4,4-diphenyl-3,4-dihydroquinolin-2(1H)-one | 14354-89-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 4,4-diphenyl-3,4-dihydroquinolin-2(1H)-one
• 英文别名: 4,4-Diphenyl-3,4-dihydrocarbostyril；4,4-diphenyl-3,4-dihydro-1H-quinolin-2-one；4,4-Diphenyl-3,4-dihydro-1H-chinolin-2-on；2-Oxo-4,4-diphenyl-1,2,3,4-tetrahydro-chinolin；2-Oxo-4,4-diphenyl-1,2,3,4-tetrahydrochinolin；4,4-Diphenyl-3,4-dihydro-carbostyril；4,4-Diphenyl-3,4-dihydroquinolin-2-one；4,4-diphenyl-1,3-dihydroquinolin-2-one
• CAS: 14354-89-3
• 化学式: C₂₁H₁₇NO
• 分子量: 299.372
• InChiKey: OAPIFWOIYZYDOM-UHFFFAOYSA-N

物化性质

• 熔点：
  242.5-243.5 °C(Solv: ethanol (64-17-5))
• 沸点：
  476.4±45.0 °C(Predicted)
• 密度：
  1.171±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4,4-diphenyl-3,4-dihydroquinolin-2(1H)-one 在 三氯化铝 作用下， 以 氯苯 为溶剂， 反应 3.0h， 以78%的产率得到4-苯基-喹啉-2-醇
  参考文献：
  名称：

  Natarajan, M.; Ramakrishnan, V. T., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1984, vol. 23, # 8, p. 720 - 727

  摘要：

  DOI：
• 作为产物：
  描述：

  N,3,3-三苯基丙-2-烯酰胺 以 苯 为溶剂， 生成 4,4-diphenyl-3,4-dihydroquinolin-2(1H)-one
  参考文献：
  名称：

  Reactions of N-phenylamide and phenyl (thio)esters of 3-phenylpropiolic acid with benzene under superelectrophilic activation

  摘要：

  在 CF3SO3H 或 AlX3（X = Cl、Br）存在下，3-苯基丙炔酸的 N-苯酰胺和苯基（硫）酯加入苯，分别得到 4,4-二苯基-3,4-二氢喹啉-2-酮、4,4-二苯基-3,4-二氢香豆素和 4,4-二苯基-3,4-二氢硫代香豆素。

  DOI：

  10.1007/s11172-012-0117-3

文献信息

• Revisiting Arene C(sp² )−H Amidation by Intramolecular Transfer of Iridium Nitrenoids: Evidence for a Spirocyclization Pathway
  作者：Yeongyu Hwang、Yoonsu Park、Yeong Bum Kim、Dongwook Kim、Sukbok Chang

  DOI：10.1002/anie.201808892

  日期：2018.10.8

  Two mechanistic pathways, that is, electrocyclization and electrophilic aromatic substitution, are operative in most intramolecular C−H amination reactions proceeding by metal nitrenoid catalysis. Reported here is an alternative mechanistic scaffold leading to benzofused δ‐lactams selectively. Integrated experimental and computational analysis revealed that the reaction proceeds by a key spirocyclization

  在通过金属类固醇催化进行的大多数分子内CH胺化反应中，有两种机理途径，即电环化和亲电子芳族取代。此处报道的是另一种机制性支架，可以选择性地导致苯并稠合的δ-内酰胺。综合的实验和计算分析表明，该反应通过关键的螺环化步骤进行，然后进行骨架重排。基于这种机理的见解，已开发出合成螺内酰胺的新途径。
• Visible‐Light Induced C(sp ² )−H Amidation with an Aryl–Alkyl σ‐Bond Relocation via Redox‐Neutral Radical–Polar Crossover
  作者：Hyeyun Keum、Hoimin Jung、Jiwoo Jeong、Dongwook Kim、Sukbok Chang

  DOI：10.1002/anie.202108775

  日期：2021.11.22

  Herein, a photocatalyzed, intramolecular C(sp2)−H amidation of N-benzoyloxyamides has been developed to afford δ-benzolactams with an aryl-alkyl σ-bond relocation. Upon the formation of amidyl radical via reductive N−O bond cleavage, selective radical ipso-addition followed by a redox-neutral radical–polar crossover was suggested to be responsible for the preferential C−C bond migration.

  在此，已开发出N-苯甲酰氧基酰胺的光催化分子内 C(sp 2 )-H 酰胺化，以提供具有芳基-烷基σ -键重定位的δ -苯内酰胺。一旦经由还原N-O键断裂形成酰胺基的基团，选择性自由基本位-addition接着是氧化还原中性基极交叉建议负责优先C-C键的迁移。
• Reactions of <i>N</i>,3-diarylpropiolamides with arenes under superelectrophilic activation: synthesis of 4,4-diaryl-3,4-dihydroquinolin-2(1<i>H</i>)-ones and their derivatives
  作者：Larisa Yu Gurskaya、Diana S Belyanskaya、Dmitry S Ryabukhin、Denis I Nilov、Irina A Boyarskaya、Aleksander V Vasilyev

  DOI：10.3762/bjoc.12.93

  日期：——

  The reaction of 3-aryl-N-(aryl)propiolamides with arenes in TfOH at room temperature for 0.5 h led to 4,4-diaryl-3,4-dihydroquinolin-2-(1H)-ones in yields of 44-98%. The obtained dihydroquinolinones were further transformed into the corresponding N-acyl or N-formyl derivatives. For the latter, the superelectrophilic activation of the N-formyl group by TfOH in the reaction with benzene resulted in the

  3-芳基-N-（芳基）丙酰胺与芳烃在TfOH中于室温下反应0.5小时，得到4,4-二芳基-3,4-二氢喹啉-2-（1H）-酮，产率为44-98 ％。将获得的二氢喹啉酮进一步转化为相应的N-酰基或N-甲酰基衍生物。对于后者，在与苯的反应中，TfOH对N-甲酰基的超亲电活化导致形成N-（二苯甲基）-取代的二氢喹啉酮。
• METHOD FOR PRODUCING LACTAM COMPOUND, AND LACTAM COMPOUND PRODUCED THEREBY
  申请人：INSTITUTE FOR BASIC SCIENCE

  公开号：US20200331871A1

  公开（公告）日：2020-10-22

  The present invention relates to a method for producing a lactam compound from dioxazolone in the presence of a catalyst having a particular ligand, and to a lactam compound produced thereby, and can produce a lactam compound with excellent selectivity and an excellent yield by using the combination of a starting material having a particular functional group and a particular catalyst having a particular ligand.

  本发明涉及一种在具有特定配体的催化剂存在下从二氧杂环酮中生产内酰胺化合物的方法，以及由此生产的内酰胺化合物，通过使用具有特定功能基团的起始材料和具有特定配体的特定催化剂的组合，可以产生具有优异选择性和优异收率的内酰胺化合物。
• Method for producing lactam compound, and lactam compound produced thereby
  申请人：INSTITUTE FOR BASIC SCIENCE

  公开号：US11046661B2

  公开（公告）日：2021-06-29

  The present invention relates to a method for producing a lactam compound from dioxazolone in the presence of a catalyst having a particular ligand, and to a lactam compound produced thereby, and can produce a lactam compound with excellent selectivity and an excellent yield by using the combination of a starting material having a particular functional group and a particular catalyst having a particular ligand.

  本发明涉及一种在具有特定配位体的催化剂存在下从二恶唑酮生产内酰胺化合物的方法，以及由此生产的内酰胺化合物，通过将具有特定官能团的起始原料和具有特定配位体的特定催化剂结合使用，可以生产出具有优异选择性和优异产率的内酰胺化合物。