7,9-dibromo-2,3-dihydro-1-oxa-3a-azonia-phenalene bromide | 1231156-93-6

• 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: 7,9-dibromo-2,3-dihydro-1-oxa-3a-azonia-phenalene bromide
• 英文别名: 6,8-Dibromo-4-oxa-1-azoniatricyclo[7.3.1.05,13]trideca-1(12),5,7,9(13),10-pentaene;bromide
• CAS: 1231156-93-6
• 化学式: Br*C₁₁H₈Br₂NO
• 分子量: 409.903
• InChiKey: ZSVILUKESWRTOA-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  0.05
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  13.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  5,7-二溴-8-羟基喹啉 、 1,2-二溴乙烷 在 Amberlite IRA 402(OH) resin 作用下， 以 水 为溶剂， 反应 3.0h， 以97%的产率得到7,9-dibromo-2,3-dihydro-1-oxa-3a-azonia-phenalene 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.