5-methyl-2-(1-piperidinyl)-2-cyclopenten-1-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 5-methyl-2-(1-piperidinyl)-2-cyclopenten-1-one
• 英文别名: 5-Methyl-2-piperidin-1-ylcyclopent-2-en-1-one
• 化学式: C₁₁H₁₇NO
• 分子量: 179.262
• InChiKey: WOGFGTKDXAXGHQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  哌啶 、 甲基环戊烯醇酮 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以7%的产率得到3-methyl-2-(1-piperidinyl)-2-cyclopenten-1-one
  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

• 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。
• Use of alpha-keto enamine derivatives as ingredients
  申请人：Société des Produits Nestlé S.A.

  公开号：EP1157617A2

  公开（公告）日：2001-11-28

  The present invention concerns the use of a compound of general formula alone or in combination, as an ingredient for food, cosmetic, pharmaceutical and perfume compositions, wherein R1 is N-Pyrrolidinyl, R2 is Methyl, X is Ethyliden and Y is Oxy radical.

  本发明涉及通式化合物的用途 作为食品、化妆品、药物和香水组合物的成分、 其中 R1 是 N-吡咯烷基、 R2 是甲基 X 是亚乙基 Y 是氧基基。
• Method and compositions for imparting cooling effect to tobacco products
  申请人：Bereman D. Robert

  公开号：US20050000529A1

  公开（公告）日：2005-01-06

  The present invention relates to smoking articles such as cigarettes, and in particular to a method and composition for providing a cooling effect to cigarettes. The tobacco rod of the cigarette contains a compound that imparts a cooing effect and sensation of freshness to tobacco smoke.

  本发明涉及香烟等烟具，特别是一种为香烟提供冷却效果的方法和组合物。 香烟的烟杆中含有一种化合物，它能使烟草烟雾产生 "咕咕 "的效果和清新的感觉。
• METHOD AND COMPOSITIONS FOR IMPARTING COOLING EFFECT TO TOBACCO PRODUCTS
  申请人：Vector Tobacco Inc.

  公开号：EP1455609A2

  公开（公告）日：2004-09-15