(S)-3-methyl-2-(2-carboxy-1-pyrrolidinyl)-2-cyclopenten-1-one

• 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: (S)-3-methyl-2-(2-carboxy-1-pyrrolidinyl)-2-cyclopenten-1-one
• 英文别名: (2S)-1-(2-methyl-5-oxocyclopenten-1-yl)pyrrolidine-2-carboxylic acid
• 化学式: C₁₁H₁₅NO₃
• 分子量: 209.245
• InChiKey: XBKDTCRJSSQWAP-QMMMGPOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  57.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  甲基环戊烯醇酮 、 L-脯氨酸 以 乙醇 为溶剂， 反应 4.0h， 以7%的产率得到(S)-3-methyl-2-(2-carboxy-1-pyrrolidinyl)-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 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
• [EN] METHOD AND COMPOSITIONS FOR IMPARTING COOLING EFFECT TO TOBACCO PRODUCTS<br/>[FR] PROCEDES ET COMPOSITIONS POUR CONFERER UN EFFET RAFRAICHISSANT AUX ARTICLES DE TABAC
  申请人：VECTOR TOBACCO INC

  公开号：WO2003053176A2

  公开（公告）日：2003-07-03

  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 cyclic alpha-keto enamine that imparts a cooling effect and sensation of freshness to tobacco smoke.
• Systematic Studies on Structure and Physiological Activity of Cyclic α-Keto Enamines, a Novel Class of “Cooling” Compounds
  作者：Harald Ottinger、Tomislav Soldo、Thomas Hofmann

  DOI：10.1021/jf010857v

  日期：2001.11.1

  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.