碱催化2,5-己二酮脱水制3-甲基-2-环戊烯-1-酮

doi:10.13218/j.cnki.csdc.2016.05.011

日用化学工业 ›› 2016, Vol. 46 ›› Issue (5): 292-295.doi: 10.13218/j.cnki.csdc.2016.05.011

碱催化2,5-己二酮脱水制3-甲基-2-环戊烯-1-酮

李岳秦,杨永兴,侯相林

中国科学院大学中国科学院山西煤炭化学研究所山西省生物炼制工程技术研究中心,山西太原 030001

出版日期:2016-05-22 发布日期:2016-05-22
通讯作者: 侯相林,研究员,E-mail:houxianglin@sxicc.ac.cn。
作者简介:李岳秦,女,山西人,硕士研究生,电话:(0351)4049501,E-mail:liyueqin1214@aliyun.com。
基金资助:
国家自然科学基金资助项目(21403273);国家重点基础研究发展计划(973计划)资助项目(2012CB215305)

Preparation of 3-methyl-2-cyclopentene-1-ketone by base catalyzed dehydration of 2,5-hexanedione

LI Yue-qin,YANG Yong-xing,HOU Xiang-lin

Shanxi Engineering Research Center of Biorefinery,Institute of Coal Chemistry, Chinese Academy of Sciences,Taiyuan,Shanxi 030001,China

Online:2016-05-22 Published:2016-05-22

摘要/Abstract

摘要： 以2,5-己二酮为原料,选用碱催化剂在弱极性有机溶剂中实现2,5-己二酮脱水制备3-甲基-2-环戊烯-1-酮。考察了碱催化剂种类、催化剂加入量、反应温度和时间等因素对产物收率的影响。得出的较佳实验条件为:以硅酸钠为碱催化剂,反应温度为180 ℃,反应时间为5.0 h,反应溶剂为环己烷,在此条件下可以得到收率为98%的3-甲基-2-环戊烯-1-酮。

关键词: 香料, 2,5-己二酮, 3-甲基-2-环戊烯-1-酮, 碱催化

Abstract: 3-Methyl-2-cyclopentane-1-ketone was synthesized via base catalyzed dehydration of 2,5-hexanedione in a weakly polar organic solvent.Effects of separate kinds of base catalyst,different dosages of the catalyst,as well as different reaction conditions on the yield of the product were investigated.The optimum experimental conditions were determined as following:sodium silicate as the base catalyst;reaction temperature,180 ℃;reaction time,5.0 h;cyclohexane as the solvent.Under such experimental conditions,the yield of 3-methyl-2-cyclopentane-1-ketone can achieve 98%.

Key words: spice, 2,5-hexanedione, 3-methyl-2-cyclopentane-1-ketone, base catalysis

中图分类号:

TQ655

李岳秦,杨永兴,侯相林. 碱催化2,5-己二酮脱水制3-甲基-2-环戊烯-1-酮[J]. 日用化学工业, 2016, 46(5): 292-295.

LI Yue-qin,YANG Yong-xing,HOU Xiang-lin. Preparation of 3-methyl-2-cyclopentene-1-ketone by base catalyzed dehydration of 2,5-hexanedione[J]. China Surfactant Detergent & Cosmetics, 2016, 46(5): 292-295.

参考文献

[1] TIAN J,LI D L,ZHAI F Y,et al.Synthesis and biological evaluation of cyclopentent-1-one mannich base oxovanadium compound [J].Medicinal Chemistry Research,2009,19(9):1162-1173.
[2] DUY H H,VENKATARAMAN S,ROCH C Y K,et al.Enantioselective total synthesis of (+)-12,13-epoxytrichothec-9-ene and its antipode [J].American Chemical Society,1988,110:4741-4748.
[3] JOHN C G,ROBERT D S.Enantioselective synthesis of an ent-trichothecene [J].Tetrahedron,1994,50(6):1651-1664.
[4] NICOS A P,MICHAEL A P.A claisen rearrangement strategy for the three-atoom ring expansion of cyclic ketones.A total synthesis of (±) precapnelladiene [J].Tetrahedron Letters,1990,31(47):6799-6802.
[5] ACHESON R M,ROBINSON R.Experiments bearing on the synthesis of cortisone.Part I.Some cyclopentenone derivatives [J].Journal of the Chemical Society,1952,198:1127-1133.
[6] STRUNZ G M.Synthetic routes to 2-hydroxyl-3-methylcyclopent-2-en-l-one and related cyclopentane-l,2-diones:A Review [J].Journal of Agricultural and Food Chemistry,1983,31(2):186-190.
[7] FRANCO D O,GIOVANNI P,MASSIMO N.Photo-oxidation of 2-furyl-alkyl-phosphonates:synthesis of new cyclopentenone derivatives [J].Tetrahedron,1995,51(14):4083-4088.
[8] ELLISON R A,LUKENBACH E R,CHIU C W.Cyclopentenone synthesis via aldol condensation-synthesis of a key prostaglandin intermediate [J].Tetrahedron Letters,1975(8):499-502.
[9] PAOLO C,MASSIMO C,MARIA C M,et al.A new synthetic route to 2-carbomethoxycyclopent-2-enone via rhodium (II)-mediated decompoaition of diazoesters [J].Organic Preparations and Procedures International,1992,24(4):497-499.
[10] JANSSEN C G M,SIMONS L,GODEFROI E F.3-methyl-cyclopentenone-derived synthons [J].Synthesis-Stuttgart,1982(5):389-391.
[11] MATTHEW L K,DALE N,JOHN C G.An improved procedure for the preparation of 3-methyl-2-cyclopenten-1-one [J].Organic Preparations and Procedures International,1995,27(5):569-570.
[12] SACIA E R,DEANER M H,LOUIE Y L,et al.Synthesis of biomass-derived methylcyclopentane as a gasoline additive via aldol condensation/hydrodeoxygenation of 2,5-hexanedione [J].Green Chemistry,2015,17(4):2393-2397.
[13] BAGNELL L,BLIESE M,CABLEWSKI T,et al.Environmentally benign procedures for the preparation and isolation of 3-methyl-cyclopent-2-en-1-one [J].Australian Journal of Chemistry,1997,50(9):921-925.
[14] ROSINI G,BALLINI R,SORRENTI P.A new route to 1,4-diketones and its application to (Z)-jasmone and dihydrojasmoe synthesis [J].Tetrahedron,1983,39:4127-4132.
[15] AN JINGYI,BAGNELL L,CABLEWSKI T,et al.Applications of high-temperature aqueous media for synthetic organic reactions [J].J Org Chem,1997,62:2505-2511.
[16] 侯相林,李岳秦,邓天昇.一种制备3-甲基-2-环戊烯-1-酮的方法:CN201510764423.5 [P].2016-02-03.
[17] 谭露璐,钱君律,伍艳辉.羟醛缩合催化剂研究进展[J].化学工业与工程,2006,23(1):70-74.

碱催化2,5-己二酮脱水制3-甲基-2-环戊烯-1-酮

Preparation of 3-methyl-2-cyclopentene-1-ketone by base catalyzed dehydration of 2,5-hexanedione

PDF (PC)

赞

可视化

摘要/Abstract

引用本文

使用本文

参考文献

相关文章 13

Metrics

本文评价

推荐阅读 10

[1]	王玮, 邢玉瑾, 张雪. 气相色谱-质谱法测定化妆品中19种香精香料[J]. 日用化学工业（中英文）, 2023, 53(5): 581-587.
[2]	张永涛,赵净沙,蒋雁冰,赵丹,王昌涛,李萌. 代谢工程改造酵母生产香料的研究进展[J]. 日用化学工业, 2022, 52(6): 645-655.
[3]	杨婷婷,易路遥,王绎,李杰,吉伟佳,章红. 采用DPRA替代方法评价3种香料的皮肤致敏性[J]. 日用化学工业, 2021, 51(5): 438-442.
[4]	王玉健,梁振纲,符灵梅,董存柱. 高效液相色谱-串联质谱法测定香水中24种香料类过敏原物质残留量[J]. 日用化学工业, 2018, 48(8): 472-477.
[5]	王久标, 储鸿. 抗紫外聚多巴胺香料纳米胶囊缓释体系的研究[J]. 日用化学工业, 2018, 48(10): 582-588.
[6]	王玉健, 庞道标, 符灵梅, 梁振纲, 董存柱. 化妆品中过敏性香料及检测技术研究进展[J]. 日用化学工业, 2018, 48(1): 51-56.
[7]	向诗银, 杨水金. H₆P₂Mo₉W₉O₆₂/Cu₃(BTC)₂的制备及催化合成缩醛(酮)[J]. 日用化学工业, 2017, 47(5): 281-285.
[8]	王玥, 于海园, 施雁勤, 潘仙华, 卢艳花, 曹平. 当归净油抗衰老及抗炎祛痘功效的体外实验研究[J]. 日用化学工业, 2017, 47(2): 87-89.
[9]	向诗银, 李志鹏, 杨水金. SBA-15复合材料的制备及其催化合成环己酮乙二醇缩酮[J]. 日用化学工业, 2017, 47(11): 641-644.
[10]	王中天,于凤丽,袁冰,解从霞,于世涛. α-蒎烯催化环氧化研究进展[J]. 日用化学工业, 2016, 46(6): 353-358.
[11]	刘显明, 汤小芳. 6,7-二甲氧基香豆素的合成[J]. 日用化学工业, 2014, 44(9): 517-520.
[12]	沈德立, 穆旻, 何昕, 刘玉平, 田红玉, 孙宝国. 玫瑰麝香酯的合成研究[J]. 日用化学工业, 2014, 44(9): 508-511.
[13]	陈娟, 尹学琼. 香料香精的安全性及防范措施与评价标准[J]. 日用化学工业, 2014, 44(2): 100-104.