1-benzyl-5-(4-methoxyphenyl)-2,3-dihydropyridin-4(1H)-one | 1001078-59-6

• 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-benzyl-5-(4-methoxyphenyl)-2,3-dihydropyridin-4(1H)-one
• 英文别名: 1-Benzyl-5-(4-methoxyphenyl)-2,3-dihydropyridin-4-one
• CAS: 1001078-59-6
• 化学式: C₁₉H₁₉NO₂
• 分子量: 293.365
• InChiKey: TWAKGOTVUIHGAY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2,3-dihydro-1-(phenylmethyl)-4(1H)-pyridinone 、 (4-甲氧基苯基)三氟硼酸钾 在 palladium diacetate 、 copper diacetate potassium carbonate 、 溶剂黄146 作用下， 以 二甲基亚砜 、 叔丁醇 为溶剂， 反应 7.0h， 以82%的产率得到1-benzyl-5-(4-methoxyphenyl)-2,3-dihydropyridin-4(1H)-one
  参考文献：
  名称：

  Palladium(II)-Catalyzed Direct Arylation of Enaminones Using Organotrifluoroborates

  摘要：

  A Pd(II)-catalyzed reaction for the direct aryation of cyclic enaminones is reported. The reactivity of electron-rich, electron-poor, and sterically encumbered organotrifluoroborates was investigated. This reaction represents a unique use for organotrifluoroborates as coupling partners and discloses the utility of enaminones for direct-functionalization reactions. It provides immediate access to arylpiperidine, indolizidine, and quinolizidine scaffolds from the corresponding mono- and bicyclic, unattenuated enaminones.

  DOI：

  10.1021/ja710221c

文献信息

• Copper-Assisted Palladium(II)-Catalyzed Direct Arylation of Cyclic Enaminones with Arylboronic Acids
  作者：Yong Wook Kim、Micah J. Niphakis、Gunda I. Georg

  DOI：10.1021/jo301531k

  日期：2012.11.2

  Described herein is a palladium(II)-catalyzed direct arylation of cyclic enaminones with arylboronic acids. The versatility of this method is that both electron-rich and electron-poor boronic acids can be coupled in high yields. A mixture of two Cu(II) additives was crucial for efficient cross-coupling. The role of each Cu(II) reagent appears to be distinct and complementary serving to assist catalyst

  本文描述的是钯(II)-催化的环状烯胺酮与芳基硼酸的直接芳基化。这种方法的多功能性在于富电子和缺电子硼酸都可以高产率耦合。两种 Cu(II) 添加剂的混合物对于有效的交叉耦合至关重要。每个 Cu(II) 试剂的作用似乎是不同的和互补的，有助于通过假定的芳基铜中间体帮助催化剂再氧化和金属转移。
• Palladium-Catalyzed Direct C–H Arylation of Cyclic Enaminones with Aryl Iodides
  作者：Yi-Yun Yu、Lei Bi、Gunda I. Georg

  DOI：10.1021/jo400830t

  日期：2013.6.21

  A ligand-free method for the Pd-catalyzed direct arylation of cyclic enaminones using aryl iodides was developed. This method can be applied to a wide range of cyclic enaminones and aryl iodides with excellent C5-regioselectivity. Using widely available aryl iodides, the generality of this transformation provides easy access to a variety of 3-arylpiperidine structural motifs.

  开发了一种使用芳基碘对环烯胺酮进行 Pd 催化直接芳基化的无配体方法。该方法可应用于范围广泛的环状烯胺酮和芳基碘化物，并具有出色的 C5 区域选择性。使用广泛可用的芳基碘化物，这种转化的普遍性提供了对各种 3-芳基哌啶结构基序的轻松访问。
• Palladium(II)-Catalyzed Direct Arylation of Enaminones Using Organotrifluoroborates
  作者：Haibo Ge、Micah J. Niphakis、Gunda I. Georg

  DOI：10.1021/ja710221c

  日期：2008.3.1

  A Pd(II)-catalyzed reaction for the direct aryation of cyclic enaminones is reported. The reactivity of electron-rich, electron-poor, and sterically encumbered organotrifluoroborates was investigated. This reaction represents a unique use for organotrifluoroborates as coupling partners and discloses the utility of enaminones for direct-functionalization reactions. It provides immediate access to arylpiperidine, indolizidine, and quinolizidine scaffolds from the corresponding mono- and bicyclic, unattenuated enaminones.