(E)-1-(3-phenyl-1-propenyl)-2-pyrrolidinone | 960397-85-7

• 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: (E)-1-(3-phenyl-1-propenyl)-2-pyrrolidinone
• 英文别名: 1-((E)-3-phenylprop-1-enyl)pyrrolidin-2-one；1-[(E)-3-phenylprop-1-enyl]pyrrolidin-2-one
• CAS: 960397-85-7
• 化学式: C₁₃H₁₅NO
• 分子量: 201.268
• InChiKey: PWDXXGAFHGMEKA-ONNFQVAWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (E)-1-(3-phenyl-1-propenyl)-2-pyrrolidinone 、 苯硒酚 在 palladium diacetate 作用下， 以 四氢呋喃 为溶剂， 反应 20.0h， 以80%的产率得到1-[3-phenyl-(1-phenylseleno)propyl]-2-pyrrolidinone
  参考文献：
  名称：

  Palladium-Catalyzed Markovnikov-Selective Hydroselenation of N-Vinyl Lactams with Selenols Affording N,Se-Acetals

  摘要：

  The highly regioselective hydroselenation of N-vinyl lactams has been revealed to successfully afford the corresponding N,Se-acetals as Markovnikov adducts. In the case of terminal N-vinyl lactams, Markovnikov-selective hydroselenation proceeds efficiently in the absence of any catalyst (or additive), owing to the acidity of the selenols. In contrast, the self-promoted hydroselenation is inefficient with internal N-vinyl lactams. In the presence of palladium diacetate (Pd(OAc)(2)), however, the desired hydroselenation of internal N-vinyl lactams proceeds efficiently to afford the corresponding N,Se-acetals.

  DOI：

  10.1021/acs.joc.5b02431
• 作为产物：
  描述：

  2-吡咯烷酮 、 3-苯-1-丙炔 在 十羰基二铼 作用下， 以 甲苯 为溶剂， 反应 30.0h， 以77%的产率得到(E)-1-(3-phenyl-1-propenyl)-2-pyrrolidinone
  参考文献：
  名称：

  Rhenium-Catalyzed Hydroamidation of Unactivated Terminal Alkynes:  Synthesis of (E)-Enamides

  摘要：

  Reactions of cyclic amides with unactivated terminal alkynes in the presence of a catalytic amount of a rhenium complex provided (E)enamides in high regio- and stereoselectivity (E:Z = > 99:< 1).

  DOI：

  10.1021/ol702564e

文献信息

• Synthesis of sterically hindered enamides via a Ti-mediated condensation of amides with aldehydes and ketones
  作者：Julien Genovino、Bharat Lagu、Yaping Wang、B. Barry Touré

  DOI：10.1039/c2cc32538a

  日期：——

  The first TiCl(4)-mediated condensation of secondary amides with aldehydes and ketones has been achieved. The reaction proceeds at room temperature and is complete within 5 h in most cases. The optimized procedure used 5 equiv of an amine base hinting that the in situ activation of both the amide and the Lewis acid is required. The reaction affords polysubstituted (E)-enamides.

  已经实现了第一个TiCl（4）介导的仲酰胺与醛和酮的缩合。反应在室温下进行，在大多数情况下，反应会在5小时内完成。优化的程序使用了5当量的胺碱，这暗示着需要酰胺和路易斯酸的原位活化。反应得到多取代的（E）-酰胺。
• Regioselective Hydrothiolation of Alkenes Bearing Heteroatoms with Thiols Catalyzed by Palladium Diacetate
  作者：Taichi Tamai、Akiya Ogawa

  DOI：10.1021/jo500586a

  日期：2014.6.6

  examples of transition-metal-catalyzed hydrothiolation of alkynes, the corresponding catalytic addition of thiols to alkenes has remained undeveloped. However, a novel Pd-catalyzed addition of thiols to alkenes bearing a heteroatom, such as oxygen and nitrogen, is found to proceed under mild conditions to give the corresponding Markovnikov adducts, regioselectively, in good yields.

  与过渡金属催化的炔烃氢硫醇化反应的许多实例形成鲜明对比的是，尚未开发出相应的硫醇向烯烃的催化加成反应。然而，发现在温和的条件下，新型的钯催化的硫醇向带有杂原子的烯烃（如氧和氮）进行新型的Pd催化加成反应，可以区域选择性地以高收率得到相应的马尔可夫尼科夫加合物。