[1]许招会,熊斌,雷志伟.无溶剂下磷钨酸镧催化合成5-亚烃基-2,2-亚丁基-1,3-二噁烷-4,6-二酮[J].江西师范大学学报(自然科学版),2013,(04):337-341.
　XU Zhao-hui,XIONG Bin,LEI Zhi-wei.Solvent-Free Synthesis of 5-Alkenyl-2,2-Butylidene-1,3-Dioxane-4,6-Diones with LaPW12O40 as Catalyst[J].Journal of Jiangxi Normal University:Natural Science Edition,2013,(04):337-341.
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无溶剂下磷钨酸镧催化合成5-亚烃基-2,2-亚丁基-1,3-二噁烷-4,6-二酮()
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《江西师范大学学报》（自然科学版）[ISSN:1006-6977/CN:61-1281/TN]

卷:
期数:
2013年04期
页码:
337-341
栏目:
出版日期:
2013-09-01

文章信息/Info

Title:
Solvent-Free Synthesis of 5-Alkenyl-2,2-Butylidene-1,3-Dioxane-4,6-Diones with LaPW12O40 as Catalyst
作者:
许招会;熊斌;雷志伟
江西师范大学化学化工学院,江西南昌,330027
Author(s):
XU Zhao-hui；XIONG Bin；LEI Zhi-wei
关键词:
2; 2-亚丁基-1; 3-二噁烷-4; 6-二酮; 磷钨酸镧; 芳香醛; 缩合反应
Keywords:
2; 2-butylidene-1; 3-dioxane-4; 6-dione; LaPW12O40; aromatic aldehydes; condensation reaction
分类号:
O621.25
文献标志码:
A
摘要:
在LaPW12O40催化下,芳香醛和2,2-亚丁基-1,3-二噁烷-4,6-二.酮在无溶剂条件下合成了8种新型5-亚烃基-2,2-亚丁基-1,3-二噁烷-4,6-二酮.当催化剂的用量为5；(摩尔分数)时,室温反应20 ～40 min,收率为87.6；～94.3；.此外,还探讨了LaPW12O40的催化机理.该方法具有条件温和,反应时间短且收率高的优点.催化剂LaPW12O40对环境友好且可循环利用.
Abstract:
Eight kinds of 5-alkenyl-2,2-butylidene-1,3-dioxane-4,6-diones were synthesized by the Knoevenagel condensation reaction of aromatic aldehydes with 2,2-pentamethylene -1,3-dioxane-4,6-dione using LaPW12O40 as catalyst,without solvent.The results indicate that the yields ranged from 87.6%～94.3%,when using 5%( molar fraction)LaPW12O40 and reacting at room temperature for 20～40 min.Furthermore,a proposed reaction mechanism for the reaction catalyzed by LaPW12O40 was speculated.Compared to the classical Knoevenagel condensation reaction,the main advantages of the present procedure were milder conditions,shorter reaction time and higher yields,which afforded an effective method to synthesize 5-alkenyl-isopropylidene malonate derivatines.Further study showed that LaPW12O40 was environmentally friendly and reused for four times without any noticeable decrease in the catalytic activity.

参考文献/References:

[1] Jacobs R T,Wright A D,Smith F X.Condensation of monosubstituted isopropylidene malonates with mannich bases [J].J Org Chem,1982,47(16):3769-3772.
[2] Bruns R,Wernicke A,Koll P.Application of the reaction of D-glucose with Meldrum's acid:Total synthesis of the styryl lactones(+)-goniofufurone and(+)-7-epi-goniofufurone [J].Tetrahedron,1999,55(32):9793-9800.
[3] 黄志真,吴露玲,黄宪.微波作用下2-烃基-4-喹啉酮的简便合成法 [J].有机化学,2000,20(1):88-90.
[4] Watanabe T,Knöpfel T F,Carreira E M.Asymmetric conjugate addition reactions of Meldrum's acid derived acceptors employing chiral phosphoramidite ligands [J].Org Lett,2003,24(5):4557-4558.
[5] Fillion E,Dumas A M,Hogg S A.Modular synthesis of tetrahydrofluorenones from 5-alkylidene Meldrum's acids [J].J Org Chem,2006,71(26):9899-9902.
[6] Huang Xian,Xie Lin.One pot synthesis of 5-monosubstituted Meldrum's acid [J].Synth Commun,1988,18(13):1701-1707.
[7] Desai U V,Pore D M,Mane R B,et al.One pot synthesis of monoalkylated and mixed dialkylated Meldrum's acid derivatives [J].SynthCommun,2004,34(1):25-32.
[8] Rao Pengshan,Venkataratnam R V.Zinc chloride as a new catalyst for knoevenagel condensation [J].Tetrahedron Lett,1991,32(41):5821-5822.
[9] Davidson D,Bernhard S A.The Structure of Meldrum's supposed β-lactonic acid [J].J Am Chem Soc,1948,70(10)3426-3428.
[10] Corey E J.The mechanism of the decarboxylation of α,β- and β,γ-unsaturated malonic acid derivatives and the course of decarboxylative condensation reactions in pyridine [J].J Am Chem Soc,1952,74(23):5897-5905.
[11] Kraus G A,Krolski M E.Synthesis of a precursor to quassimarin [J].J Org Chem,1986,51(7):3347-3350.
[12] Scuster P,Polansky O E,Wessely F.Zur Kenntnis cyclischer Acylale,6.Mitt.[J].Monatsch Chem,1964,95(36):53-58.
[13] 许招会,严楠,廖维林.六甲基二硅胺烷催化芳香醛与2,2-二甲基-1,3-二噁烷-4,6-二酮的缩合反应 [J].江西师范大学学报:自然科学版,2012,36(5):524-526.
[14] Dumas A M,Seed A,Zorzitto A K,et al.A general and practical preparation of alkylidene Meldrum's acids [J].Tetrahedron Letters,2007,48(40):7072-7074.
[15] 许招会,廖维林,王甡.磷钨酸镧催化合成缩醛(酮)的研究 [J].分子催化,2008,22(1):39-42.
[16] 许招会,刘显亮,张世金,等.磷钨酸铈催化合成苯甲醛乙二醇缩醛 [J].江西师范大学学报:自然科学版,2006,30(5):453-455.
[17] 严楠,熊斌,廖维林,等.La(OTf)3催化合成1,3-二噁烷-4,6-二酮化合物的研究 [J].有机化学,2010,30(9):1391-1394.
[18] 徐福培,丁维钰,竺宝林.2,2-五甲叉-1,3-二氧六环-4,6-二酮与芳香醛的反应 [J].上海科技大学学报,1991(1):96-98.

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备注/Memo

备注/Memo:
江西科技国际合作课题(kj082563)；江西省研究生创新专项基金(YC10A051)
更新日期/Last Update: 1900-01-01