1,1-dimethylethyl 3-(methoxymethyl)-7α-methoxy-8-oxo-5-thia-1-azabicyclo<4.2.0>oct-3-ene-2-carboxylate | 95570-51-7

• 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: 1,1-dimethylethyl 3-(methoxymethyl)-7α-methoxy-8-oxo-5-thia-1-azabicyclo<4.2.0>oct-3-ene-2-carboxylate
• CAS: 95570-51-7
• 化学式: C₁₄H₂₁NO₅S
• 分子量: 315.39
• InChiKey: SWTOBYXXXLUGOP-OJBNZGHXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.16
• 重原子数：
  21.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  65.07
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  1,1-dimethylethyl 3-(methoxymethyl)-7α-methoxy-8-oxo-5-thia-1-azabicyclo<4.2.0>oct-3-ene-2-carboxylate 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 以34%的产率得到1,1-dimethylethyl 3-(methoxymethyl)-7α-methoxy-8-oxo-5-thia-1-azabicyclo<4.2.0>oct-2-ene-2-carboxylate 5,5-dioxide
  参考文献：
  名称：

  Inhibition of human leukocyte elastase. 3. Synthesis and activity of 3'-substituted cephalosporins

  摘要：

  Several 3'-substituted cephalosporin sulfones were synthesized from 3-(hydroxymethyl)cephalosporin, which was prepared by Ti(OiPr)4 hydrolysis of the corresponding acetate. A method was also developed to prepare a 3-vinylcephalosporin. Some of these compound were found to be potent time-dependent inhibitors of human leukocyte elastase (HLE). The HLE inhibitory activity was correlated with sigma 1 and it was concluded that the potency was determined by the electron-withdrawing ability as well as the size of the substituent. A mechanism for inhibition of HLE by cephalosporin sulfones is proposed.

  DOI：

  10.1021/jm00171a030
• 作为产物：
  描述：

  1,1-dimethylethyl 3-<(acetyloxy)methyl>-7α-methoxy-8-oxo-5-thia-1-azabicyclo<4.2.0>oct-3-ene-2-carboxylate 在 titanium(IV) isopropylate 作用下， 以 异丙醇 为溶剂， 反应 16.0h， 生成 1,1-dimethylethyl 3-(methoxymethyl)-7α-methoxy-8-oxo-5-thia-1-azabicyclo<4.2.0>oct-3-ene-2-carboxylate
  参考文献：
  名称：

  Inhibition of human leukocyte elastase. 3. Synthesis and activity of 3'-substituted cephalosporins

  摘要：

  Several 3'-substituted cephalosporin sulfones were synthesized from 3-(hydroxymethyl)cephalosporin, which was prepared by Ti(OiPr)4 hydrolysis of the corresponding acetate. A method was also developed to prepare a 3-vinylcephalosporin. Some of these compound were found to be potent time-dependent inhibitors of human leukocyte elastase (HLE). The HLE inhibitory activity was correlated with sigma 1 and it was concluded that the potency was determined by the electron-withdrawing ability as well as the size of the substituent. A mechanism for inhibition of HLE by cephalosporin sulfones is proposed.

  DOI：

  10.1021/jm00171a030