12-fluorobenzathracene | 77450-63-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: 12-fluorobenzathracene
• 英文别名: 12-Fluorobenzoanthracen；Benz(a)anthracene, 12-fluoro-；12-fluorobenzo[a]anthracene
• CAS: 77450-63-6
• 化学式: C₁₈H₁₁F
• 分子量: 246.284
• InChiKey: AJQIAXVJFGHYFS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  苯并[a]蒽 在 N-fluoro-2,4-dinitroimidazole 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 72.0h， 生成 7-氟苯并蒽 、 12-fluorobenzathracene 、 7,12-difluorobenzathracene
  参考文献：
  名称：

  Facile one-pot fluorination of polycyclic aromatic hydrocarbons (PAHs) with N-fluoro-2,4-dinitroimidazole; scope and limitation

  摘要：

  The synthetic utility of N-fluoro-2,4-dinitro-imidazole 'NF-2,4-DNI', a recently introduced NF fluorinating agent, has been tested for direct one-pot fluorination of several classes of polycyclic aromatic hydrocarbons, PAHs, namely pyrene, crowded alkyl(cycloalkyl)-pyrenes; hexahydro- and tetrahydro-pyrene; benzo[a] anthracene; benzo[a]- and benzo[e]pyrene; perylene; 2,7-di-tert-butylphenanthrene; chrysene; 9-methylanthracene and anthracene, as well as trans-15, 16-dimethyl-dihydropyrene; azuleno[1,2-a] acenaphthylene and azulene. Although the isolated yields are modest, the ease of handling of the reagent, simple operation (reflux in dichloroethane for 3 days) and the use of 1.1 equivalent of the reagent makes the procedure quite attractive for polynuclear aromatics, avoiding multi-step operations (NO2-PAH-->NH2-PAH-->N-2(+)-PAH-->F-PAH) or the use of toxic or costly reagents (CF3OF, XeF2, etc.); it provides direct one-pot access to a variety of F-PAHs that are not readily made using other fluorinating agents. (C) 1998 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0022-1139(98)00224-3

文献信息

• Anodic fluorination of benz[a]anthracene
  作者：Robert F. O'Malley、Henry A. Mariani、Donald R. Buhler、Donald M. Jerina

  DOI：10.1021/jo00326a051

  日期：1981.6
• Facile one-pot fluorination of polycyclic aromatic hydrocarbons (PAHs) with N-fluoro-2,4-dinitroimidazole; scope and limitation
  作者：Kenneth K. Laali、Mutsuo Tanaka、Farhad Forohar、Michael Cheng、John C. Fetzer

  DOI：10.1016/s0022-1139(98)00224-3

  日期：1998.9

  The synthetic utility of N-fluoro-2,4-dinitro-imidazole 'NF-2,4-DNI', a recently introduced NF fluorinating agent, has been tested for direct one-pot fluorination of several classes of polycyclic aromatic hydrocarbons, PAHs, namely pyrene, crowded alkyl(cycloalkyl)-pyrenes; hexahydro- and tetrahydro-pyrene; benzo[a] anthracene; benzo[a]- and benzo[e]pyrene; perylene; 2,7-di-tert-butylphenanthrene; chrysene; 9-methylanthracene and anthracene, as well as trans-15, 16-dimethyl-dihydropyrene; azuleno[1,2-a] acenaphthylene and azulene. Although the isolated yields are modest, the ease of handling of the reagent, simple operation (reflux in dichloroethane for 3 days) and the use of 1.1 equivalent of the reagent makes the procedure quite attractive for polynuclear aromatics, avoiding multi-step operations (NO2-PAH-->NH2-PAH-->N-2(+)-PAH-->F-PAH) or the use of toxic or costly reagents (CF3OF, XeF2, etc.); it provides direct one-pot access to a variety of F-PAHs that are not readily made using other fluorinating agents. (C) 1998 Elsevier Science S.A. All rights reserved.