6-chlorobenzo[pqr]tetraphen-3-yl acetate | 121962-93-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 芘
• 英文名称: 6-chlorobenzo[pqr]tetraphen-3-yl acetate
• CAS: 121962-93-4
• 化学式: C₂₂H₁₃ClO₂
• 分子量: 344.797
• InChiKey: QZNGJBBTWPXTIZ-UHFFFAOYSA-N

物化性质

• 沸点：
  554.1±23.0 °C(Predicted)
• 密度：
  1.403±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.32
• 重原子数：
  25.0
• 可旋转键数：
  1.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  sodium acetate 、 以 水 、 乙腈 为溶剂， 反应 0.25h， 生成 苯并[b]芘-1,6-二酮 、 苯并[b]芘-3,6-二酮 、 6-chlorobenzo[pqr]tetraphen-3-yl acetate 、 6-chlorobenzo[pqr]tetraphen-1-yl acetate
  参考文献：
  名称：

  Radical Cations of Benzo[a]pyrene and 6-Substituted Derivatives: Synthesis and Reaction with Nucleophiles

  摘要：

  Radical cations of benzo[a]pyrene (BP) and 6-substituted derivatives were synthesized by two methods: reaction of the hydrocarbon with I-2 and AgClO4 in benzene, and reaction of the hydrocarbon with NOBF4 in CH3CN/CH2Cl2. Both the radical cation perchlorates and tetrafluoroborates were stable for prolonged periods of time when stored under argon at subzero temperatures. The radical cations were reacted with nucleophiles of various strengths, namely H2O, AcO- and F-, as a means of best characterizing these intermediates, as well as determining their chemical properties. Reaction of BP, 6-FBP, 6-ClBP, and 6-BrBP radical cation perchlorates with H2O produced BP 1,6- 3,6-, and 6,12-dione, whereas the radical cation derived from 6-CH3BP yielded 6-CH2OHBP. When (BPClO4-)-Cl-.+ and 6-(FBPClO4-)-Cl-.+ were reacted with NaOAc in H2O/CH3CN (9:1), 6-OAcBP was formed, in addition to the quinones. 6-(ClBPClO4-)-Cl-.+ formed a small amount of 1-OAc-6-ClBP and 3-OAc-6-ClBP, in addition to the diones, whereas for 6-(BrBPClO4-)-Cl-.+ and 6-(CH3BPClO4-)-Cl-.+ the reaction products were BP diones and 6-CH2OHBP, respectively. Reactions conducted under anhydrous conditions, using tetramethylammonium acetate in CH3CN, gave similar results, except that no quinones were formed. These results confirm the reactivity of nucleophiles at the positions of high charge localization in the BP.+, i.e. C-6, followed by C-1 and C-3.

  DOI：

  10.1021/jo00104a024

文献信息

• One-electron oxidation of 6-substituted benzo[a]pyrenes by manganic acetate. A model for metabolic activation
  作者：Paolo Cremonesi、Ercole L. Cavalieri、Eleanor G. Rogan

  DOI：10.1021/jo00276a013

  日期：1989.7