16,18-Dioxa-2,11-diazapentacyclo[11.7.0.03,11.04,9.015,19]icosa-1(20),2,4,6,8,13,15(19)-heptaen-12-one | 1182366-42-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 16,18-Dioxa-2,11-diazapentacyclo[11.7.0.03,11.04,9.015,19]icosa-1(20),2,4,6,8,13,15(19)-heptaen-12-one
• CAS: 1182366-42-2
• 化学式: C₁₆H₁₀N₂O₃
• 分子量: 278.267
• InChiKey: USSMEEGABIONEJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  21
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  51.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  在 1,1'-双(二苯基膦)二茂铁 、 potassium phosphate 、 palladium diacetate 作用下， 以 1,4-二氧六环 为溶剂， 反应 8.0h， 以39 mg的产率得到16,18-Dioxa-2,11-diazapentacyclo[11.7.0.03,11.04,9.015,19]icosa-1(20),2,4,6,8,13,15(19)-heptaen-12-one
  参考文献：
  名称：

  Palladium-Catalyzed Sequential Cyanation/N-Addition/N-Arylation in One-Pot: Efficient Synthesis of Luotonin A and Its Derivatives

  摘要：

  With the catalysis of palladium, a number of 2-bromo-N-(2-iodobenzyl)benzamides underwent sequential cyanation/N-addition/N-arylation leading to the efficient construction of isoindolo[1,2-b]quinazolin-10(12H)-ones in a two-stage, one-pot manner. This method also allowed the convenient synthesis of luotonin A and its derivatives.

  DOI：

  10.1021/ol901305q

文献信息

• Nickel-Catalyzed Intramolecular Dual Annulation Reaction of Aryl Nitrile-Containing 1,2,3-Benzotriazin-4(3<i>H</i>)-ones: A Pathway To Synthesize Luotonin A and Related Polycyclic Pyrroloquinazolinones
  作者：Vijaykumar H. Thorat、Jen-Chieh Hsieh

  DOI：10.1021/acs.orglett.3c03142

  日期：2023.11.10

  Herein, we report a nickel-catalyzed intramolecular denitrogenative dual annulation reaction of aryl nitrile-containing 1,2,3-benzotriazine-4(3H)-ones to synthesize polycyclic pyrroloquinazolinones with a tolerance of a wide diversity of substituents. This catalytic reaction is the first denitrogenative transannulation of 1,2,3-benzotriazine-4(3H)-one with nitrile, which can be applied as the critical

  在此，我们报道了含芳基腈的1,2,3-苯并三嗪-4(3 H )-酮的镍催化分子内脱氮双环化反应，合成了具有多种取代基的多环吡咯并喹唑啉酮。该催化反应是1,2,3-苯并三嗪-4(3H)-酮与腈的首次脱氮转环反应，可作为合成洛托宁A的关键步骤，具有较高的步骤经济性。