2-(1-Pyrrolidinyl)cyclohex-2-en-1-one | 18543-93-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(1-Pyrrolidinyl)cyclohex-2-en-1-one
• 英文别名: 2-(1-pyrrolidinyl)-2-cyclohexen-1-one；2-(1-pyrrolidino)cyclohex-2-en-1-one；2-pyrrolidinocyclo-2-hexen-1-one；2-pyrrolidin-1-yl-cyclohex-2-enone；2-(Pyrrolidin-1-yl)cyclohex-2-en-1-one；2-pyrrolidin-1-ylcyclohex-2-en-1-one
• CAS: 18543-93-6
• 化学式: C₁₀H₁₅NO
• 分子量: 165.235
• InChiKey: XXWXPRMRPAPIRE-UHFFFAOYSA-N

物化性质

• 沸点：
  305.8±32.0 °C(Predicted)
• 密度：
  1.118±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 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

反应信息

• 作为反应物：
  描述：

  2-(1-Pyrrolidinyl)cyclohex-2-en-1-one 生成
  参考文献：
  名称：

  双环腈酸酯的环收缩反应

  摘要：

  六氢-4H-1,2-苯并恶嗪N-氧化物衍生物重排成1（2H）-六氢戊烯酮系统。

  DOI：

  10.1016/s0040-4039(00)81726-8
• 作为产物：
  描述：

  四氢吡咯 、 2-羟基-2-环己烯-1-酮 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以16%的产率得到2-(1-Pyrrolidinyl)cyclohex-2-en-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
• 作为试剂：
  描述：

  N-phenyliminobenzamide 在 盐酸 、 2-(1-Pyrrolidinyl)cyclohex-2-en-1-one 作用下， 生成 2-pyrrolidino-1,3-cyclohexandione 、 2-苯基苯并肼
  参考文献：
  名称：

  Forchiassin, Mirella; Pitacco, Giuliana; Russo, Claudio, Gazzetta Chimica Italiana, 1982, vol. 112, # 7/8, p. 335 - 338

  摘要：

  DOI：

文献信息

• Polyfunctionalized hexahydro-1 (2H)-pentalenones by rearrangement of bicyclic 1,2-oxazine N-oxide derivatives
  作者：G. Barbarella、S. Brückner、G. Pitacco、E. Valentin

  DOI：10.1016/s0040-4020(01)83495-5

  日期：1984.1

  The title heterocycles rearrange into a mixture of diastereoisomeric hexahydro-1(2H)-pentalenone derivatives, which undergo nucleophilic eliminative ring fission by methanol to give 1-amino-2-nitroalkylated cyclopentancarboxylic esters. The X-ray structure determination of hexahydro-2-methyl-2-nitro-3-phenyl-6a- (1-piperidinyl) -1 (2H)-pentalenone – (2α, 3α, 3aα, 6aα) is also reported.

  标题杂环重排为非对映异构体六氢-1（2H）-戊烯酮衍生物的混合物，该衍生物通过甲醇进行亲核消除环裂变，得到1-氨基-2-硝基烷基化的环戊烷羧酸酯。还报告了六氢-2-甲基-2-硝基-3-苯基-6a-（1-哌啶基）-1（2H）-戊烯酮–（2α，3α，3aα，6aα）的X射线结构测定。
• Reaction of an enaminone with 1-nitrocyclopentene: synthesis of a triquinane
  作者：Melanie M. Cooper、John W. Huffman

  DOI：10.1039/c39870000348

  日期：——

  A convergent synthesis of a functionalized triquinane is reported which proceeds in three steps and 72% yield from 2-(1-pyrrolidino)cyclohex-2-en-1-one and 1-nitrocyclopentene.

  据报道，官能化的三喹烷的会聚合成分三步进行，由2-（1-吡咯烷基）环己二-2-烯-1-酮和1-硝基环戊烯的产率为72％。
• 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。
• Reactions of enaminones with 1-nitroolefins. Scope and limitations of a polyquinane synthesis
  作者：John W. Huffman、Melanie M. Cooper、Barnabe B. Miburo、William T. Pennington

  DOI：10.1016/s0040-4020(01)80490-7

  日期：1992.1

  The reaction of several 2-aminocyclohex-2-en-1-ones with cyclic nitroolefins has been explored as a possible synthetic approach to polyquinanes. 2-Pyrrolidino, 2-piperidino and 2-morpholinocyclohex-2-en-1-one react with 1-nitrocyclopentene to provide substituted triquinanes. Reactions involving 5,5-dimethyl-2-morpholinocyclohex-2-en-1-one were unsuccessful as were those using 4,4-dimethyl-1-nitrocyclopentene. 5-Methyl-2-morpholinocyclohex-2-en-1-one and 1-nitrocyclopentene provide the corresponding triquinane, plus a by-product in which the amino substituent has been lost. The reactions of other selected nitroolefins have been carried out, and the products are described. The results of these reactions are rationalized in terms of an inverse electron demand Diels-Alder reaction to afford an intermediate oxazine N-oxide, which then undergoes further transformations to afford the observed products.
• Forchiassin, M.; Pitacco, G.; Risaliti, A., Journal of Heterocyclic Chemistry, 1983, vol. 20, p. 305 - 309
  作者：Forchiassin, M.、Pitacco, G.、Risaliti, A.、Russo, C.、Valentin, E.

  DOI：——

  日期：——