CN1227837A - 芳基丙烯酸酯 - Google Patents
芳基丙烯酸酯 Download PDFInfo
- Publication number
- CN1227837A CN1227837A CN99101847A CN99101847A CN1227837A CN 1227837 A CN1227837 A CN 1227837A CN 99101847 A CN99101847 A CN 99101847A CN 99101847 A CN99101847 A CN 99101847A CN 1227837 A CN1227837 A CN 1227837A
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- China
- Prior art keywords
- alkyl
- formula
- compound
- described compound
- branched
- Prior art date
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- 150000001875 compounds Chemical class 0.000 claims abstract description 67
- 230000000845 anti-microbial effect Effects 0.000 claims abstract description 3
- 239000002243 precursor Substances 0.000 claims description 26
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 20
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 claims description 15
- 150000001299 aldehydes Chemical class 0.000 claims description 13
- 125000003545 alkoxy group Chemical group 0.000 claims description 13
- 150000002576 ketones Chemical class 0.000 claims description 13
- 229920006395 saturated elastomer Polymers 0.000 claims description 11
- 230000008786 sensory perception of smell Effects 0.000 claims description 11
- 125000003118 aryl group Chemical group 0.000 claims description 10
- 235000013599 spices Nutrition 0.000 claims description 10
- 125000000623 heterocyclic group Chemical group 0.000 claims description 9
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 7
- 125000000217 alkyl group Chemical class 0.000 claims description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- 239000000975 dye Substances 0.000 claims description 6
- 238000005282 brightening Methods 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 125000005842 heteroatom Chemical group 0.000 claims description 4
- 150000002790 naphthalenes Chemical class 0.000 claims description 4
- 125000002723 alicyclic group Chemical group 0.000 claims description 3
- 238000004140 cleaning Methods 0.000 claims description 3
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 150000002632 lipids Chemical class 0.000 claims description 2
- 235000019505 tobacco product Nutrition 0.000 claims description 2
- 125000002587 enol group Chemical group 0.000 claims 2
- 101710094902 Legumin Proteins 0.000 claims 1
- 125000003710 aryl alkyl group Chemical group 0.000 claims 1
- NEKNNCABDXGBEN-UHFFFAOYSA-L disodium;4-(4-chloro-2-methylphenoxy)butanoate;4-(2,4-dichlorophenoxy)butanoate Chemical compound [Na+].[Na+].CC1=CC(Cl)=CC=C1OCCCC([O-])=O.[O-]C(=O)CCCOC1=CC=C(Cl)C=C1Cl NEKNNCABDXGBEN-UHFFFAOYSA-L 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 239000003205 fragrance Substances 0.000 abstract description 23
- 239000003795 chemical substances by application Substances 0.000 abstract description 8
- 230000000873 masking effect Effects 0.000 abstract description 4
- 239000000796 flavoring agent Substances 0.000 abstract description 3
- 125000005396 acrylic acid ester group Chemical group 0.000 abstract 1
- 235000019634 flavors Nutrition 0.000 abstract 1
- 239000006081 fluorescent whitening agent Substances 0.000 abstract 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 26
- -1 heterocyclic radical Chemical class 0.000 description 24
- 239000000203 mixture Substances 0.000 description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 18
- 238000005406 washing Methods 0.000 description 18
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
- 239000000243 solution Substances 0.000 description 14
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 13
- HHSARRMUXPDGJD-UHFFFAOYSA-N butyl(dimethyl)silicon Chemical group CCCC[Si](C)C HHSARRMUXPDGJD-UHFFFAOYSA-N 0.000 description 11
- 239000000047 product Substances 0.000 description 11
- 239000011541 reaction mixture Substances 0.000 description 11
- 239000012074 organic phase Substances 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- 238000001816 cooling Methods 0.000 description 8
- 238000001035 drying Methods 0.000 description 8
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 7
- 238000000354 decomposition reaction Methods 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- 239000003921 oil Substances 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000004744 fabric Substances 0.000 description 6
- ZAAJFIBQWOITJV-UHFFFAOYSA-N 2-but-2-en-2-yl-5-(diethylamino)phenol Chemical compound CCN(CC)C1=CC=C(C(C)=CC)C(O)=C1 ZAAJFIBQWOITJV-UHFFFAOYSA-N 0.000 description 5
- 241000208125 Nicotiana Species 0.000 description 5
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 235000013409 condiments Nutrition 0.000 description 5
- 238000010790 dilution Methods 0.000 description 5
- 239000012895 dilution Substances 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 description 5
- GLZPCOQZEFWAFX-UHFFFAOYSA-N Geraniol Chemical compound CC(C)=CCCC(C)=CCO GLZPCOQZEFWAFX-UHFFFAOYSA-N 0.000 description 4
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 4
- 238000011097 chromatography purification Methods 0.000 description 4
- 235000019504 cigarettes Nutrition 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- OTTZHAVKAVGASB-UHFFFAOYSA-N hept-2-ene Chemical compound CCCCC=CC OTTZHAVKAVGASB-UHFFFAOYSA-N 0.000 description 4
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 238000003860 storage Methods 0.000 description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 3
- KSMVZQYAVGTKIV-UHFFFAOYSA-N decanal Chemical compound CCCCCCCCCC=O KSMVZQYAVGTKIV-UHFFFAOYSA-N 0.000 description 3
- 239000003599 detergent Substances 0.000 description 3
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 3
- 238000003818 flash chromatography Methods 0.000 description 3
- 239000002304 perfume Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 230000008521 reorganization Effects 0.000 description 3
- SMQUZDBALVYZAC-UHFFFAOYSA-N salicylaldehyde Chemical compound OC1=CC=CC=C1C=O SMQUZDBALVYZAC-UHFFFAOYSA-N 0.000 description 3
- 239000000779 smoke Substances 0.000 description 3
- BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 3
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 3
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- PWVUXRBUUYZMKM-UHFFFAOYSA-N 2-(2-hydroxyethoxy)ethyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCCOCCO PWVUXRBUUYZMKM-UHFFFAOYSA-N 0.000 description 2
- ZAAJFIBQWOITJV-VZUCSPMQSA-N 2-[(E)-but-2-en-2-yl]-5-(diethylamino)phenol Chemical compound CCN(CC)C1=CC=C(\C(C)=C\C)C(O)=C1 ZAAJFIBQWOITJV-VZUCSPMQSA-N 0.000 description 2
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 2
- OXYRENDGHPGWKV-UHFFFAOYSA-N 3-methyl-5-phenylpentan-1-ol Chemical compound OCCC(C)CCC1=CC=CC=C1 OXYRENDGHPGWKV-UHFFFAOYSA-N 0.000 description 2
- ALHUZKCOMYUFRB-UHFFFAOYSA-N 3-methylcyclopentadecan-1-one Chemical compound CC1CCCCCCCCCCCCC(=O)C1 ALHUZKCOMYUFRB-UHFFFAOYSA-N 0.000 description 2
- MQWCXKGKQLNYQG-UHFFFAOYSA-N 4-methylcyclohexan-1-ol Chemical compound CC1CCC(O)CC1 MQWCXKGKQLNYQG-UHFFFAOYSA-N 0.000 description 2
- 241000213006 Angelica dahurica Species 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- 229920000858 Cyclodextrin Polymers 0.000 description 2
- 102000004190 Enzymes Human genes 0.000 description 2
- 108090000790 Enzymes Proteins 0.000 description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 2
- 239000005792 Geraniol Substances 0.000 description 2
- GLZPCOQZEFWAFX-YFHOEESVSA-N Geraniol Natural products CC(C)=CCC\C(C)=C/CO GLZPCOQZEFWAFX-YFHOEESVSA-N 0.000 description 2
- 239000004367 Lipase Substances 0.000 description 2
- 102000004882 Lipase Human genes 0.000 description 2
- 108090001060 Lipase Proteins 0.000 description 2
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 2
- NFLGAXVYCFJBMK-UHFFFAOYSA-N Menthone Chemical compound CC(C)C1CCC(C)CC1=O NFLGAXVYCFJBMK-UHFFFAOYSA-N 0.000 description 2
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 230000004913 activation Effects 0.000 description 2
- AKGGYBADQZYZPD-UHFFFAOYSA-N benzylacetone Chemical compound CC(=O)CCC1=CC=CC=C1 AKGGYBADQZYZPD-UHFFFAOYSA-N 0.000 description 2
- 230000003115 biocidal effect Effects 0.000 description 2
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 2
- ULDHMXUKGWMISQ-UHFFFAOYSA-N carvone Chemical compound CC(=C)C1CC=C(C)C(=O)C1 ULDHMXUKGWMISQ-UHFFFAOYSA-N 0.000 description 2
- 229960000541 cetyl alcohol Drugs 0.000 description 2
- QMVPMAAFGQKVCJ-UHFFFAOYSA-N citronellol Chemical compound OCCC(C)CCC=C(C)C QMVPMAAFGQKVCJ-UHFFFAOYSA-N 0.000 description 2
- 239000012230 colorless oil Substances 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- HFJRKMMYBMWEAD-UHFFFAOYSA-N dodecanal Chemical compound CCCCCCCCCCCC=O HFJRKMMYBMWEAD-UHFFFAOYSA-N 0.000 description 2
- 238000005538 encapsulation Methods 0.000 description 2
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- 238000000605 extraction Methods 0.000 description 2
- 239000002979 fabric softener Substances 0.000 description 2
- 235000013355 food flavoring agent Nutrition 0.000 description 2
- 229940113087 geraniol Drugs 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
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- JARKCYVAAOWBJS-UHFFFAOYSA-N hexanal Chemical compound CCCCCC=O JARKCYVAAOWBJS-UHFFFAOYSA-N 0.000 description 2
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- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
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- 229910052760 oxygen Inorganic materials 0.000 description 2
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- 230000004044 response Effects 0.000 description 2
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 description 2
- 239000003352 sequestering agent Substances 0.000 description 2
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- 239000001074 1-methoxy-4-[(E)-prop-1-enyl]benzene Substances 0.000 description 1
- FSKGFRBHGXIDSA-UHFFFAOYSA-N 2-(4-propan-2-ylphenyl)acetaldehyde Chemical compound CC(C)C1=CC=C(CC=O)C=C1 FSKGFRBHGXIDSA-UHFFFAOYSA-N 0.000 description 1
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- GESSJUAZQLNAOJ-UHFFFAOYSA-N CC(CC[O])CCC=C(C)C Chemical compound CC(CC[O])CCC=C(C)C GESSJUAZQLNAOJ-UHFFFAOYSA-N 0.000 description 1
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- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
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- 239000003109 Disodium ethylene diamine tetraacetate Substances 0.000 description 1
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- A24—TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
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- A24B15/00—Chemical features or treatment of tobacco; Tobacco substitutes, e.g. in liquid form
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- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/37—Esters of carboxylic acids
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Abstract
式Ⅰ的丙烯酸酯可用于供给特殊感觉化合物,特别是调料、香料、掩蔽剂和抗菌剂。它们也可以产生荧光增白剂。
Description
本发明涉及3-(2-取代芳基)-丙烯酸酯,特别是3-(2-羟基芳基)-丙烯酸酯和3-(2-氨基芳基)丙烯酸酯。这些化合物通常用作某些特殊感觉化合物(organoleptic compounds),特别是调料、香料和掩蔽剂、抗菌剂和荧光增白剂的前体。
目前,向消费品中引入气味的主要途径就是把香料直接混入产品中。但这种方法有几个缺点。由于香料极易挥发和/或极易溶,从而导致在产品的制造、储存及使用过程中香味散失。很多香料不具有长期稳定性,这也造成储存过程中的气味损耗。
对很多消费品,人们希望其香味能够随着时间的推移而缓慢释放出来,具有环糊精的微封装(micro-encapsulation)和包含(inclusion)复合物可用来帮助降低其挥发性、提高稳定性并且提供缓释性能。然而,由于某些原因,这些方法通常无法奏效。另外,环糊精的价格十分昂贵。
能使织物在用含有脂肪酶的洗涤剂洗涤过程中,具有香味的香料前体已在WO95/04809中有描述。脂肪酶能够分解洗涤剂和/或软化剂中所含的香料前体,得到一种单一的活性化合物,或者是有气味的醇,或者是醛,或者是酮。因此织物上的香味能够持久。但对于含脂肪酶的洗涤剂的需求是有限的。在世界上许多国家中,洗涤剂不含脂肪酶。还有一些消费者喜欢用“非生物”洗涤剂。
早在20世纪50年代,荧光增白剂或增亮剂就被加入衣物洗涤剂中以使白色衣物保持本色。
本发明的一个目的就是要提供新的化合物前体,该化合物可具有不同的活性,因此只需加入一种化合物就能使产品具有不同的活性。本发明另外一个目的是要提供在储存和运输过程中都很稳定的新化合物。本发明的第三个目的是要提供能同时或依次产生不同活性化合物的前体分子。
本发明涉及式Ⅰ的3-(2-取代芳基)-丙烯酸酯,
其中
A代表苯环或萘环,
R1代表饱和或不饱和、直链、支链的脂环或芳香C1-C30烃基,其可含有杂原子或可被离子型取代基取代,
2-或3-位的R2代表H、直链或支链C1-C6烃基;任选取代的芳基或任选取代的杂环基,
R3和R4代表H、直链或支链C1-C6烷基、C1-C6烷氧基,取代或稠合杂环基、-OH、-NO2、-NH2、-N(C1-C6烷基)2、-N(羟烷基)2、-NHCO2CH3或-NH(杂环),
R2、R3、R4可以相同也可以不同,
X代表-OH或NHR6,其中R6是H、饱和或不饱和、直链或支链C1-C20烃、任选取代的芳基或杂环基,
丙烯酸酯中的双键是E构型。
上式Ⅰ中,所有可能的对映体、非对映体以及所有的混合物都包含在本发明范围内。
其中,R1代表饱和或不饱和、直链或支链C10-C30烃基,该烃基可以含有一个或多个O原子和/或N原子和/或C(O)基团和/或烷氧基团,或者被式为NR5 3 +的离子型取代基取代,其中R5代表脂肪酸的残基或具有1-30个C原子的烷基基团,具有上述基团的化合物是优选化合物。
R3和/或R4优选代表H、-N(C1-C6烷基)2、-NH2、任选含N和/或O原子的五元杂环基,其可以被C1-C6脂族或芳族取代基取代。
R1可以是式为R1OH的嗅觉醇(olfactory alcohol)的残基,式为R1HO的嗅觉醛或式为R1O的嗅觉酮的烯醇式。R1也可以是任选取代的烷基、链烯基或带有1-烷氧基、1-芳氧基或1-芳烷氧基取代基的芳烷基。
其中X1代表O或NR6,R2、R3、R4的含义如前所述。结构式为Ⅱ的香豆素具有特殊感觉和/或抗菌性能和/或光增强活性。尤其令人感兴趣的是具有嗅觉性能的香豆素。如果R1是嗅觉醇的残基、嗅觉醛或酮的烯醇式的残基,则通过分解可以得到具有以上性质的两种活性化合物。因此可利用式Ⅰ化合物开发出具有增强的特殊感觉和/或抗菌和/或光增强性质的产品。所得到的特殊感觉的香豆素和醇或醛或酮可用作香料、调料、掩蔽剂和抗菌剂。
导致分解,产生预期化合物的活化条件包括紫外光、例如太阳光,以及高温的存在。
A代表苯环或萘环,
R1代表H、饱和或不饱和、直链或支链的C1-C30脂环烃基或芳烃基,其可以含有杂原子并可被离子型取代基取代,
2-或3-位的R2代表H、直链或支链C1-C6基、任选取代的芳基或任选取代的杂环基,
R3和R4代表H、直链或支链的C1-C6烷基或C1-C6烷氧基、取代或稠合杂环基、-OH、-NO2、-NH2、-N(C1-C6烷基)2、-N烃基烷基)2、-NHCO2CH3或-NH(杂环),
R2、R3、R4可以相同也可以不同,
X代表-OH或NHR6,其中R6代表H,饱和或不饱和、直链或支链C1-C20烃基,也可以是任选取代的芳基或杂环基,
并且丙烯酸中的双键是E构型,
该式Ⅰ化合物可用作特殊感觉化合物(例如调料、香料、气味掩蔽剂)的前体,还可以用作抗菌剂的前体和荧光增白剂的前体。
优选的取代基如上所述。
式Ⅰ的酯类可用作洗涤产品中的香料前体。它们还可以在同一种产品中既用作气味掩蔽剂的前体,也用作香料的前体。它们还可以用作抗菌剂及荧光增白剂的前体。本发明所涉及的香料前体、气味掩蔽剂前体和调料前体可分别以有效量使用,以增强或掩盖物质的特殊气味或味道。但更通常的情况是这些化合物与其它的足量的香料或调料组分混合以产生所期望的气味或味道特征。
增亮剂前体可以以有效量单独使用,也可以和一种或多种其它增亮剂或着色剂混合使用。
由于在使用处就地产生活性化合物,所以延长了所需的效果并且在不同基质上的实质作用也得到了提高。如果一种式Ⅰ的酯能够提供两种活性化合物,那么取决于该前体和/或活化条件,或同时、或依次产生这两种活性化合物。再者,本发明的前体能够使活性化合物产生缓释功能。
式Ⅰ化合物分解后,R1重组而产生的醇R1OH的实例是:戊醇己醇*2-己醇*庚醇*辛醇*壬醇*癸醇*十一烷醇*月桂醇*肉豆蔻醇3-甲基-丁-2-烯-1-醇*3-甲基-1-戊醇顺式-3-己烯醇*顺式-4-己烯醇*3,5,5-三甲基己醇3,4,5,6,6-五甲基庚-2-醇*香茅醇*香叶醇*辛-1-烯-3-醇2,5,7-三甲基辛-3-醇2-顺式-3,7-二甲基-2,6-辛二烯-1-醇6-乙基-3-甲基-5-辛烯-1-醇*3,7-二甲基辛-3,6-二烯醇*3,7-二甲基辛醇*7-甲氧基-3,7-二甲基辛-2-醇*顺式-6-壬醇*5-乙基-2-壬醇6,8-二甲基-2-壬醇*2,2,8-三甲基-7(8)-壬烯-3-醇壬-2,6-二烯-1-醇4-甲基-3-癸烯-5-醇*癸-9-烯-1-醇苯甲醇2-甲基-十一醇10-十一烯-1-醇1-苯基-乙醇*2-苯基-乙醇*2-甲基-3-苯基-3-丙烯醇2-苯基-1-丙醇*3-苯基-1-丙醇*4-苯基-2-丁醇2-甲基-5-苯基-戊醇*2-甲基-4-苯基-戊醇*3-甲基-5-苯基-戊醇*2-(2-苯甲基)-乙醇*4-(1-甲基乙基)-苯甲醇4-(4-羟苯基)-丁-2-酮*2-苯氧基-乙醇*4-(1-甲基乙基)-2-羟基-1-甲基苯2-甲氧基-4-甲基苯酚4-甲基苯酚茴香醇*对-甲苯基甲醇*肉桂醇*香兰素*乙基香兰素*丁子香酚*异丁子香酚*百里酚对丙烯基茴香醚(anethol)*十氢-2-萘酚冰片*雪松烯醇*法呢醇*葑醇*薄荷醇*3,7,11-三甲基-2,6,10-十二碳三烯-1-醇α-芷香醇(ionol)*四氢芷香醇*2-(1,1-二甲基乙基)环己醇*3-(1,1-二甲基乙基)环己醇*4-(1,1-二甲基乙基)环己醇*4-异丙基-环己醇6,6-二甲基-双环[3.3.1]庚-2-烯-2-乙醇6,6-二甲基-双环[3.1.1]庚-2-烯-甲醇*对--8-烯-3-醇*3,3,5-三甲基-环己醇2,4,6-三甲基-3-环己烯基甲醇*4-(1-甲基乙基)-环己基甲醇*4-(1,1-二甲基乙基)-环己醇2-(1,1-二甲基乙基)-环己醇2,2,6-三甲基-α-丙基-环己烷丙醇*5-(2,2,3-三甲基-3-环戊烯基)-3-甲基戊-2-醇*3-甲基-5-(2,2,3-三甲基环戊-3-烯基)戊-4-烯-2-醇*2-乙基-4-(2,2,3-三甲基-3-环戊-3-烯基)丁-2-烯-1-醇*4-(5,5,6-三甲基双环[2.2.1]庚-2-基)-环己醇*2-(2-甲基丙基)-4-羟基-4-甲基-四氢吡喃*2-环己基丙醇*2-(1,1-二甲基乙基)-4-甲基-环己醇*1-(2-叔丁基-环己基氧)-2-丁醇*1-(4-异丙基-环己基)-乙醇*2,6-二甲基-辛-7-烯-2-醇**2,6-二甲基-庚-2-醇**3,7-二甲基-辛-1,6-二烯-3-醇**其中,*表示优选醇,**表示更优选的醇。式Ⅰ化合物分解,R1基团重组而得到的醛R1HO的实例是:2,6,10-三甲基-十一碳-9-烯醛(enal)*1,2,3,4,5,6,7,8-八氢-8,8-二甲基-2-萘甲醛十三醛(tridecanal)2-[4-(1-甲基乙基)苯基]-乙醛2,4-二甲基-环己-3-烯-1-醛(carboxaldehyde)*4-醛-1,3,5-三甲基-环己-1-烯*1-醛-2,4-二甲基-环己-3-烯*1-醛-4-(4-羟基-4-甲基戊基)-环己-3-烯*3,5,5-三甲基己醛庚醛*2,6-二甲基-庚-5-烯醛*癸醛**癸-9-烯醛癸-4-烯醛2-甲基癸醛*十一碳-10-烯醛**十一醛*十二醛**2-甲基-十一醛**十三醛*辛醛**壬醛*3,5,5-三甲基己醛十一碳-9-烯醛**2-苯基丙醛*4-甲基-苯基-乙醛*3,7-二甲基辛醛*二氢法呢醛**7-羟基-3,7-二甲基-辛醛*2,6-二甲基辛-5-烯醛2-[4-(1-甲基乙基)苯基]-乙醛*3-(3-异丙基-苯基)-丁醛**2-(3,7-二甲基辛-6-烯氧基)-乙醛1-醛-4-(4-甲基-3-戊烯基)-环己-3-烯*2,3,5,5-四甲基-己醛长叶醛2-甲基-4-(2,6,6-三甲基环己-2-烯-1-基)-丁醛*2-甲基-3-(4-叔丁基苯基)-丙醛**4-(1,1-二甲基-乙基)-苯-丙醛*2-[4-(1-甲基-乙基)-苯基]-丙醛α-甲基-1,3-苯并间二氧杂环戊烯(dioxole)-5-丙醛*3,7-二甲基-辛-6-烯醛*2-甲基-3-(4-异丙基苯基)-丙醛*4-(4-羟基-4-甲基-戊基)-环己-3-烯-1-甲醛**α-甲基-1-3-苯并间二氧杂环戊烯-5-丙醛*1-醛4-(1,1-二甲基乙基)-环己烷4-八氢-4,7-亚甲基-5H-亚茚-5-基)-丁醛(3,7-二甲基-6-辛烯基-氧基)-乙醛**其中,*表示优选醛,**表示更优选的醛。酮R1O的实例如下:2-庚基-环戊酮2,2,6,10-四甲基三环-[5.4.0.0(6,10)]-十一烷-4-酮苄基丙酮*香芹酮*1,2,3,5,6,7-六氢-1,1,2,3,3-五甲基-4H-茚基-4-酮*甲基庚烯酮*二甲基辛烯酮*
2-(丁-2-基)-环己酮*
2-己基-环戊-2-烯-1-酮*
2-(1-甲基乙基)-5-甲基环己酮*
2-(2-甲基乙基)-5-甲基环己酮*
3-甲基-环十五酮
4-叔戊基-环己酮
3-氧代-2-戊基-环戊烷-乙酸甲酯**
1-(1,2,3,4,5,6,7,8-八氢-2,3,8,8-四甲基-2-萘基)-乙酮*
3-甲基-5-丙基-环己-2-烯-1-酮*
其中*表示优选酮,**表示更优选的酮。
式Ⅰ化合物分解并且相应的残基重组形成的式Ⅱ的荧光增白香豆素的实例是:
7-(3-甲基-1H-吡唑-1-基)-3-苯基-2H-1-苯并吡喃-2-酮
7-(4-甲基-5-苯基-2H-1,2,3-三唑-2-基)-3-苯基-2H-1-苯并吡喃-2-酮
7-(2H-萘并[1,2-d]三唑-2-基)-3-苯基-2H-1-苯并吡喃-2-酮
3-(1H-吡唑-1-基)-7-(2H-1,2,3-三唑-2-基)-2H-1-苯并吡喃-2-酮
7-二甲基氨基-1-甲基-3-苯基-2(1H)-喹啉酮
7-二乙基氨基-1-乙基-3-苯基-2(1H)-喹啉酮
7-氨基-4-甲基-2H-1-苯并吡喃-2-酮
7-二甲基氨基-4-甲基-2H-1-苯并吡喃-2-酮
7-二乙基氨基-4-甲基-2H-1-苯并吡喃-2-酮
7-羟基-4-甲基-2H-1-苯并吡喃-2-酮
6,7-二羟基-2H-1-苯并吡喃-2-酮
式Ⅰ化合物分解后,相应的残基重组后生成的且有嗅觉性质的式Ⅱ香豆素的实例是:
2H-1-苯并吡喃
3-甲基-苯并吡喃-2-酮
8-(1,1-二甲基乙基)-6-甲基-苯并吡喃酮
4-甲基-7-乙氧基-香豆素
6-甲基-2H-1-苯并吡喃
当然,我们不可能列出式Ⅰ的丙烯酸酯在紫外光或高温条件下分解所得到的所有的具有活性的香豆素、醇、醛、酮。但本领域普通技术人员会清楚地意识到那些能够提供所需的特殊感觉,诸如香味、气味掩蔽、抗菌和/或增白作用的香豆素、醇、醛、酮。
式Ⅰ化合物可被优选用作气味和香味的持久释放剂,也可用作掩盖或稀释难闻气味或提供洗衣剂、织物柔软剂、卫生用品、化妆品(如防晒用品)等本身所没有的味道。该化合物还可进一步被用作上述产品的光亮剂或抗菌剂。光亮剂尤其被广泛用于羊毛、人造纤维和多聚酰胺中。其还可作为调味剂和芳香剂使用,例如加入烟草中。
至于产生上述不同效果所需的用量依赖于式Ⅰ化合物的具体选择,应用该化合物的产品以及所需的特定效果而定。
例如,取决于所选的化合物及其浓度,例如当式Ⅰ化合物单独或以混合物形式,以大约0.001-10%的重量加入到一种洗涤组合物中,在使用该组合物时,产生对特殊感觉有效量的香豆素和(如果需要)有气味的醇或醛或酮。这些新形成的增味剂被用来增加香料的香味。当使用不同的式Ⅰ化合物时,也可以产生抗菌剂或增亮剂。
取决于式Ⅰ化合物的选择和浓度以及添加量,式Ⅰ化合物可单独或以混合物形式加入到烟草制品中,其用量为大约5ppm-50′000ppm,用以提高烟草的香味并掩盖其不希望具有的烟味。这类化合物Ⅰ的一个重要性质是由于该香味剂或增味剂是共价键形成的非挥发性化合物,因此使烟草只有在被点燃的情况下才能发出气味。
在包括烟草的介质中以适宜的、5ppm-50000ppm的量单独或以混合物形式加入化合物Ⅰ,可向烟草的侧向烟(side-stream smoke)中引入某种气味/香味。因此在空气中产生了香味和/或某种气味。取决于式Ⅰ化合物的选择和用量,该新产生的气味或香味可用来增强或掩蔽烟味。
从以上对醇、醛、酮和香豆素所进行的叙述中可以看出,可以利用本发明的前体制备出使用范围很广的已知的增味剂、香味剂或其混合物。可根据香料工业中已知的方法(如W.A.Poucher,Perfumes,Cosmetics,Soaps,2,7th Edition,Chapman and Hall,London 1974),使用本发明的前体生产组合物。也可以使用相同的方式引入荧光增白剂。
化合物Ⅰ可以采用本领域普通技术人员已知的标准方法制备,此外,以下的实例中也概述了一些简便的制备方法,但不应局限于此。
实施例1
(E)-3-(2-羟基-苯基)-2-甲基-丙烯酸乙酯
在350mL甲苯中加入75.0g(乙酯基亚乙基)三苯基膦,将23.2g水杨醛于20℃、冰浴冷却下滴加到上述溶液中,然后在室温下搅拌90分钟。所得反应混合物用甲苯稀释,并用水洗涤至中性。将有机相干燥、过滤、蒸干。所得的黄色油状物用色谱法纯化,得到35.5g无色固体。
NMR(CDCl3)δ7.82(s,1H),7.30-6.85(m,4H),6.6(s,OH),4.35-4.17(q,
2H),2.04(s,3H),1.40-1.28(t,3H)
实施例2
(E)-3-(2-羟基-苯基)-丙烯酸甲酯
根据实例1的步骤,由(三苯基-亚膦基)乙酸甲酯和水杨醛得到(E)-3-(2-羟基-苯基)-2-甲基-丙烯酸甲酯。
实施例3
(E)-3-(2-羟基-苯基)-丙烯酸乙酯
根据实施例1的步骤,由(三苯基亚膦基)乙酸乙酯和水杨醛得到(E)-3-(2-羟基-苯基)-2-甲基丙烯酸甲酯。
实施例4
(E)-3-(2-羟基-苯基)-2-甲基-丙烯酸
将35.3g(E)-3-(2-羟基-苯基)-2-甲基-丙烯酸乙酯加入600ml乙醇中,得到一溶液。将10.66g KOH溶入500mL水后所得溶液加入上述溶液中。回流5小时后,加入5.0g KOH,再回流19小时。待反应混合物冷却后,用乙醚稀释,再分别用浓度为2N的HCl和水洗涤至pH值为4。将得到的有机相干燥、过滤、蒸干。所得无色晶体无需提纯。
NMR(CDCl3)δ7.90(s,1H),7.31-6.83(m,4H),2.07(s,3H)
实施例5
(E)-3-(2-羟基-苯基)-2-甲基-丙烯酸-3,7-二甲基-辛-6-烯酯
将6.0g(E)-3-(2-羟基-苯基)-2-甲基-丙烯酸、5.3g香茅醇、1g对甲苯磺酸加入150mL环己烷中,使用一种水分离器,将该溶液回流6.5小时。待反应混合物冷却后,用己烷稀释,分别用饱和碳酸氢钠和水洗涤至中性。有机相经干燥、过滤、蒸干得到黄色油状物,经色谱法提纯,得到6.45g无色油状物。
NMR(CDCl3)δ7.80(s,1H),7.38-6.83(m,4H),6.4(s,OH),5.09(t,1H),
4.25(t,2H),2.01-1.90(m,5H),1.88-1.08(m,11H),0.93(d,
3H)。
实施例6
(E)-3-(2-羟基-苯基)-2-甲基-丙烯酸苯乙酯
根据与实施例3相同的步骤,由3-(2-羟基-苯基)-2-甲基-丙烯酸、苯乙醇和对甲苯磺酸制得(E)-3-(2-羟基-苯基)-2-甲基-丙烯酸苯乙酯。
实施例7
3-(4-二乙基氨基-2-羟基-苯基)-丁-2-烯酸乙酯
将5.27g乙氧基羰基亚甲基三苯基膦加入10ml甲苯后得到悬浮液,再将2.02g1-(4-二乙基氨基-2-羟基-苯基)-乙烯酮溶液(DE 2844606)在室温下滴加入其中。反应混合物加热回流31小时后,冷却、蒸干溶剂。所得黑色油状物用色谱法纯化得无色油状物。
NMR(CDCl3)δ7.22-7.09(m,1H),6.57-6.42(m,1H),6.32-6.20(m,2H),
5.01(s,1H),4.18-4.01(q,2H),3.42-3.24(q,4H),2.49(s,
3H),1.31-1.08(m,9H).
实施例1-4中的化合物分解得到特殊感觉香豆素,实施例5-6中的化合物分解得到特殊感觉香豆素和醇,实例7中的化合物分解得到增亮香豆素。
实施例8
(E)-3-(2-羟基-5-甲基-苯基)-丙烯酸乙酯
将193.7g3-[5-甲基-2-(四氢吡喃-2-基氧)-苯基]-丙烯酸乙酯(Bunce,R.,Moore,J.,Org.Prep.Proc.,29(3),293(1997))与2g对甲基苯磺酸的2.51乙醇溶液,在室温下搅拌24小时。将反应混合物浓缩后的残余物用乙醚稀释,用饱和碳酸氢钠及盐水洗涤,干燥、蒸干。所得黄色固体经重结晶得到97.7g无色晶体。
NMR(CDCl3)δ8.10-7.93(d,1H),7.27(s,1H),7.10-6.98(d,1H),6.82-
6.70(d,1H),6.69-6.55(d,1H),4.38-4.20(q,2H),2.27(s,
3H),1.42-1.28(t,3H)ppm(E)-3-(2-羟基-苯基)-丙烯酸
将50.9g KOH溶入500mL水,将其在室温下滴加入100.0g3-(2-羟基-苯基)-丙烯酸乙酯的500mL乙醇溶液中。搅拌回流28小时后,将反应混合物浓缩。剩余物用500mL2N的HCl稀释,再用乙醚萃取。有机相分别用2N的HCl和水洗涤、干燥、蒸干。所得固体经重结晶得到44.3g无色晶体。
NMR(DMSO)δ12.2(brs,1H),10.2(brs,1H),7.95-7.75(d,1H),7.65-
7.50(d,1H),7.32-7.15(m,1H),6.99-6.76(m,2H),6.62-
6.45(d,1H)ppm
(E)-3-(2-羟基-苯基)-丙烯酸-癸-9-烯酯
将5.0g3-(2-羟基-苯基)-丙烯酸乙酯、6.1g癸-9-烯-1-醇和1.0g四异丙基原钛酸酯的混合物加热至150℃以除掉生成的乙醇。在该温度下搅拌2.5小时后,将反应混合物冷却,用乙醚稀释,再用盐水洗涤。将有机相干燥后蒸干。所得油状物经Kuqelrohr-蒸馏、结晶和重结晶得到1.69g无色晶体。
NMR(CDCl3)δ8.11-7.96(d,1H),7.55-7.40(d,1H),7.32-7.15(M,
1H),6.99-6.72(m,2H),6.71-6.57(d,1H),5.93-
5.69(m,1H),5.07-4.88(m,2H),4.31-4.15(t,2H),
2.12-1.93(m,2H),1.85-1.55(m,2H),1.54-1.15(m,
10H),ppm
(E)-3-(2-羟基-苯基)-丙烯酸-2-乙基-4-(2,2,3-三甲基-环戊-3-烯基)-丁-2-烯酯
根据相同的反应步骤,由3-(2-羟基-苯基)-丙烯酸乙酯、2-乙基-4-(2,2,3-三甲基-环戊-3-烯-1-基)-丁-2-烯-1-醇和四异丙基原钛酸酯制得3-(2-羟基-苯基)-丙烯酸-2-乙基-4-(2,2,3-三甲基-环戊-3-烯基)-丁-2-烯酯。
(E)-3-(2-羟基-5-甲基-苯基)-丙烯酸-2-乙基-4-(2,2,3-三甲基-环戊-3-烯基)-丁-2-烯酯
根据相同的反应步骤,由3-(2-羟基-5-甲基-苯基)-丙烯酸乙酯、2-乙基-4-(2,2,3-三甲基环戊-3-烯-1-基)-丁-2-烯-1-醇和四异丙基原钛酸酯制得3-(2-羟基-5-甲基-苯基)-丙烯酸-2-乙基-4-(2,2,3-三甲基-环戊-3-烯基)-丁-2-烯酯。
(E)-3-(2-羟基-5-甲基-苯基)-丙烯酸-3-甲基-5-苯基-戊基酯
根据相同的反应步骤,由3-(2-羟基-5-甲基-苯基)-丙烯酸乙酯、3-甲基-5-苯基-戊醇和四异丙基原钛酸酯制得3-(2-羟基-5-甲基-苯基)-丙烯酸-3-甲基-5-苯基-戊酯。
(E)-3-(4-二乙基氨基-2-羟基-苯基)-丁-2-烯酸-癸-9-烯酯
根据相同的反应步骤,由3-(4-二乙基氨基-2-羟基-苯基)-丁-2-烯酸乙酯、癸-9-烯-1-醇和四异丙基原钛酸酯制得3-(4-二乙基氨基-2-羟基-苯基)-丁-2-烯酸-癸-9-烯酯。
(E)-3-(4-二乙基氨基-2-羟基-苯基)-丁-2-烯酸-3-甲基-5-苯基-戊酯
根据相同的反应步骤,由3-(4-二乙基氨基-2-羟基-苯基)-丁-2-烯酸乙酯、3-甲基-5-苯基-戊醇和四异丙基原钛酸酯制得3-(4-二乙基氨基-2-羟基-苯基)-丁-2-烯酸-3-甲基-5-苯基-戊酯。
实施例9
3-[2-(叔丁基-二甲基-硅烷(silanyl)氧基)-苯基]-丙烯酸-叔丁基-二甲基-甲硅烷基酯
在室温下,将10.1g叔丁基二甲基氯硅烷加入5.0g(E)-3-(2-羟基-苯基)-丙烯酸、4.6g咪唑的100mL二甲基甲酰胺溶液中,搅拌过夜,倒入200mL冷水中,并用150mLMTBE萃取3次。将合并的有机相用MgSO4干燥,蒸发至干。所得的油状物在0.08托/120-170℃下干燥以除去过量的叔丁基二甲基氯硅烷,得到11.4g黄色油状的3-[2-叔丁基-二甲基-硅烷氧基)-苯基]-丙烯酸-叔丁基-二甲基-甲硅烷基酯。
NMR(CDCl3)δ7.96(d,1H),7.52(dd,1H),7.23(m,1H),6.94(m,
1H),6.82(dd,1H),6.37(d,1H),1.00(s,9H),0.97(s,
9H),0.32(s,6H),0.22(s,6H)
实施例10
3-[2-(叔丁基-二甲基-硅烷氧基)-苯基]-丙烯酰氯
在0℃冷却的15mLCH2Cl2中加入6.3g3-[2-(叔丁基-二甲基-硅烷氧基)-苯基]-丙烯酸-叔丁基-二甲基-甲硅烷基酯和8滴二甲基甲酰胺,得到一溶液,再向其中滴加2.0mL草酰氯。添加完成后,将反应混合物升至室温,继续搅拌60小时。将反应混合物过滤、蒸干,再导入MTBE中,所得溶液在冷藏箱内冷却过夜,过滤、蒸干得到4.4g3-[2-叔丁基-二甲基-硅烷氧基)-苯基]-丙烯酰氯。
NMR(CDl3)δ8.28(d,1H),7.55(dd,1H),7.35(m,1H),7.01(m,1H),
6.87(dd,1H),6.63(d,1H),1.04(s,9H),0.26(s,6H)
实施例11
3-(2-羟基-苯基)-丙烯酸-3-(3-异丙基-苯基)-丁-1-烯酯
将0.72g事先用己烷冲洗过的NaH(55%的油液)溶于22.5mL四氢呋喃中,并在12分钟内滴加1.67mL叔丁醇。反应混合物在室温下搅拌1.25小时,冷却至-15℃,缓慢加入2.85g3-(3-异丙基-苯基)-丁醛(Florhydral),继续搅拌45分钟,将此冷却的烯醇化的溶液通过聚四氟乙烯套管加入-5℃的4.44g3-[2-(叔丁基-二甲基-硅烷氧基)-苯基]-丙烯酰氯的7.5mL四氢呋喃的冷却溶液中。完成添加后在-5℃下搅拌1小时,将反应混合物用80mL水/40mL盐水的混合液骤冷,再用MTBE萃取。用(水/盐水2∶1洗涤合并的有机相,用MgSO4干燥,再蒸发至干,得到6.65g黄色粘油状3-[2-(叔丁基-二甲基-硅烷氧基)-苯基]-丙烯酸-3-(3-异丙基-苯基)-丁-1-烯酯粗品。
将此油状物6.2g在0℃下加入70mL四氢呋喃中,再缓慢加入13.7mL、浓度为1M的氟化四丁基铵/四氢呋喃溶液。反应混合物在0℃下搅拌1.5小时,倒入200mL水中,再用150mLMTBE萃取3次。用盐水冲洗合并的有机相,用MgSO4干燥,再蒸发至干。所得油状物经色谱法提纯,得到2.64g3-(2-羟基-苯基)-丙烯酸-3-(3-异丙基-苯基)-丁-1-烯酯的黄色油状物。
NMR(CDCl3)δ8.12(d,1H),8.01(d,1H),7.50-6.80(d,10H),6.66和
6.56(d,1H),5.75和5.13(m,1H),4.13(m,CH),
3.53(m,CH),2.89(m,CH),1.42(d,3H),1.25(d,6H)
实施例12
(E)-3-[2-(叔丁基-二甲基-硅烷氧基)-苯基]-丙烯酸
将8.2g(E)-3-(2-羟基-苯基)-丙烯酸、15.2g叔丁基二甲基氯硅烷加入10mL二甲基甲酰胺后,再将11.9g咪唑加入该混合物中,在室温下将其搅拌24小时,待液相形成(aqueous work-up)后,用2.1g溶于四氢呋喃-H2O的LiOH溶液在0℃下皂化0.5小时。混合物在真空条件下浓缩,再用己烷萃取除叔丁基二甲基羟基硅烷(TBDMS-OH)。水层用KHSO4酸化至pH值为4,再以乙酸乙酯萃取。有机相用盐水洗涤、NaSO4干燥后、再蒸发至干。将半固体状残余物悬浮于己烷中,过滤,将滤液蒸干得到7.5g浅黄色油状物,该物在储藏过程中会固化。
NMR(CDCl3)δ8.08(d,1H),7.46(dd,1H),7.18(dt,1H),6.87(t,
1H),6.75(dd,1H),6.31(d,1H),0.93(s,9H),0.13(s,
6H),
实施例13
(E)-3-(2-羟基-苯基)-丙烯酸-1-乙氧基-3-(3-异丙基-苯基)-丁酯
根据P.D.Bartlett和A.A.Frimer在Heterocycles 11,419-435,(1978)中叙述的二步法,将由3-(3-异丙基-苯基)-丁醛得到的(E)-3-[2-(叔丁基-二甲基-硅烷氧基)-苯基]-丙烯酸6.5g和5.5g1-(3-乙氧基-1-甲基-烯丙基)-3-异丙基苯加入25mL甲苯中,加热回流并搅拌16小时。混合物浓缩后用闪蒸色谱纯化得到7.5g为浅黄色油状物的中间体(E)-3-[2-(叔丁基-二甲基-硅烷氧基)-苯基]-丙烯酸-1-乙氧基-3-(3-异丙基-苯基)-丁酯。将其溶于50mL四氢呋喃中,在0℃下用4.7g氟化四丁基铵·3H2O处理。20分钟后,将混合物浓缩,经闪蒸色谱纯化得到2.2g标题酯。
NMR(CDCl3)δ8.12和8.08(d,1H),7.47(dt,1H),7.35(brs,1H),
7.31-7.18(m,2H),7.12-6.98(m,3H),6.92(dt,1H),
6.83(dd,1H),6.68和6.61(d,1H),5.96和5.77(dd,
1H),3.82-3.65(m,1H),3.63-3.40(m,1H),3.05-
2.77(m,2H),2.22-1.95(m,2H),1.38-1.12(m,12H)
实施例14
(E)-3-(2-羟基-苯基)-丙烯酸-3-(4-叔丁基-苯基)-1-乙氧基-丙酯
根据P.D.Bartlett和A.A.Frimer的Heterocycles11,419-435,(1978)的两步法,将由3-(4-叔丁基-苯基)-2-甲基丙醛得到的3.1g(E)-3-[2-(叔丁基-二甲基-硅烷氧基)-苯基]-丙烯酸和3.0g1-叔丁基-4-(3-乙氧基-2-甲基-烯丙基)-苯,和20毫克对甲苯磺酸的25mL甲苯溶液,在0℃下搅拌4小时,再在室温下搅拌14小时。反应混合物在饱和碳酸钠和己烷分配开,有机相用盐水洗涤,Na2SO4干燥、蒸干,得到5.3g粗品中间体(E)-3-[2-(叔丁基-二甲基-硅烷氧基)-苯基]-丙烯酸-3-(4-叔丁基-苯基)-1-乙氧基-丙酯,为淡黄色油状物。在0℃下将其溶于20mL的四氢呋喃中,再用3.2g固体氟化四丁基铵·3H2O处理。30分钟后,将混合物浓缩后,再用闪蒸色谱反复纯化,得到1.2g浅黄色标题酯的油状物(非对映异构体混合物)。
NMR(CDCl3)δ8.17和8.13(d,1H),7.50(ddd,1H),7.36-7.18(m,
4H),7.11(br dd,2H),6.98-6.83(m,2H),6.73和
6.69(d,1H),5.94(t,1H),3.92-3.70(m,1H),3.71-
3.54(m,1H),3.05-2.81(m,1H),2.52-2.34(m,1H),
2.30-2.12(m,1H),1.31(s,9H),1.33-1.20(m,3H),
0.97和0.90(t,3H)
实施例15
将实施例1-14中的前体加入某种洗涤剂中,用其洗涤样品布,将洗涤后的样品布晾干(line dried),在阳光下晒干的样品有很明显的香味,该结果是经经过训练的专门人员(trained panel)测定的。与此相反,未经阳光照射的样品就没有气味。
实施例16
样品布用洗涤剂洗涤,然后将织物柔软剂加入漂洗循环中,在该柔软剂中含有实施例1-14中的一种或多种前体。将该布晾干。在阳光下晒干的样品有很明显的香味,该结果是经过训练的专门人员测定的。相反,未经阳光照射的样品就没有气味。
实施例17
用一种或多种实施例1-14的产品的1%的乙醇溶液处理烟纸,以使每种香味达到5-50000ppm的水平。点燃用该种烟纸包装的香烟,发出香味。
实施例18
一种油/水型广谱(UV-A、UV-B)防晒乳液由下面的配方制得,其含量为0.5%。
A部分:
配方% 化合物 化学名称
2% PARSOLMCX 甲氧基肉桂酸辛酯
3% PARSOL1789 4-4-丁基-4-甲氧基-二苯甲酰基甲烷
12% Cetiol LC 可可-辛酸酯/癸酸酯
4% Dermol185 新戊酸异硬脂酯
0.25% 二甘醇单硬脂酸酯 PEG-2-硬脂酸酯
1% 十六烷醇 十六烷醇
0.25% MPOB/PPOB 甲基-对羟基苯甲酸丙酯
0.1% EDTABD 乙二胺四乙酸钠盐
1% Amphisol DEA(Giv.) 二乙醇胺-十六烷基膦酸酯
B部分:
20% Permulene TR-1(+%) 丙烯酸酯C1-C30烷基丙烯酸酯
50.1% 去离子水 去离子水
5% 丙二醇 1,2-丙二醇
0.8% KOH(10%) 氢氧化钾
在反应器内加热A部分到85℃,在10分钟内缓慢加入B部分,再加入KOH以及0.5%实施例5的产品。然后将所得乳液冷却和脱气。
Claims (18)
1.式Ⅰ所述化合物,
其中
A为苯或萘环,
R1是饱和或不饱和、直链或支链、脂环或芳族C10-C30烃基,该烃基中可以含有杂原子,也可以被离子型取代基取代,
R2取代于2-或3-位上,可以是H、直链或支链C1-C6基团、任选取代的芳香基或任选取代的杂环基,
R3和R4为H、直链或支链的C1-C6烷基或C1-C6烷氧基、取代或稠合杂环基、-OH、-NO2、-NH2、-N(C1-C6烷基)2、-N(羟基烷基)2、-NHCO2CH3或-NH(杂环),
R2、R3、R4可以相同或不同,
X为-OH或NHR6,其中R6为H、饱和或不饱和、直链或支链的C1-C20烃基或任选取代的芳基或杂环基,
丙烯酸酯中的双键为E构型。
2.根据权利要求1所述的化合物,其中R1为饱和或不饱和、直链或支链的C10-C30烃基,其可以含有一个或多个O和/或N和/或C(O)基和/或烷氧基。
3.根据上述权利要求之一所述的化合物,其中R1是饱和或不饱和、直链或支链的C10-C30烃基,该烃基可被式NR5 3 +的离子型取代基取代,其中R5为脂肪酸的残基或具有1至30个碳原子的烷基。
5.根据上述权利要求之一所述的化合物,其中R3和/或R4为含有N和/或O的五元杂环。
6.根据上述权利要求之一所述的化合物,其中R3和/或R4为H、-N(C1-C6烷基)2、-NH2、五元杂环基,其可以被C1-C6的脂肪族或芳香族取代基取代。
7.根据上述权利要求之一所述的化合物,其中R2为H或甲基。
8.根据上述权利要求之一所述的化合物,其中的R1为嗅觉醇R1OH的残基。
9.根据上述权利要求1~7之一所述的化合物,其中的R1为式R1HO的嗅觉醛的烯醇式的残基。
10.根据上述权利要求1~7之一所述的化合物,其中R1为式R1O的嗅觉酮的烯醇式的残基。
11.根据上述权利要求1~7之一所述的化合物,其中的R1为任选取代的烷基、链烯基、具有1-烷氧基、1-芳氧基或1-芳烷氧基的芳烷基。
15.式Ⅰ化合物的应用,其可以用作特殊感觉化合物、抗菌化合物和/或荧光增白剂的前体,
其中
A为苯环或萘环,
R1为H、饱和或不饱和、直链或支链、脂环族或芳族的C1-C30烃基,其可以含有杂原子,也可以被离子型取代基取代,
R2位于2-或3-位,可以为H、直链或支链的C1-C6基团、任选取代的芳基或任选取代的杂环基,
R3和R4为H、直链或支链的C1-C6烷基、C1-C6的烷氧基、取代或稠合杂环基、-OH、-NO2、-NH2、-N(C1-C6烷基)2、-N羟烷基)2、-NHCO2CH3或-NH(杂环),
R2、R3、R4可以相同或不同,
X为-OH或-NHR6,其中的R6为H、饱和或不饱和、直链或支链的C1-C20烃基或任选取代的芳基或杂环基,
丙烯酸酯中的双键为E构型。
16.根据权利要求15的应用,式Ⅰ化合物可用于洗涤产品中。
17.根据权利要求15的应用,式Ⅰ化合物可用于烟草制品中。
18.根据权利要求15的应用,式Ⅰ化合物可用于化妆品和盥洗用品中。
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CN100506782C (zh) * | 2004-02-12 | 2009-07-01 | 吉万奥丹股份有限公司 | 3-(2-烷氧基羰基氧基-苯基)丙烯酸酯及其作为传递嗅觉化合物的前体的用途 |
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- 1999-01-13 SG SG9900082A patent/SG93823A1/en unknown
- 1999-01-19 ES ES99810036T patent/ES2347307T3/es not_active Expired - Lifetime
- 1999-01-19 DE DE69942555T patent/DE69942555D1/de not_active Expired - Lifetime
- 1999-01-26 ZA ZA9900567A patent/ZA99567B/xx unknown
- 1999-02-02 ID IDP990074D patent/ID22095A/id unknown
- 1999-02-02 CN CNB991018478A patent/CN1289460C/zh not_active Expired - Lifetime
- 1999-02-10 BR BRPI9900443-7A patent/BR9900443B1/pt not_active IP Right Cessation
- 1999-02-12 US US09/249,384 patent/US6096918A/en not_active Ceased
- 1999-02-12 AU AU16430/99A patent/AU725999B2/en not_active Expired
- 1999-02-12 JP JP03390699A patent/JP4329885B2/ja not_active Expired - Lifetime
-
2002
- 2002-07-30 US US10/209,628 patent/USRE43006E1/en not_active Expired - Lifetime
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2008
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Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN100390261C (zh) * | 2001-09-11 | 2008-05-28 | 宝洁公司 | 包括光不稳定性香料递送体系的组合物 |
CN1802342B (zh) * | 2003-06-07 | 2010-05-26 | 吉万奥丹股份有限公司 | 改进或涉及有机化合物 |
CN100506782C (zh) * | 2004-02-12 | 2009-07-01 | 吉万奥丹股份有限公司 | 3-(2-烷氧基羰基氧基-苯基)丙烯酸酯及其作为传递嗅觉化合物的前体的用途 |
CN100400497C (zh) * | 2004-12-29 | 2008-07-09 | 浙江海正药业股份有限公司 | 苯丙烯酸苯丙烯酯和苯丙酸苯丙酯类化合物及其制备方法和制备药物的用途 |
Also Published As
Publication number | Publication date |
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AU1643099A (en) | 1999-10-21 |
ID22095A (id) | 1999-09-02 |
ZA99567B (en) | 1999-07-26 |
SG93823A1 (en) | 2003-01-21 |
BR9900443B1 (pt) | 2011-06-28 |
BR9900443A (pt) | 2000-05-02 |
US6096918A (en) | 2000-08-01 |
CN1289460C (zh) | 2006-12-13 |
AU725999B2 (en) | 2000-10-26 |
DE69942555D1 (de) | 2010-08-19 |
JP2000063328A (ja) | 2000-02-29 |
JP2009114194A (ja) | 2009-05-28 |
ES2347307T3 (es) | 2010-10-27 |
JP4329885B2 (ja) | 2009-09-09 |
USRE43006E1 (en) | 2011-12-06 |
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