3-<1-<1-<(tert-butyldimethylsilyl)oxy>ethyl>>-4-<2-(1-azido-2-methylethyl)>azetidin-2-one | 139976-60-6

• 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-<1-<1-<(tert-butyldimethylsilyl)oxy>ethyl>>-4-<2-(1-azido-2-methylethyl)>azetidin-2-one
• 英文别名: (3S,4R)-4-[(2S)-1-azidopropan-2-yl]-3-[(1R)-1-[tert-butyl(dimethyl)silyl]oxyethyl]azetidin-2-one
• CAS: 139976-60-6
• 化学式: C₁₄H₂₈N₄O₂Si
• 分子量: 312.487
• InChiKey: QCHPVUYBGIDJNU-IRCOFANPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.46
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  52.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-<1-<1-<(tert-butyldimethylsilyl)oxy>ethyl>>-4-<2-(1-azido-2-methylethyl)>azetidin-2-one 在 4-甲基苯磺酸吡啶 、 L-Selectride 作用下， 以 四氢呋喃 为溶剂， 反应 0.67h， 生成 7-<1-<1-<(tert-butyldimethylsilyl)oxy>ethyl>>-1-hydroxy-6-methyl-9a-carbobenzoxy-8-oxoazetidino<1,2-c>perhydropyrrolo<1,2-a>pyrimidine
  参考文献：
  名称：

  Addition of amino amides to vinyl vicinal tricarbonyls. Formation of tricyclic 3-azadethiacephams

  摘要：

  Amino amides react as trinucleophiles with vinyl vicinal tricarbonyl esters. Reaction of the primary amino group takes place at the beta-position of the alpha,beta-unsaturated ketone along with addition to the central carbonyl group. In a third-stage reaction, the amide residue adds to the iminium ion formed from the intermediate carbinolamine. The resulting product is a bicyclic or tricyclic (acylamino)pyrrolidone carboxylate. A novel tricyclic 3-azadethiacepham of biological interest has been prepared using this reaction.

  DOI：

  10.1021/jo00035a019
• 作为产物：
  描述：

  (3S,4R)-3-<(R)-1-(t-Butyldimethylsilyloxy)ethyl>-4-<(R)-1-((S)-4-benzyl-2-oxazolidone-3-carbonyl)ethyl>-2-azetidinone 在 锂硼氢 、 偶氮二甲酸二异丙酯 、 二苯基膦叠氮化物 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 5.17h， 生成 3-<1-<1-<(tert-butyldimethylsilyl)oxy>ethyl>>-4-<2-(1-azido-2-methylethyl)>azetidin-2-one
  参考文献：
  名称：

  Addition of amino amides to vinyl vicinal tricarbonyls. Formation of tricyclic 3-azadethiacephams

  摘要：

  Amino amides react as trinucleophiles with vinyl vicinal tricarbonyl esters. Reaction of the primary amino group takes place at the beta-position of the alpha,beta-unsaturated ketone along with addition to the central carbonyl group. In a third-stage reaction, the amide residue adds to the iminium ion formed from the intermediate carbinolamine. The resulting product is a bicyclic or tricyclic (acylamino)pyrrolidone carboxylate. A novel tricyclic 3-azadethiacepham of biological interest has been prepared using this reaction.

  DOI：

  10.1021/jo00035a019

文献信息

• Addition of amino amides to vinyl vicinal tricarbonyls. Formation of tricyclic 3-azadethiacephams
  作者：Harry H. Wasserman、Susan L. Henke、Eiji Nakanishi、Gayle Schulte

  DOI：10.1021/jo00035a019

  日期：1992.4

  Amino amides react as trinucleophiles with vinyl vicinal tricarbonyl esters. Reaction of the primary amino group takes place at the beta-position of the alpha,beta-unsaturated ketone along with addition to the central carbonyl group. In a third-stage reaction, the amide residue adds to the iminium ion formed from the intermediate carbinolamine. The resulting product is a bicyclic or tricyclic (acylamino)pyrrolidone carboxylate. A novel tricyclic 3-azadethiacepham of biological interest has been prepared using this reaction.