CN101072857A - 有机化合物 - Google Patents
有机化合物 Download PDFInfo
- Publication number
- CN101072857A CN101072857A CN 200580042243 CN200580042243A CN101072857A CN 101072857 A CN101072857 A CN 101072857A CN 200580042243 CN200580042243 CN 200580042243 CN 200580042243 A CN200580042243 A CN 200580042243A CN 101072857 A CN101072857 A CN 101072857A
- Authority
- CN
- China
- Prior art keywords
- phenyl
- methyl
- compound
- nitrile
- fragrance
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
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- 150000002894 organic compounds Chemical class 0.000 title description 2
- 239000003205 fragrance Substances 0.000 claims abstract description 35
- 239000002304 perfume Substances 0.000 claims abstract description 15
- 239000004615 ingredient Substances 0.000 claims abstract description 7
- 239000002537 cosmetic Substances 0.000 claims abstract description 5
- 150000001875 compounds Chemical class 0.000 claims description 38
- 239000000203 mixture Substances 0.000 claims description 25
- -1 methoxyl group Chemical group 0.000 claims description 11
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 8
- 239000000463 material Substances 0.000 claims description 7
- IWOSBVMKLPSAAJ-UHFFFAOYSA-N 3-methyl-2-phenylbut-2-enenitrile Chemical compound CC(C)=C(C#N)C1=CC=CC=C1 IWOSBVMKLPSAAJ-UHFFFAOYSA-N 0.000 claims description 6
- WTGMOKSFTZAETA-UHFFFAOYSA-N 3-methyl-2-(4-methylphenyl)but-2-enenitrile Chemical compound CC(C)=C(C#N)C1=CC=C(C)C=C1 WTGMOKSFTZAETA-UHFFFAOYSA-N 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- HYVSCAYUKJYEOR-KAMYIIQDSA-N (E)-2-phenyloct-2-enenitrile Chemical compound CCCCC\C=C(\C#N)C1=CC=CC=C1 HYVSCAYUKJYEOR-KAMYIIQDSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 18
- 239000003921 oil Substances 0.000 description 12
- 235000019198 oils Nutrition 0.000 description 12
- 239000000047 product Substances 0.000 description 10
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- GLZPCOQZEFWAFX-UHFFFAOYSA-N Geraniol Chemical compound CC(C)=CCCC(C)=CCO GLZPCOQZEFWAFX-UHFFFAOYSA-N 0.000 description 8
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- 239000000796 flavoring agent Substances 0.000 description 7
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- 235000013599 spices Nutrition 0.000 description 7
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- 238000009835 boiling Methods 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000012044 organic layer Substances 0.000 description 6
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- 239000012230 colorless oil Substances 0.000 description 5
- 230000006837 decompression Effects 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 4
- 241000675108 Citrus tangerina Species 0.000 description 4
- 239000005792 Geraniol Substances 0.000 description 4
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- 229920006395 saturated elastomer Polymers 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- JKRWZLOCPLZZEI-UHFFFAOYSA-N alpha-Trichloromethylbenzyl acetate Chemical compound CC(=O)OC(C(Cl)(Cl)Cl)C1=CC=CC=C1 JKRWZLOCPLZZEI-UHFFFAOYSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 150000002596 lactones Chemical class 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
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- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
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- XRHCAGNSDHCHFJ-UHFFFAOYSA-N Ethylene brassylate Chemical compound O=C1CCCCCCCCCCCC(=O)OCCO1 XRHCAGNSDHCHFJ-UHFFFAOYSA-N 0.000 description 2
- 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 2
- WRQNANDWMGAFTP-UHFFFAOYSA-N Methylacetoacetic acid Chemical compound COC(=O)CC(C)=O WRQNANDWMGAFTP-UHFFFAOYSA-N 0.000 description 2
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- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
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- 239000003513 alkali Substances 0.000 description 2
- 150000001728 carbonyl compounds Chemical class 0.000 description 2
- HQKQRXZEXPXXIG-VJOHVRBBSA-N chembl2333940 Chemical compound C1[C@]23[C@H](C)CC[C@H]3C(C)(C)[C@H]1[C@@](OC(C)=O)(C)CC2 HQKQRXZEXPXXIG-VJOHVRBBSA-N 0.000 description 2
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- 230000005494 condensation Effects 0.000 description 2
- 235000009508 confectionery Nutrition 0.000 description 2
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 2
- 235000013399 edible fruits Nutrition 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 229940093468 ethylene brassylate Drugs 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- IFYYFLINQYPWGJ-UHFFFAOYSA-N gamma-decalactone Chemical compound CCCCCCC1CCC(=O)O1 IFYYFLINQYPWGJ-UHFFFAOYSA-N 0.000 description 2
- HIGQPQRQIQDZMP-DHZHZOJOSA-N geranyl acetate Chemical compound CC(C)=CCC\C(C)=C\COC(C)=O HIGQPQRQIQDZMP-DHZHZOJOSA-N 0.000 description 2
- JMANVNJQNLATNU-UHFFFAOYSA-N glycolonitrile Natural products N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- JARKCYVAAOWBJS-UHFFFAOYSA-N hexanal Chemical compound CCCCCC=O JARKCYVAAOWBJS-UHFFFAOYSA-N 0.000 description 2
- 235000012907 honey Nutrition 0.000 description 2
- WPFVBOQKRVRMJB-UHFFFAOYSA-N hydroxycitronellal Chemical compound O=CCC(C)CCCC(C)(C)O WPFVBOQKRVRMJB-UHFFFAOYSA-N 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 229940067107 phenylethyl alcohol Drugs 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- CZCBTSFUTPZVKJ-UHFFFAOYSA-N rose oxide Chemical compound CC1CCOC(C=C(C)C)C1 CZCBTSFUTPZVKJ-UHFFFAOYSA-N 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 2
- 229960001860 salicylate Drugs 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 230000008786 sensory perception of smell Effects 0.000 description 2
- 239000002453 shampoo Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
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- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- 239000000341 volatile oil Substances 0.000 description 2
- NOOLISFMXDJSKH-UTLUCORTSA-N (+)-Neomenthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@@H]1O NOOLISFMXDJSKH-UTLUCORTSA-N 0.000 description 1
- WTOYNNBCKUYIKC-JMSVASOKSA-N (+)-nootkatone Chemical compound C1C[C@@H](C(C)=C)C[C@@]2(C)[C@H](C)CC(=O)C=C21 WTOYNNBCKUYIKC-JMSVASOKSA-N 0.000 description 1
- ORHSGDMSYGKJJY-SAIIYOCFSA-N (1'r,6's)-2,2,4',7',7'-pentamethylspiro[1,3-dioxane-5,5'-bicyclo[4.1.0]heptane] Chemical compound C12([C@H]3[C@H](C3(C)C)CCC2C)COC(C)(C)OC1 ORHSGDMSYGKJJY-SAIIYOCFSA-N 0.000 description 1
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- BVDMQAQCEBGIJR-UHFFFAOYSA-N 1-(2,2,6-trimethylcyclohexyl)hexan-3-ol Chemical compound CCCC(O)CCC1C(C)CCCC1(C)C BVDMQAQCEBGIJR-UHFFFAOYSA-N 0.000 description 1
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Abstract
2-苯基-2-烯腈作为芳香成分的用途和含有它们的芳香用品。这些芳香用品可以是例如香水、家用产品、洗衣用产品、身体护理用产品和美容品。
Description
本发明涉及2-苯基-2-烯腈和它们作为芳香成分的用途。
在香料工业中,一直需要香调得到增强或改善、或赋予新香调的新化合物。
现已发现,某些2-苯基-2-烯腈构成新的有效增味剂。尽管一些2-苯基-2-烯腈作为中间体是已知的(例如参见美国专利5,389,608),但没有文献指出这些中间体(即α,β-不饱和腈)具有使它们适用于香料工业的香味性能。仅有E.C.Knowles等(Journal of the AmericanChemical Society(1932),54,2028-2037页)指出某些2-苯基-2-烯腈的香味性能,它公开了2-苯基-丁-2-烯腈作为具有令人不快的霉味的化合物。
已出人意料地发现,某些2-苯基-2-烯腈非常适于作为芳香成分,这不仅由于它们的非常令人愉快的鲜花香、清新、类似Rosacetol的香调,而且由于它们的非常低的气味阈值,即比饱和化合物低约7-9倍。因此,本发明的2-苯基-2-烯腈比它们的饱和对应物更强效。
其中:
R1和R2独立地是H,C1-8烷基例如甲基、乙基、丙基、异丁基、正丁基、叔戊基、异戊基和正戊基,或C2-8链烯基例如乙烯基、烯丙基和1-丁烯基,条件是残基R1和R2中的至少一个不是氢;
R3是H,甲氧基,C1-4烷基例如甲基、乙基或丙基,或C2-4链烯基例如乙烯基或烯丙基;
和通式I的化合物的碳原子总数为≤18,优选为11-16。
本发明的化合物可含有一个或多个立体单元,例如手性中心和/或E/Z-构型的双键,和就此它们可以是以立体异构体的混合物形式存在,或者它们可以异构体纯形式被拆分。立体异构体的拆分会增加制备和纯化这些化合物的复杂性,所以,出于经济原因,优选简单地以它们的立体异构体混合物的形式来使用这些化合物。然而,如果期望制备单一的立体异构体,则可以根据本领域已知的方法来实现,所述已知的方法例如制备型HPLC和GC或通过立体有择性合成。
通式I的特别优选的化合物是3-甲基-2-苯基-丁-2-烯腈、3-乙基-2-苯基-戊-2-烯腈、(2E)-2-苯基-辛-2-烯腈、3-甲基-2-苯基-戊-2-烯腈、3-甲基-2-对甲苯基-丁-2-烯腈、3,7-二甲基-2-苯基-辛-2,6-二烯腈、(2E)-5-甲基-2-苯基-己-2,4-二烯腈、2-(2-甲氧基-苯基)-3-甲基-丁-2-烯腈和2-(3-甲氧基-苯基)-3-甲基-丁-2-烯腈。
最优选的是3-甲基-2-苯基-丁-2-烯腈,这是由于其香调非常接近Rosacetol的香调(三氯-甲基-苯基-甲基乙酸酯)。
本发明的化合物可单独或者结合已知的增味剂分子使用,所述已知的增味剂分子选自宽范围的目前可获得的天然与合成分子,例如精油、醇类、醛类和酮类、醚类和缩醛类、酯类和内酯类、大环化合物类和杂环化合物类,和/或与一种或多种在芳香组合物中常规地与增味剂结合使用的成分或赋形剂混合,例如载体材料和本领域中常用的其它辅助剂。
下面所列的物质包括可以与本发明的化合物结合的已知增味剂分子的实例:
-香精油和提取物,例如纯橡树苔藓油、罗勒油,热带水果油,例如香柠檬油和红桔油、纯乳香脂油、桃金娘油、玫瑰草油、广藿香油、橙叶油、苦艾油、熏衣草油、玫瑰油、茉莉油、衣兰油和檀香油。
-醇类,例如顺-3-己烯醇、肉桂醇、香茅醇、EbanolTM、丁子香酚、法呢醇、香叶醇、薄荷醇、橙花醇、香草醇、Super MuguetTM、芳樟醇、苯乙醇、SandaloreTM、萜品醇和TimberolTM(1-(2,2,6-三甲基环己基)己醇-3)。
-醛类和酮类,例如柠檬醛、羟基香茅醛、Lilial、甲基壬基乙醛、茴香醛、烯丙基紫罗兰酮、马鞭草烯酮、努特卡酮、香叶基丙酮、α-戊基肉桂醛、GeorgywoodTM、羟基香茅醛、Iso E Super、Isoraldeine(甲基紫罗兰酮)、Hedione、麦芽酚、甲基柏木基酮和香草醛。
-醚类和缩醛类,例如AmbroxTM、香叶基甲基醚、氧化玫瑰或SpirambreneTM。
-酯类和内酯类,例如乙酸苄酯、乙酸柏木酯、γ-癸内酯、Helvetolide、γ-十一内酯、乙酸岩兰草酯、肉桂醇丙酸酯、香茅醇乙酸酯、乙酸癸酯、二甲基苄基甲基乙酸酯、乙酰乙酸乙酯、乙酰乙酸乙酯、异丁酸顺-3-己烯酯、乙酸芳樟酯和乙酸香叶酯。
-大环化合物类,例如黄葵内酯、巴西酸亚乙酯和Exaltolide。
-杂环化合物类,例如异丁基喹啉。
本发明的化合物可以例如在精细和功能香料的任何领域中的宽范围的芳香用品中使用,所述芳香用品例如香水、家用产品、洗衣用产品、身体护理用产品和美容品。取决于特定的用品和其它增味剂成分的性质与用量,本发明的化合物可以宽泛变化的用量使用。其比例典型地为该用品的0.001-5wt%。在一个实施方案中,本发明的化合物可在织物柔软剂中以0.001-0.05wt%的用量使用。在另一实施方案中,本发明的化合物可在精细香料中以0.1-5wt%,更优选0.1-2wt%的用量使用。然而,这些数值仅仅以实例方式给出,这是因为有经验的香料制造者以更低或更高的浓度也可实现效果或者产生新的谐香。
已出人意料地发现,通式I的化合物具有抑制或者至少减少皮肤内前列腺素形成的能力,这样潜在地使它们适合于皮肤抚慰。因此,通式I的化合物特别适合于身体护理产品和美容品,例如软膏、除臭剂和晒黑乳液,和它们可以直接涂敷到皮肤上。
通过将芳香组合物直接与芳香用品混合,即可将本发明的化合物用于芳香用品中,或者可以将所述化合物在先前的步骤中用截留材料截留(所述截留材料例如聚合物、胶囊、微胶囊和纳米胶囊、脂质体、成膜剂、吸收剂例如碳或沸石、环状低聚糖及其混合物),或者可以将所述化合物与基底化学键合(当施加外部刺激,例如光、酶等时,所述截留材料或者基底适于释放芳香分子),然后与用品混合,也可将本发明的化合物用于芳香用品中。
因此,本发明还提供了一种芳香用品的制备方法,包括使用常规工艺和方法,通过将通式I的化合物直接混合到用品中,或者通过混合含通式I化合物的芳香组合物、然后混合该芳香组合物到芳香用品中,从而将通式I的化合物掺入作为芳香成分。
本文所用的“芳香用品”是指任意产品,例如高级芳香剂,例如香水和化妆水;家用产品,例如洗碗机用洗涤剂、表面清洗剂;洗衣用产品,例如软化剂、漂白剂、洗涤剂;身体护理产品,例如洗发香波、洗浴凝胶;和美容品,例如除臭剂、粉底霜,其中包括增味剂。该系列产品是以说明方式给出的,不认为是以任何方式限制性的。
如方案1所示,通式I的化合物可以通过将通式III的苄基氰与相应的羰基化合物的缩合反应制备,其中R1、R2和R3具有与上面给出的相同含义。
方案1:
将苄基氰(III)溶解在过量的相应羰基化合物(II)中,然后加入碱,例如叔丁醇钾或氢氧化钾,和将所得混合物加热至50-100℃,优选50-70℃。通过本领域技术人员已知的标准提取工艺将反应产物(I)分离并通过在减压下蒸馏来进行纯化。
现在参照下面的非限制性实施例进一步描述本发明。
实施例1:3-甲基-2-苯基-丁-2-烯腈
将苄基氰(50.0g、0.43mol)溶解在丙酮(150ml)和甲醇(20ml)的混合物中,然后在搅拌下加入KOH(10g、0.15mol)。完全溶解之后,在90分钟内将棕色混合物加热至65℃(油浴)。在旋转蒸发器中浓缩混合物,将残余物溶解在甲苯中,和用半饱和NaCl水溶液洗涤3次。在MgSO4上干燥有机层,减压下除去溶剂,并在短程设备中在0.07mbar下蒸馏残余物。收集77℃下的馏分(33g)并在Widmer柱内进行精馏,获得31.3g(47%)的3-甲基-2-苯基-丁-2-烯腈,为无色油状物(沸点85℃/0.05mbar)。
13C-NMR:154.6(s),134.1(s),129.1(d),128.6(d),128.2(d),118.8(s),111,0(s),24.9(q),21.6(q).MS:157(100,[M]+),142(79),129(51),115(76).
气味描述:鲜花香、Rosacetol、清新、柑橘香、干草香、烟草味。
实施例2:(2E)-2-苯基-辛-2-烯腈
将钠(27.6g、1.2mol)溶解在甲醇(550ml)中并加入苄基氰(140.4g、1.2mol),接着在45分钟内滴加己醛(164.2g、1.44mol),将内部温度保持在20-25℃。室温下将该混合物进一步搅拌90分钟,然后用己烷萃取3次。依次用水、2N HCl水溶液和盐水洗涤有机层。在MgSO4上干燥有机层,减压下除去溶剂并在短程设备中在0.04mbar下蒸馏将残余物。收集114-121℃下的馏分(172g)并在Widmer柱内进行精馏,获得嗅觉纯的2-苯基-辛-2-烯腈(113g、44%),为无色油状物(沸点113-115℃/0.03mbar)。
13C-NMR:147.1(d),133.2(s),128.8(d),128.7(d),125.5(d), 116.5(s),115.7(s),32.0(t),31.2(t),28.2(t),22.3(t),13.8(q).MS:199(18, [M]+),184(3),170(4),156(3),143(15),124(100),115(35).
气味描述:清新、青香、茉莉香、水杨酸酯味。
实施例3:3-甲基-2-苯基-戊-2-烯腈
将丁酮(45.0g、0.63mol)加入到苄基氰(58.5g、0.50mol)和甲醇钠(30%于MeOH中、34.3ml、0.185mol)的混合物中,和将所得悬浮液加热至60℃(油浴)并在该温度下搅拌6h。产物用环己烷萃取,用稀NaHCO3溶液和盐水洗涤。在MgSO4上干燥有机层,减压下除去溶剂并在短程设备中在0.05mbar蒸馏残余物。收集90℃下的馏分(45g)并在Widmer柱内进行精馏,获得嗅觉纯的3-甲基-2-苯基-戊-2-烯腈(19g、22%),为无色油状物(沸点102℃/0.05mbar)。(E/Z)比约为55∶45。
13C-NMR:160.1/159.9(s),134.2/134.1(s),129.1/128.9(d),128.7/128.6(d),128.3/128.2(d),118.9/118.6(s),110.7/110.2(s),31.8/27.5(t),21.8/19.0(q),12.5/12.4(q).MS:171(50,[M]+),156(48),129(100),115(29).
气味描述:甜、鲜花香、青香、蜂蜜、水杨酸酯味、橙鲜花香。
实施例4:3-甲基-2-对甲苯基-丁-2-烯腈
将对甲苯基乙腈(18.5g、0.14mol)溶解在丙酮(50ml)和甲醇(6.7ml)的混合物中并加入KOH(3.33g、0.05mol)。将所得混合物加热至65℃(油浴)并搅拌3h。在旋转蒸发器中除去挥发物,将残余物溶解在甲苯中并用半饱和NaCl水溶液洗涤3次。在MgSO4上干燥有机层,减压下除去溶剂并短程设备中在0.06mbar下蒸馏残余物。收集77℃下的馏分(11g)并在Widmer柱内进行精馏,获得3.54g(15%)的3-甲基-2-对甲苯基-丁-2-烯腈,为无色油状物(沸点90-95℃/0.05mbar)。
13C-NMR:154.1(s),138.1(s),131.2(s),129.3(d),128.9(d),118.9(s),110.8(s),24.9(q),21.6(q),21.2(q).MS:171(100,[M]+),156(94),129(92),115(27).
气味描述:柑橘味、玫瑰香、水果香、薄荷味。
实施例5:3,7-二甲基-2-苯基-辛-2,6-二烯腈
向6-甲基-庚-5-烯-2-酮(90.86g、0.72mol)和苄基氰(46.8g、0.40mol)的混合物中滴加KOH在MeOH中的4N溶液(25.0ml、0.10mol)。在4.5h期间将所得悬浮液加热至回流。然后蒸馏除去甲醇并且依次用6N HCl水溶液、水、饱和NaHCO3水溶液和盐水洗涤残余物。在MgSO4上干燥有机层,减压下除去溶剂并在Widmer柱内蒸馏将残余物2次,获得3,7-二甲基-2-苯基-辛-2,6-二烯腈(21.5g、24%、(E/Z)混合物),为无色油状物(沸点122℃/0.1mbar)。
13C-NMR:158.3/158.1(s),134.3/134.1(s),133.3/133.1(s),129.1(2 d),128.7/128.6(d),128.2(2d),122.4(2d),118.9/118.7(s),111.4/111.2(s),38.6/34.3(t),26.6/26.2(t),25.7/25.6(q),22.2/19.7(q),17.7/17.5(q).MS:225(4,[M]+),157(52),140(7),128(11),115(15),69(100).
气味描述:鲜花香、蜂蜜、肉桂香、甜味。
实施例6:(2E)-5-甲基-2-苯基-己-2,4-二烯腈
将钠(9.2g、0.4mol)溶解在甲醇(130ml)中并加入苄基氰(46.8g、0.40mol),接着小心加入3-甲基-2-丁烯醛(40.3g、0.48)的甲醇(100ml)溶液。将所得悬浮液在室温下搅拌20h,然后按照实施例2中所述工序进行操作。用己烷结晶粗产物2次,获得5-甲基-2-苯基-己-2,4-二烯腈(44.9g、61%),沸点66-67℃。
13C-NMR:148.0(s),138.1(d),133.8(s),128.9(d),128.6(d),125.5(d),123.1(d),117.3(s),110.5(s),26.9(q),19.4(q).MS:183(31,[M]+),168(100),153(17),141(19),128(11),115(26)
气味描述:粉末、肉桂香、苯甲醛味道。
实施例7:2-(2-甲氧基-苯基)-3-甲基-丁-2-烯腈
按照实施例1所述的工序,使对甲氧基苄基氰(18.6g、127mmol)与丙酮(50ml)在加入甲醇(6.5ml)和KOH(3.33g、50mmol)的条件下进行缩合,加工并在106-110℃/0.05mbar下蒸馏之后,获得2-(2-甲氧基苯基)-3-甲基-丁-2-烯腈(1.7g、7%)。
13c-NMR:156.9(s),155.6(s),131.0(d),130.1(d),122.6(s),120.5(d),118.4(s),111.3(d),107.1(s),55.6(q),24.2(q),21.5(q).MS:187(100,[M]+),172(59),156(27),145(61),115(48).
气味描述:柑橘味、风信子香(hyacinthe)、香豆素味。
实施例8:2-(4-甲氧基-苯基)-3-甲基-丁-2-烯腈
按照实施例1所述的工序,将对甲氧基苄基氰(18.6g、127mmol)与丙酮(50ml)在加入甲醇(6.5ml)和KOH(3.33g、50mmol)的条件下进行缩合,在加工并于111-113℃/0.05mbar下蒸馏之后,获得2-(4-甲氧基苯基)-3-甲基-丁-2-烯腈(14.3g、18%)。
13C-NMR:159.3(s),153.7(s),130.3(d),126.4(s),119.0(s),114.0(d),110.4(s),55.3(q),24.8(q),21.5(q).MS:187(100,[M]+), 172(69),115(38).
气味描述:鲜花香、茴香味、甜。
实施例9:3-乙基-2-苯基-戊-2-烯腈
按照实施例1中所述的工序,通过使苄基氰与3-戊酮在有碱的情况下反应,制得标题化合物。
13C-NMR:165.5(s),134.2(s),128.9(d),128.7(d),128.2(d),118.7(s),110.2(s),28.2(t),24.6(t),12.8(q),12.5(q).MS:185(33,[M]+),170(11),156(18),143(67),129(100),115(32).
气味描述:青香、鲜花香、玫瑰香。
实施例10:香味评价。
按照本领域技术人员已知的标准工序,在配备有鼻吸口的气相色谱仪上由经过培训的专家小组来确定挥发性香料化合物的阈值。将每个人闻到的最后浓度记录为个人阈值,以ng表示(在鼻吸口释放的化合物的绝对量)。由相同专家小组来评价所有化合物。在同一天评价饱和及不饱和化合物。结果列于表1。
表1:
实施例11:洗发香波用芳香组合物的制备
组分 重量份
苯乙醇 80
正癸醛 5
10-癸烯醇 5
月桂醛 5
麝香内酯 65
Bergamote Base 130
巴西酸亚乙酯 250
香茅醇 50
Georgywood 18
香叶醇 50
Iso E Super 160
铃兰醛 150
衣兰精油 16
二丙二醇 16
合计 1000
用16重量份实施例1的3-甲基-2-苯基-丁-2-烯腈代替该配方中的二丙二醇提高了它的鲜花香-玫瑰香特征,和使其闪光且更有亲和性。
Claims (6)
2、权利要求1的化合物的用途,所述化合物选自3-甲基-2-苯基-丁-2-烯腈、3-乙基-2-苯基-戊-2-烯腈、(2E)-2-苯基-辛-2-烯腈、3-甲基-2-苯基-戊-2-烯腈、3-甲基-2-对甲苯基-丁-2-烯腈、3,7-二甲基-2-苯基-辛-2,6-二烯腈、(2E)-5-甲基-2-苯基-己-2,4-二烯腈、2-(2-甲氧基-苯基)-3-甲基-丁-2-烯腈和2-(3-甲氧基-苯基)-3-甲基-丁-2-烯腈。
3、一种芳香组合物,含有权利要求1或2中定义的通式I的化合物。
4、一种制备芳香组合物的方法,包括将权利要求1或2中定义的通式I的化合物掺入到基料中的步骤。
5、一种增强或改善香调或者赋予芳香用品新香调的方法,包括将权利要求1或2中定义的通式I的化合物掺入到基料中的步骤。
6、权利要求5的方法,其中所述芳香用品选自香水、家用产品、洗衣用产品、身体护理用产品和美容品。
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CN107532111A (zh) * | 2015-04-23 | 2018-01-02 | 弗门尼舍有限公司 | 桂花气味剂 |
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CN107532111A (zh) * | 2015-04-23 | 2018-01-02 | 弗门尼舍有限公司 | 桂花气味剂 |
CN107532111B (zh) * | 2015-04-23 | 2020-11-27 | 弗门尼舍有限公司 | 桂花气味剂 |
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