1-phenyl-2,3-dihydropyridin-4(1H)-one | 35487-96-8

• 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-2,3-dihydropyridin-4(1H)-one
• 英文别名: 1-Phenyl-2,3-dihydro-4(1h)-pyridinone；1-phenyl-2,3-dihydropyridin-4-one
• CAS: 35487-96-8
• 化学式: C₁₁H₁₁NO
• 分子量: 173.214
• InChiKey: KMDBZRHHPWYQQJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-phenyl-2,3-dihydropyridin-4(1H)-one 、 丙烯酸叔丁酯 在 palladium(II) trifluoroacetate 、 氧气 、 copper diacetate 、 邻苯二酚 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以32%的产率得到(E)-5-[2-(tert-butoxycarbonyl)vinyl]-1-phenyl-2,3-dihydropyridin-4(1H)-one
  参考文献：
  名称：

  室温下环状烯胺酮的仿生有氧 C?H 烯烃化：1,3,5-三取代苯的合成进展

  摘要：

  使用氧气作为末端氧化剂，在室温下通过钯催化设计了一种绿色温和的环状烯胺酮脱氢烯烃化方案。烯化环烯胺酮的合成效用通过意想不到的 Diels-Alder 串联反应提供了一系列独特的 1,3,5-三取代苯。这种新协议实现了广泛的底物范围和良好的产量，为芳烃功能化提供了另一种途径。

  DOI：

  10.1002/adsc.201300904
• 作为产物：
  描述：

  1-苯基-4-哌啶酮 在 氧气 、 rhodamine 6G 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 16.0h， 以70%的产率得到1-phenyl-2,3-dihydropyridin-4(1H)-one
  参考文献：
  名称：

  可见光光催化好氧脱氢合成2,3-二氢-4-吡啶酮，4-喹诺酮和2,3-二氢-4-偶氮酮

  摘要：

  已开发出用于合成三种类型的N-杂环的协议。环烯胺酮是在环境友好的条件下通过使用罗丹明6G作为廉价的光催化剂并使用氧气作为末端氧化剂进行光催化脱氢制备的。通过一锅法中的[2 + 2]环加成/扩环序列，将该方法扩展为可使用偶氮酮。

  DOI：

  10.1002/ejoc.201900584

文献信息

• Dual C(sp³ )−H Bond Functionalization of N-Heterocycles through Sequential Visible-Light Photocatalyzed Dehydrogenation/[2+2] Cycloaddition Reactions
  作者：Guo-Qiang Xu、Ji-Tao Xu、Zhi-Tao Feng、Hui Liang、Zhu-Yin Wang、Yong Qin、Peng-Fei Xu

  DOI：10.1002/anie.201710523

  日期：2018.4.23

  through a sequential visible‐light photocatalyzed dehydrogenation/[2+2] cycloaddition procedure. As a complementary approach to the well‐established use of iminium ion and α‐amino radical intermediates, the elusive cyclic enamine intermediates were effectively generated by photoredox catalysis under mild conditions and efficiently captured by acetylene esters to form a wide array of bicyclic amino acid

  在这里，我们描述了一种温和的方法，用于通过顺序可见光光催化脱氢/ [2 + 2]环加成程序对饱和含氮杂环进行双C（sp 3）-H键官能化。作为完善使用亚胺离子和α-氨基自由基中间体的一种补充方法，难以捉摸的环状烯胺中间体是在温和条件下通过光催化氧化有效产生的，并被乙炔酯有效捕获，从而形成多种双环氨基酸衍生物，从而使两个邻位C（sp 3）-H键同时功能化。
• 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。
• Synthesis of 6- and 7-Membered Cyclic Enaminones: Scope and Mechanism
  作者：Micah J. Niphakis、Brandon J. Turunen、Gunda I. Georg

  DOI：10.1021/jo100907u

  日期：2010.10.15

  Six- and seven-membered cyclic enaminones can be prepared using common. environmentally benign reagents. Ammo acids are used as synthetic precursors allowing diversification and the incorporation of chirality The key reaction in this multistep process involves deprotection Boc-amino ynones and subsequent treatment with methanolic K2CO3 to induce cyclization. A beta-amino elimination side reaction was identified in a few labile substrates that led to loss of stereochemical purity of degradation. This process can be mitigated in specific cases using mild deprotection conditions NMR and deuteitum-labeling experiments provided valuable insight into the work kings and limitations of this reaction Although disguised as a 6-endo-dig cyclization, the reagents employed in the transformation play a direct role in bond-making and bond-breaking. thus changing die mode of addition to a 6-endo-trig cyclization This method can be used to construct an array of monocyclic and bicyclic scaffolds. many of which me found in well-known natural products (e g indolizidine, quinolizidine, and Stemona alkaloids).
• Palladium(II)-Catalyzed Dehydrogenative Alkenylation of Cyclic Enaminones via the Fujiwara–Moritani Reaction
  作者：Yi-Yun Yu、Micah J. Niphakis、Gunda I. Georg

  DOI：10.1021/ol202677g

  日期：2011.11.4

  A new Pd(II)-catalyzed dehydrogenative alkenylation reaction involving two alkenes was developed. A variety of nonaromatic, cyclic enaminones were successfully coupled to primary and secondary alkenes yielding a series of unique 1,3-dienes. The generality of this transformation presents a useful strategy for directly cross-coupling alkenes and offers an attractive new approach to functionallze enaminones.