methyl (2R,3R)-3-ethyl-4-oxoazetidine-2-carboxylate | 120522-68-1

• 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: methyl (2R,3R)-3-ethyl-4-oxoazetidine-2-carboxylate
• CAS: 120522-68-1
• 化学式: C₇H₁₁NO₃
• 分子量: 157.169
• InChiKey: VNMPZKJTANRMRB-RFZPGFLSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl (2R,3R)-3-ethyl-4-oxoazetidine-2-carboxylate 在 三甲基氯硅烷 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  A concise stereoselective approach to β-Alkylaspartates from β-Lactams via [2 + 2] cycloaddition reaction of ketenes to glyoxylic ester-derived imines.

  摘要：

  syn beta-Alkyl aspartates were obtained with high stereoselectivities from cis 4-alkoxycarbonyl-beta-lactams prepared via [2 + 2] cycloaddition reaction of monoalkylketenes and glyoxalate derived imines.

  DOI：

  10.1016/s0040-4039(00)61295-9
• 作为产物：
  描述：

  在 ammonium cerium(IV) nitrate 作用下， 以 水 、 乙腈 为溶剂， 反应 0.5h， 生成 methyl (2R,3R)-3-ethyl-4-oxoazetidine-2-carboxylate
  参考文献：
  名称：

  A concise stereoselective approach to β-Alkylaspartates from β-Lactams via [2 + 2] cycloaddition reaction of ketenes to glyoxylic ester-derived imines.

  摘要：

  syn beta-Alkyl aspartates were obtained with high stereoselectivities from cis 4-alkoxycarbonyl-beta-lactams prepared via [2 + 2] cycloaddition reaction of monoalkylketenes and glyoxalate derived imines.

  DOI：

  10.1016/s0040-4039(00)61295-9

文献信息

• A novel method for generation of enolizable N-trimethylsilylaldimines and application to β-lactam synthesis
  作者：Tadao Uyehara、Ichiro Suzuki、Yoshinori Yamamoto

  DOI：10.1016/s0040-4039(01)80709-7

  日期：1989.1

  A new method to generate N-trimethylsilylaldimines has been developedby the combination of bis(trimethylsilyl)formamide and organolithium reagents and applied successfully to β-lactam synthesis.

  通过双（三甲基甲硅烷基）甲酰胺和有机锂试剂的结合，开发了一种新的生成N-三甲基甲硅烷基亚胺的方法，并成功地应用于β-内酰胺的合成。
• TiCl4-mediated reactions of silyl ketene acetals derived from n-methylephedrine esters:asymmetric synthesis ofβ-lactams
  作者：Cesare Gennari、Giuliana Schimperna、Isabella Venturini

  DOI：10.1016/s0040-4020(01)86668-0

  日期：1988.1

  TiCl4 mediated addition of silyl ketene acetals derived from N-methylephedrine esters to various aldehydes and imines was used as the key-step in the enantio- and diastereo-controlled synthesis ofβ-lactams.

  TiCl 4介导的从N-甲基麻黄碱酯衍生的甲硅烷基乙烯酮缩醛向各种醛和亚胺的加成反应是β-内酰胺对映体和非对映体控制合成的关键步骤。
• GENNARI, CESARE;SCHIMPERNA, GIULIANA;VENTURINI, ISABELLA, TETRAHEDRON, 44,(1988) N 13, 4221-4232
  作者：GENNARI, CESARE、SCHIMPERNA, GIULIANA、VENTURINI, ISABELLA

  DOI：——

  日期：——
• A concise stereoselective approach to β-Alkylaspartates from β-Lactams via [2 + 2] cycloaddition reaction of ketenes to glyoxylic ester-derived imines.
  作者：Claudio Palomo、Jesus M. Aizpurua、Jesus M. Ontoria、Miren Iturburu

  DOI：10.1016/s0040-4039(00)61295-9

  日期：1992.8

  syn beta-Alkyl aspartates were obtained with high stereoselectivities from cis 4-alkoxycarbonyl-beta-lactams prepared via [2 + 2] cycloaddition reaction of monoalkylketenes and glyoxalate derived imines.