tert-butyl (3R,4S)-3-methyl-2-oxo-4-thiophen-2-yl-3-triethylsilyloxyazetidine-1-carboxylate | 496918-81-1

• 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: tert-butyl (3R,4S)-3-methyl-2-oxo-4-thiophen-2-yl-3-triethylsilyloxyazetidine-1-carboxylate
• CAS: 496918-81-1
• 化学式: C₁₉H₃₁NO₄SSi
• 分子量: 397.611
• InChiKey: NJDCNHPRIMLVFU-DNVCBOLYSA-N

物化性质

• 沸点：
  469.8±45.0 °C(Predicted)
• 密度：
  1.11±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.35
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  84.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  tert-butyl (3R,4S)-3-methyl-2-oxo-4-thiophen-2-yl-3-triethylsilyloxyazetidine-1-carboxylate 在 4-二甲氨基吡啶 、 四丁基氟化铵 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 生成 (2R,3S)-3-(tert-butoxycarbonylamino)-2-hydroxy-2-methyl-3-(2-thienyl)propionic acid methyl ester
  参考文献：
  名称：

  Synthesis of Optically Active Constrained 2-Substituted Norstatines:  A Straightforward Application of Seebach's “SRS” Synthetic Principle

  摘要：

  A straightforward two-step methodology of synthesis of optically active (2,R)-substituted norstatines via addition of N-tert-butoxycarbonyl-substituted aldimines to (2S)-chiral enolates of 1,3-dioxolan-4-ones has been developed. In particular, the use of the natural (2S)-malic acid is examined for the synthesis of potential GABAergic spirocyclic gamma-lactams.

  DOI：

  10.1021/jo0486793
• 作为产物：
  描述：

  E-3-hydroxy-3-methyl-4-thien-2-yl-azetidin-2-one 在 咪唑 、 4-二甲氨基吡啶 作用下， 生成 tert-butyl (3R,4S)-3-methyl-2-oxo-4-thiophen-2-yl-3-triethylsilyloxyazetidine-1-carboxylate
  参考文献：
  名称：

  Synthesis of Optically Active Constrained 2-Substituted Norstatines:  A Straightforward Application of Seebach's “SRS” Synthetic Principle

  摘要：

  A straightforward two-step methodology of synthesis of optically active (2,R)-substituted norstatines via addition of N-tert-butoxycarbonyl-substituted aldimines to (2S)-chiral enolates of 1,3-dioxolan-4-ones has been developed. In particular, the use of the natural (2S)-malic acid is examined for the synthesis of potential GABAergic spirocyclic gamma-lactams.

  DOI：

  10.1021/jo0486793

文献信息

• Synthesis of Optically Active Constrained 2-Substituted Norstatines:  A Straightforward Application of Seebach's “SRS” Synthetic Principle
  作者：Arturo Battaglia、Andrea Guerrini、Carlo Bertucci

  DOI：10.1021/jo0486793

  日期：2004.12.1

  A straightforward two-step methodology of synthesis of optically active (2,R)-substituted norstatines via addition of N-tert-butoxycarbonyl-substituted aldimines to (2S)-chiral enolates of 1,3-dioxolan-4-ones has been developed. In particular, the use of the natural (2S)-malic acid is examined for the synthesis of potential GABAergic spirocyclic gamma-lactams.