2,3-dimethyl-2-13C3-1,4-naphthoquinone

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2,3-dimethyl-2-13C3-1,4-naphthoquinone
• 英文别名: 2-methyl-3-(113C)methylnaphthalene-1,4-dione
• 化学式: C₁₂H₁₀O₂
• 分子量: 187.199
• InChiKey: LGFDNUSAWCHVJN-OUBTZVSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,3-dimethyl-2-13C3-1,4-naphthoquinone 、 在 氧气 作用下， 以 水 为溶剂， 生成 Phosphoric acid (2R,3S,5R)-5-(4-amino-2-oxo-2H-pyrimidin-1-yl)-3-hydroxy-tetrahydro-furan-2-ylmethyl ester (2R,3S,5R)-5-(6-formylamino-2,3-dihydro-purin-9-yl)-2-hydroxymethyl-tetrahydro-furan-3-yl ester 、 Phosphoric acid (2R,3S,5R)-5-(6-acetylamino-2,3-dihydro-purin-9-yl)-2-hydroxymethyl-tetrahydro-furan-3-yl ester (2R,3S,5R)-5-(4-amino-2-oxo-2H-pyrimidin-1-yl)-3-hydroxy-tetrahydro-furan-2-ylmethyl ester 、 、
  参考文献：
  名称：

  Mechanisms for the Formation of Major Oxidation Products of Adenine upon 365-nm Irradiation with 2-Methyl-1,4-naphthoquinone as a Sensitizer

  摘要：

  Recently we reported the isolation and characterization of N-6-formyl- and M-acetyladenine from 365-nm irradiation of dinucleoside monophosphates d(ApA), d(ApC), and d(CpA) in the presence of 2-methyl-1,4-naphthoquinone (menadione) (Wang et al. Biochem. Biophys. Res. Commun. 2002, 291, 1252-7). In this article we investigated the mechanisms for the formation of the two major products by carrying out photoirradiation with isotopically labeled menadione and 2,3-dimethyl-1,4-naphthoquinone. HPLC and electrospray ionization (ESI)-mass spectrometry (MS) and tandem MS studies of the products unambiguously established that the carbonyl group in the products arises from the photosensitizer: The N-6-formyl group comes from oxidation of the methyl group and the N-6-acetyl group stems from the methyl group and the adjacent ring carbon in menadione. From above results, we proposed mechanisms for the formation of the two products.

  DOI：

  10.1021/jo0264170
• 作为产物：
  描述：

  乙酸-2-13C 、 甲萘醌 在 ammonium peroxydisulfate 、 silver nitrate 作用下， 以 水 、 乙腈 为溶剂， 反应 5.0h， 生成 2,3-dimethyl-2-13C3-1,4-naphthoquinone
  参考文献：
  名称：

  Mechanisms for the Formation of Major Oxidation Products of Adenine upon 365-nm Irradiation with 2-Methyl-1,4-naphthoquinone as a Sensitizer

  摘要：

  Recently we reported the isolation and characterization of N-6-formyl- and M-acetyladenine from 365-nm irradiation of dinucleoside monophosphates d(ApA), d(ApC), and d(CpA) in the presence of 2-methyl-1,4-naphthoquinone (menadione) (Wang et al. Biochem. Biophys. Res. Commun. 2002, 291, 1252-7). In this article we investigated the mechanisms for the formation of the two major products by carrying out photoirradiation with isotopically labeled menadione and 2,3-dimethyl-1,4-naphthoquinone. HPLC and electrospray ionization (ESI)-mass spectrometry (MS) and tandem MS studies of the products unambiguously established that the carbonyl group in the products arises from the photosensitizer: The N-6-formyl group comes from oxidation of the methyl group and the N-6-acetyl group stems from the methyl group and the adjacent ring carbon in menadione. From above results, we proposed mechanisms for the formation of the two products.

  DOI：

  10.1021/jo0264170