2,2'-bis(3,5-dihydro-4H-dinaphtho[2,1-c:1',2'-e]azepin-4-yl)-1,1'-binaphthalene | 1015486-97-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 2,2'-bis(3,5-dihydro-4H-dinaphtho[2,1-c:1',2'-e]azepin-4-yl)-1,1'-binaphthalene
• CAS: 1015486-97-1；1015487-00-9；1015487-69-0
• 化学式: C₆₄H₄₄N₂
• 分子量: 841.067
• InChiKey: LUZRIUXVBYWESL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  16.65
• 重原子数：
  66.0
• 可旋转键数：
  3.0
• 环数：
  14.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  6.48
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  2,2'-bis(3,5-dihydro-4H-dinaphtho[2,1-c:1',2'-e]azepin-4-yl)-1,1'-binaphthalene 在 nickel dichloride lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 生成 N-[[1-(2-methylnaphthalen-1-yl)naphthalen-2-yl]methyl]-1-[2-[[1-(2-methylnaphthalen-1-yl)naphthalen-2-yl]methylamino]naphthalen-1-yl]naphthalen-2-amine
  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'-(3,5-dihydro-4H-dinaphtho[2,1-c:1',2'-e]azepin-4-yl)-[1,1'-binaphthalen]-2-amine 、 (S)-2,2'-双(溴甲基)-1,1'-联萘 在 N,N-二异丙基乙胺 作用下， 以 甲苯 、 乙腈 为溶剂， 反应 192.0h， 以49%的产率得到2,2'-bis(3,5-dihydro-4H-dinaphtho[2,1-c:1',2'-e]azepin-4-yl)-1,1'-binaphthalene
  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