2-(trimethylsilyl)ethyl 8-cyclopropyl-7-(naphthalen-1-ylmethyl)-5-oxo-2-(thiophen-3-ylethynyl)-5H-thiazolo[3,2-a]-pyridine-3-carboxylate | 1345974-56-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(trimethylsilyl)ethyl 8-cyclopropyl-7-(naphthalen-1-ylmethyl)-5-oxo-2-(thiophen-3-ylethynyl)-5H-thiazolo[3,2-a]-pyridine-3-carboxylate
• CAS: 1345974-56-2
• 化学式: C₃₃H₃₁NO₃S₂Si
• 分子量: 581.832
• InChiKey: BWIXSSLJBHCGHB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.94
• 重原子数：
  40.0
• 可旋转键数：
  7.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  47.78
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  2-(trimethylsilyl)ethyl 8-cyclopropyl-7-(naphthalen-1-ylmethyl)-5-oxo-2-(thiophen-3-ylethynyl)-5H-thiazolo[3,2-a]-pyridine-3-carboxylate 以 二氯甲烷 、 三氟乙酸 为溶剂， 反应 20.0h， 以99%的产率得到6-cyclopropyl-7-(naphthalen-1-ylmethyl)-3-(thiophen-3-yl)-1H,9H-pyrano[3',4':4,5][1,3]thiazolo[3,2-a]pyridine-1,9-dione
  参考文献：
  名称：

  A Selective Intramolecular 5-exo-dig or 6-endo-dig Cyclization en Route to 2-Furanone or 2-Pyrone Containing Tricyclic Scaffolds

  摘要：

  Ringfused bicyclic 2-pyridones exhibit interesting biological properties against pili assembly in uropathogenic Escherichia coli (Pinkner, J. S. et al. Proc. Natl. Acad. Sci. U. S. A. 2006, 103, 17897-17902; Aberg, V. et al. Org. Biomol. Chem. 2007, 5, 1827-1834) as well as curli formation (Cegelski, L. et al. Nat. Chem. Biol. 2009, 5, 913-919). In the search for new ring-fused central fragments, highly selective synthetic routes to the 2-furanone or 2-pyrone containing tricyclic scaffolds 1 and 2 have been developed.

  DOI：

  10.1021/jo201952p
• 作为产物：
  描述：

  在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三氯溴甲烷 、 sodium hydride 、 三乙胺 作用下， 以 二氯甲烷 、 2-(三甲硅基)乙醇 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 8.5h， 生成 2-(trimethylsilyl)ethyl 8-cyclopropyl-7-(naphthalen-1-ylmethyl)-5-oxo-2-(thiophen-3-ylethynyl)-5H-thiazolo[3,2-a]-pyridine-3-carboxylate
  参考文献：
  名称：

  A Selective Intramolecular 5-exo-dig or 6-endo-dig Cyclization en Route to 2-Furanone or 2-Pyrone Containing Tricyclic Scaffolds

  摘要：

  Ringfused bicyclic 2-pyridones exhibit interesting biological properties against pili assembly in uropathogenic Escherichia coli (Pinkner, J. S. et al. Proc. Natl. Acad. Sci. U. S. A. 2006, 103, 17897-17902; Aberg, V. et al. Org. Biomol. Chem. 2007, 5, 1827-1834) as well as curli formation (Cegelski, L. et al. Nat. Chem. Biol. 2009, 5, 913-919). In the search for new ring-fused central fragments, highly selective synthetic routes to the 2-furanone or 2-pyrone containing tricyclic scaffolds 1 and 2 have been developed.

  DOI：

  10.1021/jo201952p