3,4,5,6,8,8-六氯-1a,7a-二甲基-1a,2,2a,3,6,6a,7,7a-八氢-3,6-亚甲基萘并[2,3-b]噁丙烯 | 81536-58-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噁庚英
• 中文名称: 3,4,5,6,8,8-六氯-1a,7a-二甲基-1a,2,2a,3,6,6a,7,7a-八氢-3,6-亚甲基萘并[2,3-b]噁丙烯
• 英文名称: (2S,3S,4S,5R,6S)-3,4,5-Trihydroxy-6-[2-(11-oxo-6,11-dihydro-dibenzo[b,e]oxepin-2-yl)-acetoxy]-tetrahydro-pyran-2-carboxylic acid
• 英文别名: Isoxepac glucuronide；(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[2-(11-oxo-6H-benzo[c][1]benzoxepin-2-yl)acetyl]oxyoxane-2-carboxylic acid
• CAS: 81536-58-5
• 化学式: C₂₂H₂₀O₁₀
• 分子量: 444.395
• InChiKey: NCYWNHLOMITKET-SXFAUFNYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  32
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  160
• 氢给体数：
  4
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  3,4,5,6,8,8-六氯-1a,7a-二甲基-1a,2,2a,3,6,6a,7,7a-八氢-3,6-亚甲基萘并[2,3-b]噁丙烯 在 potassium phosphate buffer 作用下， 反应 24.0h， 生成 (2S,3S,4S,5R,6R)-3,5,6-Trihydroxy-4-[2-(11-oxo-6,11-dihydro-dibenzo[b,e]oxepin-2-yl)-acetoxy]-tetrahydro-pyran-2-carboxylic acid 、 (2S,3S,4S,5R,6S)-3,5,6-Trihydroxy-4-[2-(11-oxo-6,11-dihydro-dibenzo[b,e]oxepin-2-yl)-acetoxy]-tetrahydro-pyran-2-carboxylic acid 、 (2S,3S,4R,5R,6S)-4,5,6-Trihydroxy-3-[2-(11-oxo-6,11-dihydro-dibenzo[b,e]oxepin-2-yl)-acetoxy]-tetrahydro-pyran-2-carboxylic acid 、 (2S,3S,4R,5R,6R)-4,5,6-Trihydroxy-3-[2-(11-oxo-6,11-dihydro-dibenzo[b,e]oxepin-2-yl)-acetoxy]-tetrahydro-pyran-2-carboxylic acid 、 (2S,3S,4S,5R,6R)-3,4,6-Trihydroxy-5-[2-(11-oxo-6,11-dihydro-dibenzo[b,e]oxepin-2-yl)-acetoxy]-tetrahydro-pyran-2-carboxylic acid 、 (2S,3S,4S,5R,6S)-3,4,6-Trihydroxy-5-[2-(11-oxo-6,11-dihydro-dibenzo[b,e]oxepin-2-yl)-acetoxy]-tetrahydro-pyran-2-carboxylic acid 、 alkaline earth salt of/the/ methylsulfuric acid
  参考文献：
  名称：

  750 MHz HPLC−NMR Spectroscopic Studies on the Separation and Characterization of the Positional Isomers of the Glucuronides of 6,11-Dihydro-11- oxodibenz[b,e]oxepin-2-acetic Acid

  摘要：

  Ester glucuronides (β-1-O-acyl-d-glucopyranuronates) of many drugs can undergo a series of acyl migration reactions, resulting in positional isomers and anomers which can react with serum proteins with possible toxicological consequences. We have investigated the acyl migration of the ester glucuronides of the model drug 6,11-dihydro-11-oxodibenz[b,e]oxepin-2-acetic acid in pH 7.4 buffer using directly coupled 750 MHz stopped-flow HPLC−NMR spectroscopy. Using a reversed phase isocratic HPLC method with 21% acetonitrile and 79% D2O in the mobile phase, it was possible to separate and hence identify the individual positional isomers of the model drug glucuronide by 750 MHz HPLC−NMR. The order of elution of the isomers from the C18 column was 4α-, 4β-, aglycon, 1β-, 3β-, 3α-, 2α-, 2β- (α- and β- referring to the anomerization state at C1 on the glucuronide ring and the numbers referring to the carbon number on the glucuronide ring to which the drug moiety has migrated). It is shown that directly coupled ultra-high-field HPLC−NMR spectroscopy offers a unique analytical advantage for obtaining structural information of interconverting compounds in equilibrium mixtures, and this method will be of value in the study of reactive drug glucuronides of toxicological importance.

  DOI：

  10.1021/ac950752p