新型树状化合物1,3,5-三{3-[2,4,8,10-四氧杂\|9(3,5-二(2,6-二氧杂-4,4-二羟甲基环己基)苯基]螺[5.5]十一烷基}苯的制备

本实验采用季戊四醇与苯三甲醛缩合, 制成树状化合物1,3,5-三{3-|2,4,8,10-四氧杂-9(3,5-二(2,6-二氧杂-4,4-二羟甲基环己基)苯基)螺5.5]十一烷基}苯. 该类树状分子具有手性螺环结构, 手性密度很高, 可开发成理想的高效手性催化剂3~8], 具有诱人的应用前景.

Synthesis of 1,3,5-Tri{3-[2,4,8,10-tetra-oxa-9(3,5-di(2,6-dioxa-4,4-dihydroxymethylcyclohexyl)phenyl]spiro[5.5] undecyl}benzene for Novel Dendrimer

Dendrimers are the subject of intense attention recently because of their anticipated potentialities and the peculiar structural properties.A novel synthetic route for the preparation of functionalized dendrons built on the 1,3,5-benzenetricarboxaldehyde core and endowed with a periphery of pentaerythritol groups has been developed.1,3,5-Tri(2,6-dioxa-4,4-dihydroxymethyl cyclohexyl) benzene(1) was synthesized by the condensation of 1,3,5-benzenetricarboxaldehyde with pentaerythritol in the presence of hot CHCl_3 and p-methyl benzene sulfonic acid with 55% yield.By turning 1,3,5-benzenetricarboxaldehyde into its trioxime,it was protected to decrease the cross-linked reaction with compound 1 both including many groups.The reaction of compound 1 with 1,3,5-benzenetricarboxaldehyde trioxime and pentaerythritol afforded 1,3,5-tri{3-2,4,8,10 -tetra-oxa-9(3,5-di(2,6-dioxa-4,4-dihydroxymethylcyclohexyl) phenyl]spiro\undecyl}benzene(2) by using I_2 as the catalyst,and the yield was 25.2%.Product 2 and its intermediates were identified by IR,~1H NMR,MS spectra and elemental analysis.