1-octyl-2-phenylquinolin-4(1H)-one | 1395418-40-2

• 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: 1-octyl-2-phenylquinolin-4(1H)-one
• 英文别名: 1-octyl-2-phenyl-1H-quinolin-4-one；1-Octyl-2-phenylquinolin-4-one；1-octyl-2-phenylquinolin-4-one
• CAS: 1395418-40-2
• 化学式: C₂₃H₂₇NO
• 分子量: 333.473
• InChiKey: IEHJSHQFHUPAFP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-(2-chlorophenyl)-3-phenyl-2-propyn-1-ol 在 manganese(IV) oxide 、 potassium phosphate monohydrate 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 14.0h， 生成 1-octyl-2-phenylquinolin-4(1H)-one
  参考文献：
  名称：

  Synthesis of N-Alkyl-Substituted 4-Quinolones via Tandem Alkenyl and Aryl C-N Bond Formation

  摘要：

  N-Alkyl-substituted 4-quinolones are present as the key structural motif in many marketed drugs. An efficient one-step tandem amination approach was developed to afford N-alkyl-substituted 4-quinolones in high yields from easily accessible o-chloroaryl acetylenic ketones and functionalized alkyl amines. The approach complements and extends our previous work. Compared with other reported methods, the current method provides a very simple and convenient route.

  DOI：

  10.1055/s-0031-1290775

文献信息

• Hydrogen Bond Assisted Three-Component Tandem Reactions to Access N-Alkyl-4-Quinolones
  作者：Huanhuan Liu、Huadan Liu、Enhua Wang、Liangqun Li、Zhongsheng Luo、Jiafu Cao、Jialin Chen、Lishou Yang、Xiaosheng Yang

  DOI：10.3390/molecules28052304

  日期：——

  Hydrogen-bonding catalytic reactions have gained great interest. Herein, a hydrogen-bond-assisted three-component tandem reaction for the efficient synthesis of N-alkyl-4-quinolones is described. This novel strategy features the first proof of polyphosphate ester (PPE) as a dual hydrogen-bonding catalyst and the use of readily available starting materials for the preparation of N-alkyl-4-quinolones. The method provides a diversity of N-alkyl-4-quinolones in moderate to good yields. The compound 4h demonstrated good neuroprotective activity against N-methyl-ᴅ-aspartate (NMDA)-induced excitotoxicity in PC12 cells.

  氢键催化反应备受关注。本文介绍了一种氢键辅助的三组分串联反应，用于高效合成 N-烷基-4-喹啉酮。这一新颖策略的特点是首次证明了聚磷酸酯（PPE）是一种双重氢键催化剂，并利用容易获得的起始材料制备 N-烷基-4-喹啉酮。该方法提供了多种 N-烷基-4-喹啉酮，收率中等至良好。化合物 4h 对 PC12 细胞中 N-甲基-ᴅ-天冬氨酸（NMDA）诱导的兴奋性毒性具有良好的神经保护活性。
• CN116120227
  申请人：——

  公开号：——

  公开（公告）日：——
• Synthesis of N-Alkyl-Substituted 4-Quinolones via Tandem Alkenyl and Aryl C-N Bond Formation
  作者：Bin Xu、Jun Shao、Xiaomei Huang、Xiaohu Hong、Bingxin Liu

  DOI：10.1055/s-0031-1290775

  日期：2012.6

  N-Alkyl-substituted 4-quinolones are present as the key structural motif in many marketed drugs. An efficient one-step tandem amination approach was developed to afford N-alkyl-substituted 4-quinolones in high yields from easily accessible o-chloroaryl acetylenic ketones and functionalized alkyl amines. The approach complements and extends our previous work. Compared with other reported methods, the current method provides a very simple and convenient route.