5-(dec-1-ynyl)-1,3-dimethyl-1H-pyrazole-4-carbaldehyde | 1418137-15-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-(dec-1-ynyl)-1,3-dimethyl-1H-pyrazole-4-carbaldehyde
• 英文别名: 5-Dec-1-ynyl-1,3-dimethylpyrazole-4-carbaldehyde；5-dec-1-ynyl-1,3-dimethylpyrazole-4-carbaldehyde
• CAS: 1418137-15-1
• 化学式: C₁₆H₂₄N₂O
• 分子量: 260.379
• InChiKey: JIEIKRHIBGWRSV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  19
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  34.9
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-癸炔 、 5-氯-1,3-二甲基-1H-吡唑-4-甲醛 在 双[二叔丁基-(4-二甲基-氨基苯基)磷]钯(0) 、 caesium carbonate 作用下， 以 乙腈 为溶剂， 反应 5.0h， 以86%的产率得到5-(dec-1-ynyl)-1,3-dimethyl-1H-pyrazole-4-carbaldehyde
  参考文献：
  名称：

  Heck Alkynylation (Copper-Free Sonogashira Coupling) of Aryl and Heteroaryl Chlorides, Using Pd Complexes of t-Bu₂(p-NMe₂C₆H₄)P: Understanding the Structure–Activity Relationships and Copper Effects

  摘要：

  L2Pd(0) and L2Pd(II) complexes, where L=t-Bu-2(p-NMe2C6H4)P, have been identified as efficient catalyst systems for the Heck alkynylation of a variety of aryl bromides (17 examples) and aryl/heteroaryl chlorides (31 examples) with a range of aryl- and alkyl-acetylenes in excellent yields, under relatively low Pd loadings. The single-crystal X-ray structure determination of the presumably active catalytic species, L2Pd(0), was carried out in this study to better understand the superior activity of the current catalyst system from a structure activity relationship point of view. The P-Pd-P bond angle indicates that the complex is bent (174.7 degrees) in comparison to the perfectly linear (180.0 degrees) structure of the analogous Pd(t-Bu3P)(2). Preliminary mechanistic studies on the negative copper effect and substrate effect of aryl acetylenes were conducted to better understand the cross-coupling pathway of Heck alkynylation.

  DOI：

  10.1021/jo302195y

文献信息

• Heck Alkynylation (Copper-Free Sonogashira Coupling) of Aryl and Heteroaryl Chlorides, Using Pd Complexes of <i>t</i>-Bu₂(<i>p</i>-NMe₂C₆H₄)P: Understanding the Structure–Activity Relationships and Copper Effects
  作者：Xiaotao Pu、Hongbo Li、Thomas J. Colacot

  DOI：10.1021/jo302195y

  日期：2013.1.18

  L2Pd(0) and L2Pd(II) complexes, where L=t-Bu-2(p-NMe2C6H4)P, have been identified as efficient catalyst systems for the Heck alkynylation of a variety of aryl bromides (17 examples) and aryl/heteroaryl chlorides (31 examples) with a range of aryl- and alkyl-acetylenes in excellent yields, under relatively low Pd loadings. The single-crystal X-ray structure determination of the presumably active catalytic species, L2Pd(0), was carried out in this study to better understand the superior activity of the current catalyst system from a structure activity relationship point of view. The P-Pd-P bond angle indicates that the complex is bent (174.7 degrees) in comparison to the perfectly linear (180.0 degrees) structure of the analogous Pd(t-Bu3P)(2). Preliminary mechanistic studies on the negative copper effect and substrate effect of aryl acetylenes were conducted to better understand the cross-coupling pathway of Heck alkynylation.