2-methyl-3-(1-pyrrolidinyl)-2-cyclopenten-1-one | 3335-02-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: 2-methyl-3-(1-pyrrolidinyl)-2-cyclopenten-1-one
• 英文别名: 2-methyl-3-pyrrolidinocyclopent-2-en-1-one；2-methyl-3-pyrrolidino-2-cyclopentenone；2-methyl-3-pyrrolidino-cyclopent-2-enone；2-Methyl-3-pyrrolidino-cyclopent-2-enon；2-Methyl-3-(pyrrolidin-1-yl)cyclopent-2-en-1-one；2-methyl-3-pyrrolidin-1-ylcyclopent-2-en-1-one
• CAS: 3335-02-2
• 化学式: C₁₀H₁₅NO
• 分子量: 165.235
• InChiKey: ZJUWVCPWYGFQMS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  2-methyl-3-(1-pyrrolidinyl)-2-cyclopenten-1-one 在 lithium diisopropyl amide 作用下， 以 Petroleum ether 为溶剂， 反应 4.0h， 生成 2,4-dimethyl-3-butyl-2-cyclopentenone
  参考文献：
  名称：

  一种合成 α, β-不饱和羰基化合物的简便方法

  摘要：

  多种α,β-不饱和酮可以方便地由烯氨基酮和有机锂化合物合成，特别是当反应在石油醚中进行时；该反应为合成α,β,γ-三取代的2-环戊烯酮以及烯氨基酮的区域选择性烷基化提供了一种简便的方法。

  DOI：

  10.1246/cl.1983.875
• 作为产物：
  描述：

  四氢吡咯 、 3-羟基-2-甲基-2-环戊烯酮 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以5%的产率得到2-methyl-3-(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

• Synthesis of<i>N</i>-Substituted 2-Alkyl-3-amino-2-cyclopenten-1-ones
  作者：André Otto、Hans Schick

  DOI：10.1055/s-1991-26392

  日期：——

  Several 2-alkyl-3-amino-2-cyclopenten-1-ones are prepared in 45-92 % yield from 2-alkyl-1,3-cyclopentanediones and a slight excess of an equimolar mixture of various primary and secondary amines and acetic or propionic acid in boiling toluene.

  几种2-烷基-3-氨基-2-环戊烯-1-酮以45-92%的产率从2-烷基-1,3-环戊烯二酮和过量的等摩尔混合的各种初级和次级胺以及乙酸或丙酸在沸腾的甲苯中制备。
• Addition reactions of cyclic s-trans-enaminones with Grignard reagents.
  作者：Thomas T. Shawe、Darren B. Hansen、Kelly Ann Peet、Anthony S. Prokopowicz、Patrice M. Robinson、Annatina Cannon、Kathleen E. Dougherty、Andrew A. Ross、Linda M. Landino

  DOI：10.1016/s0040-4020(96)01133-7

  日期：1997.2

  Addition of Grignard reagents to s-trans-enaminones derived from 1,3-cycloalkanediones are described. In dichloromethane, addition of phenylmagnesium bromide gave 3-phenyl substituted cycloalkenones. Alkylmagnesium halides underwent multiple addition reactions, giving mixtures of the 3-alkylcycloalkenones and 1,3-dialkyl-3-(dialkylamino)cyclohexenes. In tetrahydrofuran, only the 3-alkylcycloalkenone

  描述了将格氏试剂添加到衍生自1，3-环烷二酮的s-反式-烯胺酮上。在二氯甲烷中，加入苯基溴化镁得到3-苯基取代的环烯酮。烷基卤化镁经历多次加成反应，得到3-烷基环烯酮和1，3-二烷基-3-（二烷基氨基）环己烯的混合物。在四氢呋喃中，仅获得3-烷基环烯酮。
• 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。
• Panouse; Sannie, Bulletin de la Societe Chimique de France, 1956, p. 1374,1377
  作者：Panouse、Sannie

  DOI：——

  日期：——
• Lis, L. G.; Zheldakova, T. A.; Pap, A. A., Journal of Organic Chemistry USSR (English Translation), 1992, vol. 28, # 9.1, p. 1485 - 1490
  作者：Lis, L. G.、Zheldakova, T. A.、Pap, A. A.、Lakhvich, F. A.

  DOI：——

  日期：——