaphthalene-2,2'-diamine
  作者：Ivan Stibor、Roman Holakovský、Asiya R. Mustafina、Pavel Lhoták

  DOI：10.1135/cccc20040365

  日期：——

  Simple bis(arylureido)binaphthalenes and (arylamido)binaphthalenes have been synthesized in both racemic as well as optically active forms. One of these compounds has been found to complex chiral anions with modest enantioselectivity.

  已合成简单的双(芳基脲基)联苯和(芳基氨基)联苯，既有外消旋形式也有光学活性形式。其中一种化合物被发现能与手性阴离子形成复合物，并具有适度的对映选择性。
• Stabilized well-dispersed Pd(0) nanoparticles for aminocarbonylation of aryl halides
  作者：Yinghuai Zhu、Li Chuanzhao、Algin Oh Biying、Meriska Sudarmadji、Anqi Chen、Dang Thanh Tuan、Abdul M Seayad

  DOI：10.1039/c1dt10927h

  日期：——

  Well-dispersed palladium (0) nanoparticles stabilized with phosphonium based ionic liquid were synthesized conveniently and fully characterized. A catalyst system comprising of the Pd(0) nanoparticles and a base was found to be recyclable and efficient for the aminocarbonylation reaction of aryl iodide in ionic liquid media. In the presence of potassium tert-butyloxide, for the relatively stable aryl chloride and bromide substrates, medium activities were achieved for the catalyst. The catalyst composites can be recycled at least five times with sustained activity.

  很好分散的镍(0)纳米颗粒使用基于膦的离子液体进行合成，并进行了全面表征。由Pd(0)纳米颗粒和碱组成的催化剂系统被发现对于离子液体介质中芳基碘化物的氨基羰基化反应具有可回收性和高效性。在存在氟化钾叔丁基氧化物的情况下，对于相对稳定的芳基氯和溴底物，催化剂显示出中等活性。催化剂复合材料至少可以回收五次且保持活性。
• Retention of strong intramolecular hydrogen bonds in high polarity solvents in binaphthalene–benzamide derivatives: extensive NMR studies
  作者：Arun Kumar Patel、Sandeep Kumar Mishra、Kiran Krishnamurthy、N. Suryaprakash

  DOI：10.1039/c9ra07299c

  日期：——

  Advanced multidimensional NMR techniques have been employed to investigate the intramolecular hydrogen bonds (HBs) in a series of N,N′-([1,1′-binaphthalene]-2,2′-diyl)bis(benzamide) derivatives, with the site-specific substitution of different functional groups. The existence of intramolecular HBs and the elimination of any molecular aggregation and possible intermolecular HBs are ascertained by various

  先进的多维 NMR 技术已被用于研究一系列N , N '-([1,1'-binaphthalene]-2,2'-diyl)bis(benzamide) 衍生物中的分子内氢键 (HBs) ，其中不同官能团的位点特异性取代。分子内 HBs 的存在和任何分子聚集和可能的分子间 HBs 的消除通过各种实验 NMR 技术确定，包括 HB 强度的溶剂极性依赖性修改。在氟取代衍生物中，有机氟参与HBs的直接证据是通过检测异核空间相关性和两个NMR活性核之间的耦合，其中自旋极化的传输是通过HBs介导的（1h J FH )。用高极性溶剂稀释后1h J FH强度的降低程度直接提供了 HB 强度的定性测量。HB 虽然变弱，但即使在纯高极性溶剂中也不会失效，这归因于结构限制。不稳定的氢原子与溶剂的氘的交换率允许测量它们的半衰期，这与 HBs 的相对强度相关。NMR 实验结果通过 XRD 和基于 DFT 的理论计算（例如
• 65. Some dinaphthyl bases. Part I. Syntheses and properties
  作者：William Murdoch Cumming、George Howie

  DOI：10.1039/jr9320000528

  日期：——
• New axially chiral atropos and tropos secondary diamines as ligands for enantioselective intramolecular hydroamination
  作者：Isabelle Aillaud、Karen Wright、Jacqueline Collin、Emmanuelle Schulz、Jean-Paul Mazaleyrat

  DOI：10.1016/j.tetasy.2007.11.029

  日期：2008.1

  The highly constrained, axially chiral atropos diamines (R',S,S)-1, (R',R,R)-1 and (R',S,R)-1 and their tropos analogue (R')-2 have been prepared via bis-N,N-dialkylation of (R)-2,2'-diamino-1,1'-binaphthyl, using either (R)- or (S)-2,2'-bis(bromomethyl)-1,1'-binaphthyl and 2,2'-bis(bromomethyl)-1,1'-biphenyl as alkylating agents, followed by selective nickel chloride-catalysed bis(monohydrogenolysis) of the tertiary amino groups of the so-obtained (R',R,R)-4, (R',S,S)4, (R',R,)-4 and (R')-6, respectively, by lithium aluminium hydride in refluxing THF or THF/diglyme. The diamines (R',S,S)-1, (R',R,R)-1, (R',S,R)-1 and (R')-2 have been evaluated as ligands for ytterbium-catalysed intramolecular hydroamination and compared to the ligand 1,1'-binaphthyl-2,2'-bis(benzylamine) (R')-3. They afforded highly active catalysts for the cyclisation of aminopentenes and ammohexenes with up to 58% ee. (c) 2007 Elsevier Ltd. All rights reserved.