N,N'-dicyclohexyloct-2-ynamidine | 1604047-29-1

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N,N'-dicyclohexyloct-2-ynamidine
• 英文别名: N,N'-dicyclohexyloct-2-ynimidamide
• CAS: 1604047-29-1
• 化学式: C₂₀H₃₄N₂
• 分子量: 302.503
• InChiKey: QVTRBUJXMRKLOI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  24.4
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  1-庚炔 、 N,N'-二环己基碳二亚胺 在 bis[2-(3-benzyl-2H-imidazol-1-ium-2-id-1-yl)-4-methylphenyl]azanide;bis(trimethylsilyl)azanide;europium(3+) 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以68%的产率得到N,N'-dicyclohexyloct-2-ynamidine
  参考文献：
  名称：

  CNC-Pincer Rare-Earth Metal Amido Complexes with a Diarylamido Linked Biscarbene Ligand: Synthesis, Characterization, and Catalytic Activity

  摘要：

  In preparation of CNC-pincer rare-earth metal amido complexes with a diarylamido linked biscarbene ligand, it is found that conditions have a key influence on final products. Reaction of a THF suspension of bis[2-(3-benzylimidazolium)-4-methylphenyl]amine dichlorides (H3LCl2) with [(Me3Si)(2)N](3)RE(mu-Cl)Li(THF)(3) (RE = Yb, Eu, Sm) in THF at room temperature afforded the only unexpected fused-heterocyclic compound 8,9-dibenzyl-3,14-dimethyl-8a,9-dihydro-8H-benzo[4,5]imidazo-[2',1':2,3]imidazo[1,2-a]imidazo[2,1-c]quinoxaline (1) containing an imidazolyl ring and a piperidyl ring, which formed through carbene C-C and C-N coupling. However, the reaction of H3LCl2 with [(Me3Si)(2)N](3)Er(mu-Cl)Li(THF)(3) in toluene afforded the CNC-pincer erbium amido complex incorporating a diarylamido linked biscarbene ligand LEr[N(SiMe3)(2)](2) (2) in low yield and the above fused-heterocyclic compound 1. The stepwise reaction of H3LCl2 with strong bases (n-BuLi or LiCH2SiMe3) in THF for 4 h, followed by treatment with [(Me3Si)(2)N](3)RE(mu-Cl)Li(THF)(3), generated zwitterion complexes [L2RE][RECl{N(SiMe3)(2)}(3)] (L = [4-CH3-2-{(C6H4CH2-[N(CH)(2)CN]}C6H3](2)N; RE = Y (3), Er (4), Yb (5)) in less than 20% yields together with fused-heterocyclic compound 1. Additionally, the reaction of H3LCl2 with 6 equiv of NaN(SiMe3)(2) in THF for 4 h, followed by treatment with YbCl3, generated a novel discrete complex [L2Yb][{Na(mu-N(SiMe3)(2))}(5)(mu(5)-Cl)] (6). The one-pot reaction of H3LCl2 with n-BuLi, followed by reaction with [(Me3Si)(2)N](3)RE(mu-Cl)Li(THF)(3) in THF at -78 degrees C, generated the CNC-pincer lanthanide bisamido complexes LRE[N(SiMe3)(2)](2) (RE = Er (2), Y (7), Sm (8), Eu (9)) in moderate yields. These kinds of biscarbene supported pincer bisamido complexes could also be prepared by a one-pot reaction of bis(imidazolium) salt (H3LCl2) with 5 equiv of NaN(SiMe3)(2), followed by treatment with RECl3, in good yields at -78 degrees C. Investigation of the catalytic activity of complexes 2 and 7-9 indicated that all complexes showed a high activity toward the addition of terminal alkynes to carbodiimides producing propiolimidines, which represents the first example of rare-earth metal CNC-pincer-type catalysts applied for catalytic C-H bond addition of terminal alkynes to carbodiimides at room temperature.

  DOI：

  10.1021/om500354s