1-(4-烯丙氧基-1,6-庚二烯-4-基)-4-甲氧基苯的合成与表征
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摘要
以尼泊金甲酯为初始原料,经甲基化、格氏试剂加成和醚化3步反应,设计合成了新型AB_3型树枝状标题化合物,利用红外光谱、核磁共振氢谱和元素分析对其结构进行了表征。对影响醚化反应的条件进行了优化,确定了最优反应条件:氢化钠为碱、四氢呋喃为溶剂、反应温度为65℃、反应时间为4 h,收率可达95%。
A novel dendron was designed and synthesized by methylation,nucleophilic addition of Grignard reagent and etherification using nipagin ester as starting material. The structure of product was confirmed by IR,1HNMR and elemental analysis. The reaction conditions of 1-( 4-( allyloxy) hepta-1,6-dien-4-yl)-4-methoxybenzene were optimized. In the presence of sodium hydride as base,THF as solvent,the yield of the etherification was up to 95%.
A novel dendron was designed and synthesized by methylation,nucleophilic addition of Grignard reagent and etherification using nipagin ester as starting material. The structure of product was confirmed by IR,1HNMR and elemental analysis. The reaction conditions of 1-( 4-( allyloxy) hepta-1,6-dien-4-yl)-4-methoxybenzene were optimized. In the presence of sodium hydride as base,THF as solvent,the yield of the etherification was up to 95%.
引文
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[3]RUIZ J,LAFUENTE G,MARCEN S,et al.Construction of giant dendrimers using a tripodal building block[J].J.Am.Chem.Soc.,2003,125(24):7 250-7 257.
[4]ORNELAS C,RUIZ J,BELIN C,et al.Giant dendritic molecular electrochrome batteries with ferrocenyl and pentamethylferrocenyl termini[J].J.Am.Chem.Soc.,2009,131(2):590-601.
[5]汪剑,赵辉,蔡春根,等.带树枝状侧链聚苯乙炔的合成与结构表征[J].高分子学报,2009,(4):293-297.
[6]李迎迎,韩镭,陈金平,等.双枝芳醚树枝形聚合物构象研究[J].化学学报,2008,66(15):1 803-1 809.
[7]林志忠,刘敬欣,李良春,等.新型含寡聚乙二醇链的苄醚树状化合物的合成及其溶液性质[J].合成化学,2013,21(4):432-435.
[8]王永亮.树枝状分子共价键修饰质子化多金属氧酸盐有序结构的研究[D].天津:南开大学,2010:17-20.
[9]JIANG Jing,LIU Hong-wei,ZHAO You-liang,et al.Synthesis and characterization of dendronized poly(methylsiloxane)with appendent Fréchet-type dendrons[J].Sci.China,2002,45(6):633-639.
[10]SARTOR V,DJAKOVITCH L,FILLAUT J L,et al.Organoiron route to a new dendron for fast dendritic syntheses using divergent and convergent methods[J].J.Am.Chem.Soc.,1999,121(12):2 929-2 930.
[11]OOI T,KAMEDA M,MARUOKA K.Design of N-spiro C2-symmetric chiral quaternary ammonium bromides as novel chiral phase-transfer catalysts:synthesis and application to practical asymmetric synthesis ofα-amino acids[J].J.Am.Chem.Soc.,2003,125(17):5 139-5 151.
[12]NLATE S,PLAULT L,FELPIN F X,et al.Fast and scalable route to aryl polyallyl dendrons and dendrimers[J].Adv.Synth.Catal.,2008,350(1):1 419-1 424.