5-chloro-2-phenylfuro[3,2-h]quinoline | 1218818-87-1

• 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-2-phenylfuro[3,2-h]quinoline
• 英文别名: 5-Chloro-2-phenylfuro[3,2-h]quinoline
• CAS: 1218818-87-1
• 化学式: C₁₇H₁₀ClNO
• 分子量: 279.725
• InChiKey: YHQNRGASTLBXRW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  26
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-chloro-2-phenylfuro[3,2-h]quinoline 在 aluminum oxide 作用下， 以 氯仿 、 乙腈 为溶剂， 生成 10-benzoyl-5-chloro-2-phenyl-1-oxa-10a-aza-dicyclopenta[a,h]naphthalene-8-carboxylic acid methyl ester
  参考文献：
  名称：

  Traceless synthetic approach towards oxaza-dicyclopenta[a,h]naphthalenes under solvent-free condition: a basic alumina-supported green protocol

  摘要：

  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.

  DOI：

  10.1016/j.tetlet.2013.03.095
• 作为产物：
  描述：

  氯碘羟喹 、 苯乙炔 在 copper(l) iodide 、 palladium diacetate 、 potassium carbonate 、 三苯基膦 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.5h， 以75%的产率得到5-chloro-2-phenylfuro[3,2-h]quinoline
  参考文献：
  名称：

  First Synthesis of 5- and 7-Phenylethynyl-8-hydroxyquinolines by Sonogashira Reaction

  摘要：

  通过 Pd-CuI 催化 8-(苄氧基)-5-氯-7-碘喹啉和 8-(苄氧基)-5,7-二碘喹啉与 1-乙炔苯的 Sonogashira 型交叉偶联，合成了 5-氯-7-(2-苯乙炔基)喹啉-8-醇和 7-碘-5-(2-苯乙炔基)喹啉-8-醇。偶联产物在二氯甲烷中被三氯化硼顺利脱苄基，得到相应的产物，产率良好。

  DOI：

  10.2174/15701786113109990045

文献信息

• One-Pot Tandem Synthesis of Furo[3,2-h]quinolines by a Sonogashira Cross-Coupling and Cyclization Reaction Supported by Basic Alumina Under Microwave Irradiation
  作者：Nirup Mondal、Pritam Saha、Subhendu Naskar、Rupankar Paira、Shyamal Mondal、Arindam Maity、Krishnendu Sahu、Priyankar Paira、Abhijit Hazra、Diptendu Bhattacharya、Sukdeb Banerjee

  DOI：10.1055/s-0029-1217143

  日期：2010.2

  Acetylenic 8-quinolinols generated in situ by the Sonogashira cross-coupling reaction are efficiently converted into furo[3,2-h]quinolines by microwave-assisted, copper-catalyzed, intramolecular cyclization in the presence of basic alumina. heterocycles - furoquinoline - cross-coupling - cyclizations - solid-phase synthesis - microwave irradiation

  在碱性氧化铝的存在下，通过微波辅助的铜催化的分子内环化作用，通过Sonogashira交叉偶联反应原位生成的乙炔8-喹啉醇可有效地转化为呋喃并[3,2- h ]喹啉。 杂环-呋喃喹啉-交叉偶联-环化-固相合成-微波辐射
• Copper–phenanthroline catalysts for regioselective synthesis of pyrrolo[3′,4′:3,4]pyrrolo[1,2-<i>a</i>]furoquinolines/phenanthrolines and of pyrrolo[1,2-<i>a</i>]phenanthrolines under mild conditions
  作者：Rupankar Paira、Tarique Anwar、Maitreyee Banerjee、Yogesh P Bharitkar、Shyamal Mondal、Sandip Kundu、Abhijit Hazra、Prakas R Maulik、Nirup B Mondal

  DOI：10.3762/bjoc.10.62

  日期：——

  A new series of pyrrolo[3',4':3,4]pyrrolo[1,2-a]furoquinolines/phenanthrolines and pyrrolo[1,2-a]phenanthrolines were efficiently built up from an 8-hydroxyquinoline derivative or phenanthroline via 1,3-dipolar cycloaddition reaction involving non-stabilized azomethine ylides, generated in situ from the parent furo[3,2-h]quinoliniums/phenanthroliums, in presence of a copper(II) chloride-phenanthroline

  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。
• 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。
• A green approach for highly regioselective syntheses of furo[3,2-h]quinolines in aqueous medium
  作者：Swarbhanu Sarkar、Rammyani Pal、Nivedita Chatterjee、Samrat Dutta、Subhendu Naskar、Asish Kumar Sen

  DOI：10.1016/j.tetlet.2013.05.038

  日期：2013.7

  An environmentally benign, high yielding, and operationally simple protocol has been developed for the regioselective synthesis of furo[3,2-h]quinolines in aqueous micellar medium involving Cu-free domino Sonogashira reaction followed by 5-endo-dig-cyclization of substituted 8-hydroxyquinolines and terminal allcyne by using Pd(C6H5CN)Cl-2 as catalyst and 2-pyridinecarboxaldehyde methylphenyl hydrazone as ligand under aerobic condition. (C) 2013 Elsevier Ltd. All rights reserved.
• 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.