N-(sulfonatooxy)-N-acetyl-4-aminostilbene | 211029-25-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: N-(sulfonatooxy)-N-acetyl-4-aminostilbene
• 英文别名: [N-acetyl-4-[(E)-2-phenylethenyl]anilino] sulfate
• CAS: 211029-25-3
• 化学式: C₁₆H₁₄NO₅S
• 分子量: 332.357
• InChiKey: XLTJYOJNFBEHRL-BQYQJAHWSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  95.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-(sulfonatooxy)-N-acetyl-4-aminostilbene 在 sodium azide 作用下， 以 乙腈 为溶剂， 生成 3-azido-N-acetyl-4-aminostilbene 、 N-[4-((1S,2R)-2-Azido-1-hydroxy-2-phenyl-ethyl)-phenyl]-acetamide 、 N-[4-((1R,2R)-1,2-Diazido-2-phenyl-ethyl)-phenyl]-acetamide 、 N-[4-((1R,2S)-1,2-Diazido-2-phenyl-ethyl)-phenyl]-acetamide
  参考文献：
  名称：

  Azide and Solvent Trapping of Electrophilic Intermediates Generated during the Hydrolysis of N-(Sulfonatooxy)-N-acetyl-4-aminostilbene

  摘要：

  Hydrolysis of the carcinogenic title compound 1a in 5 vol % CH3CN-H2O, mu = 0.5, 20 degrees C at pH 7.2 in 0.02 M phosphate buffer, yields the rearranged material 3-(sulfonatooxy)-N-acetyl-4-aminostilbene (4) (23 +/- 1%), threo-1,2-dihydroxy-1-phenyl-2-(4-acetamidophenyl)ethane (5) (57 +/- 2%), and erythro-1,2-dihydroxy-1-phenyl-2-(4-acetamidophenyl)ethane (6) (20 +/- 2%) in the absence of added nucleophiles. Addition of N-3(-) has no effect on the rate constant for decomposition of 1a (ca. 1.9 x 10(-2) s(-1)), but generates a number of adducts that result from trapping of three different electrophilic intermediates. The ortho-N-3 adduct 3-azido-N-acetyl-4-aminostilbene (7) is produced from trapping of the nitrenium ion 2. A fit of the product yield data as a function of [N-3(-)] provides the ratio k(az)/k(s) of 280 +/- 10 M-1 for competitive trapping of 2 by N-3(-) and H2O. The nucleophilic aromatic substitution product 7 is a minor reaction product. The predominant site of attack by N-3(-) On 2 (ca. 85%) is at the beta-vinyl carbon to produce the quinone imide methide 3b. Attack of H2O at the same site produces the analogous intermediate 3a. Both of these electrophilic species are competitively trapped by N-3(-) and H2O with trapping ratios k(az)'/k(s)' for 3b of 107 +/- 8 M-1 and k(az)"/ k(s)" for 3a of 39 +/- 2 M-1. The reactivity patterns of 2 are unlike those of other N-arylnitrenium ions that undergo predominant nucleophilic aromatic substitution with nucleophiles such as N-3(-). The quinone imide methides that are produced by nucleophilic attack on the beta-carbon of 2 react selectively enough with nonsolvent nucleophiles that they may be physiologically relevant.

  DOI：

  10.1021/jo980500z
• 作为产物：
  描述：

  a-D-吡喃葡萄糖基溴化,6-C-溴-6-S-苯基-6-硫代-,三乙酸酯(9CI) 在 硫酸 、 N,N'-二环己基碳二亚胺 作用下， 生成 N-(sulfonatooxy)-N-acetyl-4-aminostilbene
  参考文献：
  名称：

  Azide and Solvent Trapping of Electrophilic Intermediates Generated during the Hydrolysis of N-(Sulfonatooxy)-N-acetyl-4-aminostilbene

  摘要：

  Hydrolysis of the carcinogenic title compound 1a in 5 vol % CH3CN-H2O, mu = 0.5, 20 degrees C at pH 7.2 in 0.02 M phosphate buffer, yields the rearranged material 3-(sulfonatooxy)-N-acetyl-4-aminostilbene (4) (23 +/- 1%), threo-1,2-dihydroxy-1-phenyl-2-(4-acetamidophenyl)ethane (5) (57 +/- 2%), and erythro-1,2-dihydroxy-1-phenyl-2-(4-acetamidophenyl)ethane (6) (20 +/- 2%) in the absence of added nucleophiles. Addition of N-3(-) has no effect on the rate constant for decomposition of 1a (ca. 1.9 x 10(-2) s(-1)), but generates a number of adducts that result from trapping of three different electrophilic intermediates. The ortho-N-3 adduct 3-azido-N-acetyl-4-aminostilbene (7) is produced from trapping of the nitrenium ion 2. A fit of the product yield data as a function of [N-3(-)] provides the ratio k(az)/k(s) of 280 +/- 10 M-1 for competitive trapping of 2 by N-3(-) and H2O. The nucleophilic aromatic substitution product 7 is a minor reaction product. The predominant site of attack by N-3(-) On 2 (ca. 85%) is at the beta-vinyl carbon to produce the quinone imide methide 3b. Attack of H2O at the same site produces the analogous intermediate 3a. Both of these electrophilic species are competitively trapped by N-3(-) and H2O with trapping ratios k(az)'/k(s)' for 3b of 107 +/- 8 M-1 and k(az)"/ k(s)" for 3a of 39 +/- 2 M-1. The reactivity patterns of 2 are unlike those of other N-arylnitrenium ions that undergo predominant nucleophilic aromatic substitution with nucleophiles such as N-3(-). The quinone imide methides that are produced by nucleophilic attack on the beta-carbon of 2 react selectively enough with nonsolvent nucleophiles that they may be physiologically relevant.

  DOI：

  10.1021/jo980500z