4-carbomethoxy-8a-carbo-tert-butoxy-2,8-dioxoperhydropyrrolo<1,2-a>pyrimidine | 130762-37-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 4-carbomethoxy-8a-carbo-tert-butoxy-2,8-dioxoperhydropyrrolo<1,2-a>pyrimidine
• 英文别名: 8a-O-tert-butyl 4-O-methyl (4S)-2,8-dioxo-3,4,6,7-tetrahydro-1H-pyrrolo[1,2-a]pyrimidine-4,8a-dicarboxylate
• CAS: 130762-37-7
• 化学式: C₁₄H₂₀N₂O₆
• 分子量: 312.323
• InChiKey: HAXWGKMPISWHBP-BVVIDWAXSA-N

物化性质

• 沸点：
  477.6±45.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  102
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  2,2-Dihydroxy-3-oxo-pent-4-enoic acid tert-butyl ester 在 4-甲基苯磺酸吡啶 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 4-carbomethoxy-8a-carbo-tert-butoxy-2,8-dioxoperhydropyrrolo<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

文献信息

• Addition of amino lactams to vinyl vicinal tricarbonyls. Formation of tricyclic 2-azadethiapenams and 3-azadethiacephams
  作者：Harry H. Wasserman、Susan L. Henke、Patrick Luce、Eiji Nakanishi、Gayle Schulte

  DOI：10.1021/jo00310a012

  日期：1990.11
• 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.