1-(3,5-Dichloro-4-hydroxy-phenyl)-4-(2H-tetrazol-5-ylmethyl)-azetidin-2-one | 145887-42-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 英文名称: 1-(3,5-Dichloro-4-hydroxy-phenyl)-4-(2H-tetrazol-5-ylmethyl)-azetidin-2-one
• 英文别名: 1-(3,5-dichloro-4-hydroxyphenyl)-4-(2H-tetrazol-5-ylmethyl)azetidin-2-one
• CAS: 145887-42-9
• 化学式: C₁₁H₉Cl₂N₅O₂
• 分子量: 314.131
• InChiKey: TVUVUZBLWFNAAM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  95
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (+/-)-1-(4-methoxyphenyl)-4-(tetrazol-5-ylmethyl)azetidin-2-one 在 ammonium cerium(IV) nitrate 、 sodium chloride 作用下， 生成 1-(4-hydroxyphenyl)-4-(tetrazol-5-ylmethyl)azetidin-2-one 、 RS-1-(3-chloro-4-hydroxyphenyl)-4-(tetrazol-5-ylmethyl)azetidin-2-one 、 1-(3,5-Dichloro-4-hydroxy-phenyl)-4-(2H-tetrazol-5-ylmethyl)-azetidin-2-one
  参考文献：
  名称：

  Simple and condensed β-lactams. Part 14. Anomalous behaviour of 1-(4-methoxyphenyl)-4-(tetrazol-5-ylmethyl)azetidin-2-one towards cerium(IV) ammonium nitrate

  摘要：

  Treatment of 1-(4-methoxyphenyl)azetidin-2-one 7 with cerium(IV) ammonium nitrate (CAN) fails to yield the N-deprotected product 6. Depending on the mode of work-up, N-substituted products 8-13 are obtained instead. The formation of these products may be rationalized by assuming interaction of the nucleophilic tetrazole and electrophilic quinone imine moieties of intermediate 21 to afford, after deprotonation, the spirocyclic quinone aminal 25. The latter, in contrast to quinone imine derivatives of type 3, is stable to hydrolysis under the conditions applied but reacts readily both with added sodium chloride and bromide as well as with reducing agents (NaHSO3, I-).

  DOI：

  10.1039/p19920003061

文献信息

• Simple and condensed β-lactams. Part 14. Anomalous behaviour of 1-(4-methoxyphenyl)-4-(tetrazol-5-ylmethyl)azetidin-2-one towards cerium(<scp>IV</scp>) ammonium nitrate
  作者：József Fetter、Ernő Keskeny、Tibor Czuppon、Károly Lempert、Mária Kajtár-peredy、József Tamás

  DOI：10.1039/p19920003061

  日期：——

  Treatment of 1-(4-methoxyphenyl)azetidin-2-one 7 with cerium(IV) ammonium nitrate (CAN) fails to yield the N-deprotected product 6. Depending on the mode of work-up, N-substituted products 8-13 are obtained instead. The formation of these products may be rationalized by assuming interaction of the nucleophilic tetrazole and electrophilic quinone imine moieties of intermediate 21 to afford, after deprotonation, the spirocyclic quinone aminal 25. The latter, in contrast to quinone imine derivatives of type 3, is stable to hydrolysis under the conditions applied but reacts readily both with added sodium chloride and bromide as well as with reducing agents (NaHSO3, I-).