5-(4-hydroxyphenyl)-3,5-diphenyl-1,5-dihydro-2H-pyrrol-2-one | 1076206-79-5

• 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: 5-(4-hydroxyphenyl)-3,5-diphenyl-1,5-dihydro-2H-pyrrol-2-one
• 英文别名: 3,5-diphenyl-5-(4-hydroxyphenyl)-3-pyrrolin-2-one；5-(4-hydroxyphenyl)-3,5-diphenyl-1H-pyrrol-2-one
• CAS: 1076206-79-5
• 化学式: C₂₂H₁₇NO₂
• 分子量: 327.382
• InChiKey: YSIQDJRZXMZZBS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (Z)-3-氰基-l-苯基-3-苯基-2-丙烯-1-酮 、 苯酚 在 水 、 copper(II) bis(trifluoromethanesulfonate) 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 3.0h， 以90%的产率得到5-(4-hydroxyphenyl)-3,5-diphenyl-1,5-dihydro-2H-pyrrol-2-one
  参考文献：
  名称：

  Copper-catalyzed Addition Reactions of Aromatics and Ketones to 2-Aza-2,4-cyclopentadienone: Facile and Efficient Transformation of Carbonyl-ene-nitriles to 1H-Pyrrolin-2(5H)-ones

  摘要：

  Copper-catalyzed reactions of carbonyl-ene-nitriles with carbon nucleophiles, such as aromatics and ketones, afforded pyrrolin-2-ones (gamma-lactam) in excellent yield. The reaction mechanism involves addition reactions with a ketimine moiety of the 2-aza-2,4-cyclopentadienone intermediate, which is formed via hydration of a nitrile moiety followed by dehydrative cyclization.

  DOI：

  10.1021/jo801776v

文献信息

• Preparation of 3,5-diarylsubstituted 5-hydroxy-1,5-dihydro-2<i>H</i>-pyrrol-2-ones <i>via</i> base-assisted cyclization of 3-cyanoketones
  作者：Nicolai A. Aksenov、Dmitrii A. Aksenov、Igor A. Kurenkov、Alexander V. Aksenov、Anton A. Skomorokhov、Lidiya A. Prityko、Michael Rubin

  DOI：10.1039/d1ra02279b

  日期：——

  A convenient preparative method is developed allowing for expeditious assembly of 3,5-diarylsubstituted 5-hydroxy-1,5-dihydro-2H-pyrrol-2-ones from routinely available inexpensive synthetic precursors. These compounds could not be prepared via the previously known protocols, as 2-aminofuran derivatives were produced instead.

  开发了一种方便的制备方法，允许从常规可用的廉价合成前体快速组装 3,5-二芳基取代的 5-羟基-1,5-二氢-2H-吡咯-2-酮。这些化合物无法通过先前已知的方案制备，而是生产 2-氨基呋喃衍生物。
• Copper-catalyzed Addition Reactions of Aromatics and Ketones to 2-Aza-2,4-cyclopentadienone: Facile and Efficient Transformation of Carbonyl-ene-nitriles to 1<i>H</i>-Pyrrolin-2(5<i>H</i>)-ones
  作者：Masahito Murai、Koji Miki、Kouichi Ohe

  DOI：10.1021/jo801776v

  日期：2008.11.21

  Copper-catalyzed reactions of carbonyl-ene-nitriles with carbon nucleophiles, such as aromatics and ketones, afforded pyrrolin-2-ones (gamma-lactam) in excellent yield. The reaction mechanism involves addition reactions with a ketimine moiety of the 2-aza-2,4-cyclopentadienone intermediate, which is formed via hydration of a nitrile moiety followed by dehydrative cyclization.