[1]宋蕴丽,徐崇福,赵萌萌,等.反应合成2-[(4-硝基苯基)羟甲基]丙烯酸酯[J].常州大学学报(自然科学版),2013,(01):35-38.[doi:10.3969/j.issn.2095-0411.2013.01.007]
　SONG Yun-li,XU Chong-fu,ZHAO Meng-meng,et al.Syntheses of 2-[(4-Nitrophenyl)Hydroxy Methyl]Acrylates Via MBH Reaction[J].Journal of Changzhou University(Natural Science Edition),2013,(01):35-38.[doi:10.3969/j.issn.2095-0411.2013.01.007]
点击复制

反应合成2-[(4-硝基苯基)羟甲基]丙烯酸酯()
分享到：

常州大学学报(自然科学版)[ISSN:2095-0411/CN:32-1822/N]

卷:
期数:
2013年01期
页码:
35-38
栏目:
出版日期:
2013-01-01

文章信息/Info

Title:
Syntheses of 2-[(4-Nitrophenyl)Hydroxy Methyl]Acrylates Via MBH Reaction
作者:
宋蕴丽; 徐崇福; 赵萌萌; 富利祥
常州大学 石油化工学院,江苏 常州 213164
Author(s):
SONG Yun-li; XU Chong-fu; ZHAO Meng-meng; FU Li-xiang
School of Petrochemical Engineering,Changzhou University, Changzhou 213164,China
关键词:
丙烯酸酯;  对硝基苯甲醛;  亲核加成反应;  离子液体催化
Keywords:
acrylates;  p-nitrobenzaldehyde aldehydes;  nucleophillic addition;  ionic-liquid catalysis
分类号:
O 625
DOI:
10.3969/j.issn.2095-0411.2013.01.007
文献标志码:
A
摘要:
通过MBH反应,用路易斯碱催化丙烯酸酯与对硝基苯甲醛的亲核加成反应,合成了一系列2-[(4-硝基苯基)羟甲基]丙烯酸酯。研究了各种因素对产率的影响,优化了反应条件。离子液体[N-μ-(CH2CH2)3N+H][CH3COO-]为催化剂; THF为溶剂; 反应物最佳配料比为:n(丙烯酸酯):n(对硝基苯甲醛):n(离子液催化剂)=3:1:1; 在室温下反应24 h。目标产物经柱色谱分离提纯,对其分子结构进行了1H NMR,13C NMR,IR表征。
Abstract:
A serious of 2-[(4-nitrophenyl)hydroxy methyl]acrylates were synthesized by nucleophillic addition of acrylates and p-nitrophenyl aldehyde via MBH reaction catalyzed by Lewis bases. Various factorsaffecting the productivity of target products in the process were investigatedand reaction conditions were optimized. The most effective catalyst was found tobe liquid ion [N-μ-(CH2CH2)3N+H][CH3COO-].The most suitable solvent was chosen to be THF.The optimal ratio of reactants was determined as n(acrylates):n(p-nitrophenyl aldehyde):n(the liquid ion catalyst)=3:1:1.The reaction was best carried out at ambient temperature for 24 h. The targeted products were isolated by column chromatography and their molecular structures were characterized by 1H NMR,13C NMR and IR spectroscopy respectively.

参考文献/References:

[1]Declan J Maher,Stephen J Connon.Acceleration of the DABCO-promoted Baylis-Hillman reaction using a recoverable H-bonding organocatalyst[J]. Tetrahedron Letters, 2004,45:1301-1305.
[2]Marília O F,Goulart A A,de Souza E M Sales. Electrochemical study of methyl 2-[p-nitrophenyl(hydroxy)methyl]acrylate, an anticancer drug, In the presence of GSH and dsDNA[J].ECS Transactions, 2007, 3(29): 137-146.
[3]Zhao Sanhu,Chen Zhaobin.The N,N,N',N'-tetramethylethylenediamine mediated Baylis-Hillman reaction[J]. Synthetic Communications, 2005, 35: 121-127.
[4]Gong Jingjing,Yuan Kui,Wu Xinyan. Valine-derived phosphinothiourea as organocatalyst in enantioselective Morita-Baylis-Hillman reactions of acrylates witharomatic aldehydes[J]. Tetrahedron:Asymmetry, 2009, 20: 2117-2120.
[5]Fernando Coelho, Demetrius Veronese, Cesar H Pavam. Palladium-catalyzed carbonylative cyclization of Baylis-Hillman adducts. An efficient approach for thestereoselective synthesis of 3-alkenyl phthalides[J]. Tetrahedron, 2006, 62:4263-4572.
[6]崔朋雷, 王春, 果秀敏,等.膦催化的Baylis-Hillman反应[J].有机化学, 2008,28(2): 194-200.
[7]Song Ying,Ke Haihua,Wang Nan.Baylis-Hillman reaction promoted by a recyclable protic-ionic-liquid solvent-catalyst system: DABCO-AcOH-H2O[J]. Tetrahedron, 2009, 65: 9086-9090.
[8]Fernando Coelho, Wanda P Almeida, Demetrius Veronese. Ultrasound in Baylis-Hillman reactions with aliphatic and aromatic aldehydes: scope and limitations[J]. Tetrahedron, 2002, 58: 7437-7447.
[9]David Cantillo, Oliver Kappe C. A unified mechanistic view on the Morita-Baylis-Hillman Reaction: Computational and Experimental Investigations[J].Journal of Organic Chemistry, 2010, 75: 8615-8626.

备注/Memo

备注/Memo:
作者简介:宋蕴丽(1988-),女,山东济南人,硕士生。
更新日期/Last Update: 2013-01-01