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左旋β蒎烯选择性氧化合成右旋诺蒎酮的研究

DOI: 10.3969/j.jssn.1000-2006.2010.02.021, PP. 89-94

Keywords: (-)β蒎烯,选择性氧化,(+)诺蒎酮

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Abstract:

以(-)β蒎烯为原料,经选择性氧化合成(+)诺蒎酮,分析了在不同氧化剂及溶剂体系下β蒎烯的氧化行为。研究了β蒎烯与高锰酸钾摩尔比、硫酸与高锰酸钾摩尔比、溶剂类型、反应温度、反应时间等因素对β蒎烯氧化转化率和诺蒎酮产物选择性的影响。结果表明,左旋β蒎烯选择性氧化合成右旋诺蒎酮适宜的氧化工艺条件:β蒎烯与高锰酸钾摩尔比为1∶3,硫酸与高锰酸钾摩尔比0.054∶1,以丙酮为溶剂,反应温度为15~25℃,反应时间为5h。此条件下β蒎烯转化率为94.15%,诺蒎酮选择性为89.19%,诺蒎酮得率为83.97%,纯度为95.29%,比旋光度为[α]18d+33.86°(c1.01,chcl3)。另外,采用ir、gc-ms、1hnmr和13cnmr等对诺蒎酮结构进行了表征。

References

[1]  秦民坚,徐珞珊.滑叶山姜的挥发油成分[j].中草药,1999(10):734-734.
[2]  江苏省植物研究所.新华本草纲要:第一卷[m].上海:上海科学技术出版社,1988.
[3]  baucherelx,uzielj,juges.unexpectedcatalyzedc=cbondcleavagebymolecularoxygenpromotedbyathiylradical[j].jorgchem,2001,66(13):4504-4510.
[4]  changws,shiaks,liuhj,etal.thefirsttotalsynthesisofxenitorinsbandc:assignmentofabsoluteconfiguration[j].organic&biomolecularchemistry,2006,4:3751-3753.
[5]  malkovav,bellam,langerv,etal.pindy:anovel,pinene?derivedbipyridineligandanditsapplicationinasymmetric,copper(ⅰ)catalyzedallylicoxidation[j].organicletters,2000,2(20):3047-3049.
[6]  yasuhikoi,isaon.preparationof(+)nopinone:jp,60146843[p].1985-08-02.
[7]  李家其,郭丹,尹笃林,等.苯甲酸氧钒催化过氧化氢氧化β蒎烯的研究[j].林产化学与工业,2008,28(2):97-100.
[8]  mayercf,crandalljk.thepyrolysisofnopinone[j].jorgchem,1970,35(8):2688-2690.
[9]  金建忠,沈敏敏.β蒎烯氧化反应研究进展[j].广州化学,2006,31(3):51-56.
[10]  williamad,kobayashiy.synthesisoftetrahydrocannabinolsbasedonanindirect1,4additionstrategy[j].jorgchem,2002,67(25):8771-8782.
[11]  honys,linsw,lul,etal.themechanisticstudyandsyntheticapplicationsofthebasetreatmentintheozonolyticreactions[j].tetrahedron,1995,51(17):5019-5034.
[12]  krzeminskimp,wojtczaka.chiralterpeneauxiliaries.part1:highlyenantioselectivereductionofketoneswithboranecatalyzedbyanoxazaborolidinederivedfrom(-)βpinene[j].tetrahedronletters,2005,46:8299-8302.
[13]  kozminan,paquetela.(1r,5s)(+)nopinoneofhighenantiomericpurity[j].syntheticcommunication,1996,26(10):2027-2030.
[14]  winsteins,holnessnj.neighboringcarbonandhydrogen.ⅹⅷ.solvolysisofthenopinylpbromobenzenesulfonates[j].jacs,1955,77:3054-3060.
[15]  saueram,crowewe,lainera,etal.efficientandeconomicasymmetricsynthesisofnootkatone,tetrahydronootkatone,theirprecursorsandderivatives:us,7112700[p].2006-09-26.
[16]  姜红宇,哈成勇,金建忠,等.用β蒎烯为原料合成高纯度对异丙基苯酚[j].林产化学与工业,2004,24(4):53-55.
[17]  coxonjm,garlandrp,hartshornmp.somederivativesofnopinone[j].austjchem,1970,23:1069-1071.
[18]  silvajuniorrc,ferreiravf,pinheiros.thestereoselectivesynthesisofnopinonebasedtriazoleketones[j].tetrahedron:asymmetry,2004,15:3719-3722.
[19]  camposkr,journetm,caidw,etal.apracticalsynthesisforthecorestructureofafamilyofselectiveprostaglandind2receptorantagonists[j].jorgchem,2003,68:2338-2342.
[20]  camposkr,lees,journetm,etal.ageneralmethodforthehighlydiastereoselective,kineticallycontrolledalkylationof(+)nopinone[j].tetrahedronletters,2002,43:6957-6959.
[21]  goralskict,chrismanw,hashadl,etal.boranesinsynthesis―ⅶ.synthesisof2dialkylamino6,6dimethylbicyclo[3.1.1]heptan3olsfrom(r)(+)nopinone.chiralauxiliariesfortheadditionofdiethylzinctoaromaticaldehydes[j].tetrahedron:asymmetry,1997,8(23):3863-3871.
[22]  liuc,sowajr.synthesisof(1r)(+)nopinone(1s)verbenonederivedchiralannulatedindenesviaelectrocyclicreactions[j].tetrahedronletters,1996,37(40):7241-7244.
[23]  bogerdl,mullicanmd,hellbergmr,etal.preparationofopticallyactivefunctionalizedcisδ61octalones[j].jorgchem,1985,50(11):1904-1911.

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