4-(2-methyltetrazol-5-ylmethyl)azetidin-2-one | 145887-36-1

• 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: 4-(2-methyltetrazol-5-ylmethyl)azetidin-2-one
• 英文别名: 4-[(2-Methyltetrazol-5-yl)methyl]azetidin-2-one
• CAS: 145887-36-1
• 化学式: C₆H₉N₅O
• 分子量: 167.17
• InChiKey: WNFCPHMQZQJBPB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  72.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (+/-)-4-cyanomethyl-1-(4-methoxyphenyl)azetidin-2-one 在 三氯化铝 、 sodium azide 、 ammonium cerium(IV) nitrate 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙醚 、 水 、 乙腈 为溶剂， 反应 29.0h， 生成 4-(2-methyltetrazol-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 27. Reaction of 1-(4-methoxyphenyl)-4-(tetrazol-5-yl)azetidin-2-one and 1-(4-methoxyphenyl)-5-(tetrazol-5-yl-methyl)pyrrolidin-2-one with cerium(IV) ammonium nitrate (CAN)
  作者：Le Thanh Giang、József Fetter、Károly Lempert、Mária Kajtár-Peredy、Ágnes Gömöry

  DOI：10.1016/0040-4020(96)00539-x

  日期：1996.7

  Treatment of pyrrolidinone 3a with CAN under the usual conditions leads to formation of spiro compound 12, rather than to N-demethoxyphenylation. A study of the reactions of compound 12 with sodium chloride and sodium iodide furnished the proof for our assumption that the related non-isolable compounds 6 and 11 are the intermediates of the anomalous reactions of compounds 1a and 2a, respectively, with

  在通常条件下用CAN处理吡咯烷酮3a导致形成螺环化合物12，而不是导致N-脱甲氧基苯基化。对化合物12与氯化钠和碘化钠反应的研究为我们的假设提供了证据，即相关的不可分离的化合物6和11分别是化合物1a和2a与CAN异常反应的中间产物。
• AZETIDINONE DERIVATIVES FOR THE TREATMENT OF HCMV INFECTIONS
  申请人：BOEHRINGER INGELHEIM (CANADA) LTD.

  公开号：EP1021405B1

  公开（公告）日：2002-09-25
• US6242439B1
  申请人：——

  公开号：US6242439B1

  公开（公告）日：2001-06-05
• 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-).