CN111587284B - 醛香气味剂 - Google Patents
醛香气味剂 Download PDFInfo
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- CN111587284B CN111587284B CN201980007235.4A CN201980007235A CN111587284B CN 111587284 B CN111587284 B CN 111587284B CN 201980007235 A CN201980007235 A CN 201980007235A CN 111587284 B CN111587284 B CN 111587284B
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- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 title abstract 2
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- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims abstract description 7
- 125000003542 3-methylbutan-2-yl group Chemical group [H]C([H])([H])C([H])(*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims abstract description 6
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- MRUAUOIMASANKQ-UHFFFAOYSA-N cocamidopropyl betaine Chemical compound CCCCCCCCCCCC(=O)NCCC[N+](C)(C)CC([O-])=O MRUAUOIMASANKQ-UHFFFAOYSA-N 0.000 description 6
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- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 6
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- UEUXEKPTXMALOB-UHFFFAOYSA-J tetrasodium;2-[2-[bis(carboxylatomethyl)amino]ethyl-(carboxylatomethyl)amino]acetate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]C(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CC([O-])=O UEUXEKPTXMALOB-UHFFFAOYSA-J 0.000 description 5
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- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 4
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- OALYTRUKMRCXNH-QMMMGPOBSA-N gamma-Nonalactone Natural products CCCCC[C@H]1CCC(=O)O1 OALYTRUKMRCXNH-QMMMGPOBSA-N 0.000 description 1
- PHXATPHONSXBIL-JTQLQIEISA-N gamma-Undecalactone Natural products CCCCCCC[C@H]1CCC(=O)O1 PHXATPHONSXBIL-JTQLQIEISA-N 0.000 description 1
- IFYYFLINQYPWGJ-UHFFFAOYSA-N gamma-decalactone Chemical compound CCCCCCC1CCC(=O)O1 IFYYFLINQYPWGJ-UHFFFAOYSA-N 0.000 description 1
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- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 1
- 229940061515 laureth-4 Drugs 0.000 description 1
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- 229930007744 linalool Natural products 0.000 description 1
- UWKAYLJWKGQEPM-UHFFFAOYSA-N linalool acetate Natural products CC(C)=CCCC(C)(C=C)OC(C)=O UWKAYLJWKGQEPM-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
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- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
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- BOPPSUHPZARXTH-UHFFFAOYSA-N ocean propanal Chemical compound O=CC(C)CC1=CC=C2OCOC2=C1 BOPPSUHPZARXTH-UHFFFAOYSA-N 0.000 description 1
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- 239000005056 polyisocyanate Substances 0.000 description 1
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- 238000006116 polymerization reaction Methods 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- LJCNRYVRMXRIQR-OLXYHTOASA-L potassium sodium L-tartrate Chemical compound [Na+].[K+].[O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O LJCNRYVRMXRIQR-OLXYHTOASA-L 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- GWFJURKHPPFFMD-UHFFFAOYSA-N prop-2-enyl 2-(2-methylbutoxy)acetate Chemical compound CCC(C)COCC(=O)OCC=C GWFJURKHPPFFMD-UHFFFAOYSA-N 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
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- 150000003839 salts Chemical class 0.000 description 1
- 239000002884 skin cream Substances 0.000 description 1
- ZLVSYODPTJZFMK-UHFFFAOYSA-M sodium 4-hydroxybenzoate Chemical compound [Na+].OC1=CC=C(C([O-])=O)C=C1 ZLVSYODPTJZFMK-UHFFFAOYSA-M 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000011006 sodium potassium tartrate Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
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- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- ILJSQTXMGCGYMG-UHFFFAOYSA-N triacetic acid Chemical compound CC(=O)CC(=O)CC(O)=O ILJSQTXMGCGYMG-UHFFFAOYSA-N 0.000 description 1
- URAYPUMNDPQOKB-UHFFFAOYSA-N triacetin Chemical compound CC(=O)OCC(OC(C)=O)COC(C)=O URAYPUMNDPQOKB-UHFFFAOYSA-N 0.000 description 1
- 239000001069 triethyl citrate Substances 0.000 description 1
- VMYFZRTXGLUXMZ-UHFFFAOYSA-N triethyl citrate Natural products CCOC(=O)C(O)(C(=O)OCC)C(=O)OCC VMYFZRTXGLUXMZ-UHFFFAOYSA-N 0.000 description 1
- 235000013769 triethyl citrate Nutrition 0.000 description 1
- 150000004043 trisaccharides Chemical class 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 description 1
- FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 description 1
- 235000012141 vanillin Nutrition 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
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- ZFNVDHOSLNRHNN-UHFFFAOYSA-N xi-3-(4-Isopropylphenyl)-2-methylpropanal Chemical compound O=CC(C)CC1=CC=C(C(C)C)C=C1 ZFNVDHOSLNRHNN-UHFFFAOYSA-N 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B9/00—Essential oils; Perfumes
- C11B9/0026—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring
- C11B9/0034—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring the ring containing six carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/20—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms
- C07C47/225—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms containing rings other than six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/10—Systems containing only non-condensed rings with a five-membered ring the ring being unsaturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Wood Science & Technology (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Life Sciences & Earth Sciences (AREA)
- Fats And Perfumes (AREA)
- Cosmetics (AREA)
- Detergent Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Disinfection, Sterilisation Or Deodorisation Of Air (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Abstract
本发明涉及式(I)化合物,
Description
技术领域
本发明涉及香料(日化香精)领域。更具体地,本发明涉及本文如下定义的式(I)化合物,以及其作为加香成分的用途。因此,按照本文所述,本发明包含作为加香组合物或已加香消费品的一部分的本发明化合物。
背景技术
在香料工业中,一直需要提供赋予新的感官香调的化合物。特别地,对于醛香特别感兴趣,该醛香代表山谷百合(lily of the valley)香味的关键器官感受方面(facets)之一。因此,特别需要寻找赋予所述香调的化合物以复原铃兰(muguet)的细腻花香,其即使在最温和的产生精油的提取方法下也不能存留。
本发明提供了以前从未报道过的式(I)的新型香料成分,其可用于带来铃兰香调的一个方面,从而赋予结合了醛香、奶油和香菜(coriander)特征的非常令人感兴趣的感官香调。
据我们所知,在US 20110217257和US 20110117046中描述了作为加香成分的结构类似物,其中报道了赋予花香、铃兰青香香调的3-(4-烷基)环己烷丙醛化合物,而EP1054053公开了3-(4-叔丁基)-1-环己烯-1-基)丙醛,也被称为(来自瑞士Firmenich SA的商标),具有山谷百合香调。所述现有技术化合物具有不同于式(I)化合物的感官特性。
因此,这些现有技术文献均未报道或暗示式(I)化合物的任何感官特性,或所述化合物在香料领域的任何用途。
发明内容
本发明涉及式(I)化合物,其具有作为复杂山谷百合气味的一方面特征的醛香香调,同时具有奶油和香菜香调。
因此,本发明的第一个目的是式(I)化合物的用途,
该化合物为其任何一种立体异构体或它们的混合物的形式,并且其中R代表正丁基或(3-甲基丁烷-2-基)基团。
本发明的第二个目的是一种给予、增强、改善或修饰加香组合物或已加香制品的气味特性的方法,该方法包括向所述组合物或制品中加入有效量的至少一种如上定义的式(I)化合物。
本发明的第三个目的是如上定义的式(I)化合物。
本发明的另一个目的是一种加香组合物,其包含:
i)至少一种如上定义的式(I)化合物;
ii)至少一种从由香料载体和香料基料构成的群组中选出的成分;和
iii)可选地,至少一种香料佐剂。
本发明的最后一个目的是一种已加香消费品,其包含如上定义的至少一种式(I)化合物或组合物。
具体实施方式
令人惊奇的是,现在已经发现,式(I)化合物具有山谷百合气味香调的醛香方面,并结合有奶油和香菜香调。所述式(I)化合物可以用于复原铃兰气味的香料组合物中。
本发明的第一目的是下式的化合物:
该化合物为其任何一种立体异构体或它们的混合物的形式,并且其中R代表正丁基或(3-甲基丁烷-2-基)基团。所述化合物可以用作加香成分,例如赋予带有山谷百合细微特征(aspect)的醛香、香菜和奶油类型的气味香调。
为了清楚起见,通过表述“其任何一种立体异构体或它们的混合物”或类似术语,表示本领域技术人员所理解的正常含义,即本发明化合物可以是纯对映异构体(如果是手性的),对映异构体的混合物(立体异构体的混合物),纯的非对映异构体,非对映异构体的混合物;或它们的混合形式。
根据本发明的上述实施方案中的任何一种,所述化合物(I)是C13-C14化合物。
根据本发明的上述实施方案中的任何一种,R代表正丁基或(3-甲基丁烷-2-基)基团。优选地,R代表正丁基。
作为本发明化合物的具体例子,可以列举作为非限制性例子的3-(4-正丁基-1-环己烯-1-基)丙醛,其特征在于具有作为山谷百合气味香调特征的醛香香调,并具有奶油香调和香菜香调,尤其是香菜叶香调,还具有桔子(mandarin)方面和清新的细微特征(aspect)。所述化合物还具有脂肪和水样的特性,强烈地使人联想到非常著名的成分,(2-甲基-3-[4-(2-(2-甲基-2-丙烷基)苯基]丙醛,瑞士韦尔涅的Givaudan-RoureSA的商标)。该化合物提供的总体感官效果非常浓烈,具有迸发(bloom)效果(扩散)。
作为另一个例子,可以列举3-[4-(1,2-二甲基丙基)-1-环己烯-1-基]丙醛,其具有与上述类似的气味,但浓烈度稍弱。
本发明的化合物非常浓烈。上面列举的所有对比化合物在结构上与本发明的化合物相近,赋予不太令人感兴趣的气味香调,带有金属和/或脂肪香调,并且缺乏辐射性。只有本发明的化合物没有金属和脂肪的香调。
表1:对比化合物及其气味特性
根据本发明的特定实施方案,式(I)化合物可以选自3-(4-正丁基-1-环己烯-1-基)丙醛和3-[4-(1,2-二甲基丙基)-1-环己烯-1-基]丙醛。优选地,式(I)化合物可以是3-(4-正丁基-1-环己烯-1-基)丙醛。
当将本发明化合物的气味与现有技术化合物(3-(4-叔丁基-1-环己烯-1-基)丙醛;来源:瑞士的Firmenich SA)或/>(3-[4-(2-甲基丙基)环己基]丙醛;来源:美国的International Flavors&Fragrances)的气味相比较时,本发明的化合物通过具有奶油和香菜特征香调的更浓烈的醛香并缺乏/>的花香香调和的香茅香调而与它们不同。在US 20110117046中报道的3-(4-正丁基环己基)丙醛不具有本发明化合物的典型的花香香调气味,但是赋予了不希望的脂肪和金属气味。本发明化合物的气味比现有技术化合物新鲜得多。而且,本发明化合物具有迸发作用和扩散/辐射,这是现有技术化合物所不具备的。
所述差异使本发明的化合物和现有技术的化合物各自适合于不同的用途,即赋予不同的感官印象。
如上所述,本发明涉及式(I)化合物作为加香成分的用途。换句话说,它涉及给予、增强、改善或修饰加香组合物或已加香制品或表面的气味特性的方法或工艺,该方法包括向所述组合物或制品中加入有效量的至少一种式(I)化合物,例如传达其典型的香调。应理解,最终享乐效应可能取决于本发明化合物的精确剂量和感官特性,但是本发明化合物的添加将取决于剂量而赋予最终产品以香调、触感或形态等形式的典型触感。
通过“式(I)化合物的用途”,在此还必须理解为含有式(I)化合物并且可有利地用于香料工业的任何组合物的用途。
事实上可有利地用作加香成分的所述组合物也是本发明的目的。
因此,本发明的另一个目的是一种加香组合物,其包含:
i)作为加香成分的至少一种如上定义的本发明化合物;
ii)至少一种从由香料载体和香料基料构成的群组中选出的成分;和
iii)可选地,至少一种香料佐剂。
通过“香料载体”,是指从香料的观点来看实际上是中性,即不会显著改变加香成分的感官特性的材料。所述载体可以是液体或固体。
作为液体载体,可以列举作为非限制性例子的乳化体系,即溶剂和表面活性剂体系,或通常用于香料中的溶剂。香料中通常使用的溶剂的性质和类型的详细描述是无法穷尽的。然而,可以列举作为非限制性例子的溶剂,如丁二醇或丙二醇、甘油、二丙二醇及其单醚、三乙酸1,2,3-丙三酯、戊二酸二甲酯、己二酸二甲酯、乙酸1,3-二乙酰氧基丙-2-基酯、邻苯二甲酸二乙酯、肉豆蔻酸异丙酯、苯甲酸苄酯、苄醇、2-(2-乙氧基乙氧基)-1-乙醇、柠檬酸三乙酯或它们的混合物,它们是最常用的。对于同时包含香料载体和香料基料的组合物,除之前详细说明的,其他合适的香料载体也可以是乙醇,水/乙醇混合物,柠檬烯或其他萜烯,异链烷烃,如以商标公知的那些(来源:Exxon Chemical),或二醇醚和二醇醚酯,如以商标/>公知的那些(来源:Dow Chemical Company),或氢化蓖麻油,如以商标/>RH 40公知的那些(来源:BASF)。
固体载体是指这样一种材料,加香组合物或加香组合物的某些成分可以化学地或物理地与其结合。通常,使用这样的固体载体来稳定组合物,或控制组合物或某些成分的蒸发速率。固体载体是目前在本领域中使用的,并且本领域技术人员知道如何达到期望的效果。然而,作为固体载体的非限定性例子,可以列举吸收树胶或聚合物或无机材料,例如多孔聚合物、环糊精、木基材料、有机或无机凝胶、粘土、石膏、滑石或沸石。
作为固体载体的其他非限制性例子,可以列举包封材料。这种材料的例子可包括成壁材料和增塑材料,例如单糖、二糖或三糖,天然或改性淀粉,水胶体,纤维素衍生物,聚乙酸乙烯酯,聚乙烯醇,蛋白质或果胶,或在参考文献例如H.Scherz,Hydrokolloide:Stabilisatoren,Dickungs-und Geliermittel in Lebensmitteln,Band 2derSchriftenreihe Lebensmittelchemie,Behr's Verlag GmbH&Co.,Hamburg,1996中列举的材料。包封是本领域技术人员熟知的方法,并且可以通过例如使用诸如喷雾干燥、附聚或挤出的技术进行;或由包括凝聚和复合凝聚技术的涂层包封组成。
作为固体载体的非限制性例子,可以特别列举核-壳胶囊,其使用氨基塑料、聚酰胺、聚酯、聚脲或聚氨酯类型的树脂或它们的混合物(所有所述树脂都是本领域技术人员公知的),通过使用聚合、界面聚合、凝聚等技术或这些技术一起(所有所述技术已经在现有技术中描述)引发的相分离方法,并且可选地在聚合物稳定剂或阳离子共聚物的存在下进行。
树脂可以通过醛(例如甲醛、2,2-二甲氧基乙醛、乙二醛、乙醛酸或羟乙醛及它们的混合物)与胺例如脲、苯并胍胺、甘脲基(glycoluryl)、三聚氰胺、羟甲基三聚氰胺、甲基化羟甲基三聚氰胺、胍唑等以及它们的混合物缩聚产生。或者,可以使用预先形成的树脂烷基化(alkylolated)多胺,例如以商标(来源:Cytec Technology Corp.)、Cy />(来源:Cytec Technology Corp.)、/>或/>(来源:BASF)可商购的那些。
其他树脂是通过多元醇如甘油与多异氰酸酯如六亚甲基二异氰酸酯的三聚体、异佛尔酮二异氰酸酯或苯二甲基二异氰酸酯的三聚体或六亚甲基二异氰酸酯的缩二脲、或苯二甲基二异氰酸酯与三羟甲基丙烷的三聚体(以商品名已知,来源:MitsuiChemicals)的缩聚产生的那些,其中苯二甲基二异氰酸酯与三羟甲基丙烷的三聚体和六亚甲基二异氰酸酯的缩二脲。
与通过氨基树脂即三聚氰胺基树脂与醛类缩聚而包封香料有关的一些研究文献包括诸如K.Dietrich等人发表的文章Acta Polymerica,1989,vol.40,pages 243,325和683以及1990,vol.41,page 91。这些文章已经描述了影响根据现有技术方法制备这种核-壳微胶囊的各种参数,这些方法在专利文献中也被进一步详述和示例。Wiggins TeapeGroup Limited的US 4'396'670是后者的相关早期例子。此后,许多其他作者已经丰富了这一领域的文献,这里并不可能涵盖所有发表的进展,但是包封技术的一般知识是非常重要的。更为近期的针对性的出版物也涉及这种微胶囊的合适用途,例如由H.Y.Lee等人的文章Journal of Microencapsulation,2002,vol.19,pages 559-569、国际专利公开WO01/41915或S.等人的文章Chimia,2011,vol.65,pages 177-181代表。
通过“香料基料”,这里指的是包含至少一种加香助成分的组合物。
所述加香助成分不是式(I)。此外,通过“加香助成分”,这里指的是这样一种化合物,其用于加香制剂或组合物中以赋予享乐效果。换句话说,要被认为是加香助成分的此种助成分必须被本领域技术人员公认为能够以主动或令人愉快的方式赋予或改变组合物的气味,而不仅仅是具有气味。
基料中存在的加香助成分的性质和类型在这里不保证更详细的描述,其在任何情况下都是无法穷尽的,本领域技术人员能够根据其常识并根据预期的用途或应用和所需的感官效果对它们进行选择。一般而言,这些加香助成分属于不同的化学分类,如醇类、内酯类、醛类、酮类、酯类、醚类、乙酸酯类、腈类、萜类化合物、含氮或含硫杂环化合物和精油,并且所述加香助成分可以是天然来源的或合成来源的。
特别是可以列举已知具有类似嗅觉香调的的加香助成分,例如:
特别是可以列举通常用于香料制剂中的加香助成分,例如:
-醛香成分:癸醛、十二醛、2-甲基十一醛、10-十一烯醛、辛醛和/或壬烯醛;
-芳香草本成分:桉树油、樟脑、桉油醇、薄荷醇和/或α-蒎烯;
-香脂成分:香豆素、乙基香草醛和/或香草醛;
-柑橘香成分:二氢月桂烯醇、柠檬醛、橙油、乙酸芳樟酯、香茅腈、橙萜烯、柠檬烯、乙酸1-对薄荷烯-8-基酯和/或1,4(8)-对薄荷二烯;
-花香成分:二氢茉莉酮酸甲酯、芳樟醇、香茅醇、苯乙醇、3-(4-叔丁基苯基)-2-甲基丙醛、己基肉桂醛、乙酸苄酯、水杨酸苄酯、四氢-2-异丁基-4-甲基-4(2H)-吡喃醇、β-紫罗兰酮、2-(甲基氨基)苯甲酸甲酯、(E)-3-甲基-4-(2,6,6-三甲基-2-环己烯-1-基)-3-丁烯-2-酮、水杨酸己酯、3,7-二甲基-1,6-壬二烯-3-醇、3-(4-异丙基苯基)-2-甲基丙醛、乙酸三环癸烯酯、香叶醇、对薄荷-1-烯-8-醇、乙酸4-(1,1-二甲基乙基)-1-环己酯、乙酸1,1-二甲基-2-苯基乙酯、4-环己基-2-甲基-2-丁醇、水杨酸戊酯、高顺式二氢茉莉酮酸甲酯、3-甲基-5-苯基-1-戊醇、丙酸三环癸烯酯、乙酸香叶酯、四氢芳樟醇、顺-7-对薄荷醇、(S)-2-(1,1-二甲基丙氧基)丙酸丙酯、2-甲氧基萘、乙酸2,2,2-三氯-1-苯基乙酯、4/3-(4-羟基-4-甲基戊基)-3-环己烯-1-甲醛、戊基肉桂醛、4-苯基-2-丁酮、乙酸异壬酯、乙酸4-(1,1-二甲基乙基)-1-环己酯、异丁酸三环癸烯酯和/或甲基紫罗兰酮异构体的混合物;
-果香成分:γ-十一内酯、4-癸内酯、2-甲基-戊酸乙酯、乙酸己酯、2-甲基丁酸乙酯、γ-壬内酯、庚酸烯丙酯、异丁酸2-苯氧基乙酯、2-甲基-1,3-二氧戊环-2-乙酸乙酯和/或1,4-环己烷二甲酸二乙酯;
-青香成分:2,4-二甲基-3-环己烯-1-甲醛、乙酸2-叔丁基-1-环己酯、乙酸苏合香酯、(2-甲基丁氧基)乙酸烯丙酯、4-甲基-3-癸烯-5-醇、二苯醚、(Z)-3-己烯-1-醇和/或1-(5,5-二甲基-1-环己烯-1-基)-4-戊烯-1-酮;
-麝香成分:1,4-二氧杂-5,17-环十七烷二酮、十五烯内酯、3-甲基-5-环十五碳烯-1-酮、1,3,4,6,7,8-六氢-4,6,6,7,8,8-六甲基环戊并[G]-2-苯并吡喃、丙酸(1S,1'R)-2-[1-(3',3'-二甲基-1'-环己基)乙氧基]-2-甲基丙酯、十五内酯和/或丙酸(1S,1'R)-[1-(3',3'-二甲基-1'-环己基)乙氧基羰基]甲酯;
-木香成分:1-(八氢-2,3,8,8-四甲基-2-萘基)-1-乙酮、广藿香油、广藿香油的萜烯馏分、(1'R,E)-2-乙基-4-(2',2',3'-三甲基-3'-环戊烯-1'-基)-2-丁烯-1-醇、2-乙基-4-(2,2,3-三甲基-3-环戊烯-1-基)-2-丁烯-1-醇、甲基柏木酮、5-(2,2,3-三甲基-3-环戊烯基)-3-甲基戊-2-醇、1-(2,3,8,8-四甲基-1,2,3,4,6,7,8,8a-八氢萘-2-基)乙-1-酮和/或乙酸异冰片酯;
-其他成分(例如琥珀香、粉香、辣或水样):十二氢-3a,6,6,9a-四甲基萘并[2,1-b]呋喃及其任何立体异构体、胡椒醛、茴香醛、丁子香酚、肉桂醛、丁香油、3-(1,3-苯并间二氧杂环戊烯-5-基)-2-甲基丙醛和/或3-(3-异丙基-1-苯基)丁醛。
根据本发明的香料基料可以不限于上述加香助成分,并且许多其他的这些助成分在任何情况下都在参考文献中列出,例如S.Arctander,Perfume and Flavor Chemicals,1969,Montclair,New Jersey,USA或其更新的版本,或其他相似性质的著作,以及香料业领域大量的专利文献。还应当理解,所述助成分也可以是已知以受控方式释放各种类型的加香化合物的化合物。
通过“香料佐剂”,这里我们指能够赋予附加的额外益处如颜色、特定的耐光性、化学稳定性等的成分。在加香组合物中通常使用的佐剂的性质和类型的详细描述是无法穷尽的,但是必须提及的是所述成分是本领域技术人员熟知的。作为具体的非限制性例子可以列举如下:粘性剂(例如表面活性剂、增稠剂、胶凝和/或流变改性剂),稳定剂(例如防腐剂、抗氧化剂、热/光或缓冲剂或螯合剂,例如BHT),着色剂(例如染料和/或颜料),防腐剂(例如抗菌剂或抗微生物剂或抗真菌剂或抗刺激剂),研磨剂,皮肤清凉剂,固定剂,驱虫剂,软膏,维生素及它们的混合物。
可以理解的是,本领域技术人员仅通过应用本领域的标准知识以及通过试错法来混合加香组合物的上述组分,完全能够设计用于期望效果的最佳配方。
除了包含至少一种式(I)化合物、至少一种香料载体、至少一种香料基料和可选的至少一种香料佐剂的加香组合物之外,由至少一种式(I)化合物和至少一种香料载体组成的加香组合物也构成本发明的一种特定实施方案。
根据一个特定的实施方案,上述组合物包含多于一种的式(I)化合物,其能够使调香师制备具有本发明不同化合物的气味调子的调和物或香料,从而为创造目的创造新的结构单元。
为了清楚起见,还应当理解,直接由化学合成(其中本发明的物质组合物作为起始材料、中间体或终产物)得到的任何混合物,例如没有充分纯化的反应介质,不能被认为是根据本发明的加香组合物,只要所述混合物不以合适的用于香料的形式提供本发明的化合物。因此,除非另有说明,否则未纯化的反应混合物通常被排除在本发明之外。
本发明的化合物也可以有利地用于现代香料(即精细香料或功能性香料)的所有领域中,以主动地赋予或改变添加有所述式(I)化合物的消费品的气味。因此,本发明的另一个目的在于一种已加香消费品,该消费品包含至少一种如上定义的式(I)化合物作为加香成分。
本发明的化合物可以原样加入或作为本发明加香组合物的一部分加入。
为了清楚起见,“已加香消费品”是指一种消费品,其向施覆它的表面或空间(例如皮肤、头发、织物或家庭表面)递送至少一种令人愉快的加香效果。换句话说,根据本发明的已加香消费品是这样一种已加香消费品,其包含功能性配方以及对应于期望的消费品的可选的附加益处剂,以及嗅觉有效量的至少一种本发明化合物。为了清楚起见,所述已加香消费品是不可食用的产品。
已加香消费品的成分的性质和类型不保证在这里更详细的描述,在任何情况下都是无法穷尽的,技术人员能够基于其常识并根据所述产品的特性及期望的效果对它们进行选择。
合适的已加香消费品的非限制性例子包括香水,例如精细香水、涂抹式香水(splash)或淡香精(eau de perfume)、古龙水或剃须水或须后水;织物护理产品,例如液体或固体洗涤剂、织物柔软剂、液体或固体香味增强剂、织物清新剂、熨烫水、纸张、漂白剂、地毯清洁剂、窗帘护理产品;身体护理产品,例如头发护理产品(例如洗发剂、着色剂或发胶、颜色护理产品、头发定型产品、牙齿护理产品),消毒剂,私处护理产品;化妆品制剂(例如护肤霜或护肤液、雪花膏、体香剂(除臭剂)或止汗剂(例如喷雾或走珠),脱毛剂,晒黑剂、防晒或晒后产品,指甲产品,皮肤清洁产品,化妆品);或皮肤护理产品(例如香皂、沐浴摩丝、浴油或浴液,或卫生用品或足部/手部护理产品);空气护理产品,例如空气清新剂或“即用型”粉末空气清新剂,其可用于家庭空间(房间、冰箱、橱柜、鞋或车)和/或公共空间(大厅、旅馆、商场等);或家庭护理产品,例如去霉剂、家具护理剂、擦拭物、餐具洗涤剂或硬表面(例如地板、浴室、洁具或窗户)洗涤剂;皮革护理产品;汽车护理产品,如抛光剂、蜡或塑料清洁剂。
上述已加香消费品中的一些可以代表本发明化合物的侵蚀性介质,因此可能需要保护其免于过早分解,例如通过包封或通过将其化学结合到另一种在受到合适的外部刺激,如酶、光、热或pH变化时适于释放本发明成分的化学物质。
根据本发明的化合物可以掺入到各种上述产品或组合物中的比例在很宽的数值范围内变化。当根据本发明的化合物与本领域通常使用的加香助成分、溶剂或添加剂混合时,这些值取决于待加香制品的性质和所需感官效果以及给定基料中的助成分的性质。
例如,在加香组合物的情况下,基于其所掺入到的组合物的重量,本发明化合物的典型浓度为0.001重量%~10重量%,或甚至更多。在已加香消费品的情况下,基于其所掺入到的消费品的总重量,本发明化合物的典型浓度为0.001重量%~1重量%,或甚至更多。
式(I)化合物可根据下文所述的方法制备。
实施例
现在将通过以下实施例进一步详细描述本发明,其中缩写具有本领域的通常含义,温度以摄氏度(℃)表示;使用在(400MHz(1H)和100MHz(13C)下操作的Bruker AdvanceII Ultrashield 400plus,或在(500MHz(1H)和125MHz(13C)下操作的Bruker Advance III500plus,或在(600MHz(1H)和150MHz(13C)下操作的Bruker Advance III 600冷冻探针获得NMR光谱。光谱做内部参考,化学位移δ相对于TMS 0.0ppm以ppm表示,偶合常数J以Hz表示。
实施例1
3-(4-正丁基环己-1-烯-1-基)丙醛(式(I)化合物)的合成
a)8-丁基-1-氧杂螺[4.5]癸-2-酮的制备
将4-正丁基环己醇(175g;1120mmol)放入到配备有2个加料漏斗、温度计和Dean-Stark装置的1.5升4颈烧瓶中。将该醇在N2下在155℃下加热,同时但分别地将丙烯酸正丁酯(85g;660mmol)和过氧化二叔丁基(39.3g;264mmol)加入到反应物中。内部温度最初为158℃,但随着添加过程的进行逐渐降低,因此将浴温缓慢升至165℃,以恢复155℃的内部温度。在此过程中,会蒸馏出液体(叔丁醇)(蒸气温度=79~81℃)。加料历时6小时,收集到39ml叔丁醇。将反应物冷却至50℃。加入MTBE(200ml),然后加入30%的NaOH水溶液(将50g的NaOH溶于110ml的H2O)。将混合物搅拌30分钟,然后加入水(200ml)和更多的MTBE(200ml)。将混合物冷却至室温,并转移至2升的分液漏斗中。加入乙醚(500ml)和水(400ml),并将混合物剧烈摇动。分离各相。用乙醚(500ml)再萃取水相。用水(300ml)处理各有机相。用硫酸钠干燥有机相(含有过量的4-正丁基环己醇),过滤并浓缩并蒸馏(球对球;90℃/1mbar),得到61g(390mmol)回收的4-正丁基环己醇。
将水相(含有羟基羧酸的钠盐)用50%的H2SO4水溶液(400ml,使酸的盐质子化,然后形成内酯)进行酸化,并用乙醚(2×750ml)萃取。每个有机相用水(2×1升)和饱和NaHCO3水溶液洗涤。合并的有机部分经硫酸钠干燥。粗混合物的GC显示11%的起始原料和84%的产物。大部分原料通过球对球蒸馏(80~105℃/0.028mbar)蒸馏掉。在130℃/0.028mbar下蒸馏8-丁基-1-氧杂螺[4.5]癸-2-酮,得到两种馏分:
馏分1:49.21g;通过GC,纯度为100%;39:61的非对映异构体混合物
馏分2:1.87g;通过GC,纯度为89%;15:85的非对映异构体混合物
总收率:242mmol;37%
1H-NMR:δ0.89(t J 7Hz,3H,);0.98-1.08(m,1H);1.19-1.39(m,8H);1.48(m,1H);1.60-1.91(m,5H);1.89(t,J 7Hz,0.8H);2.057(t,J 7Hz,1.2H);2.58(m,2H)ppm.
13C-NMR:δ14.08(q);14.11(q);22.89(t);22.94(t);28.63(t);28.66(t);29.17(t);.29.37(t);29.41(t);30.60(t);34.14(t);35.64(t);35.94(t);36.10(d);36.30(t);36.40(d);36.87(t);85.94(s);87.29(s);176.71(s);176.93(s)ppm.
b)3-(4-丁基环己-1-烯-1-基)丙酸丁酯的制备
在配有短Vigreux色谱柱、迪安-斯塔克分水器和冷凝器的500ml烧瓶中,将8-丁基-1-氧杂螺[4.5]癸-2-酮(50.9g;242mmol)和1-丁醇(89.7g;1210mmol)混合。加入浓硫酸(1.19g;12mmol),并将该溶液在150℃的油浴中加热9小时。蒸发出1-丁醇,残余物用正戊烷(500ml)稀释。将该溶液用NaHCO3饱和水溶液和盐水(各300ml)洗涤。用正戊烷(300ml)萃取水相。合并的萃取物用硫酸钠干燥并过滤。通过球对球蒸馏(132~160℃/0.046mbar)纯化产物。
馏分1:4.46g;通过GC,95%
馏分2:56.42g;通过GC,95%
馏分3:1.9g;通过GC,71%
总收率:222mmol;92%
1H-NMR:δ0.89(t,J 7Hz,3H);0.93(t,J 7.5Hz,3H);1.14-1.32(m,7H);1.34-1.47(m,3H);1.55-1.64(m,3H);1.71-1.77(m,1H);1.88-2.11(m,3H);2.23-2.28(m,2H);2.38-2.43(m,2H);4.07(d,J 7Hz,2H);5.38(m,1H)ppm.
13C-NMR:δ13.73(q);14.15(q);19.17(t);22.98(t);28.37(t);29.27(t);29.28(t);30.74(t);32.05(t);32.73(t);32.97(t);33.39(d);36.18(t);64.16(t);121.15(d);135.99(s);173.72(s)ppm.
c)3-(4-丁基环己-1-烯-1-基)丙醛的制备
在-70℃和N2下(用超过1小时30分)将氢化二异丁基铝(1M的二氯甲烷溶液,241ml;241mmol)滴加到8-丁基-1-氧杂螺[4.5]癸-2-酮(56.42g;95%;201mmol)的无水二氯甲烷(500ml)溶液中。将反应物在-70℃下进一步搅拌2小时30分,然后通过缓慢加入10%的酒石酸Na/K(罗谢尔盐;700g)的水溶液来淬灭。在此阶段需要非常有效的搅拌。将反应物温热至室温并搅拌过夜。分离各相。用二氯甲烷萃取水相。每个有机相用盐水洗涤。合并的萃取物经硫酸钠干燥并过滤。产物通过硅胶柱色谱法纯化(洗脱剂:庚烷/乙酸乙酯15:1至10:1),然后进行球对球蒸馏(80℃/0.04mbar)。
收率:30g(154mmol);77%
1H-NMR:δ0.89(t,J 7Hz,3H);1.15-1.33(m,7H);1.39-1.48(m,1H);1.56-1.64(m,1H);1.72-1.78(m,1H);1.88-2.12(m,3H);2.28(m,2H);2.49-2.54(m,2H);5.39(m,1H);9.76(t,J 1.9Hz,1H)ppm.
13C-NMR:δ14.14(q);22.96(t);23.23(t);28.58(t);29.25(t);29.86(t);32.02(t);33.38(d);36.14(t);41.92(t);121.54(d);135.60(s);202.78(d)ppm.
实施例2
3-(4-(仲丁基)环己-1-烯-1-基)丙醛(对比化合物)的合成
a)1-(2-(1,3-二氧戊环-2-基)乙基)-4-(仲丁基)环己-1-醇的制备
将2-(2-溴乙基-1,3-二氧戊环)(18.0g,100mmol)的THF溶液缓慢滴加到Mg(2.7g,112mmol)的THF(100mL)的搅拌悬浮液中。用MgBr2(约100mg)和/或一些碘晶体来活化Mg。一旦放热,就缓慢地逐滴加入溴化物,并使温度升至50~60℃,然后冷却至30℃。然后缓慢滴加4-(仲丁基)环己-1-酮(100mmol)的THF(20mL)溶液。添加期间的温度<35℃。将该溶液在环境温度下再搅拌4小时,然后倒入饱和氯化铵和冰(1:1,200mL)的搅拌混合物中,用EtOAc(2×100mL)再次萃取,用饱和碳酸氢钠(100mL),然后用盐水(100mL)洗涤,经MgSO4干燥,过滤并真空除去溶剂。粗醇为顺式和反式异构体的混合物,无需进一步纯化即可直接用于下一步。
b)2-(2-(4-仲丁基)环己-1-烯-1-基)乙基)-1,3-二氧戊环的制备
将POCl3(4.4g,28.5mmol)缓慢滴加到步骤a)中获得的醇(4.8g,19mmol)在冷却至0℃的吡啶(25mL)中的搅拌溶液中。将悬浮液在0℃下搅拌30分钟,然后加热至环境温度,并再搅拌1小时。然后将悬浮液倒入到冰/水中,用EtOAc(2×100mL)萃取,用饱和碳酸氢钠洗涤直至中性,然后用10%的H2SO4、盐水洗涤,经MgSO4干燥,过滤并真空除去溶剂。粗二氧戊环通过球对球蒸馏(Kügelrohr)进一步纯化,得到纯的二氧戊环3.5g。
1H(400MHz):δ0.78-0.90(m,6H),1.06-1.31(m,3H),1.32-1.49(m,2H),1.64-1.80(m,4H),1.88-2.09(m,4H),3.81-3.90(m,2H),3.91-4.01(m,2H),4.86(t,J 4.9,1H),5.42(bs,1H)ppm.
13C(100MHz):δ11.7,11.8,15.4,15.8(q),25.5,26.4,26.7,27.2,27.6,29.2,29.3,29.6,32.2,32.3(t),38.0,38.3,38.8,39.0(d),64.9(t),104.5(d),121.0,121.1(d),136.8(s)ppm.
c)3-(4-(仲丁基)环己-1-烯-1-基)丙醛的制备
将步骤b)中获得的二氧戊环(3.4g,14.4mmol)溶于丙酮(45mL)和水(15mL)中,并加入浓HCl(0.5mL),然后将混合物加热回流15小时。然后将混合物冷却,用Et2O(100mL)稀释,水相用Et2O(100mL)再次萃取。然后将合并的有机萃取物用饱和碳酸氢钠(2×50mL)、盐水(50mL)洗涤,用MgSO4干燥,过滤并真空除去溶剂,得到粗醛。通过球对球蒸馏进一步纯化,得到期望的醛2.5g。
1H(400MHz):δ0.83(t,J 6.4,3/2H),0.86(t,J 7.2,3/2H),1.09-1.32(m,4H),1.33-1-47(m,3H),1.66-1.82(m,3H),1.88-2.02(m,3H),2.28(t,J 7.4,2H),2.49-2.54(m,2H),5.41(bs,1H),9.76(t,J 2.0,1H)ppm.
13C(100MHz):δ11.7,11.8,15.4,15.8(q),25.4,26.4,26.7,27.0,27.6,29.329.4,29.5,29.8(t),37.9,38.2,38.7,38.9(d),41.9(t),121.9,122.0(d),135.6(s),202.8(d)ppm.
实施例3
3-[4-(1,2-二甲基丙基)-1-环己烯-1-基]丙醛(式(I)化合物)的合成
根据实施例2中报道的实验部分,通过在第一步中用4-(3-甲基丁烷-2-基)环己-1-酮代替4-(仲丁基)环己-1酮来制备3-[4-(1,2-二甲基丙基)-1-环己烯-1-基]丙醛。
2-(2-(4-(3-甲基丁烷-2-基)环己-1-烯-1-基)乙基)-1,3-二氧戊环
1H(400MHz):δ0.72-0.81(m,6H),0.88(d,J 2.6,3/2H),0.91(d,J 2.6,3/2H),1.00-1.31(m,3H)1.38-1.53(m,2H),1.62-1.83(m,5H),1.90-2.10(m,4H),3.82-3.87(m,2H),3.94-3.99(m,2H),4.86(t,J 4.9,1H),5.41(bs,1H)ppm.
13C(100MHz):δ11.0,11.3,17.4,17.8,21.8,21.9(q),25.8,27.9,28.1(t),28.8,29.0(d),29.1,29.2,30.731.8,32.2(t),36.236.4,43.1,43.5(d),64.9(t),104.5,121.0(d),136.7,136.8(s)ppm.
3-(4-(3-甲基丁烷-2-基)环己-1-烯-1-基)丙醛
1H(400MHz):δ0.73-0.81(m,6H),0.88(d,J 2.2,3/2H),0.90(d,J 2.2,3/2H),1.02-1.32(m,3H),1.38-1.53(m,1H),1.62-1.84(m,3H),1.88-2.06(m,3H),2.28(t,J 7.4,2H),2.49-2.55(m,2H),5.41(bs,1H),9.76(t,J 1.9,1H)ppm.
13C(100MHz):δ11.0,11.3,17.4,17.8,21.7,21.8(q),25.7,27.8,28.1(t),28.8,28.9(d),29.2,29.3,29.7,30.6(t),36.1,36.3(d),41.9(t),43.0,43.4(d),121.9(d),135.5,135.6(s),202.8(d)ppm.
实施例4
3-(4-正丙基环己-1-烯-1-基)丙醛(对比化合物)的合成
根据实施例2中报道的实验部分,通过在第一步中用4-丙基环己-1-酮代替4-(仲丁基)环己-1-酮来制备3-(4-丙基环己-1-烯-1-基)丙醛。
2-(2-(4-丙基环己-1-烯-1-基)乙基)-1,3-二氧戊环
以81%的收率获得2-(2-(4-丙基环己基-1-烯-1-基)乙基)-1,3-二氧戊环。
IR:2954,2910,2872,1465,1450,1407,1378,1360,1130,1035,963,940,916,891,807,737.
1H-NMR:δ0.90(t,J=7.2,3H);1.16-1.26(m,3H);1.30-1.36(m,2H);1.44-1.50(m,1H);1.57-1.63(m,1H);1.72-1.77(m,3H);1.90-2.0(m,2H);2.0-2.09(m,3H);3.83-3.87(m,2H);3.95-3.99(m,2H);4.86(t,J=4.7,1H);5.40(brs,1H)ppm.
13C-NMR(100MHz):δ14.4(q);20.1(t),28.5(t);29.4(t);31.9(t);32.0(t);32.2(t);33.2(d);38.8(t);64.9(2t);104.5(d);120.6(d);136.8(s)ppm.
3-(4-丙基环己-1-烯-1-基)丙醛
以74%的收率获得3-(4-正丙基环己-1-烯-1-基)丙醛。
IR:2955,2911,2872,2833,2715,1725,1464,1454,1437,1411,1388,1378,1053,916,804,737.
1H(400MHz):δ0.89(t,J=7.3,3H);1.15-1-27(m,3H);1.33(brhex,J=7.3,2H);1.42-1-50(m,1H);1.56-1.65(m,1H);1.72-1.77(m,1H);1.91(brd,J=17,1H);1.95-2.03(m,1H);2.08(brd,J=17,1H);2.28(t,J=7.5,2H);2.50-2.54(m,2H);5.39(brs,1H);9.76(t,J=1.9,1H)ppm.
13C(100MHz):δ14.3(q);20.1(t);28.6(t);29.2(t);29.8(t);31.9(t),33.1(d),38.7(t);41.9(t);121.5(d);135.6(s),202.8(d)ppm.
实施例5
2-甲基-3-(4-丙基环己-1-烯-1-基)丙醛(对比化合物)的合成
根据实施例2中报道的实验部分,通过在第一步中用4-丙基环己-1-酮代替4-(仲丁基)环己-1-酮,并用2-(1-溴丙烷-2-基)-1,3-二氧戊环(根据JP 2016084325制备)代替2-(2-溴乙基-1,3-二氧戊环来制备2-甲基-3-(4-丙基环己-1-烯-1-基)丙醛。
2-(1-(4-丙基环己-1-烯-1-基)丙-2-基)-1,3-二氧戊环
以76%的收率获得2-(1-(4-丙基环己-1-烯-1-基)丙-2-基)-1,3-二氧戊环,其为立体异构体的1:1混合物的形式。
IR:2956,2910,2872,1456,1436,1397,1376,1157,1133,1108,1080,1059,1039,997,966,940,915,800.
1H-NMR:δ0.85(d,J=6.8,3H);0.89(t,J=7.3,3H);1.15-1.25(m,3H);1.33(hept,J=7.1,2H);1.41-1.52(m,1H);1.57-1.65(m,1H);1.71-1.80(m,2H);1.84-2.00(m,3H);2.08(brd,J=16,1H);2.15-2.23(m,1H),3.84-3.96(m,4H);4.69(d,J=4.1,0.5H);4.70(d,J=3.9,0.5H);5.39(brs,1H).
13C-NMR(100MHz):δ13.3,13.1(q);14.4,14.4(q);20.1,20.1(t);28.4,28.0(t);29.4,29.4(t);32.1,32.2(t);33.1,33.3(d);34.7,34.9(d);40.0,39.6(t);38.9,38.7(t);65.1(2t);107.5,107.4(d);122.5,122.5(d);135.3,135.3(s)ppm.
2-甲基-3-(4-丙基环己-1-烯-1-基)丙醛
以75%的收率获得2-甲基-3-(4-丙基环己-1-烯-1-基)丙醛二氧戊环,其为非对映异构体的1:1混合物的形式。
IR:2956,2911,2872,2835,2706,1726,1455,1435,1394,1376,1139,916,795.
1H(400MHz):δ0.89(t,J=7.3,3H);1.04(d,J=7.1,3H);1.15-1.25(m,2H);1.33(hex,J=7.4,2H);1.42-1.51(m,1H);1.54-1.65(m,2H);1.72-1.77(m,1H);1.86-2.01(m,3H);2.09(brd,J=17,1H);2.34-2.40(m,1H);2.47-2.54(m,1H);5.42(brs,1H);9.60(d,J=2.6,1H)ppm.
13C(100MHz):δ13.2,13.4(q);14.4(q),20.1(t);28.3,28.4(t);29.1,29.2(t);32.1,32.0(t),33.0,33.(d);38.6,38.7(t);38.9,39.0(t),44.3,44.4(d),123.5,123.6(d);134.0,134.1(s),205.4(d)ppm.
实施例6
3-(4-(仲丁基)环己-1-烯-1-基)-2甲基丙醛(对比化合物)的合成
根据实施例2中报道的实验部分,通过在第一步中用2-(1-溴丙烷-2-基)-1,3-二氧戊环(根据JP 2016084325制备)代替2-(2-溴乙基-1,3-二氧戊环来制备3-(4-(仲丁基)环己-1-烯-1-基)-2甲基丙醛。
2-(1-(4-仲丁基)环己-1-烯-1-基)丙烷-2-基)-1,3-二氧戊环
以50%的收率获得2-(1-(4-仲丁基)环己-1-烯-1-基)丙烷-2-基)-1,3-二氧戊环,其为非对映异构体的1:1:1:1混合物的形式。
IR:2959,2914,2874,2838,1460,1436,1397,1377,1218,1157,1136,1108,1081,1057,1039,998,941,911,847,801,722.
1H(400MHz):δ0.81-0.89(m,9H);1.08-1.30(m,3H);1.35-1.45(m,2H);1.65-1.83(m,3H);1.85-2.00(m,4H);2.15-2.23(brt,J=14,1H);3.82-3.89(m,2H);3.91-3.98(m,2H);4.69(d,J=4.0,0.5H);4.71(d,J=3.9,0.5H);5.41(brs,1H)ppm.
13C(100MHz):δ11.8,11.7(q);13.4,13.1(q);15.8,15.8(q);25.6,25.5(t);26.4,26.4,26.7,26.7(t);27.8,27.7,28.9,28.8(t);29.1,29.0,29.6,29.6(t);34.9,34.6(d);38.1,38.1,38.4,38.3(d);38.8,38.7,39.1,39.0(d);40.0,39.5(t);65.1(2t);107.5,107.3(d);123.0,122.9(d);135.4,135.3,(s)ppm.
3-(4-(仲丁基)环己-1-烯-1-基)-2甲基丙醛
以81%的收率获得3-(4-(仲丁基)环己基-1-烯-1-基)-2甲基丙醛,其为立体异构体的1:1:1:1混合物的形式。
IR:2960,2916,2874,2836,2707,1726,1455,1435,1393,1377,1145,912,797.
1H(400MHz):δ0.81-0.89(m,6H);1.04(d,J=6.8,3H);1.09-1.32(m,4H);1.34-1.46(m,2H);1.66-1.83(m,2H);1.87-2.02(m,3H);2.33-2.40(m,1H);2.46-2.54(m,1H);5.44(brs,1H);9.61(d,J=2.5,1H)ppm.
13C(100MHz):δ11.7,11.8(q);13.2,13.4(q);15.4,15.8(q),25.3,25.4,26.4,26.7(t);27.0,27.1,27.6,27.7(t);29.1,29.2(t);29.5,29.6(t);37.9,38.0,38.2,38.2(d);38.7,38.7,38.9,38.9(d);39.8,38.9(t);44.3,44.4(d);123.9,124.0,124.1,124.1(d),134.0,134.0(s);205.4,205.4(d)ppm.
实施例7
3-(4-正丁基环己-1-烯-1-基)-2-甲基丙醛(对比化合物)的合成
将55%甲醛(Formcel,0.9g;16.5mmol)、40%二甲胺水溶液(0.15g;1.33mmol)和丙酸(0.4g;5.4mmol)在N2下在90℃下加热。加入实施例1中获得的3-(4-丁基环己-1-烯-1-基)丙醛(2g;10.3mmol)。10分钟后,将反应物冷却至室温,用MTBE稀释。将反应物用饱和NH4Cl水溶液、10%的柠檬酸水溶液、水和盐水洗涤。每个水相用MTBE萃取。合并的萃取物用硫酸钠干燥。残余物通过球对球蒸馏(100℃/0.1mbar)纯化,得到化合物,将其溶于乙醇(10ml)中,并在环境压力和温度下,在5%钯碳(50mg)存在下氢化。产物通过硅胶柱色谱纯化(洗脱液:庚烷/乙酸乙酯99:1),然后进行球对球蒸馏(90℃/0.1mbar)。
收率:0.44g(98%纯;2.1mmol;20%)。它是非对映异构体的1:1混合物。
1H-NMR:δ0.89(t;3H,J 7Hz);1.04(dd,J1 1.2Hz;J2=7Hz,3H);1.15-1.32(m,8H);1.44(m,1H);1.62(m,1H);1.75(m,1H);1.85-2.01(m,2H);2.09(m,1H);2.37(m,1H);2.50(m,1H);5.42(m,1H);9.61(t,J 2.2Hz,1H)ppm.
13C-NMR:δ13.20(q);13.40(q);14.14(q);22.97(t);28.29(t);28.36(t);29.18(t);29.23(t);29.25(t);32.07(t);32.12(t);33.30(d);33.37(d);36.06(t);36.11(t);38.94(t);38.97(t);44.34(d);44.41(d);123.59(d);123.64(d);134.04(s);134.06(s);205.36(d);205.37(d)ppm.
实施例8
3-(4-正丁基环己-1-烯-1-基)丁醛(对比化合物)的合成
a)8-丁基-4-甲基-1-氧杂螺[4.5]癸-2-酮的制备
使用以下化合物和用量修改用于制备8-丁基-1-氧杂螺[4.5]癸-2-酮的方法(参见实施例1a)):
4-正丁基环己醇(46.78g;300mmol);巴豆酸正丁酯(24.13g;166mmol);过氧化二叔丁基(9.93g;67mmol)。产物通过硅胶柱色谱纯化(洗脱液:庚烷/乙酸乙酯5:1至3:1),然后进行球对球蒸馏(100℃/0.015mbar)。
收率:10.92g(49mmol;29%)。它是4种非对映异构体的混合物。
1H-NMR:δ0.89(m,3H);1.046(m,3H);1.19-1.42(m,9H);1.54-1.89(m,6H);2.14-2.44(m,2H);2.85-2.61(m,1H)ppm.
13C-NMR:δ14.10(q);14.11(q);14.33(q);15.44(q);22.89(t);22.93(t);27.98(t);28.24(t);28.88(t);29.04(t);29.16(t);29.52(t);29.57(t);30.48(t);34.25(t);34.35(t);34.83(d);35.60(d);36.09(t);36.46(t);36.62(t);36.83(d);37.36(t);39.75(d);88.10(s);88.54(s);176.14(s);176.29(s)ppm.
b)3-(4-丁基环己-1-烯-1-基)丁酸丁酯的制备
使用以下化合物和用量修改用于制备3-(4-丁基环己-1-烯-1-基)丙酸酯的方法(参见实施例1b)):
8-丁基-4-甲基-1-氧杂螺[4.5]癸-2-酮(10.54g;47mmol);1-丁醇(17.42g;235mmol);浓硫酸(0.23g;2.35mmol)。通过球对球蒸馏(120~160℃/0.025mbar)纯化产物。
收率:12.91g(46mmol;98%)。它是2种非对映异构体的混合物。
1H-NMR:δ0.89(m,3H);0.93(t,J 7.4Hz,3H);1.029(dd,J1 Hz;J2=6.8Hz,3H);1.11-1.31(m,7H);1.33-1.46(m,3H);1.59(m,3H);1.72-1.78(m,1H);1.97(m,2H);2.07(m,1H);2.24(m,1H);2.41(m,1H);2.56(m,1H);4.05(m,2H);5.41(m,1H).
13C-NMR:δ13.72(q);14.15(q);19.15(q);19.18(t);19.20(t);19.59(q);22.97(t);23.01(t);25.43(t);25.59(t);29.25(t);29.26(t);29.33(t);29.37(t);30.74(t);30.78(t);32.03(t);32.07(t);33.57(d);33.58(d);36.16(t);36.23(t);37.87(d);37.90(d);40.53(t);40.77(t);64.03(t);64.04(t);120.25(d);120.41(d);140.39(s);140.47(s);173.16(s);173.20(s).
c)3-(4-正丁基环己-1-烯-1-基)丁醛的制备
使用以下化合物和用量修改用于制备3-(4-丁基环己-1-烯-1-基)丙醛的方法(参见实施例1c)):
3-(4-丁基环己-1-烯-1-基)丁酸丁酯(12.9g;46mmol)、二异丁基氢化铝(1M的二氯甲烷溶液,55.2ml,55.2mmol)。产物通过硅胶柱色谱纯化(洗脱液:庚烷/乙酸乙酯15:1至10:1),然后进行球对球蒸馏(80℃/0.035mbar)。它是2种非对映异构体的混合物。
收率:7.72g(92%纯度;34mmol;74%)。
1H-NMR:δ0.89(broad t,J 6.9Hz,3H);1.06(d,J 6.9Hz,3H);1.12-1.33(m,8H);1.39-1.48(m,1H);1.56-1.66(m,1H);1.72-1.85(m,1H);1.90-2.00(m,2H);2.09(m,1H);2.48(m,1H);2.65(m,1H);5.44(m,1H);9.68(m,1H)ppm.
13C-NMR:δ14.14(q);19.48(q);19.84(q);22.96(t);25.72(t);25.85(t);29.23(t);29.26(t);31.99(t);33.55(d);35.67(d);35.73(d);36.13(t);36.15(t);48.82(t);49.01(t);120.86(d);120.97(d);140.05(s);140.09(s);202.97(d);202.99(d)ppm.
实施例9
3-(4-异丁基环己-1-烯-1-基)丙醛(对比化合物)的合成
a)1-(2-(1,3-二氧戊环-2-基)乙基)-4-异丁基环己-1-醇的制备
在氩气气氛下,向镁屑(2.45g,102mmol)的THF(8ml)悬浮液中缓慢地滴加2-(2-溴乙基)-1,3-二氧戊环(16.8g,93mmol)的THF(75ml)溶液。用冷却浴将放热保持在40℃。在环境温度下再搅拌60分钟后,缓慢滴加根据WO9955811制备的酮(9.4g,61mmol)的THF(20ml)溶液。在环境温度下再静置15小时后,将反应混合物倒入到冰和饱和氯化铵溶液的混合物中,用MTBE萃取两次,合并的有机相用饱和碳酸氢钠溶液、盐水洗涤,经Na2SO4干燥、过滤、真空除去溶剂,得到16.6g粗醇,其无需进一步纯化即可直接用于下一步。
1H-NMR:主峰,由混合物推导δ0.85(d,J=6.7,6H);0.93-2.10(m,17H);3.83-3.88(m,2H);3.95-4.00(m,2H);4.88(t,J=4.6,1H)ppm.
13C-NMR:主峰,由混合物推导δ22.9(2q);24.8(d);27.5(t);28.5(2t);34.8(d);37.0(2t);37.8(t);46.5(t);64.9(2t);70.3(s);104.9(d)ppm.
b)2-(2-(4-异丁基环己-1-烯-1-基)乙基-1,3-二氧戊环的制备
将1-(2-(1,3-二氧戊环-2-基)乙基)-4-异丁基环己-1-醇(15.0g,59mmol)溶解在吡啶(80ml)中,并将溶液冷却至0℃。缓慢滴加POCl3(15.0g,98mmol)。将该溶液缓慢温热至环境温度,并再搅拌18小时。然后将混合物冷却,并小心地倒入到冰中,然后用MTBE萃取,有机相先后用饱和的NaHCO3溶液、然后是稀硫酸(5%,2次)、盐水洗涤,用Na2SO4干燥、过滤并真空去除溶剂,得到缩醛11.2g,80%。
1H NMR:δ0.86(d,J 6.5,6H),1.10(t,J 6.9,2H),1.12-1.23(m,6H),1.49-1.79(m,5H),3.82-3.88(m,2H),3.92-3.98(m,2H),4.86(t,J 4.8,1H),5.36-5.42(bs,1H)ppm.
13C NMR:δ22.7(q),23.1(q),24.9(d),28.5(t),29.6(t),31.0(d),31.9(t),32.2(t),32.2(t),46.1(t),64.8(t),104.5(d),120.6(d),136.8(s)ppm;
c)3-(4-异丁基环己-1-烯-1-基)丙醛的制备
将粗缩醛(11.9g,50mmol)溶解在丙酮(200ml)和水(70ml)的混合物中,然后缓慢加入HCl(浓,4ml),并将溶液加热回流4小时,然后冷却。溶液用饱和NaHCO3溶液稀释,然后用MTBE萃取两次,合并的有机相用盐水洗涤,然后经Na2SO4干燥、过滤并真空除去溶剂,得到粗醛13.0g。通过蒸馏(Kügelrohr,0.7mbar,110~150℃)进一步纯化,得到醛7.5g。使用环己烷:EtOAc(99:1)通过色谱法(SiO2)进一步纯化,得到醛,该醛如前所述进行蒸馏,得到纯的3-(4-异丁基环己-1-烯-1-基)丙醛,2.75g,28%。
1H NMR:δ0.86(d,J 6.5,6H),1.10(t,J 6.9,2H),1.13-1.23(m,1H),1.48-1.61(m,2H),1.66(m7,J 6.9,1H);1.86-2.11(m,3H),2.28(t,J 7.4,2H),2.53(td,J 7.7,1.82H),5.36-5.42(bs,1H)ppm.
13C NMR:δ22.7(q),23.1(q),24.9(d),28.6(t),29.4(t),29.8(t),30.9(d),32.1(t),41.9(t),46.0(t),121.5(d),135.6(s),202.8(d)ppm.
实施例10
3-(4-异丁基环己-1-烯-1-基)-2-甲基丙醛(对比化合物)的合成
a)1-(2-(1,3-二氧戊环-2-基)丙基)-4-异丁基环己-1-醇的制备
将2-(2-溴乙基)-1,3-二氧戊环(20g,93mmol,D.J.Collins,A.M.James,Aust.J.Chem.1989,42,223)滴加到Mg(2.495g,103mmol)的THF(100ml)悬浮液中,将温度保持在15~20℃。在20℃下再放置2小时后,根据滴定,该格氏试剂为1.0M。将4-异丁基环己酮(6170mg,40mmol,A.R.Pinder,J.Chem.Soc.1956,1577;M.Julia,C.Descoins,Bull.Soc.Chim.Fr.1970,1805)的THF(50ml)溶液滴加到上述格氏试剂的溶液(1.0M,40ml,40mmol)中,保持温度低于30℃。在20℃下18小时后,将反应混合物倒入到冷的饱和NH4Cl水溶液中,然后用Et2O萃取。有机相用盐水洗涤,干燥(Na2SO4),过滤、浓缩,然后通过CC/SiO2(环己烷/AcOEt 9:1)纯化,得到1-(2-(1,3-二氧戊环-2-基)丙基)-4-异丁基环己-1-醇,收率为69%,其为立体异构体的55:45混合物。
IR:3470,2951,2924,2868,1462,1398,1384,1366,1212,1104,1054,1016,999,930,870.
1H-NMR:主要δ0.85(d,J=6.5,6H);1.05(d,J=7.2,3H);1.23-1.27(m,2H);1.35-1.53(m,4H);1.55-1.69(m,6H);1.73-1.80(m,2H);1.96-2.00(m,1H);3.09(brs,1OH);3.85-3.90(m,2H);3.96-4.00(m,2H);4.69(d,J=5.2,1H).次要δ0.85(d,J=6.5,6H);1.03(d,J=7.2,3H);1.23-1.27(m,2H);1.35-1.53(m,4H);1.55-1.69(m,6H);1.73-1.80(m,2H);2.04-2.08(m,1H);2.71(brs,1OH);3.85-3.90(m,2H);3.96-4.00(m,2H);4.68(d,J=5.2,1H)ppm.
13C-NMR:主要(1r,4r)-1-(2-(1,3-二氧戊环-2-基)丙基)-4-异丁基环己-1-醇δ18.0(q);22.9(2q);25.1(d);26.9(t);30.0(t);31.9(d);34.1(d);36.6(t);39.3(t);45.6(t);45.8(t);64.9(t);65.0(t);71.4(s);108.0(d).次要(1s,4s)-1-(2-(1,3-二氧戊环-2-基)丙基)-4-异丁基环己-1-醇δ18.0(q);22.9(2q);24.8(d);28.5(t);28.6(t);31.8(d);34.8(d);36.5(t);38.9(t);45.8(t);46.6(t);64.9(t);65.0(t);70.1(s);108.0(d)ppm.
b)2-(1-(4-异丁基环己-1-烯-1-基)丙烷-2-基)-1,3-二氧戊环的制备
在0℃下,用15分钟将POCl3(6.27g,40.9mmol)滴加到1-(2-(1,3-二氧戊环-2-基)丙基)-4-异丁基环己-1-醇(7.37g,27.3mmol)的吡啶(40ml)溶液中。在0℃下15分钟,然后在20℃下60分钟,将反应混合物冷却至0℃,并缓慢加入冰/H2O(50ml)的混合物,随后加入Et2O(100ml)。在20℃下1小时后,将反应混合物分配。将水相用饱和NaHCO3水溶液、盐水洗涤至中性,干燥(Na2SO4),浓缩,然后通过CC/SiO2(环己烷/AcOEt 98:2)纯化,得到2-(1-(4-异丁基环己-1-烯-1-基)丙烷-2-基)-1,3-二氧戊环,收率为79%。
IR:2953,2907,2835,1464,1436,1397,1384,1366,1156,1135,1109,1081,1057,1037,998,969,943,915,801.
1H-NMR:δ0.86(d,J=6.9,3H);0.87(d,J=6.2,6H);1.11(t,J=7,2H);1.13-1.21(m,1H);1.53-1.79(m,6H);1.85-1.99(m,2H);2.08(brd,J=15,1H);2.20(brt,J=11,1H);3.84-3.87(m,2H);3.92-3.97(m,2H);4.70(d,J=3.8,1H);5.40(s,1H)ppm.
13C-NMR:δ13.1(q);22.7(q);23.1(q);24.9(d);28.4(t);29.6(t);31.1(d);32.2(t);34.7(d);40.0(t);46.2(t);65.1(2t);107.5(d);122.5(d);135.3(s)ppm.
c)3-(4-异丁基环己-1-烯-1-基)-2-甲基丙醛的制备
将10%的HCl(5ml)添加到2-(1-(4-异丁基环己-1-烯-1-基)丙烷-2-基)-1,3-二氧戊环(5.6g,21.1mmol)的THF(50ml)溶液中。在20℃下18小时后,将反应混合物用Et2O(50ml)稀释,并先后用饱和NaHCO3水溶液和盐水萃取。将有机相干燥(Na2SO4)、浓缩,并将得到的油状物通过CC/SiO2(环己烷/AcOEt 97:3)纯化,以48%的收率得到3-(4-异丁基环己-1-烯-1-基)-2-甲基丙醛。或者,于15℃用5分钟将5%的HCl(121ml)添加到2-(1-(4-异丁基环己-1-烯-1-基)丙烷-2-基)-1,3-二氧戊环(21.7g,80mmol)的丙酮(150ml)溶液中。回流2小时后,将冷的反应混合物用饱和NaHCO3水溶液洗涤。有机相用盐水洗涤,干燥(Na2SO4),浓缩,并通过CC/SiO2(环己烷/AcOEt 99:1)纯化,以75%的收率得到3-(4-异丁基环己-1-烯-1-基)-2-甲基丙醛。
IR:2954,2906,2870,2834,2707,1726,1691,1465,1454,1435,1384,1366,1142,915,867,795.
1H-NMR:δ0.87(d,J=6.8,6H);1.04(d,J=7,3H);1.10(t,J=7.0,2H);1.14-1.22(m,1H);1.52-1.61(m,2H);1.66(dhept,J=6.6,1.8,1H);1.70-1.75(m,1H);1.87-2.00(m,3H);2.08(d,J=15.8,1H);2.37(dt,J=14,6.6,1H);2.51(dhex,J=6.8,1.8,1H);5.42(m,1H);9.62(d,J=1.7,1H)ppm.
13C-NMR:δ13.4(q);22.7(q);23.1(q);24.9(d);28.3(t);29.4(t);30.8(d);32.2(t);38.9(t);44.4(d);46.0(t);123.6(d);134.1(s);205.4(d)ppm.
实施例11
3-(4-正戊基环己-1-烯-1-基)丙醛(对比化合物)的合成
a)8-正戊基-1-氧杂螺[4.5]癸-2-酮的制备
按照实施例1a)中所述的程序,将4-正戊基环己醇(50g;294mmol)转化为8-正戊基-1-氧杂螺[4.5]癸-2-酮,其为非对映异构体的3:2混合物(5.3g;23mmol;8%)。
通过球对球蒸馏(150℃/0.1mbar)进行纯化。
1H-RNM:δ0.89(m,3H);1.03(m,1H);1.39-1.78(m,10H);1.48(m,1H);1.63(m,1H);1.70-1.91(m,4H);1.98(t,J=7Hz;0.8H);2.056(t,J=7Hz,1.2H);2.58(m,2H)ppm.
13C-NMR:δ14.07(q);14.09(q);22.64(t);22.67(t);26.59(t);26.80(t);28.62(t);28.66(t);29.41(t);30.60(t);32.06(t);32.12(t);34.12(t);34.14(t);35.91(t);35.95(t);36.10(d);36.42(d);36.56(t);36.87(t);85.94(s);87.28(s);176.70(s);176.92(s)ppm.
b)3-(4-正戊基环己-1-烯-1-基)丙酸丁酯的制备
按照实施例1b)中所述的程序,将8-正戊基-1-氧杂螺[4.5]癸-2-酮(3.1g;13.8mmol)转化为3-(4-正戊基环己-1-烯-1-基)丙酸酯(3.32g;11.8mmol;86%)。
通过球对球蒸馏(150℃/0.2mbar)进行纯化。
1H-NMR:δ0.88(t,J=7Hz,3H);0.93(t,J=7Hz;3H);1.13-1.48(m,12H);1.60(m,3H);1.74(m,1H);1.89-2.11(m,3H);2.26(m,2H);2.40(m,2H);4.07(t,J=7Hz;2H);5.39(m,1H)ppm.
13C-NMR:δ13.73(q);14.11(q);19.17(t);22.72(t);26.68(t);28.38(t);29.28(t);30.75(t);32.05(t);32.17(t);32.74(t);32.98(t);33.40(d);36.44(t);64.15(t);121.16(d);135.99(s);173.72(s)ppm.
c)3-(4-正戊基环己-1-烯-1-基)丙醛的制备
按照实施例1c)中所述的程序,将3-(4-正戊基环己-1-烯-1-基)丙酸丁酯(3.32g;10.2mmol)转化为3-(4-正戊基环己-1-烯-1-基)丙醛(0.51g;2.5mmol;25%)。
通过硅胶柱色谱(洗脱液:庚烷/乙酸乙酯99:1),然后球对球蒸馏(125℃/1mbar)进行纯化。
1H-NMR:δ9.75(t,J=2Hz;1H);5.39(m,1H);2.51(m,2H);2.28(m,2H);2.12-1.88(m,3H);1.76-1.57(m,3H);1.34-1.15(m,9H);0.88t,J=7Hz;3H)ppm.
13C-NMR:δ14.11(q);22.71(t);26.67(t);28.59(t);29.23(t);29.87(t);32.02(t);32.15(t);33.39(d);36.41(t);41.92(t);121.53(d);135.60(s);202.75(d).
实施例12
3-(4-正己基环己-1-烯-1-基)丙醛(对比化合物)的合成
a)8-正己基-1-氧杂螺[4.5]癸-2-酮的制备
按照实施例1a)中所述的程序,将4-正己基环己醇(42g;228mmol)转化为8-正己基-1-氧杂螺[4.5]癸-2-酮,其为非对映异构体的3:2混合物(6.8g;29mmol;13%)。
通过球对球蒸馏(150℃/0.1mbar)进行纯化。
1H-NMR:δ0.88(t,J=7Hz;3H);1.03(m,2H);1.18-1.39(m,11H);1.47(m,1H);1.63(m,1H);1.69-1.91(m,4H);1.98(t,J=7Hz;0.8H);2.05(t,J=7Hz,1.2H);2.59(m,2H)ppm.
13C-NMR:δ14.11(q);176.67(s);22.66(t);26.89(t);27.11(t);28.62(t);28.66(t);29.42(t);29.53(t);29.57(t);30.61(t);31.86(t);31.89(t);34.15(t);35.96(t);36.10(t);36.44(d);36.61(t);36.88(t);85.92(s);87.27(s);176.67(s);176.89(s)ppm.
b)3-(4-正己基环己-1-烯-1-基)丙酸丁酯的制备
按照实施例1b)中所述的程序,将8-正己基-1-氧杂螺[4.5]癸-2-酮(2.47g;10.4mmol)转化为3-(4-正己基环己-1-烯-1-基)丙酸酯(1.82g;6.2mmol;59%)。
通过球对球蒸馏(130℃/0.2mbar)进行纯化。
1H-NMR:δ0.88(t,J=7Hz,3H);0.93(t,J=7Hz,3H);1.13-1.47(m,12H);1.55-1.67(m,4H);1.74(m,1H);1.88-2.11(m,4H);2.25(m,2H);2.40(m,2H);4.07(t,J=7Hz,2H);5.38(m,1H)ppm.
13C-NMR:δ13.73(q);14.13(q);19.17(t);22.71(t);26.99(t);28.38(t);29.29(t);29.62(t);30.75(t);31.96(t);32.05(t);32.74(t);32.98(t);33.41(d);36.50(t);64.15(t);121.16(d);135.99(s);173.71(s)ppm.
c)化合物3-(4-正己基环己-1-烯-1-基)丙醛的制备
按照实施例1c)中所述的程序,将3-(4-正己基环己-1-烯-1-基)丙酸丁酯(1.5g;5.1mmol)转化为3-(4-正己基环己-1-烯-1-基)丙醛(0.6g;2.7mmol;53%)。
通过硅胶柱色谱(洗脱液:庚烷/乙酸乙酯97:3),然后球对球蒸馏(125℃/1mbar)进行纯化。
1H-NMR:δ0.88(t,J=7Hz;3H);1.15-1.34(m,11H);1.38-1.57(m,2H);1.75(m,1H);1.87-2.11(m,3H);2.28(m,2H);2.52(m,2H);5.39(m,1H);9.76(t,J=2Hz;1H)ppm.
13C-NMR:δ14.12(q);22.69(t);26.95(t);28.58(t);29.22(t);29.59(t);29.86(t);31.93(t);32.01(t);33.37(d);36.44(t);41.91(t);121.54(d);135.60(s);202.83(d)ppm.
实施例13
加香组合物的制备
通过混合以下成分制备用于液体洗涤剂的加香组合物:
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1)(3ars,5asr,9asr,9brs)-3a,6,6,9a-四甲基十二氢萘并[2,1-b]呋喃;来源:瑞士日内瓦的Firmenich SA
2)来源:瑞士韦尔涅的Givaudan-Roure SA
3)来源:瑞士日内瓦的Firmenich SA
4)丙酸(+)-(1s,1'r)-2-[1-(3',3'-二甲基-1'-环己基)乙氧基]-2-甲基丙酯;来源:瑞士日内瓦的Firmenich SA
5)1-(八氢-2,3,8,8-四甲基-2-萘基)-1-乙酮;来源:美国的InternationalFlavors&Fragrances
6)(+-)-2,5-二甲基-2-茚满甲醇;来源:瑞士日内瓦的Firmenich SA
7)2-((1RS,2RS)-3-氧-2-戊基环戊基)乙酸甲酯;来源:瑞士日内瓦的FirmenichSA
8)1-(5,5-二甲基-1-环己烯-1-基)-4-戊烯-1-酮;来源:瑞士日内瓦的FirmenichSA
9)反式-1-(2,2,6-三甲基-1-环己基)-3-己醇;来源:瑞士日内瓦的Firmenich SA
10))(+-)-2,2,5-三甲基-5-戊基环戊酮;来源:瑞士日内瓦的Firmenich SA
11)乙酸2-叔丁基-1-环己酯;来源:美国的International Flavors&Fragrances
向上述组合物中添加100重量份的3-(4-正丁基-1-环己烯-1-基)丙醛,赋予该组合物以奶油、花瓣和桔子(mandarin)香调,还具有香菜的细微特征,同时为该组合物提供新鲜感。该组合物获得了更大的体量(volume),并且变得非常浓烈。3-(4-正丁基-1-环己烯-1-基)丙醛与组合物中的干净的醛香成分例如(+-)-2-甲基十一醛以及花香成分例如(+-)-3,7-二甲基-6-辛烯-1-醇、(E)-3,7-二甲基-2,6-辛二烯-1-醇和Lilyflore混合得特别好。
当使用相同量的(3-(4-叔丁基-1-环己烯-1-基)丙醛;来源:瑞士日内瓦的Firmenich SA)代替本发明的化合物时,该组合物获得了更具花香/山谷百合的的内涵,并组合有柑橘方面,但不含奶油、花瓣、桔子和香菜香调。此外,所述组合物不那么强烈。
当使用相同量的(3-[4-(2-甲基丙基)环己基]丙醛;来源:美国的International Flavors&Fragrances)代替本发明的化合物时,结果完全不同,因为该组合物获得了醛香、香茅香调。所述组合物较弱并且不那么干净,带有金属和尘土香调。
当用相同量的3-(4-异丁基环己基)-2-甲基丙醛代替本发明的化合物时,该组合物仅获得醛香香调。所述组合物是最弱的。
当使用相同量的3-(4-正丁基环己基)丙醛代替本发明的化合物时,该组合物变得更具脂肪味、更多金属味并且具有轻微的动物粪便味。
包含3-(4-正丁基-1-环己烯-1-基)丙醛的组合物是最浓烈的。24小时后,所述组合物仍然是最强烈的,对前调的影响仍然存在。
实施例14
制备包含本发明化合物的液体洗涤剂
表2:液体洗涤剂配方的组成
成分 | 浓度[wt%] |
C14-17仲烷基磺酸钠1) | 7 |
C12-18和C18-不饱和脂肪酸2) | 7.5 |
具有7mol EO的C12/14脂肪醇聚乙二醇醚3) | 17 |
三乙醇胺 | 7.5 |
丙二醇 | 11 |
柠檬酸 | 6.5 |
氢氧化钾 | 9.5 |
Properase L4) | 0.2 |
Puradax EG L4) | 0.2 |
Purastar ST L4) | 0.2 |
丙烯酸酯/硬脂醇聚醚-20甲基丙烯酸酯结构化交联聚合物5) | 6 |
去离子水 | 27.4 |
1)Hostapur SAS 60;来源:Clariant
2)Edenor K 12-18;来源:Cognis
3)Genapol LA 070;来源:Clariant
4)来源:Genencor International
5)Aculyn 88;来源:Dow Chemical
通过在轻轻摇动下将相对于液体洗涤剂总重量为1.5重量%的实施例13的本发明组合物添加到表2的未加香液体洗涤剂配方中来制备液体洗涤剂。
实施例15
包含本发明化合物的织物柔软剂的制备
表3:柔软剂配方的组成
成分 | 浓度[wt%] |
甲基双[牛油酸乙酯基]-2-羟乙基硫酸甲酯铵1) | 12.20 |
1,2-苯并异噻唑啉-3-酮2) | 0.04 |
CaCl2(10%水溶液) | 0.40 |
水 | 87.36 |
1)Stepantex VL90 A Diester Quat;来源:Stepan
2)Proxel GXL;来源:Arch
通过称重加热到65℃的甲基双[牛油酸乙酯基]-2-羟乙基硫酸甲酯铵来制备柔软剂。然后将水和1,2-苯并异噻唑啉-3-酮放入到反应器中,并在搅拌下于65℃加热。向上述混合物中加入甲基双[牛油酸乙酯基]-2-羟乙基硫酸甲酯铵。将混合物搅拌15分钟,并加入CaCl2。然后,相对于柔软剂的总重量,添加0.5至2重量%的实施例13的本发明的组合物。将混合物搅拌15分钟,并在搅拌下冷却至室温(粘度测量:结果为35+/-5mPas。(剪切速率为106秒-1))。
实施例16
包含本发明组合物的透明均质洗发剂的制备
表4:透明均质洗发剂配方的组成
1)Ucare Polymer JR-400,来源:Noveon
2)来源:Schweizerhall
3)Glydant,来源:Lonza
4)Texapon NSO IS,来源:Cognis
5)Tego Betain F 50,来源:Evonik
6)Amphotensid GB 2009,来源:Zschimmer&Schwarz
7)Monomuls 90L-12,来源:Gruenau
8)尼泊金单钠,来源:NIPA
洗发剂通过将聚季铵盐-10分散在水中来制备。将A相的其余成分逐个添加,同时在每种助剂添加后充分混合。将该预混合物加入到聚季铵盐-10分散体中,并再混合5分钟。然后,在搅拌的同时添加预混合的B相和预混合的C相(将Monomuls 90L-12加热以熔融在Texapon NSO IS中)。在搅拌的同时添加D相和E相。用柠檬酸溶液调节pH值直到pH:5.5–6.0,制得未加香的洗发剂配方。
通过在轻轻摇动下将相对于洗发剂的总重量为0.4至0.8重量%的实施例13的本发明组合物添加到表4的未加香的洗发剂配方中,以制备已加香的洗发剂。
实施例17
包含本发明组合物的结构化浴液的制备
表5:浴液(沐浴露)配方的组成
成分 | 量(%wt) |
去离子水 | 49.350 |
EDTA四钠1) | 0.050 |
丙烯酸酯共聚物2) | 6.000 |
C12-C15链烷醇聚醚硫酸钠3) | 35.000 |
氢氧化钠20%水溶液 | 1.000 |
椰油酰胺丙基甜菜碱4) | 8.000 |
甲基氯异噻唑啉酮和甲基异噻唑啉酮5) | 0.100 |
柠檬酸(40%) | 0.500 |
1)EDETA B粉末;商标和来源:BASF
2)CARBOPOL AQUA SF-1聚合物;商标和来源:NOVEON
3)ZETESOL AO 328U;商标和来源:ZSCHIMMER&SCHWARZ
4)TEGO-BETAIN F 50;商标和来源:GOLDSCHMIDT
5)KATHON CG;商标和来源:ROHM&HASS
通过在轻轻摇动下将相对于浴液总重量为0.5至1.5重量%的实施例13的本发明组合物添加到表5的未加香的浴液配方中,以制备浴液。
实施例18
包含本发明组合物的透明浴液的制备
表6:透明浴液配方的组成
成分 | 浓度(%wt) |
去离子水 | 52.40 |
EDTA四钠1) | 0.10 |
苯甲酸钠 | 0.50 |
丙二醇 | 2.00 |
C12-C15链烷醇聚醚硫酸钠2) | 35.00 |
椰油酰胺丙基甜菜碱3) | 8.00 |
聚季铵盐-7 4) | 0.20 |
柠檬酸(40%) | 1.00 |
氯化钠 | 0.80 |
1)EDETA B粉末;商标和来源:BASF
2)ZETESOL AO 328U;商标和来源:ZSCHIMMER&SCHWARZ
3)TEGO-BETAIN F 50;商标和来源:GOLDSCHMIDT
4)MERQUAT 550;商标和来源:LUBRIZOL
通过在轻轻摇动下将相对于浴液总重量为0.5至1.5重量%的实施例13的本发明组合物添加到表6的未加香的浴液配方中,以制备透明浴液。
实施例19
包含本发明组合物的乳状浴液的制备
表7:乳状浴液配方的组成
成分 | 浓度(%wt) |
去离子水 | 50.950 |
EDTA四钠1) | 0.050 |
苯甲酸钠 | 0.500 |
甘油86% | 3.500 |
十二烷基聚氧乙醚硫酸钠2) | 27.000 |
聚季铵盐-7 3) | 1.000 |
椰油酰胺丙基甜菜碱(Coco-Betaine)4) | 6.000 |
PEG-120甲基葡萄糖三油酸酯5) | 1.000 |
柠檬酸(40%) | 1.000 |
二硬脂酸乙二醇酯&月桂醇聚醚-4&椰油酰胺丙基甜菜碱6) | 3.000 |
氯化钠20% | 5.000 |
PEG-40氢化蓖麻油7) | 1.000 |
1)EDETA B粉末;商标和来源:BASF
2)Texapon NSO IS;商标和来源:COGNIS
3)MERQUAT 550;商标和来源:LUBRIZOL
4)DEHYTON AB-30;商标和来源:COGNIS
5)GLUCAMATE LT;商标和来源:LUBRIZOL
6)EUPERLAN PK 3000AM;商标和来源:COGNIS
7)CREMOPHOR RH 40;商标和来源:BASF
通过在轻轻摇动下将相对于浴液总重量为0.5至1.5重量%的实施例13的本发明组合物添加到表7的未加香的浴液配方中,以制备透明浴液。
实施例20
包含本发明组合物的珠光洗发剂的制备
表8:珠光均质洗发剂配方的组成
/>
1)EDETA B粉末,来源:BASF
2)Jaguar C14 S,来源:Rhodia
3)Ucare Polymer JR-400,来源:Noveon
4)Sulfetal LA B-E,来源:Zschimmer&Schwarz
5)Zetesol LA,来源:Zschimmer&Schwarz
6)Tego Betain F 50,来源:Evonik
7)Xiameter MEM-1691,来源:Dow Corning
8)Lanette 16,来源:BASF
9)Comperlan 100,来源:Cognis
10)Cutina AGS,来源:Cognis
11)Kathon CG,来源:Rohm&Haas
12)D-Panthenol,来源:Roche
洗发剂通过将瓜尔胶羟丙基三甲基氯化铵和聚季铵盐-10分散在水和EDTA四钠中来制备。一旦A相均匀了,就添加NaOH 10%溶液(B相)。然后,加入预混合的C相。并将混合物加热至75℃。加入D相成分并混合直至均匀。将混合物冷却。在45℃下,在混合的同时添加E相成分。用25%的NaCl溶液调节最终粘度,用10%的NaOH溶液调节pH 5.5-6。
通过在轻轻摇动下将相对于洗发剂的总重量为0.4至0.8重量%的实施例13的本发明组合物添加到表8的未加香的洗发剂配方中,以制备已加香的珠光洗发剂。
实施例21
包含本发明组合物的结构化浴液的制备
表9:乳状浴液配方的组成
成分 | 量(%wt) |
去离子水 | 49.350 |
EDTA四钠1) | 0.050 |
丙烯酸酯共聚物2) | 6.000 |
C12-C15链烷醇聚醚硫酸钠3) | 35.000 |
氢氧化钠20%水溶液 | 1.000 |
椰油酰胺丙基甜菜碱4) | 8.000 |
甲基氯异噻唑啉酮和甲基异噻唑啉酮5) | 0.100 |
柠檬酸(40%) | 0.500 |
6)EDETA B粉末;商标和来源:BASF
7)CARBOPOL AQUA SF-1聚合物;商标和来源:NOVEON
8)ZETESOL AO 328U;商标和来源:ZSCHIMMER&SCHWARZ
9)TEGO-BETAIN F 50;商标和来源:GOLDSCHMIDT
10)KATHON CG;商标和来源:ROHM&HASS
通过在轻轻摇动下将相对于浴液总重量为0.5至1.5重量%的实施例13的本发明组合物添加到表9的未加香的浴液配方中,以制备透明浴液。
实施例22
包含本发明化合物的淡香水的制备
通过在轻轻摇动下将相对于淡香水总重量为5至20重量%的实施例13的本发明组合物添加到乙醇中,以制备淡香水。
Claims (16)
1.式(I)化合物作为加香成分的用途,用于赋予山谷百合气味香调的醛香方面,并结合有奶油和香菜香调,
该化合物以其任何一种立体异构体或它们的混合物的形式存在,并且其中R代表正丁基或(3-甲基丁烷-2-基)基团。
2.根据权利要求1的用途,其特征在于R代表正丁基。
3.根据权利要求1至2中任一项的用途,其特征在于式(I)化合物选自3-(4-正丁基-1-环己烯-1-基)丙醛和3-[4-(1,2-二甲基丙基)-1-环己烯-1-基]丙醛。
4.根据权利要求3的用途,其特征在于式(I)化合物是3-(4-正丁基-1-环己烯-1-基)丙醛。
5.一种给予、增强、改善或修饰加香组合物或已加香制品的气味特性的方法,该方法包括向所述组合物或制品中加入有效量的至少一种权利要求1至4中任一项定义的式(I)化合物,用于赋予山谷百合气味香调的醛香方面,并结合有奶油和香菜香调。
6.权利要求1至5中任一项定义的式(I)化合物。
7.一种加香组合物,其包含:
i)至少一种权利要求6中定义的式(I)化合物,用于赋予山谷百合气味香调的醛香方面,并结合有奶油和香菜香调;
ii)至少一种从由香料载体和香料基料构成的群组中选出的成分;和
iv)可选地,至少一种香料佐剂。
8.一种已加香消费品,其包含至少一种权利要求6中定义的式(I)化合物或权利要求7中定义的组合物,用于赋予山谷百合气味香调的醛香方面,并结合有奶油和香菜香调。
9.根据权利要求8的已加香消费品,其特征在于该已加香消费品是香水、织物护理产品、身体护理产品或空气护理产品。
10.根据权利要求8的已加香消费品,其特征在于该已加香消费品是化妆品制剂或家庭护理产品。
11.根据权利要求8的已加香消费品,其特征在于该已加香消费品是皮肤护理产品。
12.根据权利要求8的已加香消费品,其特征在于该已加香消费品是涂抹式香水、淡香精、古龙水、剃须水、须后水、织物柔软剂、织物清新剂、熨烫水、纸张、漂白剂、地毯清洁剂、窗帘护理产品、洗发剂、着色剂、颜色护理产品、头发定型产品、牙齿护理产品、消毒剂、私处护理产品、雪花膏、体香剂、止汗剂、脱毛剂、晒黑或防晒产品、指甲产品、香皂、沐浴摩丝、浴油、浴液、足部/手部护理产品、“即用型”粉末空气清新剂、去霉剂、餐具洗涤剂、皮革护理产品或汽车护理产品。
13.根据权利要求8的已加香消费品,其特征在于该已加香消费品是化妆品、空气清新剂、家具护理剂或硬表面洗涤剂。
14.根据权利要求8的已加香消费品,其特征在于该已加香消费品是卫生用品。
15.根据权利要求8的已加香消费品,其特征在于该已加香消费品是精细香水、擦拭物、皮肤清洁剂或头发喷雾剂。
16.根据权利要求8的已加香消费品,其特征在于该已加香消费品是液体或固体洗涤剂。
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EP1054053A2 (en) * | 1999-05-19 | 2000-11-22 | Firmenich S.A. | Utilization of substituted acetaldehydes with a cyclic substituent as perfuming ingredients |
CN102070418A (zh) * | 2009-11-16 | 2011-05-25 | 国际香料和香精公司 | 新型4-烷基环己烷丙醛化合物及其在香料组合物中的应用 |
CN103030538A (zh) * | 2011-10-07 | 2013-04-10 | 西姆莱斯有限公司 | 具有铃兰香调的香料 |
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