5-chloro-1,3-dimethyl-4-(phenylethynyl)-1H-pyrazole | 65447-57-6

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 芳基卤化物
• 英文名称: 5-chloro-1,3-dimethyl-4-(phenylethynyl)-1H-pyrazole
• 英文别名: 5-Chloro-1,3-dimethyl-4-(2-phenylethynyl)pyrazole
• CAS: 65447-57-6
• 化学式: C₁₃H₁₁ClN₂
• 分子量: 230.697
• InChiKey: HWLWKZMTSBZIHK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 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：

  5-chloro-1,3-dimethyl-4-(phenylethynyl)-1H-pyrazole 在 sodium sulfide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以75%的产率得到1,3-dimethyl-5-phenyl-1H-thieno[2,3-c]pyrazole
  参考文献：
  名称：

  Sonogashira Coupling Offers a New Synthetic Route to Thieno[2,3-c]pyrazoles

  摘要：

  [image omitted] 1,3-Disubstituted-5-chloro-4-iodopyrazoles are selectively coupled with phenylacetylene under typical Sonogashira reaction conditions [PdCl2(PPh3)2, CuI, Et3N, dimethylformamide (DMF)] to obtain the corresponding 5-chloro-4-(phenylethynyl)pyrazoles in good yield. The latter are smoothly cyclized with Na2S in DMF into the corresponding thieno[2,3-c]pyrazoles. Detailed spectroscopic investigations (1H, 13C, and 15N NMR, mass, and infrared) of all compounds are reported.

  DOI：

  10.1080/00397911003629382
• 作为产物：
  描述：

  5-氯-1,3-二甲基-1H-吡唑 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 碘 、 碘酸 、 溶剂黄146 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.17h， 生成 5-chloro-1,3-dimethyl-4-(phenylethynyl)-1H-pyrazole
  参考文献：
  名称：

  Sonogashira Coupling Offers a New Synthetic Route to Thieno[2,3-c]pyrazoles

  摘要：

  [image omitted] 1,3-Disubstituted-5-chloro-4-iodopyrazoles are selectively coupled with phenylacetylene under typical Sonogashira reaction conditions [PdCl2(PPh3)2, CuI, Et3N, dimethylformamide (DMF)] to obtain the corresponding 5-chloro-4-(phenylethynyl)pyrazoles in good yield. The latter are smoothly cyclized with Na2S in DMF into the corresponding thieno[2,3-c]pyrazoles. Detailed spectroscopic investigations (1H, 13C, and 15N NMR, mass, and infrared) of all compounds are reported.

  DOI：

  10.1080/00397911003629382

文献信息

• SINYAKOV A. N.; VASILEVSKIJ S. F.; SHVARTSBERG M. S., IZV. AN CCCP, CEP. XIM., 1977, HO 10,
  作者：SINYAKOV A. N.、 VASILEVSKIJ S. F.、 SHVARTSBERG M. S.

  DOI：——

  日期：——
• Sonogashira Coupling Offers a New Synthetic Route to Thieno[2,3-<i>c</i>]pyrazoles
  作者：Gernot A. Eller、Gytė Vilkauskaitė、Eglė Arbačiauskienė、Algirdas Šačkus、Wolfgang Holzer

  DOI：10.1080/00397911003629382

  日期：2011.1.31

  [image omitted] 1,3-Disubstituted-5-chloro-4-iodopyrazoles are selectively coupled with phenylacetylene under typical Sonogashira reaction conditions [PdCl2(PPh3)2, CuI, Et3N, dimethylformamide (DMF)] to obtain the corresponding 5-chloro-4-(phenylethynyl)pyrazoles in good yield. The latter are smoothly cyclized with Na2S in DMF into the corresponding thieno[2,3-c]pyrazoles. Detailed spectroscopic investigations (1H, 13C, and 15N NMR, mass, and infrared) of all compounds are reported.