English
新闻公告
More
化学进展 2007, Vol. 19 Issue (05): 722-734 前一篇   后一篇

• 综述与评论 •

双杯芳烃研究进展

郑琴;龚淑玲**; 张春雷; 王巍; 陈远荫   

  1. 武汉大学化学与分子科学学院 武汉 430072
  • 收稿日期:2006-07-20 修回日期:2006-08-21 出版日期:2007-05-24 发布日期:2007-05-24
  • 通讯作者: 龚淑玲

Progress in Biscalixarene Research

Zheng Qin;Gong Shuling**;Zhang Chunlei;Wang Wei; Chen Yuanyin   

  1. College of Chemistry and Molecular Sciences, Wuhan Univeristy, Wuhan 430072, China
  • Received:2006-07-20 Revised:2006-08-21 Online:2007-05-24 Published:2007-05-24
双杯芳烃是杯芳烃家族中的重要一员。它由两个杯芳烃单元通过化学键联结而形成,一般常有上缘-下缘、下缘-下缘、下缘-上缘3种桥联方式,其结构更复杂,性质也更为丰富多彩。双杯芳烃具有两个相同或不相同的结合部位,可同时络合两个相同或不相同的底物,还可表现出特殊的协同作用、更强的络合能力、变构象以及粒子雾荡等新的性质。本文根据杯芳烃亚单元的种类,综述了双杯芳烃的研究进展,重点描述了不同桥联方式的双杯[4]芳烃的合成方法,而且对一些具有特殊性能的双杯芳烃进行了较为详细的介绍。最后对双杯芳烃的发展前景作了展望。
Biscalixarene is an important member of calixarene family, composed of two calixarene moieties linked at their upper (head) or lower (tail) rim through various spacers with more complicated structures and colorful properties as compared to calixarene. It can be divided into three basic types commonly known as head-to-head, tail-to-tail, and head -to- tail bridged biscalixarenen. Biiscalixarene contains two same or different recognition sites and can complex two same or different guests. Moreover, it has some high-level properties such as stronger inclusion ability, allosteric effects, oscallation between the two metal-binding sites and so on due to cooperative effect. Here, a survey of biscalixarene chemistry and recent research progress are reviewed according to the type of calixarene subunits. Thesyntheses of the biscalix[4] arene with various linked types are emphatically described, and some special biscalixarenes are described in detail as well. The prospect of biscalixarene chemistry is also discussed.

中图分类号: 

()

[ 1 ] 刘育(Liu Y) , 尤长城(You C C) , 张衡益(Zhang H Y) . 超分子化学(Tianjin : Supramolecular Chemistry) . 天津: 南开大学出版社(Tianjin : Nankai University Press) , 2000. 306 —384
[ 2 ] Asfari Z , Bêhmer V , Harrowfield J , Vicens J . Calixarenes ,2001. Netherlands : Kluwer Academic , 2001. 130 —154
[ 3 ] Asfari Z , Weiss J , Vicens J . Synlett , 1993 , (10) : 719 —725
[ 4 ] McKervey M A , Owens M, Schulten H R , et al . Angew. Chem.Int . Ed. Engl . , 1990 , 29(3) : 280 —282
[ 5 ] Ulrich G, Ziessel R , Manet I , et al . Chem. Eur. J . , 1997 , 3(11) : 1815 —1822
[ 6 ] Ohseto F , Shinkai S. Chem. Lett . , 1993 , (12) : 2045 —2048
[ 7 ] Ikeda A , Shinkai S. J . Chem. Soc. , Chem. Commun. , 1994 ,2375 —2376
[ 8 ] Nabeshima T , Saiki T , Sumitomo K, et al . Tetrahedron Lett . ,2004 , 45(24) : 4719 —4722
[ 9 ] Bêhmer V , Goldmann H , Vogt W, et al . Tetrahedron Lett . ,1989 , 30(11) : 1391 —1394
[10] Gutsche C D , Iqbal M. Org. Synth. , 1990 , 68 : 234 —237
[11] Higler I , Timmermann P , Verboom W, et al . Eur. J . Org.Chem. , 1998 , (12) : 2689 —2702
[12] Bêhmer V , Goldmann H , Vogt W, et al . Tetrahedron Lett . ,1989 , 30(11) : 1391 —1394
[13] Asfari Z , Weiss J , Vicens J . Polish J . Chem. , 1992 , 66 (4) :709 —712
[14] Arimura T , Brown C T , Springs S L , et al . Chem. Commun. ,1996 , 2293 —2294
[15] Beer P D , Keefe A D , Slawin A M Z , et al . J . Chem. Soc. ,Dalton Trans. , 1990 , (12) : 3675 —3682
[16] Wang J S , Gutsche C D. J . Am. Chem. Soc. , 1998 , 120(47) :12226 —12231
[17] Marchand A P , Chong H S , Takhi M, et al . Tetrahedron , 2000 ,56(20) : 3121 —3126
[18] 王巍(Wang W) , 龚淑玲(Gong S L) , 孟令芝(Meng L Z) , et al . 高等学校化学学报(Chem. J . Chin. Univ. ) , 2005 , 26(8) : 1467 —1470
[19] Yamamoto H , Sakaki T , Shinkai S. Chem. Lett . , 1994 , (3) :469 —472
[20] Chen C F , Lu L G, Hu ZQ , et al . Tetrahedron , 2005 , 61(15) :3853 —3858
[21] Zhong Z L , Chen Y Y, Lu X R. Tetrahedron Lett . , 1995 , 36(37) : 6735 —6738
[22] Schmitt P , Beer P D , Drew M G B , et al . Tetrahedron Lett . ,1998 , 39(35) : 6383 —6386
[23] Ulrich G, Ziessel R. Tetrahedron Lett . , 1994 , 35(34) : 6299 —6302
[24] Zheng Q Y, Chen C F , Huang Z T. Chin. Chem. Lett . , 2002 ,13(6) : 525 —527
[25] Nabeshima T , Saiki T , Sumitomo K, et al . Tetrahedron Lett . ,2004 , 45(36) : 6761 —6763
[26] Webber P R A , Beer P D , Chen G Z , et al . J . Am. Chem.Soc. , 2003 , 125 (19) : 5774 —5785
[27] Kerdpaiboon N , Tomapatanaget B , Chailapakul O , et al . J . Org.Chem. , 2005 , 70(12) : 4797 —4804
[28] Tantrakarn K, Ratanatawanate C , Pinsuk T , et al . Tetrahedron Lett . , 2003 , 44(1) : 33 —36
[29] Li J S , Zhong Z L , Chen Y Y, et al . Tetrahedron Lett . , 1998 ,39(36) : 6507 —6510
[30] Zheng Q Y, Chen C F , Huang Z T. Chin. Chem. Lett . , 2000 ,11(10) : 863 —864
[31] Zhao B T , Blesa M J , Mercier N , et al . J . Org. Chem. , 2005 ,70(16) : 6254 —6257
[32] Kraft D , Bêhmer V , Vogt W, et al . J . Chem. Soc. , Perkin Trans. 1 , 1994 , (9) : 1221 —1230
[33] Ohseto F , Sakaki T , Araki K, et al . Tetrahedron Lett . , 1993 , 34(13) : 2149 —2152
[34] Wolbers M P O , van Veggel F C J M, Heeringa R H M, et al .Liebigs Ann.PRecueil , 1997 , (12) : 2587 —2600
[35] Memon S , Yilmaz M. Sep. Sci . Technol . , 2001 , 36(3) : 473 —486
[36] Memon S , Yilmaz M. Sep. Sci . Technol . , 2000 , 35(3) : 457 —467
[37] Memon S , Uysal G, Yilmaz M. Sep. Sci . Technol . , 2000 , 35(8) : 1247 —1256
[38] Alpoguz H K, Memon S , Ersoz M, et al . NewJ . Chem. , 2002 ,26(4) : 477 —480
[39] Santoyo-Gonzalez F , Torres-Pinedo A , Sanchez-Ortega A. J . Org.Chem. , 2000 , 65(14) : 4409 —4414
[40] Al2Saraierh H , Miller D O , Georghiou P E. J . Org. Chem. ,2005 , 70(21) : 8273 —8280
[41] Xu H , Stampp S P , Rudkevich D M. Org. Lett . , 2003 , 5(24) :4583 —4586
[42] Xu H , Rudkevich D M. J . Org. Chem. , 2004 , 69(25) : 8609 —8617
[43] Xu H , Rudkevich D M. Org. Lett . , 2005 , 7(15) : 3223 —3226
[44] Kraft D , van Loon J D , Owens M, et al . Tetrahedron Lett . ,1990 , 31(34) : 4941 —4944
[45] Hu X B , Chan A S C , Han X X, et al . Tetrahedron Lett . , 1999 ,40(39) : 7115 —7118
[46] Beer P D , Drew M G B , Gradwell K. J . Chem. Soc. , Perkin Trans. 2 , 2000 , (3) : 511 —519
[47] Kumar M, Bhalla V S N , Babu J N. Tetrahedron , 2003 , 59(18) : 3267 —3273
[48] Kumar M, Mahajan R K, Sharma V , et al . Tetrahedron Lett . ,2001 , 42(31) : 5315 —5318
[49] Rudkevich D M, Verboom W, Reinhoudt D N. Tetrahedron Lett . , 1994 , 35(38) : 7131 —7134
[50] Pinkhassik E , Stibor I , Havlicek V. Collect . Czech. Chem.Commun. , 1996 , 61(8) : 1182 —1190
[51] Ohseto F , Shinkai S. J . Chem. Soc. , Perkin Trans. 2 , 1995 ,(6) : 1103 —1109
[52] Santoyo-Gonzalez F , Torres-Pinedo A , Barria C S. Eur. J . Org.Chem. , 2000 , (21) : 3587 —3593
[53] 杨发福(Yang F F) , 郑林禄(Zheng L L) , 季衍卿(Ji YQ) 等.有机化学(Chin. J . Org. Chem. ) , 2006 , 26(2) : 268 —270
[54] McKervey M A , Pitarch M. Chem. Commun. , 1996 , 1689 —1690
[55] Matthews S E , Schmitt P , Felix V , et al . J . Am. Chem. Soc. ,2002 , 124 (7) : 1341 —1353
[56] Schmitt P , Beer P D , Drew M GB , et al . Angew. Chem. Int .Ed. Engl . , 1997 , 36(17) : 1840 —1842
[57] Natthews S E , Rees N H , Felix V , et al . Inorg. Chem. , 2003 ,42(3) : 729 —734
[58] Budka J , Lhoták P , Stibor I , et al . Tetrahedron Lett . , 2002 , 43(15) : 2857 —2861
[59] Matthews S E , Felix V , Drew M G B , et al . Org. Biomol .Chem. , 2003 , 1(7) : 1232 —1239
[60] Bouoit-Montesinos S , Bassus J , Perrin M, et al . Tetrahedron Lett . , 2000 , 41(15) : 2563 —2567
[61] Neri P , Bottino A , Cunsolo F , et al . Angew. Chem. Int . Ed.Engl . , 1998 , 37(1/2) : 166 —169
[62] Bottino A , Cunsolo F , Piattelli M, et al . Tetrahedron Lett . ,2000 , 41(51) : 10065 —10069
[63] Iglesias-Sánchez J C , Fragoso A , de Mendoza J , et al . Org.Lett . , 2006 , 8(12) : 2571 —2574
[64] Lhotak P , Shinkai S. Tetrahedron Lett . , 1996 , 37 (5) : 645 —648
[65] Dondoni A , Ghiglione C , Marra A , et al . J . Org. Chem. , 1998 ,63(25) : 9535 —9539
[66] Budka J , Dudic M, Lhotak P , et al . Tetrahedron , 1999 , 55(43) : 12647 —12654
[67] Mogck O , Parzuchowski P , Nissinen M, et al . Tetrahedron ,1998 , 54(34) : 10053 —10068
[68] Beer P D , Shade M. Chem. Commun. , 1997 , 2377 —2378
[69] Beer P D , Cooper J B. Chem. Commun. , 1998 , 129 —130
[70] Fischer C , Nieger M, Mogck O , et al . Eur. J . Org. Chem. ,1998 , (1) : 155 —161
[71] Dudic M, Lhotak P , Kral V , et al . Tetrahedron Lett . , 1999 , 40(32) : 5949 —5952
[72] Tilki T , Sener I , Karci F , et al . Tetrahedron , 2005 , 61 (40) :9624 —9629
[73] Vysotsky M O , Bêhmer V , Wurthner F , et al . Org. Lett . , 2002 ,4 (17) : 2901 —2904
[74] Arduini A , Fanni S , Manfredi G, et al . J . Org. Chem. , 1995 ,60(5) : 1448 —1453
[75] Araki K, Hayashida H. Tetrahedron Lett . , 2000 , 41 ( 8 ) :1209 —1213
[76] Araki K, Watanabe T , Oda M, et al . Tetrahedron Lett . , 2001 ,42(42) : 7465 —7468
[77] Araki K, Hayashida H. Chem. Lett . , 2000 , (1) : 20 —21
[78] Stastny V , Lhoták P , MichlováV , et al . Tetrahedron , 2002 , 58(36) : 7207 —7211
[79] Struck O , Chrisstoffels L A J , Lugtenberg R J W, et al . J . Org.Chem. , 1997 , 62(8) : 2487 —2493
[80] Hwang G T , Kim B H. Tetrahedron Lett . , 2000 , 41 ( 31) :5917 —5921
[81] Zeng C C , Yuan H S , Huang Z T. Chin. J . Chem. , 2002 , 20(8) : 795 —802
[82] Hwang GT , KimB H. Tetrahedron , 2002 , 58(44) : 9019 —9028
[83] Hwang G T , Kim B H. Tetrahedron Lett . , 2000 , 41 ( 51) :10055 —10060
[84] Jorgensen M, Larsen M, SommerLarsen P , et al . J . Chem. Soc. ,Perkin Trans. 1 , 1997 , (19) : 2851 —2855
[85] Araki K, Sisido K, Hisaichi K, et al . Tetrahedron Lett . , 1993 ,34(51) : 8297 —8300
[86] Blanda M T , Griswold K E. J . Org. Chem. , 1994 , 59 (15) :4313 —4315
[87] Wasikiewicz W, Rokicki G, Kielkiewicz J , et al . Angew. Chem.Int . Ed. Engl . , 1994 , 33(2) : 214 —216
[88] Wasikiewicz W, Rokicki G, Kielkiewicz J , et al . Monatsh.Chem. , 1997 , 128 (8P9) : 863 —879
[89] Beer P D , Gale P D , Hesek D. Tetrahedron Lett . , 1995 , 36(5) : 767 —770
[90] Kanamathareddy S , Gutsche C D. J . Org. Chem. , 1994 , 59(14) : 3871 —3879
[91] Zhang W C , Zhu Y, Li E C , et al . Tetrahedron , 2000 , 56(21) :3365 —3371
[92] Le Gac S , Zeng X S , Reinaud O , et al . J . Org. Chem. , 2005 ,70(2) : 1204 —1210
[93] Arimura T , Matsumoto S , Teshima O , et al . Tetrahedron Lett . ,1991 , 32(38) : 5111 —5114
[94] Bottino A , Cunsolo F , Piattelli M, et al . J . Org. Chem. , 1999 ,64(21) : 8018 —8020
[95] Arduini A , Ferdani R , Pochini A , et al . Tetrahedron , 2000 , 56(43) : 8573 —8577
[96] Garozzo D , Gattuso G, Kohnke F H , et al . Org. Lett . , 2003 , 5(22) : 4025 —4028
[97] Haino T , Yanase M, Fukazawa Y. Angew. Chem. Int . Ed.Engl . 1998 , 37(7) : 997 —998
[98] Haino T , Yanase M, Fukunaga C , et al . Tetrahedron , 2006 , 62(9) : 2025 —2035
[99] Wang J S , Bodige S G, Watson W H , et al . J . Org. Chem. ,2000 , 65(24) : 8260 —8263
[100] Haino T , Yamanaka Y, Araki H , et al . Chem. Commun. , 2002 ,402 —403
[101] Arduini A , Pochini A , Secchi A , et al . J . Chem. Soc. , Chem.Commun. , 1995 , 879 —880
[102] Makha M, Nichols P J , Hardie M J , et al . J . Chem. Soc. ,Perkin Trans. 1 , 2002 , (3) : 354 —359
[103] Notti A , Occhipinti S , Pappalardo S , et al . J . Org. Chem. ,2002 , 67(21) : 7569 —7572

[1] 何静, 陈佳, 邱洪灯. 中药碳点的合成及其在生物成像和医学治疗方面的应用[J]. 化学进展, 2023, 35(5): 655-682.
[2] 鄢剑锋, 徐进栋, 张瑞影, 周品, 袁耀锋, 李远明. 纳米碳分子——合成化学的魅力[J]. 化学进展, 2023, 35(5): 699-708.
[3] 杨孟蕊, 谢雨欣, 朱敦如. 化学稳定金属有机框架的合成策略[J]. 化学进展, 2023, 35(5): 683-698.
[4] 王新月, 金康. 多肽及蛋白质的化学合成研究[J]. 化学进展, 2023, 35(4): 526-542.
[5] 刘雨菲, 张蜜, 路猛, 兰亚乾. 共价有机框架材料在光催化CO2还原中的应用[J]. 化学进展, 2023, 35(3): 349-359.
[6] 龚智华, 胡莎, 金学平, 余磊, 朱园园, 古双喜. 磷酸酯类前药的合成方法与应用[J]. 化学进展, 2022, 34(9): 1972-1981.
[7] 林业竣, 李艳梅. 翻译后修饰Tau蛋白及其化学全/半合成[J]. 化学进展, 2022, 34(8): 1645-1660.
[8] 宝利军, 危俊吾, 钱杨杨, 王雨佳, 宋文杰, 毕韵梅. 酶响应性线形-树枝状嵌段共聚物的合成、性能及应用[J]. 化学进展, 2022, 34(8): 1723-1733.
[9] 徐鹏, 俞飚. 聚糖化学合成的挑战和可能的凝聚态化学问题[J]. 化学进展, 2022, 34(7): 1548-1553.
[10] 李诗宇, 阴永光, 史建波, 江桂斌. 共价有机框架在水中二价汞吸附去除中的应用[J]. 化学进展, 2022, 34(5): 1017-1025.
[11] 王鹏, 刘欢, 杨妲. 烯烃的氢甲酰化串联反应研究[J]. 化学进展, 2022, 34(5): 1076-1087.
[12] 马晓清. 石墨炔在光催化及光电催化中的应用[J]. 化学进展, 2022, 34(5): 1042-1060.
[13] 赵聪媛, 张静, 陈铮, 李建, 舒烈琳, 纪晓亮. 基于电活性菌群的生物电催化体系的有效构筑及其强化胞外电子传递过程的应用[J]. 化学进展, 2022, 34(2): 397-410.
[14] 闫保有, 李旭飞, 黄维秋, 王鑫雅, 张镇, 朱兵. 氨/醛基金属有机骨架材料合成及其在吸附分离中的应用[J]. 化学进展, 2022, 34(11): 2417-2431.
[15] 杨林颜, 郭宇鹏, 李正甲, 岑洁, 姚楠, 李小年. 钴基费托合成催化剂的表界面性质调控[J]. 化学进展, 2022, 34(10): 2254-2266.
阅读次数
全文


摘要

双杯芳烃研究进展