spiro[5.2'']acenaphthene-1''-onespiro[6.3']-5'-(2-chlorophenylmethylidene)-1'-methylpiperidin-4'-one-7-(2-chlorophenyl)tetrahydro-1H-pyrrolo[1,2-c][1,3]thiazole

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: spiro[5.2'']acenaphthene-1''-onespiro[6.3']-5'-(2-chlorophenylmethylidene)-1'-methylpiperidin-4'-one-7-(2-chlorophenyl)tetrahydro-1H-pyrrolo[1,2-c][1,3]thiazole
• 化学式: C₃₅H₂₈Cl₂N₂O₂S
• 分子量: 611.592
• InChiKey: SVYRCTKZVBGWAN-ZPRFRALRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  42
• 可旋转键数：
  2
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  65.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (3E,5E)-3,5-bis(2-chlorobenzylidene)-1-methylpiperidin-4-one 、 噻莫西酸 、 苊醌 以 甲醇 为溶剂， 反应 3.0h， 以91%的产率得到spiro[5.2'']acenaphthene-1''-onespiro[6.3']-5'-(2-chlorophenylmethylidene)-1'-methylpiperidin-4'-one-7-(2-chlorophenyl)tetrahydro-1H-pyrrolo[1,2-c][1,3]thiazole
  参考文献：
  名称：

  An atom economic synthesis and AChE inhibitory activity of novel dispiro 7-aryltetrahydro-1H-pyrrolo[1,2-c][1,3]thiazole and 4-aryloctahydroindolizine N-methylpiperidin-4-one hybrid heterocycles

  摘要：

  The 1,3-dipolar cycloaddition of azomethine ylides generated in situ from acenaphthenequinone and alpha-amino acids viz. 1,3-thiazolone-4-carboxylic acid and piperidine-2-carboxylic acid to a series of 1-methyl-3,5-bis[(E)-arylmethylidene]tetrahydro-4(1H)-pyridinones afforded novel spiro[5.2 '']acenaphthene-1 ''-onespiro[6.3']-5'-arylmethylidene-1'-methylpiperidin-4'-one-7-aryltetrahydro-1H-pyrrolo[12-c][1,3]thiazoles and spiro[2.2 '']acenaphthene-1 ''-onespiro[3.3']-5'-arylmethylidene-1'-methylpiperidin-4'-one-4-aryloctahydroindolizines respectively in quantitative yields. These compounds were evaluated for their AChE inhibitory activity and compound 3c was found to be the most potent with IC50 1.86 mu mol/L. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.04.050