N-acetyl-2-amino-1-sulfonatooxynaphthalene | 6610-14-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-acetyl-2-amino-1-sulfonatooxynaphthalene
• 英文别名: sulfuric acid mono-(2-acetylamino-[1]naphthyl ester)；Schwefelsaeure-mono-(2-acetylamino-[1]naphthylester)；(2-Acetamidonaphthalen-1-yl) hydrogen sulfate
• CAS: 6610-14-6
• 化学式: C₁₂H₁₁NO₅S
• 分子量: 281.289
• InChiKey: NLFCQCWRSIUXTG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  101
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  N-sulfonatooxy-N-acetyl-2-aminonaphthalene 在 phosphate buffer 、 sodium perchlorate 作用下， 以 水 、 乙腈 为溶剂， 以25%的产率得到N-(1-hydroxynaphthalen-2-yl)acetamide
  参考文献：
  名称：

  Hydrolysis Reactions of N-Sulfonatooxy-N-acetyl-1-aminonaphthalene and N-Sulfonatooxy-N-acetyl-2-aminonaphthalene:  Limited Correlation of Nitrenium Ion Azide/Solvent Selectivities with Mutagenicities of the Corresponding Amines

  摘要：

  The hydrolysis reactions of the title compounds N-sulfonatooxy-N-acetyl-1-aminonaphthalene, 2d, and N-sulfonatooxy-N-acetyl-2-aminonaphthalene 2e, in 5% CH3CN-H2O (20 degrees C, pH 5.7-7.5, mu = 0.5) appear to involve nitrenium ion intermediates that exhibit very small azide/solvent trapping efficiencies. The azide/solvent selectivities, S, were estimated from fitting azide- and solvent-derived product yields as a function of [N-3(-)]. The derived values of S for the N-acetyl-N-(1-naphthyl)-nitrenium ion (3d) of 0.7 +/- 0.1 M-1 and the N-acetyl-N-(2-naphthyl)nitrenium ion (3e) of 1.5 +/- 0.2 M-1 show that these ions have short lifetimes (ca. 10(-10) s) in aqueous solution. In turn, these results suggest that the hydrolysis reactions of 2d and 2e should proceed, in part, through ion-pair and/or preassociation pathways. The decrease in the yield of the rearrangement products N-acetyl-1-amino-2-sulfonatooxynaphthalene, 6, and N-acetyl-2-amino-1-sulfonatooxynaphthalene 11, with increasing [N-3(-)] indicates that this is the case. Plots of log(mutagenicity) toward Salmonella typhimurium TA 98 and TA 100 for a series of polycyclic and monocyclic aromatic amines vs log(S) for ArNAc+ show that there is no general correlation of mutagenicity with nitrenium ion selectivity, but there does appear to be a limited correlation of these two quantities for five polycyclic amines for which there are reliable mutagenicity and nitrenium ion selectivity data. These results suggest that nitrenium ion selectivity is one of several factors that determines the mutagenicity of aromatic amines.

  DOI：

  10.1021/jo990580m

文献信息

• Booth et al., Biochemical Journal, 1955, vol. 60, p. 62,63
  作者：Booth et al.

  DOI：——

  日期：——
• Hydrolysis Reactions of <i>N</i>-Sulfonatooxy-<i>N</i>-acetyl-1-aminonaphthalene and <i>N</i>-Sulfonatooxy-<i>N</i>-acetyl-2-aminonaphthalene:  Limited Correlation of Nitrenium Ion Azide/Solvent Selectivities with Mutagenicities of the Corresponding Amines
  作者：Michael Novak、Amy J. VandeWater、Angie J. Brown、Sarah A. Sanzenbacher、Lori A. Hunt、Brent A. Kolb、Michael E. Brooks

  DOI：10.1021/jo990580m

  日期：1999.8.1

  The hydrolysis reactions of the title compounds N-sulfonatooxy-N-acetyl-1-aminonaphthalene, 2d, and N-sulfonatooxy-N-acetyl-2-aminonaphthalene 2e, in 5% CH3CN-H2O (20 degrees C, pH 5.7-7.5, mu = 0.5) appear to involve nitrenium ion intermediates that exhibit very small azide/solvent trapping efficiencies. The azide/solvent selectivities, S, were estimated from fitting azide- and solvent-derived product yields as a function of [N-3(-)]. The derived values of S for the N-acetyl-N-(1-naphthyl)-nitrenium ion (3d) of 0.7 +/- 0.1 M-1 and the N-acetyl-N-(2-naphthyl)nitrenium ion (3e) of 1.5 +/- 0.2 M-1 show that these ions have short lifetimes (ca. 10(-10) s) in aqueous solution. In turn, these results suggest that the hydrolysis reactions of 2d and 2e should proceed, in part, through ion-pair and/or preassociation pathways. The decrease in the yield of the rearrangement products N-acetyl-1-amino-2-sulfonatooxynaphthalene, 6, and N-acetyl-2-amino-1-sulfonatooxynaphthalene 11, with increasing [N-3(-)] indicates that this is the case. Plots of log(mutagenicity) toward Salmonella typhimurium TA 98 and TA 100 for a series of polycyclic and monocyclic aromatic amines vs log(S) for ArNAc+ show that there is no general correlation of mutagenicity with nitrenium ion selectivity, but there does appear to be a limited correlation of these two quantities for five polycyclic amines for which there are reliable mutagenicity and nitrenium ion selectivity data. These results suggest that nitrenium ion selectivity is one of several factors that determines the mutagenicity of aromatic amines.