3-methyl-1,5-diphenyl-1H-thieno[2,3-c]pyrazole | 55164-44-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-methyl-1,5-diphenyl-1H-thieno[2,3-c]pyrazole
• 英文别名: 3-Methyl-1,5-diphenylthieno[2,3-c]pyrazole；3-methyl-1,5-diphenylthieno[2,3-c]pyrazole
• CAS: 55164-44-8
• 化学式: C₁₈H₁₄N₂S
• 分子量: 290.389
• InChiKey: NDURSUMOSFELLT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  46.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  5-氯-3-甲基-1-苯基吡唑 在 sodium sulfide 、 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 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 11.42h， 生成 3-methyl-1,5-diphenyl-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

文献信息

• A new approach to the synthesis of 2-substituted benzothiophens and their hetero-analogues.
  作者：Kenneth J. Brown、Otto Meth-Cohn

  DOI：10.1016/s0040-4039(01)92086-6

  日期：1974.1
• 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.