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CN108203395B - 感官化合物 - Google Patents

感官化合物 Download PDF

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CN108203395B
CN108203395B CN201711336651.8A CN201711336651A CN108203395B CN 108203395 B CN108203395 B CN 108203395B CN 201711336651 A CN201711336651 A CN 201711336651A CN 108203395 B CN108203395 B CN 108203395B
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CN108203395A (zh
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B·阿莫雷里
I·阿梅戈尔
M·G·蒙特莱昂
V·克兰德里亚
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International Flavors and Fragrances Inc
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Abstract

本发明涉及新型化合物及其作为香味材料的用途。

Description

感官化合物
相关申请状态
本申请要求2016年12月20日提交的美国临时专利申请号62/436,523的优先权，其全部内容在此通过引用并入本文。
发明领域
本发明涉及新的化学实体及其作为香味材料的包封和用途。
发明背景
在香味工业中始终需要提供新的化学物质，以赋予调香师和其他人为香水、古龙水和个人护理产品创造新的香味的能力。本领域技术人员理解分子化学结构中的差异如何导致在气味、香调(notes)和分子特性上产生显著差异。这些变化以及在开发新香味中发现和使用新化学品的持续需求使得调香师能够应用新化合物来创造新的香味。
发明概述
本发明提供了新型化合物及其在增强、改善或修饰香水、古龙水、花露水、织物护理产品、个人产品等中的香味的意想不到的有益用途。
具体而言，本发明涉及新型的由如下式I表示的甲氧基苯基丁酰胺化合物：
Figure GDA0003629374220000011
其中R选自甲基和乙基组成的组。
本发明的另一个实施方式涉及一种包含上述新型化合物的香味制剂。
本发明的另一个实施方式涉及一种包含上述化合物的香味产品。
本发明的另一个实施方式涉及一种通过添加嗅觉可接受量的上述新型化合物来改善、增强或修饰香味制剂的方法。
通过阅读以下的说明书，本发明的这些和其他实施方式将是显而易见的。
发明详述
例如通过以下实施例来说明本发明的由式I表示的甲氧基苯基丁酰胺化合物。
N-(3-甲氧基苯基)-N,2-二甲基丁酰胺
Figure GDA0003629374220000021
结构1
2-乙基-N-(3-甲氧基苯基)-N-甲基丁酰胺
Figure GDA0003629374220000022
结构2
本领域技术人员将认识到，取决于可得的起始材料，本发明的化合物具有多个异构体如位置异构体。本文旨在说明，本文描述的化合物既包括异构体混合物，也包括通过本领域技术人员已知的技术分离的单个异构体。合适的技术包括色谱法，如高效液相色谱法(称为HPLC)，特别是硅胶色谱，以及气相色谱法捕集(称为GC捕集)。此外，市售产品大多数以异构体混合物形式提供。
本发明的化合物的制备在实施例中进行详细说明。原料均购自Aldrich ChemicalCompany，除非另有说明。
本发明的化合物的用途广泛适用于目前的加香产品，包括香水与古龙水的制备、个人护理产品(如香皂、沐浴露和护发产品)、织物护理产品以及空气清新剂和化妆品制剂的加香。本发明还可用于加香清洁剂，例如但不限于洗涤剂、洗碗剂(dishwashingmaterials)、去污组合物(scrubbing compositions)和窗户清洁剂等。
在这些制剂中，本发明的化合物可以单独使用或与其它加香组合物、溶剂和佐剂等结合使用。也可使用的其它成分的性质与种类是本领域技术人员已知的。许多类型的香味材料可用于本发明，唯一的限制是其与所使用的其它组分的相容性。合适的香味包括但不限于果香如来自杏仁、苹果、樱桃、葡萄、梨、菠萝、橙子、草莓、覆盆子；麝香等；以及花香如薰衣草样、玫瑰样、鸢尾样、康乃馨样。其它令人愉悦的气味包括衍生自松树、云杉和其它林木气味的草药和林地气味。香味还可以衍生自各种油(如精油)或衍生自植物材料(如薄荷和留兰香等)。
在美国专利号4,534,891中提供了合适的香味材料的列表，其列举的内容在此通过引用全文并入本文。合适的香味的另一来源可以在W.A.Poucher编辑的Perfumes,Cosmetics and Soaps,第二版,1959中找到。该论文中提供的香味材料包括刺槐、黑醋栗、素心兰、仙客来、蕨、栀子、山楂、天芥菜、金银花、风信子、茉莉、丁香、百合、玉兰花、含羞草、水仙、新鲜切割的干草、橙花、兰花、木犀草、香豌豆、三叶草、晚香玉、香草、紫罗兰和桂竹等。
本发明的化合物可以与互补的香味化合物组合使用。本文中使用的术语“互补的香味化合物”定义为选自由如下香味化合物组成的组：2-[(4-甲基苯基)亚甲基]-庚醛(Acalea)、异戊氧基乙酸烯丙酯(格蓬酯(Allyl Amyl Glycolate))、(3,3-二甲基环己基)乙基乙基丙烷-1,3-二酸酯(Applelide)、(E/Z)-1-乙氧基-1-癸烯(Arctical)、2-乙基-4-(2,2,3-三甲基-3-环戊烯-1-基)-2-丁烯-1-醇(白檀醇(Bacdanol))、2-甲基-3-[(1,7,7-三甲基双环[2.2.1]庚-2-基)氧基]外-1-丙醇(Bornafix)、1,2,3,5,6,7-六氢-1,1,2,3,3-五甲基-4H-茚-4-酮(开司米酮(Cashmeran))、三甲基环戊烯基甲基氧杂二环辛烷(Cassiffix)、1,1-二甲氧基-3,7-二甲基-2,6-辛二烯(柠檬醛DMA)、3,7-二甲基-6-辛烯-1-醇(香茅醇(Citronellol))、3A,4,5,6,7,7A-六氢-4,7-桥亚甲基-1H-茚-5/6-基乙酸酯(乙酸三环癸烯酯(Cyclacet))、3A,4,5,6,7,7A-六氢-4,7-桥亚甲基-1H-茚-5/6-基丙酸酯(Cyclaprop)、3A,4,5,6,7,7A-六氢-4,7-桥亚甲基-1G-茚-5/6-基丁酸酯(环丁烷(Cyclobutanate))、1-(2,6,6-三甲基-3-环己烯-1-基)-2-丁烯-1-酮(丁位突厥酮(DeltaDamascone))、3-(4-乙基苯基)-2,2-二甲基丙腈(Fleuranil)、3-(O/P-乙基苯基)2,2-二甲基丙醛(海风醛(Floralozone))、四氢-4-甲基-2-(2-甲基丙基)-2H-吡喃-4-醇(Floriffol)、1,3,4,6,7,8-六氢-4,6,6,7,8,8-六甲基环戊-γ-2-苯并吡喃(加乐麝香(Galaxolide))、1-(5,5-二甲基-1-环己烯-1-基)戊-4-烯-1-酮(Galbascone)、E/Z-3,7-二甲基-2,6-辛二烯-1-基乙酸酯(乙酸香叶酯(Geranyl Acetate))、α-甲基-1,3-苯并二氧杂环戊烯-5-丙醛(新洋茉莉醛(Helional))、1-(2,6,6-三甲基-2-环己烯-1-基)-1,6-庚二烯-3-酮(Hexalon)、(Z)-3-己烯基-2-羟基苯甲酸酯(柳酸叶醇酯(Hexenyl Salicylate)，CIS-3)、4-(2,6,6-三甲基-2-环己烯-1-基)-3-丁烯-2-酮(α-紫罗兰酮(Iononeα))、1-(1,2,3,4,5,6,7,8-八氢-2,3,8,8-四甲基-2-萘基)-乙-1-酮(Iso E Super)、甲基-3-氧代-2-戊基环戊烷乙酸甲酯(Kharismal)、2,2,4-三甲基-4-苯基-丁腈(Khusinil)、3,4,5,6,6-五甲基庚-3-烯-2-酮(Koavone)、3/4-(4-羟基-4-甲基-戊基)环己烯-1-甲醛(Lyral)、3-甲基-4-(2,6,6-三甲基-2-环己烯-1-基)-3-丁烯-2-酮(γ-甲基紫罗兰酮(Methyl Iononeγ))、1-(2,6,6-三甲基-2-环己烯-1-基)戊-1-烯-3-酮(α-甲基紫罗兰酮额外(MethylIononeαExtra)，甲基紫罗兰酮N(Methyl Ionone N))、3-甲基-4-苯基丁-2-醇(Muguesia)、环十五碳-4-烯-1-酮(Musk Z4)、3,3,4,5,5-五甲基-11,13-二氧杂三环[7.4.0.0<2,6>]十三碳-2(6)-烯(Nebulone)、3,7-二甲基-2,6-辛二烯-1-基乙酸酯(橙花醇乙酸酯(NerylAcetate))、3,7-二甲基-1,3,6-辛三烯(罗勒烯(Ocimene))、邻甲苯基乙醇(Peomosa)、3-甲基-5-苯基戊醇(苯基异己醇(Phenoxanol))、1-甲基-4-(4-甲基-3-戊烯基)环己-3-烯-1-甲醛(Precyclemone B)、4-甲基-8-亚甲基-2-金刚烷醇(Prismantol)、2-乙基-4-(2,2,3-三甲基-3-环戊烯-1-基)-2-丁烯-1-醇(Sanjinol)、2-甲基-4-(2,2,3-三甲基-3-环戊烯-1-基)-2-丁烯-1-醇(Santaliff)、萜品醇、2,4-二甲基-3-环己烯-1-甲醛(女贞醛(Triplal))、十氢-2,6,6,7,8,8-六甲基-2H-茚并[4,5-B]呋喃(Trisamber)、2-叔丁基环己乙酸酯(Verdox)、4-叔丁基环己乙酸酯(醋酸对叔丁基环己酯(Vertenex))、乙酰基柏木烯(甲基柏木酮(Vertofix))、3,6/4,6-二甲基环己-3-烯-1-甲醛(Vertoliff)和(3Z)-1-[(2-甲基-2-丙烯基)氧基]-3-己烯(Vivaldie)。
术语“烷基”指直链或支链的饱和单价烃基，例如甲基、乙基、丙基、2-丙基、丁基(包括所有异构形式)、戊基(包括所有异构形式)、己基(包括所有异构形式)等。术语“烯基”指含有至少一个碳-碳双键的直链或支链的不饱和的脂族烃基。术语“亚烷基”指二价烷基。实例包括–CH2–、–CH2CH2–、–CH2CH2CH2–、–CH2(CH3)CH2–和–CH2CH2CH2CH2–等。
术语“香味制剂(fragrance formulation)”、“香味组合物(fragrancecomposition)”和“加香组合物(perfume composition)”含义相同，指的是作为包括例如醇类、醛类、酮类、酯类、醚类、内酯类、腈类、天然油、合成油和硫醇类的化合物的混合物的消费品组合物(consumer composition)，这些化合物被混合以使得单个组分的混合气味产生令人愉悦或所需的香味。本发明的香味制剂是包含本发明的化合物的消费品组合物。本发明的香味制剂包含本发明的化合物，并且进一步包含如上定义的互补的香味化合物。
术语“香味产品“指的是含有添加香味或掩蔽臭味的香味成分的消费产品。香味产品可包括例如香水；古龙水；香皂；液体皂；沐浴露；泡泡浴；化妆品；护肤品，如霜剂、乳液和剃须产品；护发产品，如洗发剂、清洗剂、调理剂、漂白剂、着色剂、染色剂、定型剂；除臭剂和止汗剂；女性护理产品，如卫生棉条和妇女卫生巾；婴儿护理产品，如尿布、围兜和湿巾；家庭护理产品，如卫生纸(bath tissues)、面巾纸、手帕纸(paper handkerchiefs)或擦手纸(paper towels)；织物产品如织物柔软剂和织物清香剂；空气护理产品如空气清新剂和香味递送体系；化妆品制剂；清洁剂和消毒剂如洗涤剂、洗碗剂、去污组合物；玻璃和金属清洁剂，如窗户清洁剂；台面清洁剂；地板和地毯清洁剂；厕所清洁剂和漂白添加剂；洗涤剂如多用途洗涤剂、重型洗涤剂、和手洗或精细织物洗涤剂，包括衣物洗涤剂和漂洗添加剂；牙科和口腔卫生产品，如牙膏、牙胶、牙线、义齿清洁剂、义齿粘合剂、牙粉、牙齿美白和漱口水；健康护理和营养产品以及食品，如小吃和饮料产品。本发明的香味产品是含有本发明的化合物的消费产品。本发明的香味产品含有本发明的化合物并且还含有如上所定义的补充香味化合物。
短语“改善、增强或修饰香味制剂”中的术语“改善”理解为将香味制剂提升至更合意的特征(character)。术语“增强”理解为使香味制剂效力提升或为所述香味制剂提供改善的特征。术语“修饰”理解为为香味制剂提供特征上的变化。
术语“嗅觉可接受量”理解为香味制剂中化合物贡献其个别的嗅觉特性的量。然而，香味制剂的嗅觉效果将是香味成分各自效果的总和。由此本发明的化合物可用于改善或增强香味制剂的香气特征，或通过修饰香味制剂中另一成分所贡献的嗅觉反应来修饰香味制剂的香气特征。该嗅觉可接受量随着许多因素如其它成分、它们的相对量和所需嗅觉效果而改变。
在香味制剂中使用的本发明的化合物的量为大约0.005至大约70重量％、优选大约0.005至大约50重量％、更优选大约0.5至大约25重量％和甚至更优选大约1至大约10重量％不等。本领域技术人员能够使用所需量以提供所需香味效果和强度。除了本发明的化合物之外，其它物质或材料也可与香味制剂组合使用以包封和/或递送香味。公知的物质或材料例如但不限于聚合物；低聚物；其它非聚合物如表面活性剂、乳化剂；脂质包括脂肪、蜡和磷脂；有机油；矿物油；凡士林；天然油；香味固定剂；纤维；淀粉；糖和固体表面材料，例如沸石和二氧化硅。一些优选的聚合物包括聚丙烯酸酯、聚脲、聚氨酯、聚丙烯酰胺、聚酯、聚醚、聚酰胺、聚(丙烯酸酯-共-丙烯酰胺)、淀粉、二氧化硅、明胶和阿拉伯树胶、藻酸盐、壳聚糖、聚交酯、聚(三聚氰胺-甲醛)、聚(脲-甲醛)或其组合。
当用在香味制剂中时，这些成分提供额外的香调，使得该香味制剂更合意和引人注意，并增加了感知价值。在这些材料中发现的气味品质有助于美化和提高成品，协同改善了该香味中其它材料的性能。
另外，还令人惊讶地发现本发明的化合物提供优良的成分性能并在恶臭冲消应用如对身体汗液，环境气味如黑霉(mold)和白霉(mildew)，以及浴室等方面具有出乎意料的优点。本发明的化合物基本上消除了恶臭的感知和/或防止这样的恶臭形成，因此其可以用于众多的功能性产品中。
在此提供功能性产品的实例以说明本发明的各个方面。然而，其不意欲限制本发明的范围。功能性产品可以包括例如常规的房间清新剂(或除臭剂)组合物，如房间清新剂喷雾剂、气雾剂或其它喷雾剂；香味扩散剂；芯或其它液体系统，或固体，例如如香盒或塑料中的蜡烛或蜡碱；香袋或干喷雾剂中的粉末或如在固体凝胶棒中的凝胶；如洗衣机应用中使用的衣物除臭剂，如洗涤剂、粉末、液体、增白剂或织物柔软剂、织物清新剂、亚麻喷雾剂；应用在壁橱(closet blocks)、壁橱气溶胶喷雾剂(closet aerosol sprays)、或衣服存储区域中或应用在干洗中以克服衣服上残留的溶剂样香调；浴室配件如擦手纸、卫生纸、卫生巾、湿巾、一次性洗布、一次性尿布和尿布桶除臭剂；清洁剂如消毒剂和抽水马桶清洁剂；化妆品如止汗剂和除臭剂；粉剂、气雾剂、液体或固体形式的一般身体除臭剂；或头发护理产品如发胶、调理剂、冲洗剂、头发着色剂和染色剂、烫发剂、脱毛剂、直发剂；理发应用(hairgroom applications)如润发油、霜剂和乳液；含有如二硫化硒、煤焦油或水杨酸盐等成分的含药护发产品或洗发剂；或足部护理产品如爽足粉、液体或古龙水；须后水和身体乳液；或香皂和合成洗涤剂如皂条、液体、泡沫或粉末；气味控制如制造过程中，例如纺织整理业和印刷业(油墨和纸)中的气味控制；流出物控制如涉及制浆、畜牧场和肉类处理工艺中的流出物控制；污水处理；垃圾袋或垃圾处置；或者产品的气味控制，如纺织制成品、橡胶制成品或汽车空气清新剂；农业和宠物护理产品，如狗和鸡舍的废水以及家畜和宠物护理产品，如除臭剂，洗发剂或清洁剂；或动物用卫生砂材料和在大规模封闭式系统，如礼堂、地铁和运输系统中的气味控制。
因此，可以看出，本发明的组合物通常是其中恶臭冲消剂与载体一起存在的组合物，利用该载体或通过该载体所述恶臭冲消剂可以被引入到其中存在恶臭的空气空间内，或引入到其上沉积有恶臭的基底。例如，载体可以是气溶胶推进剂如氯氟甲烷，或固体如蜡、塑料材料、橡胶、惰性粉末或凝胶。在芯型空气清新剂中，载体是低挥发性的基本上无味的液体。在一些应用中，本发明的组合物含有表面活性剂或消毒剂，而在其它应用中，恶臭冲消剂存在于纤维基底上。在本发明的许多组合物中也存在香味组分，其赋予组合物香味。可以采用所有的上述香味。
恶臭冲消有效量应理解为功能性产品中采用的本发明的恶臭冲消剂在感官有效地消减给定的恶臭同时降低气味水平的组合强度方面的量，其中给定的恶臭是存在于空气空间中或已沉积于基底上。所采用的恶臭冲消剂的确切量可以随着恶臭冲消剂的类型、所采用的载体类型和所期望的恶臭冲消剂的水平而变化。在一般情况下，存在的恶臭冲消剂的量是获得希望结果所需要的普通剂量。这种剂量是本领域技术人员所熟知的。在一个优选的实施方式中，当与恶臭固体或液体功能性产品如香皂和洗涤剂结合使用时，本发明的化合物可以以约0.005至约50wt％、优选约0.01至约20wt％和更优选约0.05至约5wt％的量存在，并且当与恶臭的气态功能性产品结合使用时，本发明的化合物可以以每立方米空气约0.1至10毫克的量存在。
作为本发明的具体实施方式提供以下内容。本发明的其它修改对本领域技术人员将是显而易见的。此类修改理解为在本发明的范围内。除非另行说明，本文中所用的所有百分比是重量百分比，ppm理解为表示每百万份的份数，L理解为升，mL理解为毫升，g理解为克，Kg理解为千克，mol理解为摩尔，mmol理解为毫摩尔，psig理解为每平方英寸的磅力，以及mmHg理解为汞(Hg)的毫米数(mm)。实施例中使用的IFF是指International Flavors&Fragrances Inc.,New York,NY,USA。
具体实施方式
实施例I
Figure GDA0003629374220000081
2-乙基-N-(3-甲氧基苯基)-N-甲基丁酰胺(结构2)的制备：将2-乙基丁酰氯(8.15g)的四氢呋喃(THF)(10mL)溶液在0℃下滴加到甲胺(60.5mL，2M)的THF溶液中。将混合物在室温下老化2小时，然后浓缩。将残余物溶于乙酸乙酯(CH3COOC2H5)(50mL)中并用碳酸钠(Na2CO3)水溶液洗涤。将有机层用硫酸钠(Na2SO4)干燥，过滤并浓缩，得到粗品2-乙基-N-甲基丁酰胺。在配备有搅拌棒的1打兰小瓶中，加入碳酸钾(K2CO3)(296mg，2.14mmol)、碘化铜(I)(CuI)(10.2mg，0.053mmol)和上述步骤中获得的粗品2-乙基-N-甲基丁酰胺(166mg，1.28mmol)，接着加入1-溴-3-甲氧基苯(200mg，1.07mmol)，二噁烷(C4H8O2)(5mL)和(1R,2R)-N1,N2-二甲基环己烷-1,2-二胺(C8H18N2)(15.2mg，0.107mmol)。将小瓶密封并加热至100℃保持15小时。然后将反应混合物冷却至环境温度，通过二氧化硅(SiO2)垫(1.5×1.5cm，用二氯甲烷洗脱)过滤。将滤液真空浓缩并通过快速色谱法(硅胶，乙酸乙酯(EtOAc)/己烷5％至20％梯度)纯化，得到白色粉末状的2-乙基-N-(3-甲氧基苯基)-N-甲基丁酰胺(98mg)。
1H NMR(500MHz,CDCl3):7.30(dd,J＝8.4,7.7Hz,1H),6.87(dd,J＝8.4,2.2Hz,1H),6.75(d,J＝7.7Hz,1H),6.66-6.71(m,1H),3.81(s,3H),3.26(s,3H),2.17-2.28(m,1H),1.53-1.69(m,2H),1.30-1.44(m,2H),0.81(t,J＝7.4Hz,6H)。
2-乙基-N-(3-甲氧基苯基)-N-甲基丁酰胺被描述为具有新鲜、多汁、黑醋栗样以及葡萄柚样和甜番石榴样的香调。葡萄柚样的香调呈清新而带酸感。番石榴样的香调为清新的、成熟的、甜香的、有活力的和自然的。
实施例II
类似地制备了以下化合物。
N-(3-甲氧基苯基)-N,2-二甲基丁酰胺(结构1)
Figure GDA0003629374220000091
1H NMR(400MHz,CDCl3):7.33(dd,J＝8.1,8.1Hz,1H),6.90(dd,J＝8.1,1.9Hz,1H),6.75-6.81(m,1H),6.72(dd,J＝2.2,2.2Hz,1H),3.84(s,3H),3.27(s,3H),2.27-2.45(m,1H),1.61-1.86(m,1H),1.21-1.41(m,1H),1.04(d,J＝6.7Hz,3H),0.81(t,J＝7.4Hz,3H)
2-乙基-N-(3-甲氧基苯基)丁烷-1-亚胺(结构3)
Figure GDA0003629374220000092
1H NMR(400MHz,CDCl3):7.65(d,J＝6.7Hz,1H),7.25(dd,J＝8.4,7.3Hz,1H),6.76(ddd,J＝8.4,2.5,1.0Hz,1H),6.59-6.67(m,2H),3.83(s,3H),2.21-2.34(m,1H),1.53-1.69(m,4H),0.99(t,J＝7.5Hz,6H)
2-乙基-N-(3-甲氧基苯基)丁酰胺(结构4)
Figure GDA0003629374220000101
1H NMR(400MHz,CDCl3):7.42(s,1H),7.26-7.36(m,1H),7.22(dd,J＝8.1,8.1Hz,1H),6.99(br d,J＝7.9Hz,1H),6.68(dd,J＝8.3,1.6Hz,1H),3.82(s,3H),1.97-2.18(m,1H),1.67-1.85(m,2H),1.49-1.67(m,2H),0.98(t,J＝7.5Hz,6H)
N-(3-甲氧基苯基)-N-甲基丁-2-烯酰胺(结构5)
Figure GDA0003629374220000102
1H NMR(400MHz,CDCl3):6.81-7.33(m,4H),6.62-6.68(m,1H),5.94-6.00(m,1H),3.82(s,3H),3.32(s,3H)1.89(dd,J＝6.8,1.7Hz,3H)
N-(3-甲氧基苯基)-N-甲基异丁酰胺(结构6)
Figure GDA0003629374220000103
1H NMR(400MHz,CDCl3):7.34(dd,J＝8.1,8.1Hz,1H),6.88-6.94(m,1H),6.77-6.83(m,1H),6.74(dd,J＝2.2,2.2Hz,1H),3.84(s,3H),3.26(s,3H),2.48-2.70(m,1H),1.06(d,J＝6.7Hz,6H)
N-(3-甲氧基苯基)-N-甲基环丙烷甲酰胺(结构7)
Figure GDA0003629374220000104
1H NMR(400MHz,CDCl3):7.33(dd,J＝8.0,8.0Hz,1H),6.85-6.92(m,2H),6.81-6.85(m,1H),3.84(s,3H),3.29(s,3H),1.39-1.53(m,1H),0.94-1.09(m,2H),0.56-0.71(m,2H)
N-(3-甲氧基苯基)-N-甲基戊-4-烯酰胺(结构8)
Figure GDA0003629374220000111
1H NMR(400MHz,CDCl3):7.33(dd,J＝8.1,8.1Hz,1H),6.89(dd,J＝8.3,2.1Hz,1H),6.76-6.81(m,1H),6.72(dd,J＝2.1,2.1Hz,1H),5.63-5.85(m,1H),4.78-5.07(m,2H),3.83(s,3H),3.26(s,3H),2.30-2.40(m,2H),2.14-2.27(m,2H)
N-(3-甲氧基苯基)-N,2-二甲基丁-2-烯酰胺(结构9)
Figure GDA0003629374220000112
1H NMR(400MHz,CDCl3):7.23(dd,J＝8.1,8.1Hz,1H),6.77(ddd,J＝8.3,2.5,0.8Hz,1H),6.68-6.74(m,1H),6.62-6.68(m,1H),5.72-5.84(m,1H),3.80(s,3H),3.34(s,3H),1.59-1.62(m,3H),1.52(dd,J＝6.9,1.1Hz,3H)
N-(3-甲氧基苯基)-N,3-二甲基丁-2-烯酰胺(结构10)
Figure GDA0003629374220000113
1H NMR(400MHz,CDCl3):7.27-7.31(m,1H),6.85(ddd,J＝8.4,2.5,0.7Hz,1H),6.75-6.80(m,1H),6.71-6.73(m,1H),5.51-5.57(m,1H),3.83(s,3H),3.31(s,3H),2.15(d,J＝1.1Hz,3H),1.71(d,J＝0.9Hz,3H)
N-(3-甲氧基苯基)-N-甲基环戊烷甲酰胺(结构11)
Figure GDA0003629374220000121
1H NMR(500MHz,CDCl3):6.59-7.36(m,4H),3.83(s,3H),3.25(s,3H),2.52-2.75(m,1H),1.33-2.05(m,8H)
2-乙基-N-(3-甲氧基苯基)-N-甲基己酰胺(结构12)
Figure GDA0003629374220000122
1H NMR(500MHz,CDCl3):7.30(dd,J＝8.2,8.2Hz,1H),6.87(dd,J＝8.2,2.1Hz,1H),6.72-6.78(m,1H),6.69(dd,J＝2.1,2.1Hz,1H),3.81(s,3H),3.26(s,3H),2.27(tt,J＝8.4,5.5Hz,1H),1.04-1.67(m,8H),0.74-0.87(m,6H)
(3-甲氧基苯基)(甲基)氨基甲酸乙酯(结构13)
Figure GDA0003629374220000123
1H NMR(400MHz,CDCl3):7.23-7.30(m,1H),6.82-6.90(m,2H),6.78(ddd,J＝8.3,2.5,0.9Hz,1H),4.19(q,J＝7.0Hz,2H),3.82(s,3H),3.31(s,3H),1.26(t,J＝7.1Hz,3H)
N,2-二乙基-N-(3-甲氧基苯基)丁酰胺(结构14)
Figure GDA0003629374220000124
1H NMR(500MHz,CDCl3):7.31(dd,J＝8.1,8.1Hz,1H),6.89(br d,J＝8.1Hz,1H),6.74(br d,J＝8.1Hz,1H),6.65-6.69(m,1H),3.82(s,3H),3.75(q,J＝6.9Hz,2H),2.04-2.26(m,1H),1.53-1.65(m,2H),1.36(dt,J＝13.6,6.8Hz,2H),1.13(t,J＝7.1Hz,3H),0.82(t,J＝7.4Hz,6H)
2-乙基-N-(2-甲氧基苯基)-N-甲基丁酰胺(结构15)
Figure GDA0003629374220000131
1H NMR(500MHz,CDCl3):7.28-7.41(m,1H),7.14(dd,J＝7.7,1.7Hz,1H),6.86-7.03(m,2H),3.81(s,3H),3.19(s,3H),1.93-2.08(m,1H),1.48-1.68(m,2H),1.22-1.44(m,2H),0.81(t,J＝7.4Hz,3H),0.74(t,J＝7.4Hz,3H)
N,2-二乙基-N-(2-甲氧基苯基)丁酰胺(结构16)
Figure GDA0003629374220000132
1H NMR(500MHz,CDCl3):7.30-7.35(m,1H),7.10(dd,J＝7.6,1.6Hz,1H),6.93-7.00(m,2H),4.01(dq,J＝13.8,7.1Hz,1H),3.80(s,3H),3.37(dq,J＝13.8,7.1Hz,1H),1.93(tt,J＝7.7,5.8Hz,1H),1.49-1.69(m,2H),1.23-1.44(m,2H),1.07(t,J＝7.3Hz,3H),0.80(t,J＝7.4Hz,3H),0.74(t,J＝7.6Hz,3H)
2-乙基-N-(4-甲氧基苯基)丁酰胺(结构17)
Figure GDA0003629374220000133
1H NMR(400MHz,CDCl3):7.50(br s,1H),7.46(m,2H),6.85(m,2H),3.79(s,3H),2.04(m,1H),1.72(m,2H),1.55(m,2H),0.96(t,J＝7.4Hz,6H)
2-乙基-N-(4-甲氧基苯基)-N-甲基丁酰胺(结构18)
Figure GDA0003629374220000141
1H NMR(500MHz,CDCl3):7.07(m,2H),6.92(m,2H),3.84(s,3H),3.25(s,3H),2.19(m,1H),1.60(m,2H),1.36(m,2H),0.81(t,J＝7.5Hz,6H)
实施例III
Figure GDA0003629374220000142
N-(2,5-二甲基苯基)-2-乙基-N-甲基己酰胺(结构27)的制备：在装有搅拌棒的1打兰小瓶中加入碳酸钾(K2CO3)(296mg，2.14mmol)、碘化铜(I)(CuI)(10.2mg，0.053mmol)和2-乙基-N-甲基己酰胺(202mg，1.28mmol)，随后加入2-溴-1,4-二甲基苯(198mg，1.07mmol)、二噁烷(C4H8O2)(5mL)和(1R,2R)-N1,N2-二甲基环己烷-1,2-二胺(C8H18N2)(15.2mg，0.107mmol)。将小瓶密封并加热至100℃保持15小时。然后将反应混合物冷却至环境温度，通过二氧化硅(SiO2)垫(1.5×1.5cm，用二氯甲烷洗脱)过滤。将滤液真空浓缩并通过快速色谱法(硅胶，乙酸乙酯(EtOAc)/己烷5％至20％梯度)纯化，得到N-(2,5-二甲基苯基)-2-乙基-N-甲基己酰胺，为无色油状物(168mg)。
1H NMR(400MHz,CDCl3):7.18(d,J＝7.8Hz,1H),7.08(dd,J＝7.8,1.1Hz,1H),6.92(d,J＝1.1Hz,1H),3.19(s,3H),2.34(s,3H),2.21(s,3H),1.94-2.09(m,1H),1.52-1.68(m,2H),1.30-1.49(m,2H),1.06-1.25(m,4H),0.74-0.91(m,6H)
实施例IV
类似地制备以下化合物。
N-(2,5-二甲基苯基)-2-乙基丁-1-亚胺(结构19)
Figure GDA0003629374220000151
1H NMR(500MHz,CDCl3):7.51(d,J＝6.3Hz,1H),7.05(d,J＝7.6Hz,1H),6.89(d,J＝7.6Hz,1H),6.53(s,1H),2.32(s,3H),2.23(s,3H),2.20-2.36(m,1H),1.58-1.65(m,4H),1.00(t,J＝7.4Hz,6H)
2-乙基-N-甲基-N-(间甲苯)丁酰胺(结构20)
Figure GDA0003629374220000152
1H NMR(400MHz,CDCl3):7.24-7.34(m,1H),7.14(d,J＝7.5Hz,1H),6.90-7.03(m,2H),3.27(s,3H),2.38(s,3H),2.13-2.27(m,1H),1.52-1.70(m,2H),1.26-1.45(m,2H),0.81(t,J＝7.5Hz,6H)
2-乙基-N-甲基-N-(邻甲苯)丁酰胺(结构21)
Figure GDA0003629374220000153
1H NMR(500MHz,CDCl3):7.16-7.33(m,3H),7.08(dd,J＝7.6,1.3Hz,1H),3.16(s,3H),2.23(s,3H),1.87-1.97(m,1H),1.57(dq,J＝14.0,7.2Hz,2H),1.28-1.47(m,2H),0.77(td,J＝7.4,2.5Hz,6H)
N-(2,5-二甲基苯基)-N-甲基异丁酰胺(结构22)
Figure GDA0003629374220000161
1H NMR(400MHz,CDCl3):7.19(d,J＝7.8Hz,1H),7.09(dd,J＝7.8,1.1Hz,1H),6.94(d,J＝1.1Hz,1H),3.18(s,3H),2.35(s,3H),2.28-2.39(m,1H),2.19(s,3H),1.04(dd,J＝6.7,4.8Hz,6H)
N-(2,5-二甲基苯基)-N-甲基环丙烷甲酰胺(结构23)
Figure GDA0003629374220000162
1H NMR(500MHz,CDCl3):7.17(d,J＝7.9Hz,1H),7.07(d,J＝7.9Hz,1H),7.02(s,1H),3.19(s,3H),2.34(s,3H),2.22(s,3H),1.16-1.32(m,1H),0.91-1.02(m,2H),0.50-0.66(m,2H)
N-(2,5-二甲基苯基)-N-甲基戊-4-烯酰胺(结构24)
Figure GDA0003629374220000163
1H NMR(400MHz,CDCl3):7.15-7.21(m,1H),7.09(dd,J＝7.8,1.1Hz,1H),6.92(d,J＝1.1Hz,1H),5.75(ddt,J＝17.0,10.3,6.6Hz,1H),4.85-5.04(m,2H),3.18(s,3H),2.28-2.40(m,2H),2.34(s,3H),2.18(s,3H),2.07-2.17(m,1H),1.91-2.03(m,1H)
N-(2,5-二甲基苯基)-N,3-二甲基丁-2-烯胺(结构25)
Figure GDA0003629374220000164
1H NMR(500MHz,CDCl3):7.06(d,J＝7.9Hz,1H),6.94-7.01(m,1H),6.83(s,1H),5.17-5.38(m,1H),3.11(s,3H),2.25(s,3H),2.09(d,J＝1.3Hz,3H),2.05(s,3H),1.58(d,J＝0.9Hz,3H)
N-(2,5-二甲基苯基)-N-甲基环戊烷甲酰胺(结构26)
Figure GDA0003629374220000171
1H NMR(400MHz,CDCl3):7.18(d,J＝7.7Hz,1H),7.09(dd,J＝7.7,1.4Hz,1H),6.93(d,J＝1.4Hz,1H),3.18(s,3H),2.35(s,3H),2.30-2.47(m,1H),2.19(s,3H),1.50-1.92(m,6H),1.35-1.48(m,2H)
乙基(2,5-二甲基苯基)(甲基)甲酰胺(结构28)
Figure GDA0003629374220000172
1H NMR(400MHz,CDCl3):7.13(d,J＝7.8Hz,1H),7.03(br d,J＝7.8Hz,1H),6.94(s,1H),3.96-4.33(m,2H),3.20(s,3H),2.33(s,3H),2.18(s,3H),1.17(t,J＝7.0Hz,3H)
N,2-二乙基-N-(间甲苯)丁酰胺(结构29)
Figure GDA0003629374220000173
1H NMR(400MHz,CDCl3):7.25-7.35(m,1H),7.15(d,J＝7.4Hz,1H),6.83-6.97(m,2H),3.75(q,J＝7.2Hz,2H),2.38(s,3H),2.03-2.15(m,1H),1.52-1.74(m,2H),1.28-1.42(m,2H),1.12(t,J＝7.2Hz,3H),0.80(t,J＝7.4Hz,6H)
N,2-二乙基-N-(邻甲苯)丁酰胺(结构30)
Figure GDA0003629374220000181
1H NMR(400MHz,CDCl3):7.19-7.41(m,3H),7.10(d,J＝7.4Hz,1H),4.14-4.32(m,1H),2.99-3.26(m,1H),2.26(s,3H),1.75-1.95(m,1H),1.52-1.72(m,2H),1.30-1.49(m,2H),1.14(t,J＝7.2Hz,3H),0.81(t,J＝7.4,3H),0.80(t,J＝7.4,3H)
实施例V
使用(i)0至10的气味强度(其中0＝无，1＝非常弱，5＝中度，10＝非常强)；(ii)复杂性水平(其中0＝无，1＝非常低，5＝中度，10＝非常高)评价了上述化合物的香味性质。以下报告了平均分数。
Figure GDA0003629374220000191
实施例V(继续)
Figure GDA0003629374220000201
实施例V(继续)
Figure GDA0003629374220000211
实施例V(继续)
Figure GDA0003629374220000221
N-(3-甲氧基苯基)-N,2-二甲基丁酰胺和2-乙基-N-(3-甲氧基苯基)-N-甲基丁酰胺显示出独特和特别理想的香调。它们的气味特征强烈而复杂，优于所有其他类似化合物。这种有利的性质是出人意料的。

Claims (23)

1.一种下式的化合物，
Figure FDA0003720207190000011
其中R选自甲基或乙基。
2.一种香味制剂，其包含嗅觉可接受量的下式的化合物，
Figure FDA0003720207190000012
其中R选自甲基或乙基。
3.根据权利要求2所述的香味制剂，其中所述嗅觉可接受量为所述香味制剂的0.005至50重量％。
4.根据权利要求2所述的香味制剂，其中所述嗅觉可接受量为所述香味制剂的0.5至25重量％。
5.根据权利要求2所述的香味制剂，其中所述嗅觉可接受量为所述香味制剂的1至10重量％。
6.根据权利要求2所述的香味制剂，其还包含选自由聚合物和非聚合物组成的组中的材料，所述非聚合物选自由以下组成的组：表面活性剂、乳化剂；脂质；有机油；矿物油；凡士林；天然油；香味固定剂；纤维；糖和固体表面材料，选自沸石和二氧化硅。
7.根据权利要求6所述的香味制剂，其中所述脂质选自脂肪、蜡和磷脂。
8.根据权利要求2所述的香味制剂，其还包含选自由低聚物和非聚合物组成的组中的材料，所述非聚合物选自由以下组成的组：表面活性剂、乳化剂；脂质；有机油；矿物油；凡士林；天然油；香味固定剂；纤维；糖和固体表面材料，选自沸石和二氧化硅。
9.根据权利要求8所述的香味制剂，其中所述脂质选自脂肪、蜡和磷脂。
10.根据权利要求6所述的香味制剂，其中所述聚合物选自聚丙烯酸酯、聚脲、聚氨酯、聚丙烯酰胺、聚酯、聚醚、聚酰胺、聚(丙烯酸酯-共-丙烯酰胺)、淀粉、明胶和阿拉伯树胶、藻酸盐、壳聚糖、聚交酯、聚(三聚氰胺-甲醛)、聚(脲-甲醛)及其组合。
11.一种通过向香味制剂添加嗅觉可接受量的下式化合物来改善、增强或修饰香味制剂的方法：
Figure FDA0003720207190000021
其中R选自甲基或乙基。
12.根据权利要求11所述的方法，其中所述嗅觉可接受量为所述香味制剂的0.005至50重量％。
13.根据权利要求11所述的方法，其中所述嗅觉可接受量为所述香味制剂的0.5至25重量％。
14.根据权利要求11所述的方法，其中所述嗅觉可接受量为所述香味制剂的1至10重量％。
15.一种香味产品，其含有权利要求1所述的化合物。
16.如权利要求15所述的香味产品，其中所述香味产品选自由以下组成的组：个人护理产品、织物护理产品、清洁产品、除臭剂、家庭护理产品、织物产品、空气护理产品、香味递送系统、化妆品制剂、消毒剂以及食品。
17.如权利要求15所述的香味产品，其中所述香味产品选自由以下组成的组：花露水、化妆品、织物护理产品、空气清新剂、皮肤护理产品、头发护理产品、除臭剂、止汗剂、女性护理产品、婴儿护理产品、家庭护理产品、织物产品、香味递送系统、消毒剂、清洗剂、口腔卫生产品、以及健康护理和营养产品。
18.如权利要求16所述的香味产品，其中所述化妆品制剂是香水。
19.如权利要求17所述的香味产品，其中所述皮肤护理产品选自由以下组成的组：香皂、液体皂、沐浴露和泡沫浴。
20.如权利要求17所述的香味产品，其中所述口腔卫生产品是牙齿卫生产品。
21.如权利要求16所述的香味产品，其中所述清洁产品是去污组合物。
22.如权利要求21所述的香味产品，其中所述去污组合物选自由以下组成的组：洗碗剂、玻璃清洁剂、金属清洁剂、台面清洁剂、地板清洁剂、地毯清洁剂、厕所清洁剂和漂白添加剂。
23.如权利要求17所述的香味产品，其中所述清洗剂选自由以下组成的组：衣物洗涤剂和漂洗添加剂。
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WO1996030470A1 (en) * 1995-03-25 1996-10-03 Quest International Fragrance material
CN101563085A (zh) * 2006-08-23 2009-10-21 威朗国际制药公司 作为钾通道调节剂的4-(n-氮杂环烷基)酰苯胺的衍生物

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