(S)-1-(4-methoxybenzyl)-4-phenyl-azetidine-2,3-dione | 1024019-43-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氮杂环丁烷
• 英文名称: (S)-1-(4-methoxybenzyl)-4-phenyl-azetidine-2,3-dione
• 英文别名: (4S)-1-[(4-methoxyphenyl)methyl]-4-phenylazetidine-2,3-dione
• CAS: 1024019-43-9
• 化学式: C₁₇H₁₅NO₃
• 分子量: 281.311
• InChiKey: HWPZTJVMHJSSKZ-HNNXBMFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (3S,4S,7R)-2-(4-methoxybenzyl)-1-oxo-3-phenyl-5-thia-2,8-diazaspiro[3.4]octane-7,8-dicarboxylic acid 8-tert-butyl ester 7-methyl ester 在 盐酸 、 aluminum oxide 、 碘 作用下， 以 乙酸乙酯 、 二氯甲烷 、 水 为溶剂， 反应 44.0h， 以75%的产率得到(S)-1-(4-methoxybenzyl)-4-phenyl-azetidine-2,3-dione
  参考文献：
  名称：

  Stereoselective synthesis of 4-substituted azetidine-2,3-diones by ring opening of 1,3-thiazolidine-derived spiro-β-lactams

  摘要：

  New 3-heterocycle substituted 1,3-thiazolidine-derived 4-spiro-beta-lactams with a relative trans-configuration were stereoselectively synthesised by means of a Staudinger ketene-imine reaction between the ketene generated from the (2S,4R)-1,3-thiazolidine-2,3,4-tricarboxylic acid 3-(1,1-dimethylethyl) 4-methyl ester 1 and imines 2b-e. The 1,3-thiazolidine-derived 4-spiro-beta-lactams were transformed into the corresponding enantiomerically pure 4-heterocycle substituted azetidine-2,3-diones by means of an oxidative cleavage of the 1,3-thiazolidine ring. The opening of the 1,3-thiazolidine ring was studied under different experimental conditions and a consistent mechanism is proposed. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.02.011

文献信息

• Stereoselective synthesis of 4-substituted azetidine-2,3-diones by ring opening of 1,3-thiazolidine-derived spiro-β-lactams
  作者：Giuseppe Cremonesi、Piero Dalla Croce、Francesco Fontana、Concetta La Rosa

  DOI：10.1016/j.tetasy.2008.02.011

  日期：2008.3

  New 3-heterocycle substituted 1,3-thiazolidine-derived 4-spiro-beta-lactams with a relative trans-configuration were stereoselectively synthesised by means of a Staudinger ketene-imine reaction between the ketene generated from the (2S,4R)-1,3-thiazolidine-2,3,4-tricarboxylic acid 3-(1,1-dimethylethyl) 4-methyl ester 1 and imines 2b-e. The 1,3-thiazolidine-derived 4-spiro-beta-lactams were transformed into the corresponding enantiomerically pure 4-heterocycle substituted azetidine-2,3-diones by means of an oxidative cleavage of the 1,3-thiazolidine ring. The opening of the 1,3-thiazolidine ring was studied under different experimental conditions and a consistent mechanism is proposed. (C) 2008 Elsevier Ltd. All rights reserved.