[(3S,4R)-2-oxo-1,4-diphenylazetidin-3-yl] methanesulfonate

• 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: [(3S,4R)-2-oxo-1,4-diphenylazetidin-3-yl] methanesulfonate
• 化学式: C₁₆H₁₅NO₄S
• 分子量: 317.365
• InChiKey: KADKAJKDROANDB-CABCVRRESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [(3S,4R)-2-oxo-1,4-diphenylazetidin-3-yl] methanesulfonate 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 生成 3-methylene-1,4-diphenylazetidin-2-one
  参考文献：
  名称：

  对映体的硝酮环转移路线为3-羟基-2-氮杂环丁酮

  摘要：

  4-芳基或杂芳基3-亚甲基β-内酰胺2a–2c与各种硝酮3a–3c进行了高度立体定向的环加成反应。该方法提供了3-羟基-β-内酰胺的对映体特异性途径。©1997由Elsevier Science Ltd发布。

  DOI：

  10.1016/s0040-4039(97)00394-8
• 作为产物：
  描述：

  3-acetoxy-1,4-diphenylazetidin-2-one 在 potassium carbonate 作用下， 以 吡啶 、 甲醇 、 水 为溶剂， 反应 25.0h， 生成 [(3S,4R)-2-oxo-1,4-diphenylazetidin-3-yl] methanesulfonate
  参考文献：
  名称：

  Synthesis of 3-acetoxyazetidin-2-ones and 3-hydroxyazetidin-2-ones with antifungal and antibacterial activity

  摘要：

  The synthesis of a series of 3-acetoxyazetidin-2-ones 3a-n and 3-hydroxyazetidin-2-ones 6a-j is reported together with the antibacterial and antifungal evaluation of these compounds. An additional series of 3-acetoxyazetidin-2-ones 11a-h which possess a free carboxylic acid group on the N-1 aryl ring were obtained by treatment of suitably substituted Schiff bases 10a-h with acetoxyacetyl chloride. The novel bicyclic structures 7 acetoxy-6-phenyl-5-thia-1-azabicyclo[4.2.0]octan-8-one 13 and 7-hydroxy-6-phenyl-5-thia-1-azabicyclo[4.2.0]octan-8-one 14 were also obtained. Many of the compounds displayed antifungal activity in vitro when evaluated against the pathogenic fungi Cryptococcus neoformans, Candida albicans, Candida tropicalis, Candida parapsilosis, Candida glabrata, and Trichosporon cutaneum, while 3-acetoxyazetidin-2-ones 11a-h containing a free carboxylic acid group on the N-1 aryl ring displayed antibacterial activity against Staphylococcus aureus, Proteus vulgaris, Pseudomonas aeruginosa, Bacillus subtilis, Klebsiella aerogenes and Escherischia coli.

  DOI：

  10.1016/s0223-5234(97)86178-8

文献信息

• Yadav, Ram Naresh; Banik, Indrani; Banik, Bimal Krishna, Journal of the Indian Chemical Society, 2018, vol. 95, # 11, p. 1405 - 1408
  作者：Yadav, Ram Naresh、Banik, Indrani、Banik, Bimal Krishna

  DOI：——

  日期：——
• Synthesis of 3-acetoxyazetidin-2-ones and 3-hydroxyazetidin-2-ones with antifungal and antibacterial activity
  作者：OM Walsh、MJ Meegan、RM Prendergast、T Al Nakib

  DOI：10.1016/s0223-5234(97)86178-8

  日期：1996.1

  The synthesis of a series of 3-acetoxyazetidin-2-ones 3a-n and 3-hydroxyazetidin-2-ones 6a-j is reported together with the antibacterial and antifungal evaluation of these compounds. An additional series of 3-acetoxyazetidin-2-ones 11a-h which possess a free carboxylic acid group on the N-1 aryl ring were obtained by treatment of suitably substituted Schiff bases 10a-h with acetoxyacetyl chloride. The novel bicyclic structures 7 acetoxy-6-phenyl-5-thia-1-azabicyclo[4.2.0]octan-8-one 13 and 7-hydroxy-6-phenyl-5-thia-1-azabicyclo[4.2.0]octan-8-one 14 were also obtained. Many of the compounds displayed antifungal activity in vitro when evaluated against the pathogenic fungi Cryptococcus neoformans, Candida albicans, Candida tropicalis, Candida parapsilosis, Candida glabrata, and Trichosporon cutaneum, while 3-acetoxyazetidin-2-ones 11a-h containing a free carboxylic acid group on the N-1 aryl ring displayed antibacterial activity against Staphylococcus aureus, Proteus vulgaris, Pseudomonas aeruginosa, Bacillus subtilis, Klebsiella aerogenes and Escherischia coli.
• AN ENANTIOSPECIFIC NITRONE CYCLOADDITION ROUTE TO 3-HYDROXY-2-AZETIDINONES
  作者：Amit Basak、Hassam M.M Bdour、Gautam Bhattacharya

  DOI：10.1016/s0040-4039(97)00394-8

  日期：1997.4

  4-Aryl or heteroaryl 3-methylene β-lactams 2a–2c underwenthighly stereospecific cycloaddition with various nitrones 3a–3c. The method offers an enantiospecific route to 3-hydroxy-β-lactams. © 1997 Published by Elsevier Science Ltd.

  4-芳基或杂芳基3-亚甲基β-内酰胺2a–2c与各种硝酮3a–3c进行了高度立体定向的环加成反应。该方法提供了3-羟基-β-内酰胺的对映体特异性途径。©1997由Elsevier Science Ltd发布。