1,3-dibromo-8,9-dihydro-7H-10-oxa-6a-azacyclohepta[de]naphthalen-6-one | 1026668-06-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶嗪类
• 英文名称: 1,3-dibromo-8,9-dihydro-7H-10-oxa-6a-azacyclohepta[de]naphthalen-6-one
• 英文别名: 9,11-dibromo-3,4-dihydro-2H,6H-[1,4]-oxazepino[2,3,4-ij]quinolin-6-one；9,11-Dibromo-3,4-dihydro-2h,6h-[1,4]oxazepino[2,3,4-ij]quinolin-6-one；6,8-dibromo-10-oxa-1-azatricyclo[7.4.1.05,14]tetradeca-3,5(14),6,8-tetraen-2-one
• CAS: 1026668-06-3
• 化学式: C₁₂H₉Br₂NO₂
• 分子量: 359.017
• InChiKey: OLEWNNWZRIHKPH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,3-dibromo-8,9-dihydro-7H-10-oxa-6a-azacyclohepta[de]naphthalen-6-one 、 3-吡啶硼酸 在 四(三苯基膦)钯 作用下， 反应 0.05h， 以88%的产率得到
  参考文献：
  名称：

  微波辐射下碱性氧化铝支持的高效铃木-宫浦交叉偶联反应：在稠合三环氧杂氮杂-喹诺酮类化合物中的应用

  摘要：

  基本的 氧化铝 代替传统 矿物 基地有效地促进了 溶剂在微波辐射下，游离的Pd（PPh 3）4催化了Suzuki-Miyaura交叉偶联反应。

  DOI：

  10.1039/b902916h
• 作为产物：
  描述：

  1,3-dibromo-8,9-dihydro-7H-10-oxa-6a-azonia-cyclohepta[de]naphthalene bromide 在 sodium hydroxide 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 水 为溶剂， 反应 0.25h， 生成 1,3-dibromo-8,9-dihydro-7H-10-oxa-6a-azacyclohepta[de]naphthalen-6-one
  参考文献：
  名称：

  Facile synthesis of seven to nine-membered-fused tricyclic quinolones and quinolinium salts under phase transfer catalyzed conditions

  摘要：

  Phase transfer catalyzed one-pot syntheses of fused oxazepino, oxazocino, and oxazonino quinolinium cations and quinolones were achieved from 8-hydroxy quinoline derivatives with 1,omega-dihaloalkanes. Structures of all the products were elucidated by spectroscopic analysis. Single crystal X-ray crystallographic analysis of three compounds and graphical superposition of the structures indicate that products having seven-membered ring are less planar compared to the product having eight-membered ring. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.02.048

文献信息

• Basic Alumina-Supported Synthesis of Aryl-Heteroarylmethanes<i>via</i>Palladium Catalyzed Cross-Coupling under Microwave Irradiation
  作者：Krishnendu B. Sahu、Arindam Maity、Shyamal Mondal、Rupankar Paira、Pritam Saha、Subhendu Naskar、Abhijit Hazra、Sukdeb Banerjee、Nirup B. Mondal

  DOI：10.1002/jhet.1099

  日期：2013.2

  A basic alumina-supported microwave assisted simple methodology has been developed for the synthesis of aryl-heteroaryl methanes (benzylated quinolones) via transition metal catalyzed cross-coupling reaction of halo substituted polynuclear oxa-aza quinolones with benzyl indium, an organometallic reagent easily derived from commercially available benzyl bromide.

  已经开发了一种基本的氧化铝支持的微波辅助简单方法，该方法可通过卤素取代的多核氧杂氮杂氮杂喹啉酮与苄基铟的过渡金属催化交叉偶联反应来合成芳基-杂芳基甲烷（苄基化喹诺酮）。市售苄溴。
• Synthesis of polycyclic fused 2-quinolones in aqueous micellar system
  作者：Subhendu Naskar、Pritam Saha、Rupankar Paira、Abhijit Hazra、Priyankar Paira、Shyamal Mondal、Arindam Maity、Krishnendu B. Sahu、Sukdeb Banerjee、Nirup B. Mondal

  DOI：10.1016/j.tetlet.2010.01.030

  日期：2010.3

  A high yielding green protocol has been developed for the synthesis of tri-, tetra-, and pentacyclic fused 2-quinolones in micellar medium. The method is more effective compared to phase-transfer catalytic (PTC) method in terms of the yield of the product as well as the reaction time. It is operationally simple as well as environmentally benign. (C) 2010 Elsevier Ltd. All rights reserved.
• Combined palladium/eosin Y-catalysed direct synthesis of anticancer biarylquinolinooxazocino-quinoxaline-1-ones under visible light in one-pot sequence: a revisited proof of concept
  作者：Nilmadhab Roy、Priyankar Paira

  DOI：10.1007/s00706-020-02641-2

  日期：2020.7

  A novel, efficient, and green catalytic system under visible light irradiation has been introduced for the synthesis of anticancer biarylquinolooxazocino-quinoxaline-1-ones in one-pot sequence. The developed synthetic approach will be successfully utilized for the synthesis of various bioactive biarylquinolone in near future. Also, the cytotoxicity profile of these scaffolds has unveiled their superb cytoselectivity in HeLa and MCF-7 cell line compared to cisplatin. Graphic abstract
• Facile synthesis of seven to nine-membered-fused tricyclic quinolones and quinolinium salts under phase transfer catalyzed conditions
  作者：Priyankar Paira、Abhijit Hazra、Krishnendu B. Sahu、Sukdeb Banerjee、Nirup B. Mondal、Niranjan P. Sahu、Manuela Weber、Peter Luger

  DOI：10.1016/j.tet.2008.02.048

  日期：2008.4

  Phase transfer catalyzed one-pot syntheses of fused oxazepino, oxazocino, and oxazonino quinolinium cations and quinolones were achieved from 8-hydroxy quinoline derivatives with 1,omega-dihaloalkanes. Structures of all the products were elucidated by spectroscopic analysis. Single crystal X-ray crystallographic analysis of three compounds and graphical superposition of the structures indicate that products having seven-membered ring are less planar compared to the product having eight-membered ring. (c) 2008 Elsevier Ltd. All rights reserved.
• Basic alumina-supported highly effective Suzuki–Miyaura cross-coupling reaction under microwave irradiation: application to fused tricyclic oxa-aza-quinolones
  作者：Pritam Saha、Subhendu Naskar、Priyankar Paira、Abhijit Hazra、Krishnendu B. Sahu、Rupankar Paira、Sukdeb Banerjee、Nirup B. Mondal

  DOI：10.1039/b902916h

  日期：——

  Basic alumina used in lieu of traditional mineral bases efficiently promotes a solvent free, Pd(PPh3)4 catalyzed Suzuki–Miyaura cross-coupling reaction under microwave irradiation.

  基本的 氧化铝 代替传统 矿物 基地有效地促进了 溶剂在微波辐射下，游离的Pd（PPh 3）4催化了Suzuki-Miyaura交叉偶联反应。