tris[(1-cyclohexyl-1H-1,2,3-triazole-4-yl)methyl]amine | 1310580-25-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并三唑类
• 英文名称: tris[(1-cyclohexyl-1H-1,2,3-triazole-4-yl)methyl]amine
• 英文别名: tris[(1-cyclohexyl-1H-1,2,3-triazol-4-yl)methyl]amine；TCTA；1-(1-cyclohexyltriazol-4-yl)-N,N-bis[(1-cyclohexyltriazol-4-yl)methyl]methanamine
• CAS: 1310580-25-6
• 化学式: C₂₇H₄₂N₁₀
• 分子量: 506.697
• InChiKey: KVKPNVLUZKDWAK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  37
• 可旋转键数：
  9
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  95.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  tris[(1-cyclohexyl-1H-1,2,3-triazole-4-yl)methyl]amine 、 cobalt(II) perchlorate hexahydrate 以 甲醇 为溶剂， 以75%的产率得到bis(tris[(1-cyclohexyl-1H-1,2,3-triazol-4-yl)methyl]amine)cobalt(II) perchlorate
  参考文献：
  名称：

  Cobalt Complexes with “Click”-Derived Functional Tripodal Ligands: Spin Crossover and Coordination Ambivalence

  摘要：

  We demonstrate the use of a Cu(I) catalyzed "Click" reaction in the synthesis of novel ligands for spin crossover complexes. The reaction between azides and alkynes was used to synthesize the reported tripodal ligand tris [ (1-benzyl-1H-1,2,3-triazol-4-yl)methyl] amine, TBTA, and the new ligands tris[(1-cyclohexyl-1H-1,2,3-triazol-4-yl)methyl] amine, TCTA, and tris[(1-n-butyl-1H-1,2,3-triazol-4-yl)methyl] amine, TBuTA Reactions of TBTA with Co(ClO4)(2) lead to complexes of the form [Co(TBTA)(CH3CN)(3)](ClO4)(2), 1, and [Co(TBTA)(2)] (ClO4)(2), 2, where complex formation can be controlled by the metal/ligand ratio and the complexes 1 and 2 can be chemically and reversibly switched from one form to another in solution resulting in coordination ambivalence. The benzyl substituents of TBTA in 2 show intramolecular C-H-pi T-stacking that generates a chemical pressure to stabilize the low spin (LS) state at lower temperatures. The structural parameters of 2 are consistent with a Jahn Teller active LS Co(II) (elongation) ion showing four short and two long bonds. 2 shows spin-crossover (SCO) behavior in the solid state and in solution with a high T-0 close to room temperature which is driven by the T-stacking. 1 remains high spin (HS) between 2 and 400 K. Reversible chemical switching is observed between 1 and 2 at room temperature, with an accompanying change in the spin state from HS to LS. The importance of the intramolecular T-stacking in driving the SCO behavior is proven by comparison with two analogous compounds that lack an aromatic substituent and remain HS down to very low temperatures.

  DOI：

  10.1021/ic200246v
• 作为产物：
  描述：

  三炔丙基胺 、 叠氮基环己烷 在 copper(ll) sulfate pentahydrate 、 sodium ascorbate 、 三[(1-苄基-1H-1,2,3-三唑-4-基)甲基]胺 作用下， 以 二氯甲烷 、 水 、 叔丁醇 为溶剂， 反应 120.0h， 以65%的产率得到tris[(1-cyclohexyl-1H-1,2,3-triazole-4-yl)methyl]amine
  参考文献：
  名称：

  Cobalt Complexes with “Click”-Derived Functional Tripodal Ligands: Spin Crossover and Coordination Ambivalence

  摘要：

  We demonstrate the use of a Cu(I) catalyzed "Click" reaction in the synthesis of novel ligands for spin crossover complexes. The reaction between azides and alkynes was used to synthesize the reported tripodal ligand tris [ (1-benzyl-1H-1,2,3-triazol-4-yl)methyl] amine, TBTA, and the new ligands tris[(1-cyclohexyl-1H-1,2,3-triazol-4-yl)methyl] amine, TCTA, and tris[(1-n-butyl-1H-1,2,3-triazol-4-yl)methyl] amine, TBuTA Reactions of TBTA with Co(ClO4)(2) lead to complexes of the form [Co(TBTA)(CH3CN)(3)](ClO4)(2), 1, and [Co(TBTA)(2)] (ClO4)(2), 2, where complex formation can be controlled by the metal/ligand ratio and the complexes 1 and 2 can be chemically and reversibly switched from one form to another in solution resulting in coordination ambivalence. The benzyl substituents of TBTA in 2 show intramolecular C-H-pi T-stacking that generates a chemical pressure to stabilize the low spin (LS) state at lower temperatures. The structural parameters of 2 are consistent with a Jahn Teller active LS Co(II) (elongation) ion showing four short and two long bonds. 2 shows spin-crossover (SCO) behavior in the solid state and in solution with a high T-0 close to room temperature which is driven by the T-stacking. 1 remains high spin (HS) between 2 and 400 K. Reversible chemical switching is observed between 1 and 2 at room temperature, with an accompanying change in the spin state from HS to LS. The importance of the intramolecular T-stacking in driving the SCO behavior is proven by comparison with two analogous compounds that lack an aromatic substituent and remain HS down to very low temperatures.

  DOI：

  10.1021/ic200246v