dimethyl 2,4-dioxo-3,8-diphenyl-1,3,5-triazabicyclo[3.3.0]octane-6,6-dicarboxylate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: dimethyl 2,4-dioxo-3,8-diphenyl-1,3,5-triazabicyclo[3.3.0]octane-6,6-dicarboxylate
• 英文别名: Dimethyl 1,3-dioxo-2,7-diphenyl-6,7-dihydropyrazolo[1,2-a][1,2,4]triazole-5,5-dicarboxylate
• 化学式: C₂₁H₁₉N₃O₆
• 分子量: 409.398
• InChiKey: AQVRIVKOHMMJIX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  96.5
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  (1'S,2'R,4S)-4-isopropyl-3-(1'-methoxycarbonyl-2'-phenylcyclopropylcarbonyl)oxazolidin-2-one 在 gallium(III) trichloride 、 sodium hydroxide 、 双氧水 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 72.0h， 生成 dimethyl 2,4-dioxo-3,8-diphenyl-1,3,5-triazabicyclo[3.3.0]octane-6,6-dicarboxylate
  参考文献：
  名称：

  GaCl₃-Catalyzed Insertion of Diazene Derivatives into the Cyclopropane Ring¹

  摘要：

  [GRAPHICS]GaCl3 has been found to efficiently catalyze the formal cycloadditions of diazene derivatives 6 onto 2-arylcyclopropane-1, 1-dicarboxylates 5, giving rise to the pyrazolidine derivatives 7. The insertion into the cyclopropane ring proceeds with complete regioselectivity to furnish 5-arylpyrazolidine-1,2,3,3-tetracarboxylates exclusively; however, the cis-configured azo compound N-phenyltriazolinedione gave the two possible regioisomeric pyrazolidine derivatives in ratios varying from 1:1.5 to 1:3. Conceivable mechanisms of these transformations are being discussed.

  DOI：

  10.1021/jo0704816

文献信息

• GaCl₃-Catalyzed Insertion of Diazene Derivatives into the Cyclopropane Ring¹
  作者：Vadim S. Korotkov、Oleg V. Larionov、Anja Hofmeister、Jörg Magull、Armin de Meijere

  DOI：10.1021/jo0704816

  日期：2007.9.1

  [GRAPHICS]GaCl3 has been found to efficiently catalyze the formal cycloadditions of diazene derivatives 6 onto 2-arylcyclopropane-1, 1-dicarboxylates 5, giving rise to the pyrazolidine derivatives 7. The insertion into the cyclopropane ring proceeds with complete regioselectivity to furnish 5-arylpyrazolidine-1,2,3,3-tetracarboxylates exclusively; however, the cis-configured azo compound N-phenyltriazolinedione gave the two possible regioisomeric pyrazolidine derivatives in ratios varying from 1:1.5 to 1:3. Conceivable mechanisms of these transformations are being discussed.