5-Naphthalen-1-ylthiolan-3-one | 1196893-56-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 5-Naphthalen-1-ylthiolan-3-one
• CAS: 1196893-56-7
• 化学式: C₁₄H₁₂OS
• 分子量: 228.315
• InChiKey: ATMNOZOQNZHORP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  42.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-Naphthalen-1-ylthiolan-3-one 、 2-氨基二苯甲酮 在 三氟乙酸 、 碳酸氢钠 作用下， 以 水 为溶剂， 20.0~100.0 ℃ 、100.0 kPa 条件下， 反应 0.5h， 以93%的产率得到2-(1-naphthyl)-9-phenyl-2,3-dihydrothieno[3,2-b]quinoline
  参考文献：
  名称：

  A microwave-assisted, facile, regioselective Friedländer synthesis and antitubercular evaluation of 2,9-diaryl-2,3-dihydrothieno-[3,2- b ]quinolines

  摘要：

  A series of 2,9-diaryl-2,3-dihydrothieno[3,2-b]quinolines have been synthesized regioselectively by Friedlander annulation of 5-aryldihydro-3(2H)-thiophenones and 2-aminobenzophenones in the presence of trifluoroacetic acid in good yields under microwave irradiation at 100 degrees C. The 2,9-diatyl-2,3-dihydrothieno[3,2-b]quinolines were screened for in vitro antimycobacterial activity against Mycobacterium tuberculosis H37Rv (MTB) and multi-drug resistant M. tuberculosis (MDR-TB). Among the 17 compounds screened, 7-chloro-2-(2,4-dichlorophenyl)-9-phenyl-2,3-dihydrothieno-[3,2-b]quinoline and 7-chloro-2-(3-nitrophenyl)-9-phenyl-2,3-dihydrothieno[3,2-b]quinoline display maximum activity with MIC of 0.90 and 0.95 mu M against MTB and MDR-TB respectively. (C) 2009 Elsevier Masson SAS. Ail rights reserved.

  DOI：

  10.1016/j.ejmech.2009.11.011

文献信息

• A facile domino protocol for the regioselective synthesis and discovery of novel 2-amino-5-arylthieno-[2,3-b]thiophenes as antimycobacterial agents
  作者：Kamaraj Balamurugan、Subbu Perumal、Aaramadaka Sunil Kumar Reddy、Perumal Yogeeswari、Dharmarajan Sriram

  DOI：10.1016/j.tetlet.2009.08.085

  日期：2009.11

  2-amino-5-arylthieno[2,3-b]thiophenes has been synthesized regioselectively from the reaction of 5-aryldihydro-3(2H)-thiophenones with ethyl cyanoacetate/malononitrile and sulfur powder in the presence of morpholine under thermal as well as microwave irradiation conditions. This transformation presumably occurs via domino Gewald reaction–dehydrogenation sequence. The 2-amino-5-arylthieno[2,3-b]thiophenes were

  在2-甲基苯甲酸酯存在下，由5-芳基二氢-3（2 H）-噻吩酮与氰基乙酸乙酯/丙二腈和硫粉的反应区域选择性合成了一系列新型的2-氨基-5-芳基噻吩并[2,3- b ]噻吩。热和微波照射条件下的吗啉。这种转变大概是通过多米诺骨牌Gewald反应-脱氢序列发生的。评价了2-氨基-5-芳基噻吩并[2,3- b ]噻吩在体外对结核分枝杆菌H37Rv（MTB）和耐多药结核分枝杆菌（MDR-TB）的活性。在筛选出的12种化合物中，乙基2-氨基-5-（1-萘基）噻吩并[2,3- b发现噻吩-3-羧酸盐是最具活性的化合物，其针对MTB和MDR-TB的MIC为1.1μM。
• A microwave-assisted, facile, regioselective Friedländer synthesis and antitubercular evaluation of 2,9-diaryl-2,3-dihydrothieno-[3,2- b ]quinolines
  作者：Kamaraj Balamurugan、Veerappan Jeyachandran、Subbu Perumal、Thimmappa H. Manjashetty、Perumal Yogeeswari、Dharmarajan Sriram

  DOI：10.1016/j.ejmech.2009.11.011

  日期：2010.2

  A series of 2,9-diaryl-2,3-dihydrothieno[3,2-b]quinolines have been synthesized regioselectively by Friedlander annulation of 5-aryldihydro-3(2H)-thiophenones and 2-aminobenzophenones in the presence of trifluoroacetic acid in good yields under microwave irradiation at 100 degrees C. The 2,9-diatyl-2,3-dihydrothieno[3,2-b]quinolines were screened for in vitro antimycobacterial activity against Mycobacterium tuberculosis H37Rv (MTB) and multi-drug resistant M. tuberculosis (MDR-TB). Among the 17 compounds screened, 7-chloro-2-(2,4-dichlorophenyl)-9-phenyl-2,3-dihydrothieno-[3,2-b]quinoline and 7-chloro-2-(3-nitrophenyl)-9-phenyl-2,3-dihydrothieno[3,2-b]quinoline display maximum activity with MIC of 0.90 and 0.95 mu M against MTB and MDR-TB respectively. (C) 2009 Elsevier Masson SAS. Ail rights reserved.