新型1,3-茚满二酮类螺环化合物的合成与表征  

Synthesis and Characterization of Novel 1,3-Spiroindandiones

作　　者：罗年华[1] 郑大贵[1] 祝显虹[1] 周安西[1] 彭化南[1] 胡久荣[1] 

机构地区：[1]上饶师范学院化学化工学院江西省普通高校应用有机化学重点实验室,江西上饶334001

出　　处：《化学试剂》2015年第9期827-830,833,共5页Chemical Reagents

基　　金：江西省教育厅科技计划资助项目(GJJ14717);江西省普通高校重点实验室科技资助项目(GJJ11708)

摘　　要：以1,3-茚满二酮和取代苯甲醛为原料,通过Knoevenagel缩合反应生成2-芳基亚甲基-1,3-茚满二酮,然后2-芳基亚甲基-1,3-茚满二酮与4-氯代乙酰乙酸乙酯在催化剂作用下发生Michael/γ-Alkylation串联反应,获得了6个新型1,3-茚满二酮类螺环化合物。并且进行了催化剂、溶剂和温度的筛选,发现三乙胺为最优的催化剂,在室温下,以氯仿为溶剂,反应获得了最好的收率(98%)和非对映选择性(98∶2 dr)。产物的结构经1HNMR、13CNMR、HRMS确证。With 1,3-indandione and substituted benzaldehydes as raw material,processed by Knoevenagel condensation reaction,2-arylidene-1,3-indandiones were synthesized. Then,a cascade Michael / γ-Alkylation reaction between 2-arylidene-1,3-indandiones and 4-chloro-3-oxobutanoate has been developed and six multicyclic 1,3-spiroindandiones were prepared. A series of organocatalyst,solvent and temperature were evaluated and Et3 N was identified as the best catalyst for the transformation. With CHCl3 as solvent,two multicyclic 1,3-spiroindandiones were obtained in good yields（ 98%） and enantioselectivities（ 98 ∶ 2 dr） at room temperature. The structure was confirmed by1 HNMR,13CNMR and HRMS.

关 键 词：1 3-茚满二酮 螺环化合物 合成 表征 

分 类 号：O626[理学—有机化学]