2-isopropyl-3-methyl-2-(2-methylphenylthiazol-4-yl)butanenitrile | 1431978-62-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-isopropyl-3-methyl-2-(2-methylphenylthiazol-4-yl)butanenitrile
• 英文别名: 3-Methyl-2-[2-(2-methylphenyl)-1,3-thiazol-4-yl]-2-propan-2-ylbutanenitrile
• CAS: 1431978-62-9
• 化学式: C₁₈H₂₂N₂S
• 分子量: 298.452
• InChiKey: SPBKSOYVTGSTSZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  64.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-isopropyl-3-methyl-2-(2-methylphenylthiazol-4-yl)butanenitrile 在 palladium diacetate 、 silver carbonate 、 三甲基乙酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.08h， 以24%的产率得到4-isopropyl-5-methyl-2-(o-tolyl)-5,6-dihydro-4H-cyclopenta[d]thiazole-4-carbonitrile
  参考文献：
  名称：

  Intramolecular PdII-catalyzed dehydrogenative C(sp3)–C(sp2) coupling: an alternative to Pd0-catalyzed C(sp3)–H arylation from aryl halides?

  摘要：

  The synthesis of fused thiophene-cyclopentanes by Pd-II-catalyzed dehydrogenative C(sp(2))-H/C(sp(3))-H coupling is described. This reaction shows interesting chemo- and diastereoselectivity, however a direct comparison showed that it is yet much less efficient than the two-step sequence composed of electrophilic halogenation and Pd-0-catalyzed C(sp(3))-H arylation. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.11.060
• 作为产物：
  描述：

  2-溴甲苯 、 2-isopropyl-3-methyl-2-(thiazol-4-yl)butanenitrile 在 palladium diacetate 、 potassium carbonate 、 tricyclohexylphosphine tetrafluoroborate 、 三甲基乙酸 作用下， 以57%的产率得到2-isopropyl-3-methyl-2-(2-methylphenylthiazol-4-yl)butanenitrile
  参考文献：
  名称：

  Intramolecular PdII-catalyzed dehydrogenative C(sp3)–C(sp2) coupling: an alternative to Pd0-catalyzed C(sp3)–H arylation from aryl halides?

  摘要：

  The synthesis of fused thiophene-cyclopentanes by Pd-II-catalyzed dehydrogenative C(sp(2))-H/C(sp(3))-H coupling is described. This reaction shows interesting chemo- and diastereoselectivity, however a direct comparison showed that it is yet much less efficient than the two-step sequence composed of electrophilic halogenation and Pd-0-catalyzed C(sp(3))-H arylation. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.11.060