1,2-Ethanediol, 1-(4-nitrophenyl)-2-phenyl- | 62086-77-5

• 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: 1,2-Ethanediol, 1-(4-nitrophenyl)-2-phenyl-
• 英文别名: (+/-)-erythro-1-(4-Nitrophenyl)-2-phenylethandiol
• CAS: 62086-77-5；66768-16-9；66768-17-0；110655-61-3
• 化学式: C₁₄H₁₃NO₄
• 分子量: 259.262
• InChiKey: AZYJUCGPXPLKHF-KGLIPLIRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.36
• 重原子数：
  19.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  83.6
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  1-(4-硝基苯基)-2-苯基-1,2-乙二酮 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 生成 1,2-Ethanediol, 1-(4-nitrophenyl)-2-phenyl-
  参考文献：
  名称：

  Microbial reduction of a series of substituted benzils. Optical properties and nuclear magnetic resonance spectra of products

  摘要：

  DOI：

  10.1021/jo00411a012

文献信息

• Azide and Solvent Trapping of Electrophilic Intermediates Generated during the Hydrolysis of <i>N</i>-(Sulfonatooxy)-<i>N</i>-acetyl-4-aminostilbene
  作者：Michael Novak、Kelly J. Kayser、Michael E. Brooks

  DOI：10.1021/jo980500z

  日期：1998.8.1

  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.