4-Methyl-3-(1-pyrrolidinyl)-2(5H)-furanone | 770-99-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 4-Methyl-3-(1-pyrrolidinyl)-2(5H)-furanone
• 英文别名: 2(5H)-Furanone, 4-methyl-3-(1-pyrrolidinyl)-；3-methyl-4-pyrrolidin-1-yl-2H-furan-5-one
• CAS: 770-99-0
• 化学式: C₉H₁₃NO₂
• 分子量: 167.208
• InChiKey: DARSINVAIIMSIF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  四氢吡咯 、 3-hydroxy-4-methyl-2(5H)-furanone 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 2.5h， 以14%的产率得到4-Methyl-3-(1-pyrrolidinyl)-2(5H)-furanone
  参考文献：
  名称：

  Systematic Studies on Structure and Physiological Activity of Cyclic α-Keto Enamines, a Novel Class of “Cooling” Compounds

  摘要：

  3-methyl- and 5-methyl-2-(1-pyrrolidinyl)-2-cyclopenten-1-one were recently identified as intense cooling compounds in roasted dark malt. To gain more insights into the molecular requirements of these compounds for imparting a cooling sensation, 26 cyclic alpha -keto enamine derivatives were synthesized, and their physiological cooling activities were evaluated. Any modification of the amino moiety, the carbocyclic ring size, or incorporation of additional methyl groups led to a significant increase of the cooling threshold. Insertion of an oxygen atom into the 2-cyclopenten-1-one ring, however, increased the cooling activity, e.g., the cooling threshold of the 5-methyl-4-(1-pyrrolidinyl)3(2H)-furanone was found to be 16-fold below the threshold concentration determined for the 3-methyl-2-(1-pyrrolidinyl)-2-cyclopenten-1-one. Shifting the oxygen atom from the 4- into the 5-position of the cyclopentenone ring resulted in a even more drastic increase in cooling activity, e.g., the 4-methyl-3-(1-pyrrolidinyl)-2(5H)-furanone exhibited the strongest cooling effect at the low oral threshold concentration of 0.02-0.06 mmol/L, which is 35-fold below the value determined for H-menthol. In contrast to the minty smelling (-)-menthol, most of the alpha -keto enamines were found to be virtually odorless but impart a sensation of "cooling" to the oral cavity as well as to the skin, thus illustrating that there is no physiological link between cooling activity and mint-like odors.

  DOI：

  10.1021/jf010857v

文献信息

• BITTER TASTE MODIFIERS INCLUDING SUBSTITUTED 1-BENZYL-3-(1-(ISOXAZOL-4-YLMETHYL)-1H-PYRAZOL-4-YL)IMIDAZOLIDINE-2,4-DIONES AND COMPOSITIONS THEREOF
  申请人：SENOMYX, INC.

  公开号：US20160376263A1

  公开（公告）日：2016-12-29

  The present invention includes compounds and compositions known to modify the perception of bitter taste, and combinations of said compositions and compounds with additional compositions, compounds, and products. Exemplary compositions comprise one or more of the following: cooling agents; inactive drug ingredients; active pharmaceutical ingredients; food additives or foodstuffs; flavorants, or flavor enhancers; food or beverage products; bitter compounds; sweeteners; bitterants; sour flavorants; salty flavorants; umami flavorants; plant or animal products; compounds known to be used in pet care products; compounds known to be used in personal care products; compounds known to be used in home products; pharmaceutical preparations; topical preparations; cannabis-derived or cannabis-related products; compounds known to be used in oral care products; beverages; scents, perfumes, or odorants; compounds known to be used in consumer products; silicone compounds; abrasives; surfactants; warming agents; smoking articles; fats, oils, or emulsions; and/or probiotic bacteria or supplements.

  本发明涵盖已知用于改变苦味感知的化合物和组合物，以及所述组合物和化合物与额外的组合物、化合物和产品的组合。示例组合物包括以下一种或多种：冷却剂；无活性药物成分；活性药用成分；食品添加剂或食品；调味剂或调味增强剂；食品或饮料产品；苦味化合物；甜味剂；苦味剂；酸味调味剂；咸味调味剂；鲜味调味剂；植物或动物产品；已知用于宠物护理产品中的化合物；已知用于个人护理产品中的化合物；已知用于家用产品中的化合物；制药制剂；局部制剂；大麻衍生或与大麻相关的产品；已知用于口腔护理产品中的化合物；饮料；香味、香水或除臭剂；已知用于消费品中的化合物；硅化合物；磨料；表面活性剂；发热剂；吸烟物品；脂肪、油脂或乳化剂；和/或益生菌或补充剂。
• P-menthan-3-ol alkylated derivatives and their use as refreshing agents
  申请人：Joulain Daniel

  公开号：US20090163733A1

  公开（公告）日：2009-06-25

  The invention concerns a 3-alkylated crystallized (1R,4S)-p-menthan-(3)-ol derivative, of formula A or B, wherein: either when R<2> represents hydrogen or a methyl radical, R<1> represents a —(CH2)n-OH where n can be 1, 2 and 3, or when R<2> represents a hydroxy radical, R<1> represents a methyl radical or a —(CH2)n-OH group where n can be 1, 2 and 3. The invention also concerns methods for preparing same, and perfume, cosmetic or food compositions containing said derivative.

  该发明涉及一种3-烷基化结晶(1R,4S)-p-薄荷烷-(3)-醇衍生物，化学式为A或B，其中：当R<2>代表氢或甲基基团时，R<1>代表—(CH2)n-OH，其中n可以是1、2和3；或者当R<2>代表羟基时，R<1>代表甲基基团或—(CH2)n-OH基团，其中n可以是1、2和3。该发明还涉及制备该衍生物的方法，以及含有该衍生物的香水、化妆品或食品组合物。
• COMPOUNDS USEFUL AS MODULATORS OF TRPM8
  申请人：Senomyx, Inc.

  公开号：US20170096418A1

  公开（公告）日：2017-04-06

  The present disclosure relates to compounds which are useful as cooling sensation compounds.

  本公开涉及作为冷感化合物有用的化合物。
• [EN] COOLING COMPOSITION<br/>[FR] COMPOSITION DE REFROIDISSEMENT
  申请人：FIRMENICH & CIE

  公开号：WO2019012071A1

  公开（公告）日：2019-01-17

  The present invention relates to the field of flavor or perfumery. More particularly, it concerns a composition of matter comprising : i) at least one compound of formula (I) in the form of any of its stereoisomers; and wherein R1 represents a phenyl group optionally substituted by one or two C1-3 alkyl or alkoxy groups or by one or two halides group; R2 and R3 represent, independently from each other, a heterocyclic group comprising from 1 to 3 heteroatoms selected from nitrogen, oxygen and sulfur, optionally substituted by one or two C1-3 alkyl groups; and ii) at least a C1-6 linear or branched alkyl lactate. The use of said composition of matter in a flavor or perfumery composition is also part of the invention. Therefore, following what is mentioned herein, the present invention comprises the invention's composition of matter as part of a flavoring or perfuming composition or of a flavoring or perfuming consumer product. The process to prepare the invention's composition of matter and the polymorph of compound of formula (I), in particular of N-(1H-pyrazol-3-yl)-N-(thiophen-2-ylmethyl)-2-(ptolyloxy)acetamide, are also an object of the invention.

  本发明涉及香料或香水领域。更具体地说，涉及一种物质组成，包括：i）至少一种式（I）的化合物，以其任意立体异构体的形式存在；其中R1代表苯基，可选地被一个或两个C1-3烷基或烷氧基或一个或两个卤素基取代；R2和R3分别独立地表示含有1至3个氮、氧和硫杂原子的杂环基，可选地被一个或两个C1-3烷基取代；以及ii）至少一种C1-6线性或支链酸乳酸酯。该物质组成在香料或香水组成中的使用也属于本发明的一部分。因此，根据本文所述，本发明包括作为调味或香料消费产品组成的发明物质组成。本发明还涉及制备发明物质组成和式（I）化合物的多晶形式的方法，特别是N-(1H-吡唑-3-基)-N-(噻吩-2-基甲基)-2-(p-甲氧基)乙酰胺的多晶形式。
• Method of using alpha-keto enamine derivatives as ingredients and products incorporating same
  申请人：——

  公开号：US20020022039A1

  公开（公告）日：2002-02-21

  The present invention concerns the food, cosmetic and pharmaceutical compositions including a compound of general formula: 1 alone or in combination, as an ingredient for food, cosmetic, pharmaceutical, and perfume compositions, wherein R 1 includes N-Pyrrolidinyl, N-Pyridinyl, N-(amino-diethyl), N-(2-carboxy-pyrrolidinyl), N-(2-Methoxycarbonyl-pyrrolidinyl), or a combination thereof; R 2 includes hydrogen, methyl, or a combination thereof; X includes methylene, ethylidene, 1-Propylidene, oxy radical, or a combination thereof; and Y includes methylene, ethylidene, 1-propylidene, oxy radical, ethan-1,2-diyl, ethen-1,2-diyl, propan-1,2-diyl, ethan-1,2-oxy-1,2-yl, or a combination thereof. Food products containing such compositions, as well as methods of imparting a cooling effect on a consumer's skin, are also included.

  本发明涉及一种通式为1的化合物，单独或组合地作为食品、化妆品、药品和香水配方的成分，其中R1包括N-吡咯烷基、N-吡啶基、N-(氨基二乙基)、N-(2-羧基吡咯烷基)、N-(2-甲氧基羰基吡咯烷基)或其组合；R2包括氢、甲基或其组合；X包括亚甲基、乙烯基、1-丙基基、氧自由基或其组合；Y包括亚甲基、乙烯基、1-丙基基、氧自由基、乙烷-1,2-二基基、乙烯-1,2-二基基、丙烷-1,2-二基基、乙烷-1,2-氧基-1,2-基基或其组合。还包括含有这种组合物的食品产品，以及在消费者皮肤上产生冷却效果的方法。