dimethyl 5-(4-methylphenyl)-1,2-diphenylpyrazolidine-3,3-dicarboxylate

• 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: dimethyl 5-(4-methylphenyl)-1,2-diphenylpyrazolidine-3,3-dicarboxylate
• 化学式: C₂₆H₂₆N₂O₄
• 分子量: 430.503
• InChiKey: AHEBRGNLTIVDTR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  59.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  dimethyl 2-(p-methylphenyl)cyclopropane-1,1-dicarboxylate 、 偶氮苯 在 gallium(III) trichloride 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以44%的产率得到dimethyl 5-(4-methylphenyl)-1,2-diphenylpyrazolidine-3,3-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.