1,3-dibromo-8,9-dihydro-7H-10-oxa-6a-azonia-cyclohepta[de]naphthalene bromide | 1026668-04-1

• 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-azonia-cyclohepta[de]naphthalene bromide
• 英文别名: 6,8-Dibromo-10-oxa-1-azoniatricyclo[7.4.1.05,14]tetradeca-1,3,5(14),6,8-pentaene;bromide；6,8-dibromo-10-oxa-1-azoniatricyclo[7.4.1.05,14]tetradeca-1,3,5(14),6,8-pentaene;bromide
• CAS: 1026668-04-1
• 化学式: Br*C₁₂H₁₀Br₂NO
• 分子量: 423.93
• InChiKey: FCRHYONIGOKRLM-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  0.44
• 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：
  13.1
• 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-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
• 作为产物：
  描述：

  5,7-二溴-8-羟基喹啉 、 1,3-二溴丙烷 在 Amberlite IRA 402(OH) resin 作用下， 以 水 为溶剂， 反应 4.0h， 以87%的产率得到1,3-dibromo-8,9-dihydro-7H-10-oxa-6a-azonia-cyclohepta[de]naphthalene bromide
  参考文献：
  名称：

  Amberlite IRA 402（OH）：一种高效的介体，用于独家合成稠合的三环氧杂氮杂喹啉鎓盐

  摘要：

  使用Amberlite IRA 402（OH）在水中已开发出用于合成三环氧杂氮杂喹啉鎓盐的高产率绿色方案。与先前报道的相转移催化（PTC）条件相比，该方法在产物收率，反应时间和分离容易性方面更有效。

  DOI：

  10.1016/j.tetlet.2010.04.034

文献信息

• Amberlite IRA 402(OH)-mediated synthesis and evaluation of fused tricyclic quinolinium salts as potent non-detergent type microbicidal spermicides
  作者：Maitreyee Banerjee、Shrabanti Kumar、Soma Ghosh、Rupankar Paira、Shyamal Mondal、Sanmoy Karmokar、Debprsad Chattopadhyay、Rupak K. Bhadra、Nirup B. Mondal

  DOI：10.1007/s00044-013-0758-2

  日期：2014.3

  Fused tricyclic oxazaquinolinium salts were synthesized using Amberlite IRA 402(OH) in water and assessed for their sperm-immobilizing efficacy in vitro by modified Sander-Cramer test followed by double fluoroprobe staining of rat sperm. Out of 11 derivatives 3 showed potent spermicidal effect. The mode of spermicidal action was assessed by (a) Hypoosmotic swelling tests, (b) Lipid peroxidation studies, and (c) scanning electron microscopy. Antimicrobial efficacies of the potent derivatives, assessed by disc diffusion as well as by agar and broth dilution methods using human isolates of bacteria and fungi, revealed their moderate antimicrobial potential. The compounds, found to be nontoxic to rabbit erythrocytes by haemolytic assay, may be exploited as microbicidal spermicides.
• An easy access to diversely fused dioxa-2-aza-tricyclo[n.3.1.02,n]tetra/pentadecanes under solvent-free condition
  作者：Rupankar Paira、Shyamal Mondal、Arindam Maity、Krishnendu B. Sahu、Subhendu Naskar、Pritam Saha、Abhijit Hazra、Sandip Kundu、Sukdeb Banerjee、Nirup B. Mondal

  DOI：10.1016/j.tetlet.2011.08.080

  日期：2011.10

  Efficient syntheses of phenyl/N-heterocycle fused 6,13-dioxa-2-aza-tricyclo[8.3.1.0(2,8)]tetradecanes have been accomplished from 8-hydroxy quinoline derivatives under solvent-free condition, using basic alumina as the solid support. The methodology was successfully extended for the synthesis of corresponding pentadecane derivatives under similar reaction conditions. In terms of its general applicability, product yield, reaction time and effortless separation techniques, the methodology is more valuable compared to the solution phase protocols. (C) 2011 Elsevier Ltd. All rights reserved.
• Amberlite IRA 402(OH): an efficient mediator for the exclusive synthesis of fused tricyclic oxaza quinolinium salts
  作者：Rupankar Paira、Priyankar Paira、Arindam Maity、Shyamal Mondal、Abhijit Hazra、Krishnendu B. Sahu、Subhendu Naskar、Pritam Saha、Maitreyee Banerjee、Nirup B. Mondal

  DOI：10.1016/j.tetlet.2010.04.034

  日期：2010.6

  A high yielding green protocol for the synthesis of tricyclic oxaza quinolinium salts has been developed using Amberlite IRA 402(OH) in water. This method is more effective compared to previously reported phase-transfer catalytic (PTC) condition in terms of yield of the product, reaction time and ease of separation.

  使用Amberlite IRA 402（OH）在水中已开发出用于合成三环氧杂氮杂喹啉鎓盐的高产率绿色方案。与先前报道的相转移催化（PTC）条件相比，该方法在产物收率，反应时间和分离容易性方面更有效。
• 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.