2,3-dihydro-2-(4-hydroxyphenyl)-1-phenylpyridin-4(1H)-one

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2,3-dihydro-2-(4-hydroxyphenyl)-1-phenylpyridin-4(1H)-one
• 英文别名: 2-(4-Hydroxyphenyl)-1-phenyl-2,3-dihydropyridin-4-one
• 化学式: C₁₇H₁₅NO₂
• 分子量: 265.312
• InChiKey: BCNBQFAKQCYWQW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  反-1-甲氧基-3-(三甲基硅氧基)-1,3-丁二烯 、 对羟基苯甲醛 、 硝基苯 在 indium 、 水 、 氯化铵 作用下， 以 乙醇 、 水 为溶剂， 以66%的产率得到2,3-dihydro-2-(4-hydroxyphenyl)-1-phenylpyridin-4(1H)-one
  参考文献：
  名称：

  Sustainable Synthetic Methods: Domino Construction of Dihydropyridin-4-ones and β-Amino Esters in Aqueous Ethanol

  摘要：

  Domino reactions were designed to allow the byproduct of an upstream reaction to be internally recycled to catalyze a downstream reaction in a one-pot tandem sequence. Nitroarene reduction by In(0) generates an amine and In(III) byproducts. Addition of aldehyde followed by Danishefsky's diene or silyl ketene acetal provides access to dihydropyridin-4-ones or,beta-amino esters, respectively, in yields that are comparable or superior to the reported stepwise reactions.

  DOI：

  10.1021/ol801911f

文献信息

• Solid phase synthesis of 2,3-dihydro-4-pyridones: Reaction of Danishefsky's diene with polymer-bound imines
  作者：Yihan Wang、Stephen R. Wilson

  DOI：10.1016/s0040-4039(97)00824-1

  日期：1997.6

  An efficient method for the construction of 2,3-dihydro-4-pyridones on solid support has been developed, which utilized the Lewis-acid catalyzed tandem Mannich-Michael reaction of Danishefsky's diene with polymer-bound aldimines.

  已开发出一种在固相载体上构建2,3-二氢-4-吡啶酮的有效方法，该方法利用了丹尼谢夫斯基二烯的路易斯酸催化串联曼尼希-迈克尔反应与聚合物结合的醛亚胺。
• Sustainable Synthetic Methods: Domino Construction of Dihydropyridin-4-ones and β-Amino Esters in Aqueous Ethanol
  作者：Peter J. Alaimo、Robert O’Brien、Adam W. Johnson、Sarah R. Slauson、Jeannette M. O’Brien、Elizabeth L. Tyson、Amanda-Lynn Marshall、Colleen E. Ottinger、Jon G. Chacon、Lorien Wallace、Corey Y. Paulino、Sarah Connell

  DOI：10.1021/ol801911f

  日期：2008.11.20

  Domino reactions were designed to allow the byproduct of an upstream reaction to be internally recycled to catalyze a downstream reaction in a one-pot tandem sequence. Nitroarene reduction by In(0) generates an amine and In(III) byproducts. Addition of aldehyde followed by Danishefsky's diene or silyl ketene acetal provides access to dihydropyridin-4-ones or,beta-amino esters, respectively, in yields that are comparable or superior to the reported stepwise reactions.