龙涎香香原料卷烟应用及降龙涎醚的合成研究进展
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摘要
介绍了龙涎香的组成及龙涎香香原料在卷烟工业中的应用,并从半合成的角度对降龙涎香醚的合成进行了综述。降龙涎香醚的合成主要以具有类似结构的植物提取物香紫苏醇为原料,重点阐述了合成过程中的重要中间体及副产物的生成,并详细介绍了反应机理。
The composition and application of ambergris products in tobacco industry were briefly introduced with 44 references.The synthesis of(-)-ambrox was also reviewed.The development of synthesis of(-)-Ambrox using sclareol from Salvia Sclare L.extracts as raw material was described and the reaction mechanism was discussed by analyzing the key intermediates and by-products.
The composition and application of ambergris products in tobacco industry were briefly introduced with 44 references.The synthesis of(-)-ambrox was also reviewed.The development of synthesis of(-)-Ambrox using sclareol from Salvia Sclare L.extracts as raw material was described and the reaction mechanism was discussed by analyzing the key intermediates and by-products.
引文
[1]SELL C.The chemistry of ambergris[J].Chemistry&Industry,1990,16:516-520.
[2]ROSSITER K J.Structure-odor relationships[J].Chem Rev,1996,96:3201-3240.
[3]黄明泉,孙宝国,等.龙涎香分子结构与香气关系规律研究进展[C].上海:2006年中国香料香精学术研讨会,2006,20-25.
[4]ABATE A,BRENNA E,FUGANTI C,et al.Lipasecatalysed preparation of enantiomerically enriched odorants[J].Journal of Molecular Catalysis B:Enzymatic,2004,32:33-51.
[5]Schumacher J N.Tobacco:US 2905576[P].1959.
[6]Chumacher J N.Tobacco:US 2905575[P].1959.
[7]CHRISTENSON P A.Alkyl sclareol diol carbonates in tobacco:US 5671756[P].1997.
[8]杨华武,黎艳玲,周宇,等,用于制备降龙涎醚或向卷烟烟气释放降龙涎醚的草酸酯及应用:CN1583711A[P].2005.
[9]ZORETIC P A,FANG H.Synthesis of d,l-Norlabdane oxide and related odorants:An intramolecular radical approach[J].J Org Chem,1998,63:4779-4785.
[10]TANIMOTOM H,ORITANI T.Practical synthesis of ambrox from farnesy acetate involving lipase catalyzed resolution[J].Tetrahedron:Asymmetry,1996,7(6):1695-1704.
[11]NAKAMURA S,ISHIHARA K,YAMAMOTO H.Enantioselective biomimetic cyclization of isoprenoids using lewis acid-assisted chiral brnsted acids:Abnormal claisen rearrangements and successive cyclizations[J].J Am Chem Soc,2000,122:8131-8140.
[12]ISHIHARA K,ISHIBASHI H,YAMAMOTO H.Enantio-and diastereoselective stepwise cyclization of polyprenoids induced by chiral and achiral LBAs.A new entry to(-)-Ambrox,(+)-podocarpa-8,11,13-triene diterpenoids,and(-)-tetracyclic polyprenoid of sedimentary[J].J Am Chem Soc,2002,124:3647-3655.
[13]SNOWDEN R L.Cetalox and analogues:Synthesis via acid-mediated polyene cyclizations[J].Chemistry&Biodiversity,2008,5:958-969.
[14]BARREROA F,ALTAREJOS J,ALVAREZ-MANZANEDA E J,et al.Synthesis of(±)-Ambrox from(E)-Nerolidol andβ-Ionone via allylic alcohol[2,3]Sigmatropic rearrangement[J].J Org Chem,1996,61(6):2215-2218.
[15]STOLL M,HINDER M.Odeur et constitution III.Les substances bicyclohomofarnésiques[J].Helv Chim Acta,1950,33(5),1251-1261.
[16]BARRERO A F,HERRADOR M M,ARTEAGA P,et al.Communic acids:Occurrence,properties and use as chirons for the synthesis of bioactive compounds[J].Molecules,2012,17:1448-1467.
[17]CASTRO J M,SALIDO S,ALTAREJOS J,et al.Synthesis of Ambrox from labdanolic acid[J].Tetrahedron,2002,58(29),5941-5945.
[18]CORTS M J,ARMSTRONG V,REYES M E,et al.Formal synthesis of Ambroxand 9-Epiambrox[J].Synth Commun,1996,26(10):1995-2002.
[19]KOYAMA H,KAKU Y,OHNO M.Synthesis of(-)-Ambrox from l-abietic acid[J].Tetrahedron Lett,1987,28(25):2863-2866.
[20]VERSTEGEN-HAAKSMA A A,SWARTS H J,JANSEN B J M,et al.Total synthesis of(-)-Ambroxfrom S-(+)-carvone[J].Tetrahedron,1994,50(33):10095-10106.
[21]GORO A,YOSHI T.Process for producing L-Ambrox:EP 0550889[P].1993.
[22]BARRERO A F,SNCHEZ J F,ALVAREZ-MANZANEDA E J,et al.Synthesis of nor-ambreinolide from(+)-cis-abienol[J].Tetrahedron,1994,50(22),6653-6662.
[23]NISHI Y,ISHIHARA K.Synthesis of(-)-Ambrox(R)from(-)-Levopimaric acid[J].Journal of Japan Oil Chemists'Society,1989,38(4),276-279.
[24]KUTNEY J P,CHEN Y H.The chemistry of thujone.Part 17.the synthesis of ambergris fragrances and related analogues[J].Can J Chem,2011,72(6):1570-1581.
[25]XIE Y P,LI B G,LUO Y G,et al.Preparation of two diastereoisomeric decalin synthons and(-)-Ambrox[J].Hel Chim Acta,2008,91:734-740.
[26]BARCO A,BENETTI S,BIANCHI A,et al.Formal synthesis of(±)-Ambrox[J].Tetrahedron,1995,51(30):8333-8338.
[27]MOULINESJ,LAMIDEY A M,BREUIL V D.A practical synthesis of Ambrox from Sclareol using no mentallic oxidant[J].Synth Commun,2001,31(5):749-758.
[28]王文军,陈莎,戴乾圜.龙涎香的组成及降龙涎醚的合成研究进展[J].有机化学,2001,21(3):167-172.
[29]BARTON D H R,PAREKH S I,TAYLOR D K,et al.An efficient synthesis of(-)-dodecahydro-3a,6,6,9a-tetramethylnaphtho[2,1-b]furan from(-)-sclareol[J].Tetrahedron Letter,1994,35(32):5801-5804.
[30]DECORZANT R,VIAL C,NAF F.A short synthesis of ambrox from sclareol[J].Tetrahedron,1987,43(8):1871-1879.
[31]SARRAGIOTTO M H,GOWER A E,MARSAIOLI A J.Synthesis of an enantiomerically pure indolosesquiterpene[J].J Chem Soc Perkin Trans,1989,559-562.
[32]MARTRESA P,PERFETTIA P,ZAHRAA J P,et al.A short and efficient synthesis of(-)-Ambroxfrom(-)-sclareol using a ruthenium oxide catalyzed key step[J].Tetrahedron Lett,1993,34(4):629-632.
[33]BARTON D H R,TAYLOR D K,TSE C.An efficient synthesis of(-)-dodecahydro-3a,6,6,9a-tetramethylnaphtho[2,1-b]furan from(-)-sclareol[J].Tetrahedron Lett,1994,35(51):9505-9508.
[34]JOSEPH N S,WALTER M H,EDWARD B.Two stage oxidation of sclareol:US 3050532[P].1962.
[35]Ogura T,Matsuoka H,Yamanaka T.Preparation of L-ambrox:JP 61-033184[P].1986.
[36]翟周平.香紫苏内酯合成新工艺的研究[J].香料香精化妆品,2002,6:1-2.
[37]BARRERO A F,ALVAREZ-MANZANEDA E J,CHAHBOUN R,et al.Degradation of the side chain of(-)-Sclareol:A very short synthesis of nor-Ambreinolide and Ambrox[J].Synth Commun,2004,34(19):3631-3643.
[38]MOULINES J,BATS J P,LAMIDEY A M,et al.About a practical synthesis of ambrox from sclareol:A new preparation of a ketone key intermediate and a close look at its Baeyer-Villiger oxidation[J].Helv Chim Acta,2004,87:2695-2705.
[39]CASTRO J M,SALIDO S,SNCHEZ A.et al.Synthesis of(+)-Sclareolide based on a cyclic enol ether ring contraction induced by peroxy acids[J].Synlett,2010,18:2747-2750.
[40]魏俊发,吴亚,石先莹,等.香紫苏内酯的合成方法:CN 1683352A[P].2005.
[41]翟周平,胡新予,赵新春,等.四丁基溴化铵催化过氧化氢氧化香紫苏醇合成香紫苏内酯的研究[J].香料香精化妆品,2009,4,1-3.
[42]李云政,赵俊岩,张春辉,等.一种由香紫苏醇合成香紫苏内酯的生产工艺:CN 102766123A[P].2012.
[43]STEENKAMP L H,TAKA M.Process for the production of Ambrafuran:US 20100248316[P].2010.
[44]ALVAREZ-MANZANEDA E J,CHABOUN R,ALVAREZ E,et al.Cerium(IV)ammonium nitrate(CAN):A very efficient reagent for the synthesis of tertiary ethers[J].Synlett,2006,12:1829-1834.
[2]ROSSITER K J.Structure-odor relationships[J].Chem Rev,1996,96:3201-3240.
[3]黄明泉,孙宝国,等.龙涎香分子结构与香气关系规律研究进展[C].上海:2006年中国香料香精学术研讨会,2006,20-25.
[4]ABATE A,BRENNA E,FUGANTI C,et al.Lipasecatalysed preparation of enantiomerically enriched odorants[J].Journal of Molecular Catalysis B:Enzymatic,2004,32:33-51.
[5]Schumacher J N.Tobacco:US 2905576[P].1959.
[6]Chumacher J N.Tobacco:US 2905575[P].1959.
[7]CHRISTENSON P A.Alkyl sclareol diol carbonates in tobacco:US 5671756[P].1997.
[8]杨华武,黎艳玲,周宇,等,用于制备降龙涎醚或向卷烟烟气释放降龙涎醚的草酸酯及应用:CN1583711A[P].2005.
[9]ZORETIC P A,FANG H.Synthesis of d,l-Norlabdane oxide and related odorants:An intramolecular radical approach[J].J Org Chem,1998,63:4779-4785.
[10]TANIMOTOM H,ORITANI T.Practical synthesis of ambrox from farnesy acetate involving lipase catalyzed resolution[J].Tetrahedron:Asymmetry,1996,7(6):1695-1704.
[11]NAKAMURA S,ISHIHARA K,YAMAMOTO H.Enantioselective biomimetic cyclization of isoprenoids using lewis acid-assisted chiral brnsted acids:Abnormal claisen rearrangements and successive cyclizations[J].J Am Chem Soc,2000,122:8131-8140.
[12]ISHIHARA K,ISHIBASHI H,YAMAMOTO H.Enantio-and diastereoselective stepwise cyclization of polyprenoids induced by chiral and achiral LBAs.A new entry to(-)-Ambrox,(+)-podocarpa-8,11,13-triene diterpenoids,and(-)-tetracyclic polyprenoid of sedimentary[J].J Am Chem Soc,2002,124:3647-3655.
[13]SNOWDEN R L.Cetalox and analogues:Synthesis via acid-mediated polyene cyclizations[J].Chemistry&Biodiversity,2008,5:958-969.
[14]BARREROA F,ALTAREJOS J,ALVAREZ-MANZANEDA E J,et al.Synthesis of(±)-Ambrox from(E)-Nerolidol andβ-Ionone via allylic alcohol[2,3]Sigmatropic rearrangement[J].J Org Chem,1996,61(6):2215-2218.
[15]STOLL M,HINDER M.Odeur et constitution III.Les substances bicyclohomofarnésiques[J].Helv Chim Acta,1950,33(5),1251-1261.
[16]BARRERO A F,HERRADOR M M,ARTEAGA P,et al.Communic acids:Occurrence,properties and use as chirons for the synthesis of bioactive compounds[J].Molecules,2012,17:1448-1467.
[17]CASTRO J M,SALIDO S,ALTAREJOS J,et al.Synthesis of Ambrox from labdanolic acid[J].Tetrahedron,2002,58(29),5941-5945.
[18]CORTS M J,ARMSTRONG V,REYES M E,et al.Formal synthesis of Ambroxand 9-Epiambrox[J].Synth Commun,1996,26(10):1995-2002.
[19]KOYAMA H,KAKU Y,OHNO M.Synthesis of(-)-Ambrox from l-abietic acid[J].Tetrahedron Lett,1987,28(25):2863-2866.
[20]VERSTEGEN-HAAKSMA A A,SWARTS H J,JANSEN B J M,et al.Total synthesis of(-)-Ambroxfrom S-(+)-carvone[J].Tetrahedron,1994,50(33):10095-10106.
[21]GORO A,YOSHI T.Process for producing L-Ambrox:EP 0550889[P].1993.
[22]BARRERO A F,SNCHEZ J F,ALVAREZ-MANZANEDA E J,et al.Synthesis of nor-ambreinolide from(+)-cis-abienol[J].Tetrahedron,1994,50(22),6653-6662.
[23]NISHI Y,ISHIHARA K.Synthesis of(-)-Ambrox(R)from(-)-Levopimaric acid[J].Journal of Japan Oil Chemists'Society,1989,38(4),276-279.
[24]KUTNEY J P,CHEN Y H.The chemistry of thujone.Part 17.the synthesis of ambergris fragrances and related analogues[J].Can J Chem,2011,72(6):1570-1581.
[25]XIE Y P,LI B G,LUO Y G,et al.Preparation of two diastereoisomeric decalin synthons and(-)-Ambrox[J].Hel Chim Acta,2008,91:734-740.
[26]BARCO A,BENETTI S,BIANCHI A,et al.Formal synthesis of(±)-Ambrox[J].Tetrahedron,1995,51(30):8333-8338.
[27]MOULINESJ,LAMIDEY A M,BREUIL V D.A practical synthesis of Ambrox from Sclareol using no mentallic oxidant[J].Synth Commun,2001,31(5):749-758.
[28]王文军,陈莎,戴乾圜.龙涎香的组成及降龙涎醚的合成研究进展[J].有机化学,2001,21(3):167-172.
[29]BARTON D H R,PAREKH S I,TAYLOR D K,et al.An efficient synthesis of(-)-dodecahydro-3a,6,6,9a-tetramethylnaphtho[2,1-b]furan from(-)-sclareol[J].Tetrahedron Letter,1994,35(32):5801-5804.
[30]DECORZANT R,VIAL C,NAF F.A short synthesis of ambrox from sclareol[J].Tetrahedron,1987,43(8):1871-1879.
[31]SARRAGIOTTO M H,GOWER A E,MARSAIOLI A J.Synthesis of an enantiomerically pure indolosesquiterpene[J].J Chem Soc Perkin Trans,1989,559-562.
[32]MARTRESA P,PERFETTIA P,ZAHRAA J P,et al.A short and efficient synthesis of(-)-Ambroxfrom(-)-sclareol using a ruthenium oxide catalyzed key step[J].Tetrahedron Lett,1993,34(4):629-632.
[33]BARTON D H R,TAYLOR D K,TSE C.An efficient synthesis of(-)-dodecahydro-3a,6,6,9a-tetramethylnaphtho[2,1-b]furan from(-)-sclareol[J].Tetrahedron Lett,1994,35(51):9505-9508.
[34]JOSEPH N S,WALTER M H,EDWARD B.Two stage oxidation of sclareol:US 3050532[P].1962.
[35]Ogura T,Matsuoka H,Yamanaka T.Preparation of L-ambrox:JP 61-033184[P].1986.
[36]翟周平.香紫苏内酯合成新工艺的研究[J].香料香精化妆品,2002,6:1-2.
[37]BARRERO A F,ALVAREZ-MANZANEDA E J,CHAHBOUN R,et al.Degradation of the side chain of(-)-Sclareol:A very short synthesis of nor-Ambreinolide and Ambrox[J].Synth Commun,2004,34(19):3631-3643.
[38]MOULINES J,BATS J P,LAMIDEY A M,et al.About a practical synthesis of ambrox from sclareol:A new preparation of a ketone key intermediate and a close look at its Baeyer-Villiger oxidation[J].Helv Chim Acta,2004,87:2695-2705.
[39]CASTRO J M,SALIDO S,SNCHEZ A.et al.Synthesis of(+)-Sclareolide based on a cyclic enol ether ring contraction induced by peroxy acids[J].Synlett,2010,18:2747-2750.
[40]魏俊发,吴亚,石先莹,等.香紫苏内酯的合成方法:CN 1683352A[P].2005.
[41]翟周平,胡新予,赵新春,等.四丁基溴化铵催化过氧化氢氧化香紫苏醇合成香紫苏内酯的研究[J].香料香精化妆品,2009,4,1-3.
[42]李云政,赵俊岩,张春辉,等.一种由香紫苏醇合成香紫苏内酯的生产工艺:CN 102766123A[P].2012.
[43]STEENKAMP L H,TAKA M.Process for the production of Ambrafuran:US 20100248316[P].2010.
[44]ALVAREZ-MANZANEDA E J,CHABOUN R,ALVAREZ E,et al.Cerium(IV)ammonium nitrate(CAN):A very efficient reagent for the synthesis of tertiary ethers[J].Synlett,2006,12:1829-1834.