1-氨基环己甲酸甲酯可用作生化试剂;作为合成聚氨酯基础原料异氰酸酯的中间体,通过碳酸二甲酯与有机胺反应制得,再经热裂解生成异氰酸酯,可避免光气污染;用于化学合成。
生化试剂;聚氨酯原料
路线1:1-氨基环己烷羧酸与(三甲基甲硅烷基)重氮甲烷反应
- 步骤:在冰冷却下搅拌1-氨基环己烷羧酸的四氢呋喃-甲醇溶液,滴加(三甲基甲硅烷基)重氮甲烷溶液并搅拌过夜;真空浓缩反应混合物,向残余物中加入乙醚-己烷(1/1),再加入4M HCl-乙酸乙酯,过滤收集沉淀物并干燥得产物。
- 条件:四氢呋喃、甲醇为溶剂,0℃反应。
- 收率:52%。
- 参考文献:[1] Patent: WO2007/46550, 2007, A1. Location in patent: Page/Page column 124 [2] Patent: WO2008/4698, 2008, A2. Location in patent: Page/Page column 130 [3] Patent: WO2011/144584, 2011, A1. Location in patent: Page/Page column 52-53
路线2:1-氨基环己烷羧酸与亚硫酰氯、甲醇反应
- 步骤:将1-氨基环己烷羧酸溶于甲醇,在-10℃下滴加亚硫酰氯,回流4小时后真空除去溶剂;将残余物在NaHCO₃溶液中浆化,用乙酸乙酯萃取,蒸馏除去溶剂得产物。
- 收率:71%。
- 表征:¹HNMR(DMSO + D₂O):δ4.12(2H,s),3.54(3H,s),1.70-1.77(2H,m),1.44-1.51(2H,m),1.22-1.33(6H,m);LC/MS [m/z] C₈H₁₅NO₂计算值157.1,实测值157.1。
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