(+/-)-4-(methylsulfonyloxymethyl)-1-(4-methoxyphenyl)azetidin-2-one | 156516-63-1

• 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-(methylsulfonyloxymethyl)-1-(4-methoxyphenyl)azetidin-2-one
• 英文别名: [1-(4-Methoxyphenyl)-4-oxoazetidin-2-yl]methyl methanesulfonate
• CAS: 156516-63-1
• 化学式: C₁₂H₁₅NO₅S
• 分子量: 285.321
• InChiKey: DNGOHJYCWBWCLJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  81.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (+/-)-4-(methylsulfonyloxymethyl)-1-(4-methoxyphenyl)azetidin-2-one 在 sodium iodide 作用下， 以 丙酮 为溶剂， 反应 12.0h， 以89%的产率得到rac-4-iodomethyl-1-(4-methoxyphenyl)-4-oxoazetidin-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：

  甲基磺酰氯 、 4-羟甲基-1-(4-甲氧基苯基)-2-氮杂环丁酮 在 吡啶 作用下， 反应 3.0h， 以85%的产率得到(+/-)-4-(methylsulfonyloxymethyl)-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

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。
• Simple and condensed β-lactams. Part 20. Reaction of some 1-(4-methoxyphenyl)azetidin-2-ones with cerium(IV) ammonium nitrate (CAN): Trapping of the quinone imine intermediate with chloride and iodide anions
  作者：József Fetter、Le Thanh Giang、Tibor Czuppon、Károly Lempert、Mária Kajtár-Peredy、Gábor Czira

  DOI：10.1016/s0040-4020(01)86713-2

  日期：1994.4

  1-(4-methoxyphenyl)azetidin-2-ones 12 and 13, when treated with cerium(IV) ammonium nitrate (CAN), afford either their N-deprotected derivatives (19, 26) or the chlorinated compounds 22 and 27, respectively, as the main products, depending on whether sodium chloride was present or not. A series of minor products (20, 21, 23–25 and 29, respectively) are formed in addition. 1-(4-Methoxyphenyl)azetidin-2-ones

  1-（4-甲氧基苯基）氮杂环丁烷-2-酮12和13，当与铈（IV）铵（CAN）处理，得到任一其Ñ -deprotected衍生物（19，26）或氯化化合物22和27分别，作为主要产品，取决于是否存在氯化钠。一系列的次要产物（20，21，23-25和29被形成在除了分别）。1-（4-甲氧基苯基）氮杂环丁烷-2-酮13和14当依次用CAN和碘化钠处理时，分别以良好的收率得到相应的1-（4-羟基苯基）氮杂环丁烷-2-酮28和30。后面的反应可能为详细阐述N-（2-和4-烷氧基苯基）羧酰胺的脱烷氧基-羟基化的一般方法奠定基础。机制被建议用于化合物的形成19 - 30。
• 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-).