(+/-)-4-cyanomethyl-1-(4-methoxyphenyl)azetidin-2-one | 145887-50-9

• 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: (+/-)-4-cyanomethyl-1-(4-methoxyphenyl)azetidin-2-one
• 英文别名: 2-[1-(4-Methoxyphenyl)-4-oxoazetidin-2-yl]acetonitrile
• CAS: 145887-50-9
• 化学式: C₁₂H₁₂N₂O₂
• 分子量: 216.239
• InChiKey: DRRBYOGVNPVIGD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  53.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (+/-)-4-cyanomethyl-1-(4-methoxyphenyl)azetidin-2-one 在 三氯化铝 、 sodium azide 、 sodium ethanolate 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 40.0h， 生成 4-(1-benzyltetrazol-5-ylmethyl)-1-(4-methoxyphenyl)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
• 作为产物：
  描述：

  hydroxy-[1-(4-methoxyphenyl)-4-oxo-azetidin-2-yl]acetonitrile 在 氯化亚砜 、 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 甲苯 为溶剂， 反应 0.25h， 生成 (+/-)-4-cyanomethyl-1-(4-methoxyphenyl)azetidin-2-one
  参考文献：
  名称：

  Boros, Eva; Bertha, Ferenc; Fetter, Jozsef, Journal of Chemical Research, 2004, # 8, p. 558 - 563

  摘要：

  DOI：

文献信息

• Acetoxylation of β-lactams with lead(IV) Acetate
  作者：Le Thanh Giang、József Fetter、Mária Kajtár-Peredy、Károly Lempert、Gábor Czira

  DOI：10.1016/s0040-4020(99)00857-1

  日期：1999.11

  1-(4-Methoxypheny])azetidin-2-ones 5a–5g were acetoxylated by lead(IV) acetate to afford the corresponding compounds 6a, 6b, 6c' and 6d–6g. In the d series elimination products 9 and 10 were also formed. Ring homologue 7a afforded the hydrotylated derivative 8'a.

  用乙酸铅（IV）对1-（4-甲氧基苯基））氮杂环丁烷-2-酮5a-5g进行乙酰氧基化，得到相应的化合物6a，6b，6c '和6d-6g。在d系列中，还形成消除产物9和10。环同系物7a得到加氢衍生的衍生物8'a。
• Boros, Eva; Bertha, Ferenc; Fetter, Jozsef, Journal of Chemical Research, 2004, # 8, p. 558 - 563
  作者：Boros, Eva、Bertha, Ferenc、Fetter, Jozsef、Vida, Laszlo、Kajtar-Peredy, Maria、Czira, Gabor

  DOI：——

  日期：——
• 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-).