五环[5.4.0.0^(2,6).0^(3,10).0^(5,9)]十一烷的合成和表征  

Synthesis and Characterization of Pentacyclo[5.4.0.0^(2,6).0^(3,10).0^(5,9)]undecane

作　　者：史胜斌[1,2] 范桂娟[1] 杨世源[2] 廖龙渝[1] 张红梨 李金山[1] 

机构地区：[1]中国工程物理研究院化工材料研究所,四川绵阳621999 [2]西南科技大学,四川绵阳621010

出　　处：《含能材料》2015年第2期120-124,共5页Chinese Journal of Energetic Materials

基　　金：国家重大基础研究资助项目(00401010201)

摘　　要：将二聚环戊二烯裂解生成的环戊二烯,与对苯二醌进行Diels-Alder加成反应,得到了1,4,4a,8a-四氢-1,4-桥亚甲基萘-5,8-二酮,经[2+2]环加成和黄鸣龙还原反应,最终得到目标产物五环[5.4.0.02,6.03,10.05,9]十一烷,产物总收率为51.6%,采用熔点测定、核磁共振氢谱、碳谱、红外光谱和质谱对各步产物进行了表征。探讨了Diels-Alder加成和[2+2]环加成反应的影响因素,确定了Diels-Alder加成反应的最佳反应条件:滴加环戊二烯时溶液温度-11℃,时间3 h。[2+2]环加成反应的最佳条件是:以丙酮做溶剂,原料浓度2 g·125mL-1,光照时间23 h。Cyclopentadiene was prepared from its dimeric form by pyrolysis at 200℃ . By using cyclopentadiene and 1 ,4-benzo- quinone as starting materials, pentacyclo [ 5.4.0.0^2,6.0^3,10.0^5,9 ]undecane was synthesized with total yield 51.6% via Diels-Alder, 12＋21photo-cycloaddition and Huang-Minlong reduction. The products were characterized by 1^H NMR, 13^C NMR, IR spectra and MS. The optimal conditions of Diels-Alder and [ 2 ＋2] photo-cycloaddition were discussed and confirmed. The optimum conditions for Diels-Alder reaction are： the reaction temperature of dropwise is -11℃, the reaction time 3 h. The best condition of [2＋2 ] photo-cycloaddition are as following： the acetone as solvent, the raw materials concentration is 2 g · 125mL^-1 and the reaction time 23 h.

关 键 词：[2+2]环加成反应 五环[5.4.0.0^2 6.0^3 10.0^5 9]]十一烷 合成 

分 类 号：TQ560.1[化学工程—炸药化工]