(S)-1-(tert-butyldimethylsilyl)-4-(1H-imidazole-1-carbonyl)azetidin-2-one | 1313226-63-9

• 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: (S)-1-(tert-butyldimethylsilyl)-4-(1H-imidazole-1-carbonyl)azetidin-2-one
• 英文别名: (4S)-1-[tert-butyl(dimethyl)silyl]-4-(imidazole-1-carbonyl)azetidin-2-one
• CAS: 1313226-63-9
• 化学式: C₁₃H₂₁N₃O₂Si
• 分子量: 279.414
• InChiKey: VFSMIDXCQNVWQK-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.13
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  55.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-1-(tert-butyldimethylsilyl)-4-(1H-imidazole-1-carbonyl)azetidin-2-one 在 三乙胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 32.67h， 生成 (S)-1-(tert-butyldimethylsilyl)-4-(7-hydroxy-2,2-dimethyl-4-oxo-4H-benzo[d][1,3]dioxin-5-yl)azetidin-2-one
  参考文献：
  名称：

  Conversion of α-Amino Acids into Bioactive o-Aminoalkyl Resorcylates and Related Dihydroxyisoindolinones

  摘要：

  The synthesis of biologically active o-aminoalkyl resorcylates and related dihydroxyisoindolinones from functionalized alpha-amino acids without the use of phenolic protection is described. The key aminoalkyl-diketo-dioxinone intermediates were prepared utilizing a crossed Claisen condensation reaction in the presence of diethylzinc. The aromatic unit was constructed via late stage cyclization and aromatization, and subsequent modification provided the novel resorcylates which showed activity against a selection of receptors and kinases, including 5-HT and CDK.

  DOI：

  10.1021/jo2009356
• 作为产物：
  描述：

  (4S)-N-(叔丁基二甲基硅)氮杂环丁烷-2-酮-4-羧酸 、 N,N'-羰基二咪唑 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 (S)-1-(tert-butyldimethylsilyl)-4-(1H-imidazole-1-carbonyl)azetidin-2-one
  参考文献：
  名称：

  Conversion of α-Amino Acids into Bioactive o-Aminoalkyl Resorcylates and Related Dihydroxyisoindolinones

  摘要：

  The synthesis of biologically active o-aminoalkyl resorcylates and related dihydroxyisoindolinones from functionalized alpha-amino acids without the use of phenolic protection is described. The key aminoalkyl-diketo-dioxinone intermediates were prepared utilizing a crossed Claisen condensation reaction in the presence of diethylzinc. The aromatic unit was constructed via late stage cyclization and aromatization, and subsequent modification provided the novel resorcylates which showed activity against a selection of receptors and kinases, including 5-HT and CDK.

  DOI：

  10.1021/jo2009356