1-phenyl-2-(2-pyrrolidinylidene)ethanone | 126381-47-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-phenyl-2-(2-pyrrolidinylidene)ethanone
• 英文别名: 1-phenyl-2-(pyrrolidin-2-ylidene)-ethanone；Z-2-benzoylmethylenepyrrolidine；(Z)-1-phenyl-2-pyrrolidinylideneethanone；(Z)-1-phenyl-2-(pyrrolidin-2-ylidene)ethanone；(Z)-1-phenyl-2-(2-pyrrolidinylidene)-1-ethanone；(2Z)-1-phenyl-2-(2-pyrrolidinylidene)ethanone；(2Z)-1-phenyl-2-pyrrolidin-2-ylideneethanone
• CAS: 126381-47-3
• 化学式: C₁₂H₁₃NO
• 分子量: 187.241
• InChiKey: ZOACWAMVLLJLOA-LUAWRHEFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-phenyl-2-(2-pyrrolidinylidene)ethanone 、 alkaline earth salt of/the/ methylsulfuric acid 在 potassium tert-butylate 、 potassium carbonate 作用下， 生成 [2-(2-oxo-2-phenyl-ethylidene)-pyrrolidin-1-yl]-acetic acid
  参考文献：
  名称：

  非甾体抗炎药，第 24 部分 [1] 吡咯烷烯胺酮作为模拟花生四烯酸的模型

  摘要：

  羧酸链固定在氮原子上的吡咯烷烯胺酮比 5-脂氧合酶更有效或选择性地抑制环加氧酶。根据所讨论的结构-活性关系，效力显着取决于羧酸的链长、杂环部分和苯基的取代模式。化合物4c是最有效的环氧合酶抑制剂。对于结合特征，比较了花生四烯酸的未折叠构象和氟比洛芬、双氯芬酸、ML 3000 和先导化合物 4a 的能量最小化构象。除了已知的结构特征外，还假设羧酸官能团和苯基残基的距离相似，可以解释与酶活性位点的相互作用。

  DOI：

  10.1002/ardp.19973300307
• 作为产物：
  描述：

  1-benzoyl-2-methylenetetrahydropyrrole 以 乙醚 为溶剂， 反应 0.5h， 以92%的产率得到1-phenyl-2-(2-pyrrolidinylidene)ethanone
  参考文献：
  名称：

  1-芳酰基-2-亚甲基哌啶和吡咯烷衍生物的光化学行为显着不同。快速合成ruspolinone

  摘要：

  在中性溶剂中辐照后，被不同取代的1-芳酰基-2-亚甲基哌啶6a-f产生光环化产物4a-f，而它们的吡咯烷同类物7a，c，得到光-弗里斯重排的烯氨基酮18a，c，d产物。

  DOI：

  10.1016/0040-4039(96)01765-0

文献信息

• Chemoselective reactions of vinylogous amides, and the synthesis of two peripentadenia alkaloids
  作者：Joseph P. Michael、Andrew S. Parsons

  DOI：10.1016/0040-4020(95)01051-3

  日期：1996.2

  Some chemoselective transformations of the vinylogous amide (E)-2-benzoylmethylene- 1-(2-cyano- ethyl)pyrrolidine (3a) and compounds derived from it have been investigated. Methodology developed during the course of these model studies has been applied to the synthesis of the alkaloids peripentadenme (1) and dinorperipentaclenine (2).

  研究了乙烯基酰胺（E）-2-苯甲酰基亚甲基-1-（2-氰基乙基）吡咯烷（3a）及其衍生化合物的一些化学选择性转化。在这些模型研究过程中开发的方法已应用于生物碱peripentadenme（1）和dinorperipentaclenine（2）的合成。
• A Convenient Protocol for the Alkylidenation of Lactams
  作者：Mark C. Elliott、Stuart V. Wordingham

  DOI：10.1055/s-2006-926390

  日期：——

  A convenient two-step preparation of alkylidenepyrrolidines is reported.

  报告了一种便捷的两步法制备亚烷基吡咯烷类化合物的方法。
• Enaminones via Ruthenium-Catalyzed Coupling of Thioamides and α-Diazocarbonyl Compounds
  作者：Naga D. Koduri、Zhiguo Wang、Garrett Cannell、Kate Cooley、Tsebaot Mesfin Lemma、Kun Miao、Michael Nguyen、Bram Frohock、Maria Castaneda、Halee Scott、Dragos Albinescu、Syed R. Hussaini

  DOI：10.1021/jo5011312

  日期：2014.8.15

  Enaminones can be prepared via the Rh2(OAc)4-catalyzed coupling of α-diazocarbonyl compounds with thioamides. However, rhodium is the most expensive and least abundant among the dominant precious metals used for catalysis. Furthermore, a very limited substrate scope is known for the intermolecular rhodium catalyzed coupling reaction. Therefore, there is a need to find a more economical catalyst substitute with a broad substrate scope. In this paper, we describe the use of Ru(II) catalysts for the synthesis of enaminones. The reaction can be performed efficiently with the Grubbs first-generation catalyst or [(Ph)3P]3RuCl2 in a sealed tube. Both catalysts are much less expensive than Rh2(OAc)4. Secondary and tertiary thioamides, when reacted with α-diazodiesters, α-diazoketoesters, α-diazodiketones, and α-diazomonoketones give enaminones. Primary thioamides give thiazole derivatives when reacted with α-diazomonoketones. However, with other diazo compounds, primary thioamides also give enaminones. All enaminones are obtained in good yields and with good diastereoselectivity. Accordingly, the method described in this paper is an efficient and economical alternative to the Rh2(OAc)4-catalyzed coupling process.
• One-Pot Eschenmoser Episulfide Contractions in DMSO: Applications to the Synthesis of Fuligocandins A and B and a Number of Vinylogous Amides
  作者：Birgitta Pettersson、Vedran Hasimbegovic、Jan Bergman

  DOI：10.1021/jo101864n

  日期：2011.3.18

  Practical total syntheses of the natural products fuligocandin A (2a) and fuligocandin B (3) have been achieved through a convergent strategy depending on the Eschenmoser episulfide contraction as a key step. Conducting the reaction in DAIS proved to be an efficient and general method for the synthesis of a variety of vinylogous amides, such as azepan-2-ylidenepropan-2-one.
• Decarboxylation of cyclic β-enaminoketoesters with boric acid
  作者：Philippe Delbecq、Jean-Pierre Celerier、Gérard Lhommet

  DOI：10.1016/s0040-4039(00)97756-6

  日期：1990.1