[1]李正义,钱纪生,殷乐,等.1,3氧杂螺环化合物的合成[J].常州大学学报(自然科学版),2016,(02):24-28.[doi:10.3969/j.issn.2095-0411.2016.02.005]
 LI Zhengyi,QIAN Jisheng,YIN Yue,et al.Synthesis of 1,3OxoSpirocyclic Compounds[J].Journal of Changzhou University(Natural Science Edition),2016,(02):24-28.[doi:10.3969/j.issn.2095-0411.2016.02.005]
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1,3氧杂螺环化合物的合成()
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常州大学学报(自然科学版)[ISSN:2095-0411/CN:32-1822/N]

卷:
期数:
2016年02期
页码:
24-28
栏目:
出版日期:
2016-03-30

文章信息/Info

Title:
Synthesis of 1,3OxoSpirocyclic Compounds
作者:
李正义钱纪生殷乐孙小强
常州大学 石油化工学院,江苏 常州 213164
Author(s):
LI Zhengyi QIAN Jisheng YIN Yue SUN Xiaoqiang
School of Petrochemical Engineering, Changzhou University, Changzhou 213164, China
关键词:
季戊四醇脂肪族芳香族13氧杂螺环合成
Keywords:
pentaerythritol aliphatic aromatic 13oxospirocycle synthesis
分类号:
O 621.3
DOI:
10.3969/j.issn.2095-0411.2016.02.005
文献标志码:
A
摘要:
系统研究了一系列不同类型脂肪族和芳香族1,3氧杂螺环化合物的合成方法。分别以脂肪族醛(酮)和季戊四醇为原料,对甲苯磺酸为催化剂,在环己烷中回流分水反应,合成了一系列脂肪族1,3氧杂螺环化合物;以芳香族醛(酮)和季戊四醇为原料,对甲苯磺酸为催化剂,在甲苯中回流分水反应,合成了一系列芳香族1,3氧杂螺环化合物,化合物结构经1H NMR,13C NMR和MS进行表征。与传统方法相比,该方法具有底物适用范围广泛、操作简单、收率较高和环境友好等优点。
Abstract:
The systematically synthetic methods for different aliphatic and aromatic 1,3oxospirocyclic compounds were studied. Aliphatic 1,3oxospirocyclic compounds were synthesized by reflux of pentaerythritol with aliphatic aldehydes or ketones in cyclohexane using ptoluenesulfonic acid as the catalyst. Aromatic 1,3oxospirocyclic compounds were synthesized by reflux of pentaerythritol with aromatic aldehydes or ketones in toluene using ptoluenesulfonic acid as the catalyst. Compared with conventional methods, this process shows some advantages such as extensive substrates,simple operation, high yield and environment friendly. The structures were characterized by 1H NMR , 13C NMR and MS.

参考文献/References:

[1] LIM C K, LEE J S, HA T H, et al. Cleavageinduced uorescence change via hydrophilicity control: A new strategy for biological application[J]. J Photochem Photobiol A,2007,188:149154.
[2]SONDHI S M, JAIN S, DINODIA M, et al. One pot synthesis of pyrimidine and bispyrimidine derivatives and their evaluation for antiinammatory and analgesic activities[J]. Bioorg Med Chem Lett,2007,15(10):33343344.
[3]SONDHI S M, DINODIA M, JAIN S, et al. Synthesis of biologically active novel bis schiff bases, bis hydrazone and bis guanidine derivatives[J]. Indian J Chem Sect B,2009,48(8):11281136.
[4]CRAWFORD E D, CONNELL G W. Polyester compositions which comprise spiroglycol, cyclohexanedimethanol, and terephthalic acid: WO 2010080117[P].20100715.
[5]GOKHAN A, HAYAL B S, FRED W, et al. Synthesis, characterization and properties of novel polyspiroacetals[J]. J Polym Res,2012,20:97101.
[6]魏荣宝.螺环化合物化学[M].北京:化学工业出版社,2007:178186.
[7]SACHSE A, WUTTKE C, LISSNER E, et al. Ordered mesoporous ZSM5 employing an imidazoliumbased ionic liquid[J]. Chem Eur J,2014,20(46):1499614999.
[8]LI Z Y, CHEN L, GE L, et al. Synthesis and crystal structure of 3,9bis(pyridin2yl)2,4,8,10tetraoxaspiro
[5.5]undecane[J]. Chin J Struct Chem,2012,31(5):728732.
[9]AKBULUT G, SONMEZ H B, WUDL F. Synthesis, characterization and properties of novel polyspiracetals[J]. J Polym Res,2013,20(3):18.
[10]KANNAN V, SREEKUMAR K, GIL A, et al. Acetalation of pentaerithritol catalyzed by an Alpillared saponite[J]. Catal Lett,2011,141(8):11181122.
[11]ZHAO Y C, ZHANG L M, WANG T, et al. Microporous organic polymers with acetal linkages: synthesis, characterization, and gas sorption properties[J]. Polym Chem,2014,5(2):614621.
[12]SHATERIAN H R, RIGI F. Acetalization of carbonyl compounds as pentaerythritol diacetals and diketals in the prensence of cellulose sulfuric acid as an efficient, biodegradable and reusable catalyst[J]. Chin J Chem,2012,30(3):695698.
[13]ALBADI J, IRAVANI N, SHIRINI F, et al. A green recyclable poly(4vinylpyridine)supported copper iodide nanoparticle catalyst for the chemoselective synthesis of pentaerythritol diacetals form aromatic aldehydes[J]. J Chem Res,2012,36(10):610611.
[14]李培,谭淼淼,毛婷婷,等. 微波辐射下季戊四醇双缩对甲氧基苯甲醛的催化合成[J]. 化工科技,2010,18(1):3234.
[15]WANG Y Y, GONG X X, WANG Z Z, et al. SO3Hfunctionalized ionic liquids as efficient and recyclable catalysts for the synthesis of pentaerythritol diacetals and diketals[J]. J Mol Catal A: Chem,2010,322(1/2):716.
[16]毛立新,廖德仲,关桂元,等. 焙烧硫酸铁铵催化合成季戊四醇双缩苯甲醛[J]. 化工时刊,2003,17(12):3941.
[17]孙勇,周忠强. 微波辐射下硫酸盐催化合成季戊四醇双缩苯甲醛[J]. 化学试剂,2008,30(4):293294.
[18]袁先友,张敏.微波促进活性炭负载磷钨酸催化合成短链季戊四醇双缩醛[J].合成化学,2007,15(4):487490.
[19]GROSU I, MAGER S, PLE G, et al. The stereochemistry of some new chiral brominated compounds with a 2,4,8,10tetraoxaspiro
[5.5]undecanic skeleton[J]. Monatsh Chem,1995,126(8/9):10211030.
[20]SUN X Q, CHEN L, JIANG Y, et al. 3,3,9,9Tetraphenyl2,4,8,10tetraoxaspiro
[5.5]undecane[J]. Acta Cryst,2010,E66(11):o3035.

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 CUI Yuan,ZHANG Xiu-qin,SUN Xiao-qiang,et al.Synthesis and NMR Analysis of Pentaerythritol Ketal with Chiral Axis[J].Journal of Changzhou University(Natural Science Edition),2011,(02):1.

备注/Memo

备注/Memo:
收稿日期:20151109。基金项目:国家自然科学基金资助项目(21572026,21002009);江苏省高校自然科学研究重大项目(14KJA150002)。作者简介:李正义(1979—),男,江苏扬州人,博士,副教授,主要从事有机化学研究。通讯联系人:孙小强(1956—),Email: sunxiaoqiang@yahoo.com
更新日期/Last Update: 2016-03-20