3-benzyloxy-1-[1-(4-methoxyphenyl)-ethyl]-4-oxo-azetidine-2-carboxylic acid methyl ester

• 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: 3-benzyloxy-1-[1-(4-methoxyphenyl)-ethyl]-4-oxo-azetidine-2-carboxylic acid methyl ester
• 化学式: C₂₁H₂₃NO₅
• 分子量: 369.417
• InChiKey: LIISTIZKKPWERE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.73
• 重原子数：
  27.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  65.07
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  3-benzyloxy-1-[1-(4-methoxyphenyl)-ethyl]-4-oxo-azetidine-2-carboxylic acid methyl ester 在 ammonium cerium(IV) nitrate 作用下， 以 水 、 乙腈 为溶剂， 反应 1.0h， 以89%的产率得到3-benzyloxy-4-oxo-azetidine-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Stereoselective synthesis of racemic α-amino-acid derivatives with a β-lactam skeleton: Application of the Staudinger reaction to chiral imines of methyl glyoxylate

  摘要：

  Selected imines of methyl glyoxylate act as good partners in the Staudinger cycloaddition reaction with a series of substituted ketenes. The cis stereoselectivity is almost complete with electron-donor substituted ketenes, but the asymmetric induction is low when imines derived From chiral 1-aryl-ethylamines are used. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00683-8
• 作为产物：
  描述：

  (R)-(+)-1-(4-甲氧基苯)乙胺 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 生成 3-benzyloxy-1-[1-(4-methoxyphenyl)-ethyl]-4-oxo-azetidine-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Stereoselective synthesis of racemic α-amino-acid derivatives with a β-lactam skeleton: Application of the Staudinger reaction to chiral imines of methyl glyoxylate

  摘要：

  Selected imines of methyl glyoxylate act as good partners in the Staudinger cycloaddition reaction with a series of substituted ketenes. The cis stereoselectivity is almost complete with electron-donor substituted ketenes, but the asymmetric induction is low when imines derived From chiral 1-aryl-ethylamines are used. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00683-8

文献信息

• Stereoselective synthesis of racemic α-amino-acid derivatives with a β-lactam skeleton: Application of the Staudinger reaction to chiral imines of methyl glyoxylate
  作者：Michel Barreau、Alain Commerçon、Serge Mignani、Dominique Mouysset、Patricia Perfetti、Lucien Stella

  DOI：10.1016/s0040-4020(98)00683-8

  日期：1998.9

  Selected imines of methyl glyoxylate act as good partners in the Staudinger cycloaddition reaction with a series of substituted ketenes. The cis stereoselectivity is almost complete with electron-donor substituted ketenes, but the asymmetric induction is low when imines derived From chiral 1-aryl-ethylamines are used. (C) 1998 Elsevier Science Ltd. All rights reserved.