5-chloro-9-(2-oxo-2-phenyl-ethyl)-2-(4-methyl-phenyl)-furo[3,2-h]quinolin-9-ium bromide | 1436840-99-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 2-芳基苯并呋喃类黄酮
• 英文名称: 5-chloro-9-(2-oxo-2-phenyl-ethyl)-2-(4-methyl-phenyl)-furo[3,2-h]quinolin-9-ium bromide
• CAS: 1436840-99-1
• 化学式: Br*C₂₆H₁₉ClNO₂
• 分子量: 492.799
• InChiKey: AFYUWTHMGMJYBF-UHFFFAOYSA-M

物化性质

• 熔点：
  244-245 °C

计算性质

• 辛醇/水分配系数(LogP)：
  3.39
• 重原子数：
  31.0
• 可旋转键数：
  4.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  34.09
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  5-chloro-9-(2-oxo-2-phenyl-ethyl)-2-(4-methyl-phenyl)-furo[3,2-h]quinolin-9-ium bromide 、 1-(2,3-二甲基苯基)-吡咯-2,5-二酮 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 1,7-菲啰啉 、 copper dichloride 作用下， 以 乙腈 为溶剂， 反应 3.5h， 以87%的产率得到3-Benzoyl-13-chloro-6-(2,3-dimethylphenyl)-17-(4-methylphenyl)-18-oxa-2,6-diazapentacyclo[10.7.0.02,9.04,8.015,19]nonadeca-1(19),10,12,14,16-pentaene-5,7-dione
  参考文献：
  名称：

  铜-菲咯啉催化剂用于在温和条件下区域选择性合成吡咯并[3',4':3,4]吡咯并[1,2-a]呋喃喹啉/菲咯啉和吡咯并[1,2-a]菲咯啉。

  摘要：

  一系列新的吡咯并[3',4':3,4]吡咯并[1,2-a]呋喃喹啉/菲咯啉和吡咯并[1,2-a]菲咯啉从8-羟基喹啉衍生物或菲咯啉通过1,3-偶极环加成反应涉及不稳定的偶氮甲碱叶立德，在氯化铜 (II)-菲咯啉催化体系存在下，由母体呋喃 [3,2-h] 喹啉鎓/菲咯鎓原位生成。该方法结合了普遍适用性和高产量。

  DOI：

  10.3762/bjoc.10.62
• 作为产物：
  描述：

  5-chloro-2-(p-tolyl)furo[3,2-h]quinoline 、 2-溴苯乙酮 在 aluminum oxide 作用下， 生成 5-chloro-9-(2-oxo-2-phenyl-ethyl)-2-(4-methyl-phenyl)-furo[3,2-h]quinolin-9-ium bromide
  参考文献：
  名称：

  铜-菲咯啉催化剂用于在温和条件下区域选择性合成吡咯并[3',4':3,4]吡咯并[1,2-a]呋喃喹啉/菲咯啉和吡咯并[1,2-a]菲咯啉。

  摘要：

  一系列新的吡咯并[3',4':3,4]吡咯并[1,2-a]呋喃喹啉/菲咯啉和吡咯并[1,2-a]菲咯啉从8-羟基喹啉衍生物或菲咯啉通过1,3-偶极环加成反应涉及不稳定的偶氮甲碱叶立德，在氯化铜 (II)-菲咯啉催化体系存在下，由母体呋喃 [3,2-h] 喹啉鎓/菲咯鎓原位生成。该方法结合了普遍适用性和高产量。

  DOI：

  10.3762/bjoc.10.62

文献信息

• Synthesis and Characterization of Furo[3,2-h]Quinoliniums as Potent Non- Detergent Spermicides
  作者：Maitreyee Banerjee、Shrabanti Kumar、Rupankar Paira、Soma Ghosh、Sanmoy Karmakar、Nirup Mondal

  DOI：10.2174/15701808113109990046

  日期：2013.11

  7-Aryl substituted furo[3,2-h]quinoliniums have been synthesised in two steps from 5-chloro-8-hydroxy-7- iodo-quinoline through a tandem Sonogashira alkynylation-cyclization pathway using aryl acetylenes followed by quaternisation reaction with alkyl halides under microwave irradiation. The compounds have been characterized spectroscopically and assessed for their sperm-immobilizing efficacy in vitro by modified Sander–Cramer test. Most of the derivatives showed potent spermicidal effect with minimum effective concentration (MEC) ranging from 125g/ml – 1mg/ml. The results were further confirmed by double fluoroprobe staining with syber14/PI (Propidium Iodide). The mode of spermicidal action was assessed by (a) Hypo-osmotic swelling tests and (b) Scanning electron microscopy. The compounds have been found to be nontoxic to lactobacillus in 36 hours of culture whereas mild to moderately effective on common vaginal pathogens. Taken together it can be inferred that the water-soluble salts prepared from facile technique are potential candidates for spermicides and could further be utilized for the preparation of vaginal contraceptives.

  通过使用芳基乙炔进行串联 Sonogashira 烷炔化-环化途径，然后在微波辐照下与烷基卤化物进行季铵化反应，分两步合成了 7-芳基取代的呋喃并[3,2-h]喹啉。对这些化合物进行了光谱表征，并通过改进的桑德尔-克拉默试验评估了它们在体外的精子固定功效。大多数衍生物都显示出强大的杀精效果，最低有效浓度（MEC）在 125g/ml - 1mg/ml 之间。用 syber14/PI（碘化丙啶）进行双荧光探针染色进一步证实了这一结果。通过（a）低渗膨胀试验和（b）扫描电子显微镜评估了杀精作用的模式。研究发现，这些化合物在 36 小时的培养过程中对乳酸杆菌无毒，而对常见的阴道病原体有轻度到中度的作用。综上所述，通过简便技术制备的水溶性盐类有可能成为杀精剂，并可进一步用于制备阴道避孕药。
• Traceless synthetic approach towards oxaza-dicyclopenta[a,h]naphthalenes under solvent-free condition: a basic alumina-supported green protocol
  作者：Rupankar Paira、Shyamal Mondal、Arpan Chowdhury、Maitreyee Banerjee、Arindam Maity、Abhijit Hazra、Nirup B. Mondal

  DOI：10.1016/j.tetlet.2013.03.095

  日期：2013.6

  A novel class of oxaza-dicyclopenta[a,h]naphthalenes was efficiently constructed from furo[3,2-h]quinoliniums through a 1,3-dipolar cycloaddition reaction employing basic alumina as the solid support. The distinguished features of this methodology encompass high yield, minimal reaction time, operational simplicity and general applicability coupled with structural novelty of the products. The intermediate furo[3,2-h]quinoliniums were easily derived through a two-step methodology, namely a tandem Sonogashira-alkynylation-cyclization, followed by quaternization of the furo[3,2-h]quinoline scaffold. (C) 2013 Elsevier Ltd. All rights reserved.