(6R,7S)-3-Acetoxymethyl-5,5,8-trioxo-7-(2,2,2-trifluoro-acetylamino)-5λ⁶-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid tert-butyl ester | 102253-56-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (6R,7S)-3-Acetoxymethyl-5,5,8-trioxo-7-(2,2,2-trifluoro-acetylamino)-5λ⁶-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid tert-butyl ester
• 英文别名: 3-Acetoxymethyl-5,5,8-trioxo-7-(2,2,2-trifluoro-acetylamino)-5lambda*6*-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid tert-butyl ester；tert-butyl (6R,7S)-3-(acetyloxymethyl)-5,5,8-trioxo-7-[(2,2,2-trifluoroacetyl)amino]-5λ6-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
• CAS: 102253-56-5
• 化学式: C₁₆H₁₉F₃N₂O₈S
• 分子量: 456.397
• InChiKey: QAXAGSAPHPPGEA-JOYOIKCWSA-N

物化性质

• 沸点：
  658.3±55.0 °C(Predicted)
• 密度：
  1.53±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  145
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  (6R,7S)-3-Acetoxymethyl-7-{[1-(4-nitro-phenyl)-meth-(E)-ylidene]-amino}-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid tert-butyl ester 在 吡啶 、 吉拉尔特试剂 T 、 间氯过氧苯甲酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 (6R,7S)-3-Acetoxymethyl-5,5,8-trioxo-7-(2,2,2-trifluoro-acetylamino)-5λ⁶-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Inhibition of human leukocyte elastase. 1. Inhibition by C-7-substituted cephalosporin tert-butyl esters

  摘要：

  Time-dependent inhibitors of the enzyme human leukocyte elastase have been developed based on the cephem nucleus. A series of cephalosporin tert-butyl esters has been examined, and the activity of these compounds has been found to be very sensitive to C-7 substituents, with small, alpha-oriented, electron-withdrawing groups showing greatest activity. Additionally, the oxidation state of the sulfur atom has been found to play a role in potency, with sulfones showing considerably greater activity than the corresponding sulfides or beta-sulfoxides. The alpha-sulfoxides were inactive.

  DOI：

  10.1021/jm00171a028