1-(4-(4-phenylquinolin-2-yl)phenyl)ethan-1-one | 929602-14-2

• 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-(4-(4-phenylquinolin-2-yl)phenyl)ethan-1-one
• 英文别名: 1-[4-(4-Phenylquinolin-2-yl)phenyl]ethanone；1-[4-(4-phenylquinolin-2-yl)phenyl]ethanone
• CAS: 929602-14-2
• 化学式: C₂₃H₁₇NO
• 分子量: 323.394
• InChiKey: ZVDDPDIDWSVTAI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  30
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以99 mg的产率得到1-(4-(4-phenylquinolin-2-yl)phenyl)ethan-1-one
  参考文献：
  名称：

  Intermolecular Dehydrative [4 + 2] Aza-Annulation of N-Arylamides with Alkenes: A Direct and Divergent Entrance to Aza-Heterocycles

  摘要：

  We disclose that following activation with trifluoromethanesulfonyl anhydride, secondary N-arylamides undergo smooth intermolecular dehydrative [4 + 2] aza-annulation with alkenes under mild conditions to give 3,4-dihydroquinolines, amenable to further functionalization. Meanwhile, conditions have been established to allow divergent one pot synthesis of tetrahydroquinolines and quinolines as well as tricyclic analogues from N-arylamides.

  DOI：

  10.1021/acs.orglett.9b00233

文献信息

• Rh-Catalyzed Sequential Hydroarylation/Hydrovinylation-Heterocyclization of β-(2-Aminophenyl)-α,β-ynones with Organoboron Derivatives: A New Approach to Functionalized Quinolines
  作者：Fabio Marinelli、Giorgio Abbiati、Antonio Arcadi、Elisabetta Rossi、Mirella Verdecchia

  DOI：10.1055/s-2006-956462

  日期：——

  4-Aryl and 4-vinyl quinolines were prepared via a sequential procedure involving regioselective Rh(acac)(C2H2)/dppf-catalyzed hydroarylation/hydrovinylation of β-(2-aminophenyl)-α,β-ynones with arylboronic acids or potassium aryl and vinyl trifluoroborates, followed by nucleophilic attack of the amino group onto the carbonyl.

  4-芳基和 4-乙烯基喹啉是通过连续程序制备的，涉及区域选择性 Rh(acac)(C2H2)/dppf 催化的 β-(2-氨基苯基)-α,β-ynones 与芳基硼酸或钾的加氢芳基化/氢乙烯基化芳基和乙烯基三氟硼酸酯，然后氨基对羰基进行亲核攻击。
• Intermolecular Dehydrative [4 + 2] Aza-Annulation of <i>N</i>-Arylamides with Alkenes: A Direct and Divergent Entrance to Aza-Heterocycles
  作者：Ying-Hong Huang、Shu-Ren Wang、Dong-Ping Wu、Pei-Qiang Huang

  DOI：10.1021/acs.orglett.9b00233

  日期：2019.3.15

  We disclose that following activation with trifluoromethanesulfonyl anhydride, secondary N-arylamides undergo smooth intermolecular dehydrative [4 + 2] aza-annulation with alkenes under mild conditions to give 3,4-dihydroquinolines, amenable to further functionalization. Meanwhile, conditions have been established to allow divergent one pot synthesis of tetrahydroquinolines and quinolines as well as tricyclic analogues from N-arylamides.