5-methyl-4H-cyclopentachrysene | 141046-12-0

• 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: 5-methyl-4H-cyclopentachrysene
• 英文别名: 2-Methylpentacyclo[14.2.1.03,8.09,18.012,17]nonadeca-1,3,5,7,9(18),10,12(17),13,15-nonaene
• CAS: 141046-12-0
• 化学式: C₂₀H₁₄
• 分子量: 254.331
• InChiKey: GCAOIDYUTOAAHK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  20
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  4H-cyclopentachrysene 在 四氯化钛 、 sodium cyanoborohydride 、 zinc(II) iodide 作用下， 以 二氯甲烷 为溶剂， 反应 51.0h， 生成 5-methyl-4H-cyclopentachrysene
  参考文献：
  名称：

  Electrophilic substitution of methylene-bridged polycyclic aromatic hydrocarbons

  摘要：

  The electrophilic bromination and formylation of the methylene-bridged polycyclic aromatic hydrocarbons 11H-benz[bc]aceanthrylene (2), 4H-cyclopenta[def]chrysene (3), 13H-dibenz[bc,l]aceanthrylene (4), and 4H-benzo[b]cyclopenta[mno]chrysene (5) were investigated. All reactions proceeded with high regioselectivity to afford predominantly a single major isomeric product. The sole exception was bromination of 3 which gave a small amount of a second isomeric product. The sites of electrophilic substitution were correlated with theoretical predictions from semiempirical molecular orbital calculations using the MNDO method, The observed sites of electrophilic substitution were in excellent agreement with the theoretical predictions in the cases of 2-4. However, in the case of 5, substitution took place in the 6-position, whereas the site predicted to be most reactive is the 5-position. In addition, the aryl aldehyde products were converted into the corresponding methyl derivatives for studies of their potential carcinogenicity.

  DOI：

  10.1021/jo00038a016

文献信息

• Electrophilic substitution of methylene-bridged polycyclic aromatic hydrocarbons
  作者：Elias Abu-Shqara、Cheng Xi Yang、Ronald G. Harvey

  DOI：10.1021/jo00038a016

  日期：1992.6

  The electrophilic bromination and formylation of the methylene-bridged polycyclic aromatic hydrocarbons 11H-benz[bc]aceanthrylene (2), 4H-cyclopenta[def]chrysene (3), 13H-dibenz[bc,l]aceanthrylene (4), and 4H-benzo[b]cyclopenta[mno]chrysene (5) were investigated. All reactions proceeded with high regioselectivity to afford predominantly a single major isomeric product. The sole exception was bromination of 3 which gave a small amount of a second isomeric product. The sites of electrophilic substitution were correlated with theoretical predictions from semiempirical molecular orbital calculations using the MNDO method, The observed sites of electrophilic substitution were in excellent agreement with the theoretical predictions in the cases of 2-4. However, in the case of 5, substitution took place in the 6-position, whereas the site predicted to be most reactive is the 5-position. In addition, the aryl aldehyde products were converted into the corresponding methyl derivatives for studies of their potential carcinogenicity.