1,4-二甲氧基柱[5]芳烃醌类的环氧衍生化
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摘要
为了扩大柱[5]芳烃衍生类型,扩展其在主客体化学与分子器件等领域的潜在应用,以1,4-二甲氧基柱[3]芳烃[2]醌(或1,4-二甲氧基柱[4]芳烃[1]醌)为原料,1,8-二氮杂二环十一碳-7-烯和过氧化叔丁醇为催化剂,制备环氧化醌类柱[5]芳烃,并采用1 H NMR、13 C NMR、高分辨质谱和X-射线衍射测试其结构性质。结果表明:合成反应条件温和,收率较高,收率分别为81%和42%;1 H NMR实验和X-射线衍射法表明,与1,4-二甲氧基柱[4]芳烃[1]醌相比,环氧化柱[4]芳烃[1]醌结构中一个对苯二甲醚单元空间位置发生约为90°偏转;而1 H NMR数据和结构模拟图表明,环氧化柱[3]芳烃[2]醌中对苯二甲醚单元并未有偏转,成规整的柱型空腔。柱[5]芳烃衍生物及其结构信息为进一步构筑柱[5]芳烃高级组装体奠定基础。
To expand derived types of pillar[5]arenes and extend its potential application in host-guest chemistry and molecular device fields,1,4-dimethoxypillar[3]arene[2]quinone(or 1.4-dimethoxypillar[4]arene[1]quinone)was used as the raw material,and 1,8-diazabicyclo 11 carbon-7 alkenetert butyl hydroperoxide was used as the catalyst to prepare epoxidation quinones pillar[5]arenes.Their structures were investigated by 1 H NMR,13 C NMR,HRMS and X-ray crystallography.The results show that,the synthetic reaction conditions are mild,and the yield is high,81% and 42%,respectively.1 H NMR experiment and X-ray diffraction method indicate that,compared with 1.4-dimethoxypillar[4]arene[1]quinone,space position of one dimethoxybenzene unit in epoxidation pillar[4]arene[1]quinone structure rotated about 90°.1 H NMR data and structural simulation diagram show that,dimethoxybenzene unit in epoxidation pillar[3]arene[2]quinone do not rotate,and present the regular columnar cavity.Pillar[5]arene derivative and its structural information lay the foundation for further constructing advanced assembly of pillar[5]arene.
To expand derived types of pillar[5]arenes and extend its potential application in host-guest chemistry and molecular device fields,1,4-dimethoxypillar[3]arene[2]quinone(or 1.4-dimethoxypillar[4]arene[1]quinone)was used as the raw material,and 1,8-diazabicyclo 11 carbon-7 alkenetert butyl hydroperoxide was used as the catalyst to prepare epoxidation quinones pillar[5]arenes.Their structures were investigated by 1 H NMR,13 C NMR,HRMS and X-ray crystallography.The results show that,the synthetic reaction conditions are mild,and the yield is high,81% and 42%,respectively.1 H NMR experiment and X-ray diffraction method indicate that,compared with 1.4-dimethoxypillar[4]arene[1]quinone,space position of one dimethoxybenzene unit in epoxidation pillar[4]arene[1]quinone structure rotated about 90°.1 H NMR data and structural simulation diagram show that,dimethoxybenzene unit in epoxidation pillar[3]arene[2]quinone do not rotate,and present the regular columnar cavity.Pillar[5]arene derivative and its structural information lay the foundation for further constructing advanced assembly of pillar[5]arene.
引文
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[19]Strutt N L,Zhang H,Stoddart J F,et al.Aminofunctionalized pillar[5]arene[J].Chemistry-A European Journal,2014,20(35):10996-11004.
[20]Han C,Zhang Z,Huang F,et al.Syntheses of a pillar[4]arene[1]quinone and a difunctionalized pillar[5]arene by partial oxidation[J].Chemical Communications,2012,48(79):9876-9878.
[21]Pan M,Xue M.A pillar[2]arene[3]hydroquinone which can selfassemble to form a molecular zipper in the solid state[J].RSC Advances,2013,3(43):20287-20290.
[22]Pan M,Xue M.Pillar[5]arene derivatives with three different kinds of repeating units:First examples,crystal structures and selective preparation[J].RSCAdvances,2014,4(1):260-263.
[23]Yadav V K,Kapoor K K.1,8-Diazabicyclo[5.4.0]undec-7-ene:a remarkable base in the epoxidation ofα,β-unsaturated-δ-lactones and other enones with anhydrous t-BuOOH[J].Tetrahedron,1995,51(31):8573-8584.
[2]Ogoshi T,Kanai S,Fujinami S,et al.Para-bridged symmetrical pillar[5]arenes:Their lewis acid catalyzed synthesis and host-guest property[J].Journal of the American Chemical Society,2008,130(15):5022-5023.
[3]Ogoshi T,Yamagishi T,Nakamoto Y.Pillar-shaped macrocyclic hosts pillar[n]arenes:New key players for supramolecular chemistry[J].Chemical Reviews,2016,116(14):7937-8002.
[4]Jie K,Liu M,Huang F,et al.Styrene purification by guest-induced restructuring of pillar[6]arene[J].Journal of the American Chemical Society,2017,139(8):2908-2911.
[5]Cao D,Kou Y,Liang J,et al.A facile and efficient preparation of pillararenes and a pillarquinone[J].Angewandte Chemie International Edition,2009,48(51):9721-9723.
[6]Yao J,Wu W,Yang C,et al.Temperature-driven planar chirality switching of a pillar[5]arene-based molecular universal joint[J].Angewandte Chemie International Edition,2017,56(24):6869-6873.
[7]Li H,Chen D X,Yang Y W,et al.Viologen-mediated assembly of and sensing with carboxylatopillar[5]arenemodified gold nanoparticles[J].Journal of the American Chemical Society,2013,135(4):1570-1576.
[8]Ogoshi T,Ueshima N,Sakakibara F,et al.Conversion from pillar[5]arene to pillar[6-15]arenes by ring expansion and encapsulation of C60 by pillar[n]arenes with nanosize cavities[J].Organic Letters,2014,16(11):2896-2899.
[9]Yao Y,Xue M,Huang F,et al.A new water-soluble pillar[5]arene:Synthesis and application in the preparation of gold nanoparticles[J].Chemical Communications,2012,48(52):6505-6507.
[10]Hu X B,Chen L,Hou J L,et al.Pillar[5]arene decaamine:Synthesis,encapsulation of very long linear diacids and formation of ion pair-stopped[2]rotaxanes[J].Chemical Communications,2011,47(16):4694-4696.
[11]Shu X,Chen W,Li C,et al.Novel binding regioselectivity in the interpenetration of a non-symmetric axle into a non-symmetric pillar[5]arene wheel[J].Chemical Communications,2014,50(37):4820-4823.
[12]Ni M,Lin C,Wang L,et al.Dramatically promoted swelling of a hydrogel by pillar[6]arene-ferrocene complexation with multistimuli responsiveness[J].Journal of the American Chemical Society,2016,138(20):6643-6649.
[13]Pan M,Xue M.Selective preparation of isomeric tetrahydroxypillar[5]arenes and pillar[3]arene[2]quinones[J].European Journal of Organic Chemistry,2013(22):4787-4793.
[14]Li C,Ma J,Zhao L,et al.Molecular selective binding of basic amino acids by a water-soluble pillar[5]arene[J].Chemical Communications,2013,49(19):1924-1926.
[15]Ma Y,Ji X,Huang F,et al.A cationic water-soluble pillar[5]arene:Synthesis and host-guest complexation with sodium 1-octanesulfonate[J].Chemical Communications,2011,47(45):12340-12342.
[16]Hu X B,Chen L,Hou J L,et al.Pillar[5]arene decaamine:Synthesis,encapsulation of very long linear diacids and formation of ion pair-stopped[2]rotaxanes[J].Chemical Communications,2011,47(16):4694-4696.
[17]Hu X B,Chen J,Hou J L,et al.Single-molecular artificial transmembrane water channels[J].Journal of the American Chemical Society,2012,134(20):8384-8387.
[18]Zhang Z,Han C,Huang F,et al.A solvent-driven molecular spring[J].Chemical Science,2012,3(10):3026-3031.
[19]Strutt N L,Zhang H,Stoddart J F,et al.Aminofunctionalized pillar[5]arene[J].Chemistry-A European Journal,2014,20(35):10996-11004.
[20]Han C,Zhang Z,Huang F,et al.Syntheses of a pillar[4]arene[1]quinone and a difunctionalized pillar[5]arene by partial oxidation[J].Chemical Communications,2012,48(79):9876-9878.
[21]Pan M,Xue M.A pillar[2]arene[3]hydroquinone which can selfassemble to form a molecular zipper in the solid state[J].RSC Advances,2013,3(43):20287-20290.
[22]Pan M,Xue M.Pillar[5]arene derivatives with three different kinds of repeating units:First examples,crystal structures and selective preparation[J].RSCAdvances,2014,4(1):260-263.
[23]Yadav V K,Kapoor K K.1,8-Diazabicyclo[5.4.0]undec-7-ene:a remarkable base in the epoxidation ofα,β-unsaturated-δ-lactones and other enones with anhydrous t-BuOOH[J].Tetrahedron,1995,51(31):8573-8584.