|本期目录/Table of Contents|

[1]何磊,郭燏.δ-辛内酯的改进合成[J].南京工业大学学报(自然科学版),2015,37(05):118-121.[doi:10.3969/j.issn.1671-7627.2015.05.020]
 HE Lei,GUO Yu.Improved synthesis of δ-octalactone[J].Journal of NANJING TECH UNIVERSITY(NATURAL SCIENCE EDITION),2015,37(05):118-121.[doi:10.3969/j.issn.1671-7627.2015.05.020]
点击复制

δ-辛内酯的改进合成()
分享到:

《南京工业大学学报(自然科学版)》[ISSN:1671-7627/CN:32-1670/N]

卷:
37
期数:
2015年05期
页码:
118-121
栏目:
出版日期:
2015-09-10

文章信息/Info

Title:
Improved synthesis of δ-octalactone
文章编号:
1671-7627(2015)05-0118-04
作者:
何磊1郭燏2
1.淮阴工学院 生命科学与化学工程学院,江苏 淮安 223003; 2.南京工业大学 化工学院,江苏 南京 210009
Author(s):
HE Lei1GUO Yu2
1.School of Life Science and Chemical Engineering,Huaiyin Institute of Technology,Huaian 223003,China; 2.College of Chemical Engineering,Nanjing Tech University,Nanjing 210009,China
关键词:
δ-辛内酯 自由基 双键加成 内酯化
Keywords:
δ-octalactone radical addition reaction lactonization
分类号:
O624.5
DOI:
10.3969/j.issn.1671-7627.2015.05.020
文献标志码:
A
摘要:
以正丁醇和戊烯酸甲酯为起始原料,通过两步反应合成高纯度的δ-辛内酯。首先在加热条件下,经自由基引发的双键加成得到6-羟基癸酸甲酯,再将6-羟基癸酸甲酯在酸性条件下内酯化得到δ-辛内酯。合成物的结构经核磁共振仪(NMR),傅里叶红外光谱仪(FT-IR)和气相色谱-质谱联用仪(GC-MS)表征。结果表明反应总产率达27%。该路线与传统工艺相比,全部采用化工中易得的原料,工艺简便,易于工业化。
Abstract:
A novel two-step synthetic route for δ-octalactone was reported.In the two-step route,methyl 6-hydroxydecanoate was prepared at first from 1-butanol and methyl pent-4-enoate raw materials.The first step was an addition reaction initiated by radicals.And via lactonization of methyl 6-hydroxydecanoate under acidic conditions,δ-octalactone was synthesized.The structures of the compounds were confirmed by nuclear magnetic resonance(NMR),Fourier transform infrared spectrometer(FT-IR)and gas chromatography mass spectrometer(GC-MS).The result showed that the total yield of the route was 27%.The main advantage of the route laid in its facility for commercial production thus raw materials were easy to get from chemical industry.

参考文献/References:

[1] Shimotori Y,Hoshi M,Seki S,et al.Preparation of optically pure δ-lactones using diastereomeric resolution with amino acid as resolving agent[J].Journal of Oleo Science,2015,64(1):75-90.
[2] Langen J,Wang C.Quantitative analysis of γ-and δ-lactones in wine using gas chromatography with selective tandem mass spectrometric
   detection[J].Rapid Communications in Mass Spectrometry,2013,27(24):2751-2759.
[3] 吴国湘,胡道华.丁位内酯系列产品的合成路线及工业化构思[J].香料香精化妆品,2000,28(2):21-24.
[4] 吴国湘,胡道华,杨承鸿,等.丁位内酯系列产品的工业化生产[J].精细与专用化学品,2001,16(14):17-18.
[5] Ijima A,Mizuno H,Takahashi K.Synthèse de δ-lactones:Ⅲ.alcény1-6 ou alcoyl-6 δ-lactones à partir de la cyclopentanone.1 [J].Chemical Pharmaceutical Bulletin,1972,20(1):197-201.
[6] Ijima A,Takahashi K.Synthèse de δ-lactones:IV.alcoyl-6 et aralcoyl-6 δ-lactones à partir de la cyclopentanone.2 [J].Chemical Pharmaceutical Bulletin,1973,21(1):215-219.
[7] 陈淑青,梁致诚.δ-癸内酯的合成[J].广州化工,1992,20(4):42-44.
[8] 俞翠娣,李美珍,张坤年.丁位癸内酯的合成[J].食品与发酵工业,1982,8(3):65-67.

备注/Memo

备注/Memo:
收稿日期:2014-05-21
基金项目:江苏省自然科学青年基金(BK20130420); 江苏省盐化工新材料工程实验室开放基金(SF201305); 淮阴工学院科研基金(HGB1203)
作者简介:何磊(1980—),男,江苏淮安人,讲师,博士,主要研究方向为有机化工合成,E-mail:heleihuaian@hyit.edu.cn.
引用本文:何磊,郭燏.δ-辛内酯的改进合成[J].南京工业大学学报:自然科学版,2015,37(5):118-121..
更新日期/Last Update: 2015-09-20