萘并[2,3-b]荧蒽 | 206-06-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 中文名称: 萘并[2,3-b]荧蒽
• 英文名称: Naphtho<2,3b>fluoranthene
• 英文别名: dibenz[e.k]acephenanthrylene；naphtho[2,3-b]fluoranthene；dibenz[e,k]acephenanthrylene；Dibenz[e,k]acephenanthrylen；Dibenzo(e,k)acephenanthrylene；hexacyclo[11.10.1.02,11.04,9.014,19.020,24]tetracosa-1(24),2,4,6,8,10,12,14,16,18,20,22-dodecaene
• CAS: 206-06-4
• 化学式: C₂₄H₁₄
• 分子量: 302.375
• InChiKey: SCQIPRLBRNOUOX-UHFFFAOYSA-N

物化性质

• 熔点：
  229-230 °C
• 沸点：
  552.3±17.0 °C(Predicted)
• 密度：
  1.313±0.06 g/cm3(Predicted)
• 保留指数：
  533.94

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  24
• 可旋转键数：
  0
• 环数：
  6.0
• 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：
  0

安全信息

• 海关编码：
  2902909090

反应信息

• 作为反应物：
  描述：

  萘并[2,3-b]荧蒽 在 dinitrogen tetraoxide 作用下， 以 二氯甲烷 为溶剂， 反应 0.3h， 以91%的产率得到9-Nitrodibenzacephenanthrylene
  参考文献：
  名称：

  Synthesis and conformational analysis of nitropolycyclic fluoranthenes

  摘要：

  Nitroarenes are ubiquitous environmental pollutants some of which exhibit mutagenic and tumorigenic activities. The first systematic investigation of the nitration reactions of the polycyclic fluoranthenes, a major class of nonalternant polyarenes, is described. The specific hydrocarbons studied were benz[e]acephenanthrylene (1), benz[a]aceanthrylene (2), indeno[1,2,3-cd]pyrene (3), indeno[1,2,3-hi]chrysene (4), dibenz[a,e]aceanthrylene (5), dibenz[a,j]aceanthrylene (6), and dibenz[e,k]acephenanthrylene (7). The nitration of all hydrocarbons, except 1, proceeded with remarkable regioselectivity to provide a single mononitro product. In the case of 1, 17 % of a second mononitro isomer was isolated. The structures of the resulting mononitrofluoranthenes (8-15) were fully characterized by analysis of their high-resolution COSY, long-range COSY, and NOESY NMR spectra and by comparison with the spectra of the parent hydrocarbons. The observed nitration sites of the polycyclic fluoranthenes were in excellent agreement with theoretical predictions made by the DEWAR-PI method based on the relative energies of the Wheland intermediates for substitutions at various ring positions. The availability of the complete H-1 chemical shift assignments of the nitropolycyclic fluoranthenes (8-15), together with those of the parent hydrocarbons (1-7) and their UV-visible spectral data, enabled the molecular conformations of the nitro groups to be probed.

  DOI：

  10.1021/jo00073a045
• 作为产物：
  描述：

  Naphtho<2,3-b>fluoranthene-8,13-dione 在 溶剂黄146 、 锌 作用下， 以 吡啶 为溶剂， 生成 萘并[2,3-b]荧蒽
  参考文献：
  名称：

  The location of double bonds in fluoranthene

  摘要：

  DOI：

  10.1016/s0040-4020(01)83070-2

文献信息

• Acephenanthrylenes from flash vacuum thermolysis of diarylmethylidenecycloproparenes
  作者：Brian Halton

  DOI：10.1016/j.tetlet.2005.12.047

  日期：2006.2

  Upon flash vacuum thermolysis at 750 °C fluorenylidenecyclopropa[b]naphthalene (1) undergoes opening of the three-membered ring and rearrangement to give a range of C24H14 polycyclic aromatic hydrocarbons. Dibenz[e.l]- and -[e.k]acephenanthrylene (7) and (12), respectively, have been identified while the plausible naphth[1,2-e]- and [2,3-e]acephenanthrylenes (9) and (14) were not detected. With di

  在750℃下的闪蒸真空热解中，亚芴基亚环丙烷[ b ]萘（1）经历三元环的开环并重排，得到一系列C 24 H 14多环芳烃。Dibenz [ e。l ]-和-[ e。已分别鉴定出k ]对苯二甲苯（7）和（12），而未检测到可能的萘[1,2- e ]-和[2,3- e ]对苯二酚（9）和（14）。与二苯基亚甲基环丙烷[ b ]萘（2）环脱氢和重排也提供C 24 H 14多环；dibenz [ e。k ]对苯乙（12）被鉴定和dibenz [ a。e ]乙炔（15）是一种提议的产品。
• Polycyclic fluoranthene hydrocarbons. 2. A new general synthesis
  作者：Bongsup P. Cho、Ronald G. Harvey

  DOI：10.1021/jo00235a005

  日期：1987.12
• 680. The preparation of some naphthofluoranthenes and their quinones
  作者：Neil Campbell、A. Marks、D. H. Reid

  DOI：10.1039/jr9500003466

  日期：——
• CHO, BONGSUP P.;HARVEY, RONALD G., J. ORG. CHEM., 52,(1987) N 26, 5668-5678
  作者：CHO, BONGSUP P.、HARVEY, RONALD G.

  DOI：——

  日期：——
• Synthesis and conformational analysis of nitropolycyclic fluoranthenes
  作者：Bongsup P. Cho、Misoo Kim、Ronald G. Harvey

  DOI：10.1021/jo00073a045

  日期：1993.10

  Nitroarenes are ubiquitous environmental pollutants some of which exhibit mutagenic and tumorigenic activities. The first systematic investigation of the nitration reactions of the polycyclic fluoranthenes, a major class of nonalternant polyarenes, is described. The specific hydrocarbons studied were benz[e]acephenanthrylene (1), benz[a]aceanthrylene (2), indeno[1,2,3-cd]pyrene (3), indeno[1,2,3-hi]chrysene (4), dibenz[a,e]aceanthrylene (5), dibenz[a,j]aceanthrylene (6), and dibenz[e,k]acephenanthrylene (7). The nitration of all hydrocarbons, except 1, proceeded with remarkable regioselectivity to provide a single mononitro product. In the case of 1, 17 % of a second mononitro isomer was isolated. The structures of the resulting mononitrofluoranthenes (8-15) were fully characterized by analysis of their high-resolution COSY, long-range COSY, and NOESY NMR spectra and by comparison with the spectra of the parent hydrocarbons. The observed nitration sites of the polycyclic fluoranthenes were in excellent agreement with theoretical predictions made by the DEWAR-PI method based on the relative energies of the Wheland intermediates for substitutions at various ring positions. The availability of the complete H-1 chemical shift assignments of the nitropolycyclic fluoranthenes (8-15), together with those of the parent hydrocarbons (1-7) and their UV-visible spectral data, enabled the molecular conformations of the nitro groups to be probed.