2,5-dimethyl-4-(1-pyrrolidinyl)-3(2H)-furanone | 80873-59-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢呋喃
• 英文名称: 2,5-dimethyl-4-(1-pyrrolidinyl)-3(2H)-furanone
• 英文别名: 2,5-dimethyl-4-pyrrolidin-1-ylfuran-3-one
• CAS: 80873-59-2
• 化学式: C₁₀H₁₅NO₂
• 分子量: 181.235
• InChiKey: FRPGHNBHIDMQGT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 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 、 2,5-二甲基-4-羟基-3(2H)-呋喃酮 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 3.5h， 以4.4%的产率得到2,5-dimethyl-4-(1-pyrrolidinyl)-3(2H)-furanone
  参考文献：
  名称：

  Characterization of Natural “Cooling” Compounds Formed from Glucose and l-Proline in Dark Malt by Application of Taste Dilution Analysis

  摘要：

  Gel permeation chromatography of the solvent extractables isolated from a thermally treated glucose/ L-proline mixture and sensory analysis of the fractions collected led to the discovery of the presence of "cooling'' compounds in Maillard reactions. To characterize the key compounds imparting this cooling sensation to the oral cavity, a taste dilution analysis was performed by determining the taste threshold of reaction products in serial dilutions of HPLC fractions to select the most intense "cooling'' compounds in the complex GPC fraction of the Maillard reaction mixture. Systematic C-13-labeling experiments and GC-MS, LC-MS, and 1D- and 2D-NMR measurements, followed by synthesis, led to the unequivocal identification of 3-methyl-2-(1-pyrralidinyl)-2-cyclopenten-1-one (3-MPC), 5-methyl-2-(1-pyrrolidinyl)-2-cyclopenten-1-one (5-MPC), and 2,5-dimethyl-4-(1-pyrrolidinyl)-3(2H)-furanone (DMPF) as the key compounds contributing the most to the cooling sensation. Although these structures were described earlier with regard to Maillard reactions, this is the first time that Maillard reaction products are reported to cause intense cooling sensations by degustation. Finally, the detection of 5-MPC (101.3 mug/kg), 3-MPC (9.4 mug/kg), and DMPF (11.5 mug/kg) in dark malt verified their natural occurrence in thermally processed foods.

  DOI：

  10.1021/jf0012594

文献信息

• SYNTHESIS OF ARYL CYCLOHEXANE CARBOXAMIDE DERIVATIVES USEFUL AS SENSATES IN CONSUMER PRODUCTS
  申请人：The Procter & Gamble Company

  公开号：US20170057911A1

  公开（公告）日：2017-03-02

  Synthesis methods to produce a series of carboxamides built off of an (S)-2-amino acid backbone or an (R)-2-amino acid backbone, depending upon the desired diastereomer of the end product.

  合成方法可用于在(S)-2-氨基酸骨架或(R)-2-氨基酸骨架上构建一系列羧酰胺，具体取决于所需的最终产物的对映异构体。
• [EN] SYNTHESIS OF CYCLOHEXANE DERIVATIVES USEFUL AS SENSATES IN CONSUMER PRODUCTS<br/>[FR] SYNTHÈSE DE DÉRIVÉS DE CYCLOHEXANE UTILES COMME AGENTS SENSORIELS DANS DES PRODUITS DE CONSOMMATION
  申请人：PROCTER & GAMBLE

  公开号：WO2010019730A1

  公开（公告）日：2010-02-18

  The present invention provides synthetic routes for preparing various isomers of cyclohexane-based coolants, such as menthyl esters and menthanecarboxamide derivatives, in particular those substituted at the amide nitrogen, for example with an aromatic ring or aryl moiety. Such structures have high cooling potency and long lasting sensory effect, which make them useful in a wide variety of consumer products. One synthetic route involves a copper catalyzed coupling of a primary menthanecarboxamide with an aryl halide, such reaction working best in the presence of potassium phosphate and water. Using this synthetic route, specific isomers can be prepared including the menthanecarboxamide isomer having the same configuration as l-menthol and new isomers such as a neoisomer having opposite stereochemistry at the carboxamide (C-1) position. The neoisomer unexpectedly has potent and long lasting cooling effect. Preparation schemes for neoisomers of other menthyl derivatives which are useful as coolants, including esters, ethers, carboxy esters and other N-substituted carboxamides are also provided.

  本发明提供了合成路径，用于制备基于环己烷的各种异构体冷却剂，例如薄荷酯和薄荷烷甲酰衍生物，特别是那些在酰胺氮上取代的，例如带有芳香环或芳基的。这些结构具有高冷却效能和持久的感官效果，使它们在各种消费品中有用。一种合成路径涉及使用铜催化剂将一种初级薄荷烷甲酰胺与芳香卤代烃偶联，这种反应在存在磷酸钾和水的情况下效果最佳。利用这种合成路径，可以制备特定的异构体，包括具有与l-薄荷醇相同构型的薄荷烷甲酰胺异构体以及具有在羧酰胺（C-1）位置上相反立体化学的新异构体，该新异构体意外地具有强效和持久的冷却效果。还提供了其他薄荷衍生物的新异构体的制备方案，这些衍生物包括酯类、醚类、羧酯类和其他N-取代羧酰胺，它们也可用作冷却剂。
• 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。
• Consumable product including consumable component and alpha-keto enamine derivatives
  申请人：——

  公开号：US20040052828A1

  公开（公告）日：2004-03-18

  The present invention relates to a consumable product that includes a consumable component and a cooling component present in an amount sufficient to provide a cooling sensation to a consumer, which cooling component includes one or more compounds each having the general formula: 1 wherein R 1 is selected from the group consisting of N-Pyrrolidinyl, N-Pyridinyl, N-(aminodiethyl), N-(2-carboxy-pyrrolidinyl), piperidinyl, or N-(2-Methoxycarbonyl-pyrrolidinyl); R 2 is selected from the group consisting of hydrogen or methyl; X is selected from the group consisting of methylene, ethylidene, 1 -Propylidene, or oxy radical; and Y is selected from the group consisting of methylene, ethylidene, 1-propylidene, oxy radical, ethan-1,2-diyl, ethen-1,2-diyl, propan-1,2-diyl, or ethan-1-oxy-1-yl, provided that when R 1 is N-pyrrolidinyl, X is methylene, and Y is ethylidene then R 2 cannot be hydrogen, and provided that when R 1 is N-pyrrolidinyl, and X and Y are each methylene, then R 2 cannot be methyl. In particular, the consumable product can be a food product, perfume, cosmetic, or pharmaceutical.

  本发明涉及一种可消耗产品，包括一种可消耗组分和一种冷却组分，其含量足以为消费者提供冷却感觉，该冷却组分包括一个或多个具有通式1的化合物：其中，R1选自N-吡咯烷基，N-吡啶基，N-(氨基二乙基)，N-(2-羧基吡咯烷基)，哌啶基或N-(2-甲氧基羰基吡咯烷基)的群组；R2选自氢或甲基的群组；X选自亚甲基，乙基亚甲基，1-丙基亚甲基或氧自由基的群组；Y选自亚甲基，乙基亚甲基，1-丙基亚甲基，氧自由基，乙烯-1，2-二基基，乙烯-1，2-二基基，丙烷-1，2-二基基或乙烷-1-氧基-1-基的群组，但当R1为N-吡咯烷基，X为亚甲基，Y为乙基亚甲基时，R2不能为氢，而当R1为N-吡咯烷基，且X和Y均为亚甲基时，R2不能为甲基。特别地，该可消耗产品可以是食品、香水、化妆品或药品。
• Synthesis of Cyclohexane Derivatives Useful as Sensates in Consumer Products
  申请人：Yelm Kenneth Edward

  公开号：US20100076080A1

  公开（公告）日：2010-03-25

  The present invention provides synthetic routes for preparing various isomers of cyclohexane-based coolants, such as menthyl esters and menthanecarboxamide derivatives, in particular those substituted at the amide nitrogen, for example with an aromatic ring or aryl moiety. Such structures have high cooling potency and long lasting sensory effect, which make them useful in a wide variety of consumer products. One synthetic route involves a copper catalyzed coupling of a primary menthanecarboxamide with an aryl halide, such reaction working best in the presence of potassium phosphate and water. Using this synthetic route, specific isomers can be prepared including the menthanecarboxamide isomer having the same configuration as l-menthol and new isomers such as a neoisomer having opposite stereochemistry at the carboxamide (C-1) position. The neoisomer unexpectedly has potent and long lasting cooling effect. Preparation schemes for neoisomers of other menthyl derivatives which are useful as coolants, including esters, ethers, carboxy esters and other N-substituted carboxamides are also provided.

  本发明提供了合成环己基冷却剂的各种异构体的合成路线，例如酯类薄荷醇和酰胺衍生物，特别是那些在酰胺氮上被取代的，例如芳香环或芳基基团。这样的结构具有高冷却效能和持久的感官效应，使它们在各种消费品中有用。一种合成路线涉及一种铜催化的一次性薄荷醇酰胺与芳基卤化物的偶联反应，这种反应在存在磷酸钾和水的情况下效果最好。使用这种合成路线，可以制备特定的异构体，包括具有与l-薄荷醇相同构型的薄荷醇酰胺异构体和新的异构体，例如在羧酰胺（C-1）位置具有相反立体化学的新异构体。这种新异构体出人意料地具有强大而持久的冷却效果。还提供了其他薄荷醇衍生物的新异构体的制备方案，这些衍生物包括酯类、醚类、羧酸酯类和其他N-取代酰胺。