1-(2-(dicyclohexylphosphino)phenyl)-3,5-dimethyl-1H-pyrazole

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-(2-(dicyclohexylphosphino)phenyl)-3,5-dimethyl-1H-pyrazole
• 英文别名: Dicyclohexyl-[2-(3,5-dimethylpyrazol-1-yl)phenyl]phosphane；dicyclohexyl-[2-(3,5-dimethylpyrazol-1-yl)phenyl]phosphane
• 化学式: C₂₃H₃₃N₂P
• 分子量: 368.502
• InChiKey: BLHWDRCUYZUYLD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  17.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  双(乙腈)氯化钯(II) 、 1-(2-(dicyclohexylphosphino)phenyl)-3,5-dimethyl-1H-pyrazole 以 二氯甲烷 为溶剂， 反应 0.33h， 以93%的产率得到
  参考文献：
  名称：

  Steric vis-à-vis electronic influence of phosphines on biaryl motif: Ligand design for coupling reactions with Chloroarenes

  摘要：

  In order to assess relative contribution of steric factors and electron-richness of phosphine ligands on biaryl-type scaffolds, a set of 1-aryl-pyrazole/pyrrole derived ligands L1-L6 featuring either aryldicyclohexylphosphino or aryldiphenylphosphino donor group was synthesized. A bidentate coordination mode of ligands L1 or L2 was evident from a representative crystal structure that implied a possible hemilabile participation to facilitate catalytic steps. With N-arylpyrroles (L3-L5), where the second nitrogen donor on the heterocycle is absent, coupling reactions of unactivated chloroarenes still proceeded with comparable efficiency. Thus, suitably endowed triarylphosphines were found to be as efficient as more expensive aryldialkylphosphine analogs in reactions with chloroarenes, extending the scope of ligand design. (C) 2014 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2014.11.008
• 作为产物：
  描述：

  2-溴苯肼盐酸盐 在 正丁基锂 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 14.5h， 生成 1-(2-(dicyclohexylphosphino)phenyl)-3,5-dimethyl-1H-pyrazole
  参考文献：
  名称：

  Steric vis-à-vis electronic influence of phosphines on biaryl motif: Ligand design for coupling reactions with Chloroarenes

  摘要：

  In order to assess relative contribution of steric factors and electron-richness of phosphine ligands on biaryl-type scaffolds, a set of 1-aryl-pyrazole/pyrrole derived ligands L1-L6 featuring either aryldicyclohexylphosphino or aryldiphenylphosphino donor group was synthesized. A bidentate coordination mode of ligands L1 or L2 was evident from a representative crystal structure that implied a possible hemilabile participation to facilitate catalytic steps. With N-arylpyrroles (L3-L5), where the second nitrogen donor on the heterocycle is absent, coupling reactions of unactivated chloroarenes still proceeded with comparable efficiency. Thus, suitably endowed triarylphosphines were found to be as efficient as more expensive aryldialkylphosphine analogs in reactions with chloroarenes, extending the scope of ligand design. (C) 2014 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2014.11.008