4-fluoro-1-methyl-9H-carbazole | 361-67-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 4-fluoro-1-methyl-9H-carbazole
• 英文别名: 4-fluoro-1-methyl-carbazole；4-Fluor-1-methyl-carbazol
• CAS: 361-67-1
• 化学式: C₁₃H₁₀FN
• 分子量: 199.228
• InChiKey: ZLDCNURIWOZRLL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  15.8
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-fluoro-1-methyl-9H-carbazole 在 喹啉 、 selenium(IV) oxide 、 copper oxide-chromium oxide 、 萘烷 作用下， 生成 4-氟-9H-咔唑
  参考文献：
  名称：

  786.杂环氟化合物。第一部分。一氟-1：2：3：4-四氢咔唑和一氟咔唑

  摘要：

  DOI：

  10.1039/jr9530003845
• 作为产物：
  描述：

  N-(2-bromophenyl)-5-fluoro-2-methylbenzenamine 在 copper(l) iodide 、 palladium diacetate 、 sodium t-butanolate 作用下， 以 1,4-二氧六环 为溶剂， 反应 10.0h， 以83%的产率得到4-fluoro-1-methyl-9H-carbazole
  参考文献：
  名称：

  Synthesis of fluorinated carbazoles via C–H arylation catalyzed by Pd/Cu bimetal system and their antibacterial activities

  摘要：

  An effective intramolecular C-H arylation reaction catalyzed by a bimetallic catalytic system Pd(OAc)(2)/Cul for the synthesis of fluorine -substituted carbazoles from corresponding N-phenyl-2-haloaniline derivatives under ligand free conditions is demonstrated. The established method is effective for both N-phenyl-2-bromoaniline and N-phenyl-2-chloroaniline, and requires the low loading of Pd(OAc)2 (0.5 mol %). A series of new fluorinated carbazoles were synthesized in excellent yields using the protocol (>83%, 19 examples) and were fully characterized by H-1, C-11 and F-19 NMR spectral data, HRMS and elemental analysis. All compounds were evaluated for their antibacterial activities against four bacteria (Bacillus subtilis, Staphylococcus aureus, Escherichia coli and methicillin-resistant S. aureus with resistance to gentamicin) by serial dilution technique. All tested compounds showed antibacterial activity against three test strains (S. aureus, B. subtilis and MRSA), and most of these compounds displayed pronounced antimicrobial activities against these three strains with low MIC values ranging from 0.39 to 6.25 mu g/mL. Among them, compounds 7 and 14 exhibited potent inhibitory activity better than reference drugs meropenem and streptomycin. Three compounds (2, 4 and 5) showed antibacterial activity against E. coli. with MIC values from 12.5 to 25 mu g/mL. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2016.02.013

文献信息

• 786. Heterocylic fluorine compounds. Part I. Monofluoro-1 : 2 : 3 : 4-tetrahydrocarbazoles and monofluorocarbazoles
  作者：F. L. Allen、H. Suschitzky

  DOI：10.1039/jr9530003845

  日期：——
• Synthesis of fluorinated carbazoles via C–H arylation catalyzed by Pd/Cu bimetal system and their antibacterial activities
  作者：Xianqiang Kong、Huizi Zhang、Changsheng Cao、Shengliang Zhou、Guangsheng Pang、Yanhui Shi

  DOI：10.1016/j.bmc.2016.02.013

  日期：2016.3

  An effective intramolecular C-H arylation reaction catalyzed by a bimetallic catalytic system Pd(OAc)(2)/Cul for the synthesis of fluorine -substituted carbazoles from corresponding N-phenyl-2-haloaniline derivatives under ligand free conditions is demonstrated. The established method is effective for both N-phenyl-2-bromoaniline and N-phenyl-2-chloroaniline, and requires the low loading of Pd(OAc)2 (0.5 mol %). A series of new fluorinated carbazoles were synthesized in excellent yields using the protocol (>83%, 19 examples) and were fully characterized by H-1, C-11 and F-19 NMR spectral data, HRMS and elemental analysis. All compounds were evaluated for their antibacterial activities against four bacteria (Bacillus subtilis, Staphylococcus aureus, Escherichia coli and methicillin-resistant S. aureus with resistance to gentamicin) by serial dilution technique. All tested compounds showed antibacterial activity against three test strains (S. aureus, B. subtilis and MRSA), and most of these compounds displayed pronounced antimicrobial activities against these three strains with low MIC values ranging from 0.39 to 6.25 mu g/mL. Among them, compounds 7 and 14 exhibited potent inhibitory activity better than reference drugs meropenem and streptomycin. Three compounds (2, 4 and 5) showed antibacterial activity against E. coli. with MIC values from 12.5 to 25 mu g/mL. (C) 2016 Elsevier Ltd. All rights reserved.