2,5-dihydroxy-3-(2-carbamoyloxy-1-methoxyethyl)-6-methyl-1,4-benzoquinone | 92778-37-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,5-dihydroxy-3-(2-carbamoyloxy-1-methoxyethyl)-6-methyl-1,4-benzoquinone
• 英文别名: [2-(2,5-dihydroxy-4-methyl-3,6-dioxocyclohexa-1,4-dien-1-yl)-2-methoxyethyl] carbamate
• CAS: 92778-37-5
• 化学式: C₁₁H₁₃NO₇
• 分子量: 271.227
• InChiKey: UKTCREQVNQTMGU-UHFFFAOYSA-N

物化性质

• 沸点：
  516.6±50.0 °C(Predicted)
• 密度：
  1.557±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.11
• 重原子数：
  19.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  136.15
• 氢给体数：
  3.0
• 氢受体数：
  7.0

反应信息

• 作为产物：
  描述：

  2-[2,5-bis(aziridin-1-yl)-4-methyl-3,6-dioxocyclohexa-1,4-dien-1-yl]ethoxymethyl carbamate 生成 2,5-dihydroxy-3-(2-carbamoyloxy-1-methoxyethyl)-6-methyl-1,4-benzoquinone
  参考文献：
  名称：

  KUSAI, AKIRA;UEDA, SEIGO, CHEM. AND PHARM. BULL., 1984, 32, N 6, 2406-2413

  摘要：

  DOI：

文献信息

• The stability of carboquone in aqueous solution. III. Kinetics and mechanisms of degradation of carboquone in aqueous solution.
  作者：AKIRA KUSAI、SEIGO UEDA

  DOI：10.1248/cpb.32.2406

  日期：——

  The kinetics and mechanisms of the degradation of carboquone (CQ) in aqueous solution were studied and compared with those of 2, 5-bis (1-aziridinyl)-3, 6-dialkyl-1, 4-benzoquinones [EBs : R=-H (EB); -CH3 (MEB); -CH (CH3)2 (IPEB)] determined previously. The degradation of CQ was essentially similar to those of EBs : it followed pseudo first-order kinetics (specific acid-base catalysis), and involved the hydrolytic cleavage of aziridine rings in acidic solutions, the substitution of aziridine rings by hydroxyl ion (radical) in basic solutions and a combination of these two mechanisms in solutions of neutral pH. High performance liquid chromatography patterns of CQ solutions at acidic pH gave two peaks corresponding to two intermediate compounds with one aziridine ring and one hydroxyethylamino group (due to the asymmetrical structure of CQ). However, we could not identify each peak component, or estimate which aziridine ring (at the 2 or 5 position of CQ) was unreacted. This was also the case for the two intermediate compounds with one aziridine ring and one hydroxyl group observed in CQ solutions at basic pH. Kinetic studies of MEB and the two intermediate compounds obtained in acidic solutions by thin-layer chromatography separation made it possible to estimate the chemical structures of these four intermediate compounds.

  卡波醌(CQ)在水溶液中的降解动力学和机理被研究,并与之前测定的2,5-双(1-氮丙啶基)-3,6-二烷基-1,4-苯醌[EBs:R=-H(EB);-CH3(MEB);-CH( )2(IPEB)]进行了比较。CQ的降解基本上与EBs相似:它遵循伪一级动力学(特定酸碱催化),并且在酸性溶液中涉及氮丙啶环的水解断裂,在碱性溶液中涉及羟基离子(自由基)对氮丙啶环的取代,以及在中性pH溶液中这两种机制的结合。酸性pH下CQ溶液的高性能液相色谱图给出了两个峰,对应于两个具有一个氮丙啶环和一个羟乙氨基的中间化合物(由于CQ的不对称结构)。然而,我们无法识别每个峰的组分,也无法估计哪个氮丙啶环(在CQ的2或5位)未反应。在碱性pH下CQ溶液中观察到的具有一个氮丙啶环和一个羟基的两个中间化合物也是如此。通过薄层色谱分离对MEB和在酸性溶液中得到的两个中间化合物进行的动力学研究,可以估计这四个中间化合物的化学结构。