[3-(1H-吡唑-1-基)苯基]甲醇 | 864068-80-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: [3-(1H-吡唑-1-基)苯基]甲醇
• 中文别名: [3-(1-吡唑)苯基]甲醇；3-(1-吡唑基)苯甲醇
• 英文名称: (3-(1H-pyrazol-1-yl)phenyl)methanol
• 英文别名: 3-(1-pyrazolyl)benzyl alcohol；[3-(1H-pyrazol-1-yl)phenyl]methanol；(3-pyrazol-1-ylphenyl)methanol
• CAS: 864068-80-4
• 化学式: C₁₀H₁₀N₂O
• mdl: MFCD06740322
• 分子量: 174.202
• InChiKey: VINVOQJANISHSK-UHFFFAOYSA-N

物化性质

• 沸点：
  338.9±25.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  38
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2933199090
• 危险性防范说明：
  P264,P270,P301+P312,P330,P501
• 危险性描述：
  H302

反应信息

• 作为反应物：
  描述：

  [3-(1H-吡唑-1-基)苯基]甲醇 在 三溴乙酸乙酯 、 三苯基膦 作用下， 以 二氯甲烷 、 丙酮 、 甲苯 为溶剂， 反应 16.5h， 生成 ditert-butyl-[(3-pyrazol-1-ylbenzene-2-id-1-yl)methyl]phosphane;palladium(2+);chloride
  参考文献：
  名称：

  Pyrazole-Based PCN Pincer Complexes of Palladium(II): Mono- and Dinuclear Hydroxide Complexes and Ligand Rollover C–H Activation

  摘要：

  Palladium complexes of the novel unsymmetrical phosphine pyrazole-containing pincer ligands PCNH (PCNH = 1-[3- [(di-tert-butylphosphino)methyl]pheny1]-1H-pyrazole) and PCNMe (PCNMe = 1-[3-(di-tert-butylphosphino)methyl]pheny1]-5-methyl-1H-pyrazole) have been prepared and characterized through single-crystal X-ray diffraction and multinudear H-1, C-13{H-1}, and P-31{H-1} NMR spectroscopy. In preparations of the monomeric hydroxide species (PCNH)Pd(OH), an unexpected N detachment followed by C-H activation on the heterocycle 5-position took place resulting in conversion of the monoanionic {P,C-,N} framework into a dianionic {P,C-,C-} ligand set. The dinuclear hydroxide-bridged species (PCNH)Pd(mu-OH)Pd(PCC) was the final product obtained under ambient conditions. The "rollover" activation was followed via P-31{H-1} NMR spectroscopy, and dinuclear cationic mu-OH and monomeric Pd-II hydroxide intermediates were identified. DFT computational analysis of the process (M06//6-31G*, THF) showed that the energy barriers for the pyrazolyl rollover and for C-H activation through a sigma-bond metathesis reaction are low enough to be overcome under ambient-temperature conditions, in line with the experimental findings. In contrast to the PCNH system, no "rollover" reactivity was observed in the PCNMe system, and the terminal hydroxide complex (PCNMe)Pd(OH) could be readily isolated and fully characterized.

  DOI：

  10.1021/acs.organomet.5b00355
• 作为产物：
  描述：

  吡唑 、 3-溴苯甲醇 在 N-甲基吡咯烷酮 、 copper(l) iodide 、 potassium carbonate 作用下， 反应 5.0h， 以78.6%的产率得到[3-(1H-吡唑-1-基)苯基]甲醇
  参考文献：
  名称：

  Pyrazole-Based PCN Pincer Complexes of Palladium(II): Mono- and Dinuclear Hydroxide Complexes and Ligand Rollover C–H Activation

  摘要：

  Palladium complexes of the novel unsymmetrical phosphine pyrazole-containing pincer ligands PCNH (PCNH = 1-[3- [(di-tert-butylphosphino)methyl]pheny1]-1H-pyrazole) and PCNMe (PCNMe = 1-[3-(di-tert-butylphosphino)methyl]pheny1]-5-methyl-1H-pyrazole) have been prepared and characterized through single-crystal X-ray diffraction and multinudear H-1, C-13{H-1}, and P-31{H-1} NMR spectroscopy. In preparations of the monomeric hydroxide species (PCNH)Pd(OH), an unexpected N detachment followed by C-H activation on the heterocycle 5-position took place resulting in conversion of the monoanionic {P,C-,N} framework into a dianionic {P,C-,C-} ligand set. The dinuclear hydroxide-bridged species (PCNH)Pd(mu-OH)Pd(PCC) was the final product obtained under ambient conditions. The "rollover" activation was followed via P-31{H-1} NMR spectroscopy, and dinuclear cationic mu-OH and monomeric Pd-II hydroxide intermediates were identified. DFT computational analysis of the process (M06//6-31G*, THF) showed that the energy barriers for the pyrazolyl rollover and for C-H activation through a sigma-bond metathesis reaction are low enough to be overcome under ambient-temperature conditions, in line with the experimental findings. In contrast to the PCNH system, no "rollover" reactivity was observed in the PCNMe system, and the terminal hydroxide complex (PCNMe)Pd(OH) could be readily isolated and fully characterized.

  DOI：

  10.1021/acs.organomet.5b00355

文献信息

• Iron complex-catalyzed N-arylation of pyrazoles under aqueous medium
  作者：Hang Wai Lee、Albert S.C. Chan、Fuk Yee Kwong

  DOI：10.1016/j.tetlet.2009.08.018

  日期：2009.10

  diamine ligand is a highly effective catalyst for N-arylation of pyrazoles using aryl and heteroaryl iodides. It is notable to show that this complex is tolerable under aqueous medium and particularly the whole reaction utilizes water as the sole solvent without any additional organic co-solvents and surfactants. Attempted study using other nitrogen nucleophiles is described. This newly developed system provides

  具有构象刚性二胺配体的市售FeCl 3 ·6H 2 O是使用芳基和杂芳基碘化物使吡唑进行N-芳基化的高效催化剂。值得注意的是，表明该络合物在水性介质中是可耐受的，特别是整个反应利用水作为唯一的溶剂，而没有任何其他的有机助溶剂和表面活性剂。描述了尝试使用其他氮亲核试剂的研究。这个新开发的系统提供了Cu和Pd催化的N-芳基化反应的替代方案。