5-((2-(3,5-dimethyl-1H-pyrazol-1-yl)phenyl)imino)-2,2-dimethylhex-3-en-3-ol | 1436386-57-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-((2-(3,5-dimethyl-1H-pyrazol-1-yl)phenyl)imino)-2,2-dimethylhex-3-en-3-ol
• CAS: 1436386-57-0
• 化学式: C₁₉H₂₅N₃O
• 分子量: 311.427
• InChiKey: JCPRNSVJIRWYIJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.07
• 重原子数：
  23.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  50.41
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  5-((2-(3,5-dimethyl-1H-pyrazol-1-yl)phenyl)imino)-2,2-dimethylhex-3-en-3-ol 、 diethylzinc 以 正己烷 、 甲苯 为溶剂， 以93%的产率得到[Zn(Et){o-(OC(t-Bu)=CHC(Me)=N)C₆H₄(3,5-Me₂C₃HN₂)}]
  参考文献：
  名称：

  Rapid and Controlled Polymerization of rac-Lactide Using N,N,O-Chelate Zinc Enolate Catalysts

  摘要：

  The synthesis and characterization of N,N,O-chelate zinc enolate complexes and the catalysis of the complexes for the ROP of rac-lactide are reported. The pyrazole-based ligand precursors o-(3,5-Me2C3HN2)C6H4N=C(Me)CH=C(OH)R-1 (R-1 = Me, 1; R-1 = Ph, 2; R-1 = t-Bu, 3; R-1 = CF3, 4) were synthesized by reaction of 2-(3,5-dimethyl-1H-pyrazol-1-yl)benzenamine with 1,3-diketones, including pentane-2,4-dione, 1-phenylbutane-1,3-dione, 5,5-dimethylhexane-2,4-dione, and 1,1,1-trifluoropentane-2,4-dione. Treatment of 1-4 with ZnEt2 generated the N,N,O-coordinated zinc complexes [Zn(Et){o-(OC(R-1)=CHC(Me)=N)C6H4(3,5-Me2C3HN2)}] (R-1 = Me, 5; R-1 = Ph, 6; R-1 = t-Bu, 7; R-1 = CF3, 8). The iminophosphoranyl-moiety-containing ligand precursors o-(3,5-Me2C3HN2)C6H4N=P(Ph-2)CH2C(O)R-2 (R-2 = Ph, 9; R-2 = t-Bu, 10) were synthesized by reaction of 1-(2-azidophenyl)-3,5-dimethyl-1H-pyrazole with 1-phenyl-2-(diphenylphosphino)ethanone and 3,3-dimethyl-1-(diphenylphosphino)butan-2-one, respectively. Treatment of 9 and 10 with ZnEt2 afforded the zinc complexes [Zn(Et){o-(OC(R-2)=CHP(Ph-2)=N)C6H4(3,5-Me2C3HN2)}] (R-2 = Ph, 11; R-2 = t-Bu, 12). The ligand precursors and complexes were characterized by NMR spectroscopy and elemental analyses. Complexes 5 and 11 were also characterized by single-crystal X-ray diffraction techniques. In the presence of BnOH complexes 5-8 efficiently catalyzed the ring-opening polymerization of rac-lactide in a controlled fashion, whereas complexes 11 and 12 showed much lower catalytic activity under the same conditions.

  DOI：

  10.1021/om400193z
• 作为产物：
  描述：

  2-(3,5-二甲基-吡唑-1-基)-苯胺 、 5,5-二甲己烷2,4-二酮 在 甲酸 作用下， 以 甲苯 为溶剂， 反应 40.0h， 以69%的产率得到5-((2-(3,5-dimethyl-1H-pyrazol-1-yl)phenyl)imino)-2,2-dimethylhex-3-en-3-ol
  参考文献：
  名称：

  Rapid and Controlled Polymerization of rac-Lactide Using N,N,O-Chelate Zinc Enolate Catalysts

  摘要：

  The synthesis and characterization of N,N,O-chelate zinc enolate complexes and the catalysis of the complexes for the ROP of rac-lactide are reported. The pyrazole-based ligand precursors o-(3,5-Me2C3HN2)C6H4N=C(Me)CH=C(OH)R-1 (R-1 = Me, 1; R-1 = Ph, 2; R-1 = t-Bu, 3; R-1 = CF3, 4) were synthesized by reaction of 2-(3,5-dimethyl-1H-pyrazol-1-yl)benzenamine with 1,3-diketones, including pentane-2,4-dione, 1-phenylbutane-1,3-dione, 5,5-dimethylhexane-2,4-dione, and 1,1,1-trifluoropentane-2,4-dione. Treatment of 1-4 with ZnEt2 generated the N,N,O-coordinated zinc complexes [Zn(Et){o-(OC(R-1)=CHC(Me)=N)C6H4(3,5-Me2C3HN2)}] (R-1 = Me, 5; R-1 = Ph, 6; R-1 = t-Bu, 7; R-1 = CF3, 8). The iminophosphoranyl-moiety-containing ligand precursors o-(3,5-Me2C3HN2)C6H4N=P(Ph-2)CH2C(O)R-2 (R-2 = Ph, 9; R-2 = t-Bu, 10) were synthesized by reaction of 1-(2-azidophenyl)-3,5-dimethyl-1H-pyrazole with 1-phenyl-2-(diphenylphosphino)ethanone and 3,3-dimethyl-1-(diphenylphosphino)butan-2-one, respectively. Treatment of 9 and 10 with ZnEt2 afforded the zinc complexes [Zn(Et){o-(OC(R-2)=CHP(Ph-2)=N)C6H4(3,5-Me2C3HN2)}] (R-2 = Ph, 11; R-2 = t-Bu, 12). The ligand precursors and complexes were characterized by NMR spectroscopy and elemental analyses. Complexes 5 and 11 were also characterized by single-crystal X-ray diffraction techniques. In the presence of BnOH complexes 5-8 efficiently catalyzed the ring-opening polymerization of rac-lactide in a controlled fashion, whereas complexes 11 and 12 showed much lower catalytic activity under the same conditions.

  DOI：

  10.1021/om400193z