N-acetyl-2-fluorenylnitrenium ion

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: N-acetyl-2-fluorenylnitrenium ion
• 英文别名: N-(3,9-dihydrofluoren-3-ylium-2-ylidene)acetamide
• 化学式: C₁₅H₁₂NO
• 分子量: 222.266
• InChiKey: DGSCGYXEFLBCOL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  29.4
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2'-脱氧鸟苷 、 N-acetyl-2-fluorenylnitrenium ion 在 disodium hydrogenphosphate 、 sodium dihydrogenphosphate 作用下， 以 水 、 乙腈 为溶剂， 生成 N-[2-氨基-9-[(4S,5R)-4-羟基-5-(羟基甲基)四氢呋喃-2-基]-6-氧代-3H-嘌呤-8-基]-N-(9H-芴-2-基)乙酰胺
  参考文献：
  名称：

  Selective Trapping of N-Acetyl-N-(4-biphenylyl)nitrenium and N-Acetyl-N-(2-fluorenyl)nitrenium Ions by 2'-Deoxyguanosine in Aqueous Solution

  摘要：

  DOI：

  10.1021/ja00106a083

文献信息

• Selective Trapping of N-Acetyl-N-(4-biphenylyl)nitrenium and N-Acetyl-N-(2-fluorenyl)nitrenium Ions by 2'-Deoxyguanosine in Aqueous Solution
  作者：Michael Novak、Sonya A. Kennedy

  DOI：10.1021/ja00106a083

  日期：1995.1
• Reactivity of the 4-biphenylyl and 2-fluorenylnitrenium ions with heterocyclic and carbon nucleophiles
  作者：Robert A. McClelland、Mary Jo Kahley、P. Adriaan Davidse

  DOI：10.1002/(sici)1099-1395(199606)9:6<355::aid-poc792>3.0.co;2-q

  日期：1996.6

  The carcinogens 4-aminobiphenyl, 2-aminofluorene and their N-acetyl derivatives form DNA adducts in vivo with the aryl nitrogen attached at C-8 of guanine. These adducts are proposed to arise through the reaction with the DNA base of a nitrenium ion obtained by N-O heterolysis of a hydroxylamine ester obtained metabolically by oxidation and esterification. Routes have now been discovered for the photochemical generation of these nitrenium ions, the N-acetyl derivatives via a photoheterolysis reaction and the N-H derivatives by protonation of the singlet nitrene photochemically generated from the azide precursor. The nitrenium ions are observed as transient intermediates with laser flash photolysis, and the kinetics of their reaction with various nucleophiles directly monitored. These results, coupled with competition kinetics experiments, show that the nitrenium ions derived from the above amines and amides are relatively long-lived in water, with a remarkably high selectivity in water for reaction with 2'-deoxyguanosine and its 5'-phosphate. The C-8 adduct is the product of this reaction. These behaviours differ considerably from those of analogous carbenium ions. Reactions with vinyl ethers have also been investigated, and also show significant differences between the two types of electrophile.