A novel receptor based on a C3v-symmetrical PN3-calix[6]cryptand

被引：45

作者：

Zeng, XS

Hucher, N

Reinaud, O

Jabin, I

机构：

[1] Univ Paris 05, Lab Chim & Biochim Pharmacol & Toxicol, CNRS, UMR 8601, F-75270 Paris 06, France

[2] Univ Havre, URCOM, Fac Sci & Tech, F-76058 Le Havre, France

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2004年 / 69卷 / 20期

关键词：

D O I：

10.1021/jo048814b

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A C-3v-symmetrical PN3-calix[6]cryptand was prepared in six steps from the known 1,3,5-tris-methylated calix[6]arene through a remarkably efficient [1 + 1] macrocyclization reaction. A H-1 NMR study showed that the P,N-crypto cap rigidifies the whole edifice in a cone conformation ideal for molecular recognition applications. The ability of this new receptor to perform selective endo-complexation is illustrated with ammonium guests.

引用

收藏

页码：6886 / 6889

页数：4

相关论文

共 30 条

[1] Synthesis, structure, and redox properties of a quinone-bridged calix[6]arene [J].

Akine, S ;

Goto, K ;

Kawashima, T .

TETRAHEDRON LETTERS, 2000, 41 (06) :897-901

[2]

Blanchard S, 1998, ANGEW CHEM INT EDIT, V37, P2732, DOI 10.1002/(SICI)1521-3773(19981016)37:19<2732::AID-ANIE2732>3.0.CO

[3]

2-7

[4] BRIDGED CALIX[6]ARENES IN THE CONE CONFORMATION - NEW RECEPTORS FOR QUATERNARY AMMONIUM CATIONS [J].

CASNATI, A ;

JACOPOZZI, P ;

POCHINI, A ;

UGOZZOLI, F ;

CACCIAPAGLIA, R ;

MANDOLINI, L ;

UNGARO, R .

TETRAHEDRON, 1995, 51 (02) :591-598

[5] A new type of amido-substituted p-tert-butylcalix[6]arene:: Double diamide bridges on the lower rim [J].

Chen, YK ;

Chen, YY .

ORGANIC LETTERS, 2000, 2 (06) :743-745

[6] An approach to calix[6]cryptands with bridgehead carbon atom: Stabilized in- and out- stereoisomers [J].

Chen, YY ;

Li, JS ;

Zhong, ZL ;

Lu, XR .

TETRAHEDRON, 1998, 54 (50) :15183-15188

[7] A novel C3v-symmetrical calix[6](aza)cryptand with a remarkably high and selective affinity for small ammoniums [J].

Darbost, U ;

Giorgi, M ;

Reinaud, O ;

Jabin, I .

JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (15) :4879-4884

[8] PHOSPHORUS POLYBRIDGED CALIXARENES [J].

GRYNSZPAN, F ;

ALEKSIUK, O ;

BIALI, SE .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1993, (01) :13-16

[9]

Gutsche C.D., 1998, CALIXARENES REVISITE

[10] First C3v-symmetrical calix[6](aza)crown [J].

Jabin, I ;

Reinaud, O .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (09) :3416-3419