12-phenyl-4b,6-dihydrobenzo[4,5][1,3]oxazino[2,3-a]isoquinoline | 1226978-10-4

• 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: 12-phenyl-4b,6-dihydrobenzo[4,5][1,3]oxazino[2,3-a]isoquinoline
• 英文别名: 12-Phenyl-4b,6-dihydroisoquinolino[2,1-a][3,1]benzoxazine
• CAS: 1226978-10-4
• 化学式: C₂₂H₁₇NO
• 分子量: 311.383
• InChiKey: SYACXZPMWGUFQP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  24
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  苯乙炔 在 bis-triphenylphosphine-palladium(II) chloride 、 silver nitrate 、 三乙胺 作用下， 以 水 、 乙腈 为溶剂， 反应 1.0h， 生成 12-phenyl-4b,6-dihydrobenzo[4,5][1,3]oxazino[2,3-a]isoquinoline
  参考文献：
  名称：

  On Water: Silver-Catalyzed Domino Approach for the Synthesis of Benzoxazine/Oxazine-Fused Isoquinolines and Naphthyridines fromo-Alkynyl Aldehydes

  摘要：

  An operationally simple domino approach for the silver-catalyzed synthesis of oxazine/benzoxazine-fused isoquinolines 5a-q and naphthyridines 6a-v by the reaction of o-alkynyl aldehydes 3a-aa with amines having embedded nucleophiles 4a-d under mild reaction condition in water is described. The reaction shows selective C-N bond formation on the more electrophilic alkynyl carbon resulting in the formation of 6-endo-dig cyclized product. The competitive experiments show the viability of an intramolecular nucleo philic attack over an intermolecular attack of the external nucleophile. This methodology accommodates wide functional group variation, which proves to be useful for structural and biological assessment.

  DOI：

  10.1021/jo4009639

文献信息

• Facile Assembly of Fused Isoquinolines by Gold(I)-Catalyzed Coupling-Cyclization Reactions between o-Alkynylbenzaldehydes and Aromatic Amines Containing Tethered Nucleophiles
  作者：Nitin T. Patil、Anil Kumar Mutyala、Pediredla G. V. V. Lakshmi、Penmatcha V. K. Raju、Balasubramanian Sridhar

  DOI：10.1002/ejoc.200901364

  日期：2010.4

  A gold(I)-catalyzed, operationally simple coupling-cyclization technique was developed for the synthesis of isoquinoline-fused polycyclic compounds. The reaction makes use of two coupling partners such as o-alkynylbenzaldehydes and aromatic amines having tethered nucleophiles. The reaction is easy to perform, broad in scope, and allows the generation of a number of biologically important heterocyclic

  开发了一种金 (I) 催化、操作简单的偶联环化技术，用于合成异喹啉稠合多环化合物。该反应利用两个偶联伙伴，例如邻炔基苯甲醛和具有系链亲核试剂的芳香胺。该反应易于进行，范围广泛，并允许从容易获得的起始材料中产生许多生物学上重要的杂环基序。讨论了反应机理。
• ‘One-pot’ Synthesis of Dihydrobenzo[4,5][1,3]oxazino[2,3-a] isoquinolines via a Silver(I)-Catalyzed Cascade Approach
  作者：Baifeng Jiang、Yu Zhou、Qingya Kong、Hualiang Jiang、Hong Liu、Jian Li

  DOI：10.3390/molecules18010814

  日期：——

  An efficient approach for the synthesis of biologically interesting fused tetracyclic isoquinolines in high yields and with a broad substrate scope has been developed. The strategy features an AgNO(3) catalyzed 'one-pot' cascade process involving formation of two new C-N bonds and one new C-O bond.

  已经开发出一种以高产率和广泛底物范围合成具有生物学意义的稠合四环异喹啉的有效方法。该策略具有 AgNO(3) 催化的“一锅”级联过程，涉及形成两个新的 CN 键和一个新的 CO 键。