Methyl 2-[2-(diethylamino)-5-methoxyindazol-3-yl]-2-hydroxyacetate | 1184730-78-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡唑类
• 英文名称: Methyl 2-[2-(diethylamino)-5-methoxyindazol-3-yl]-2-hydroxyacetate
• CAS: 1184730-78-6
• 化学式: C₁₅H₂₁N₃O₄
• 分子量: 307.349
• InChiKey: LVVVVTFGFZPLPG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  76.8
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  Methyl 3-[2-(diethylaminodiazenyl)-5-methoxyphenyl]prop-2-ynoate 在 dirhodium tetraacetate 、 水 作用下， 以 1,2-二氯乙烷 为溶剂， 以88%的产率得到Methyl 2-[2-(diethylamino)-5-methoxyindazol-3-yl]-2-hydroxyacetate
  参考文献：
  名称：

  Synthesis of α-Ketoester- and α-Hydroxyester-Substituted Isoindazoles via the Thermodynamic Coarctate Cyclization of Ester-Terminated Azo-Ene-Yne Systems

  摘要：

  The synthesis of isoindazoles bearing alpha-ketoester and alpha-hydroxyester groups via the coarctate cyclization of ester-terminated azo-ene-yne precursors is described. Whereas previous studies on isoindazole formation have shown the reaction to proceed through a kinetic coarctate pathway, functionalization of the terminal acetylene with a methyl ester sufficiently stabilizes the carbene intermediate to make the coarctate cyclization the thermodynamic pathway. Density functional theory (DFT) computations reveal ca. 8-9 kcal mol(-1) lower energy transition states for the coarctate pathway compared to the parent system.

  DOI：

  10.1021/jo9011283

文献信息

• Synthesis of α-Ketoester- and α-Hydroxyester-Substituted Isoindazoles via the Thermodynamic Coarctate Cyclization of Ester-Terminated Azo-Ene-Yne Systems
  作者：Sean P. McClintock、Nathan Forster、Rainer Herges、Michael M. Haley

  DOI：10.1021/jo9011283

  日期：2009.9.4

  The synthesis of isoindazoles bearing alpha-ketoester and alpha-hydroxyester groups via the coarctate cyclization of ester-terminated azo-ene-yne precursors is described. Whereas previous studies on isoindazole formation have shown the reaction to proceed through a kinetic coarctate pathway, functionalization of the terminal acetylene with a methyl ester sufficiently stabilizes the carbene intermediate to make the coarctate cyclization the thermodynamic pathway. Density functional theory (DFT) computations reveal ca. 8-9 kcal mol(-1) lower energy transition states for the coarctate pathway compared to the parent system.