| 设计实验:选择性保护1,4,7,10-四氮杂环十二烷的仲胺 |
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| 引用本文： | 张琴芳,王爱群,任小雨,张红素,余孝其.设计实验:选择性保护1,4,7,10-四氮杂环十二烷的仲胺[J].实验室研究与探索,2020(1):241-244. |
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| 作者姓名： | 张琴芳 王爱群 任小雨 张红素 余孝其 |
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| 作者单位： | ;1.四川大学化学基础实验教学中心;2.四川大学化学学院 |
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| 基金项目： | 四川大学实验室及设备管理处实验技术立项(20170033);新世纪高等教育教学改革工程(第八期)研究项目(SCU8165)。 |
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| 摘 要： | 氨基官能团存在于很多有生理活性的化合物中,氨基的保护策略选择对合成化学工作者非常重要。基于1,4,7,10-四氮杂环十二烷(Cyclen)的化合物应用广泛,为了合成基于Cyclen的具有不同结构和功能的产品,就需要系统的合成化学,尤其是对其仲胺的选择性保护。该设计实验以Cyclen为原料,分别采用(Boc)2O和Boc-OSu为胺基保护试剂,制备1,4,7-3 Boc-Cyclen和1,7-2 Boc-Cyclen;采用上一步合成的1,4,7-3 Boc-Cyclen为原料,Fmoc-Cl为保护试剂,制备1,4,7-3 Boc-10-Fmoc-Cyclen,再用CF3COOH脱掉Boc保护基制备Fmoc-Cyclen,以此得到单保护、对位二保护和三保护的Cyclen。结合1H NMR、13C NMR和HR-MS的鉴定结果,目标化合物结构正确。
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| 关 键 词： | 设计实验 1 4 7 10-四氮杂环十二烷 选择性保护仲胺 |
Design Experiment: Selective Protection of the Amino Groups of 1,4,7,10-Tetraazacyclododecane |
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| ZHANG Qinfang,WANG Aiqun,REN Xiaoyu,ZHANG Hongsu,YU Xiaoqi.Design Experiment: Selective Protection of the Amino Groups of 1,4,7,10-Tetraazacyclododecane[J].Laboratory Research and Exploration,2020(1):241-244. |
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| Authors: | ZHANG Qinfang WANG Aiqun REN Xiaoyu ZHANG Hongsu YU Xiaoqi |
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| Institution: | (Basic Chemistry Experiment Teaching Center,Sichua University,Chengdu 610064,China;College of Chemistry,Sichua University,Chengdu 610064,China) |
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| Abstract: | Amino functional groups are present in many physiologically active compounds,and the choice of amino protection strategy is important to synthetic chemists.Compounds based on 1,4,7,10-tetraazacyclododecane(Cyclen)are widely used.In order to synthesize Cyclen-based products with different structures and functions,systematic synthetic chemistry is required,especially selective protection of secondary amines.This design experiment uses Cyclen as raw material,and uses(Boc)2O and Boc-OSu as amino protecting reagents respectively to prepare 1,4,7-3 Boc-Cyclen and 1,7-2 Boc-Cyclen;Next,the 1,4,7-3 Boc-Cyclen synthesized in the previous step was used as a raw material,Fmoc-Cl was used as a protective reagent to prepare 1,4,7-3 Boc-10-Fmoc-Cyclen,and then the Boc protecting group was removed by CF3COOH to prepare Fmoc-Cyclen.In this way,single protected,para-double protected and triple protected Cyclen are obtained.Combining the results of 1H NMR,13C NMR and HR-MS,the structures of the target compounds are correct. |
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| Keywords: | design experiment 1 4 7 10-tetraazacyclododecane selective protection of secondary amines |
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