Methyl 3-[2-(diethylaminodiazenyl)phenyl]prop-2-ynoate | 1184730-58-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: Methyl 3-[2-(diethylaminodiazenyl)phenyl]prop-2-ynoate
• CAS: 1184730-58-2
• 化学式: C₁₄H₁₇N₃O₂
• 分子量: 259.308
• InChiKey: AZHSPWKQIBDXIG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  54.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Methyl 3-[2-(diethylaminodiazenyl)phenyl]prop-2-ynoate 在 dirhodium tetraacetate 、 水 作用下， 以 1,2-二氯乙烷 为溶剂， 以95%的产率得到Methyl 2-[2-(diethylamino)indazol-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
• 作为产物：
  描述：

  氯甲酸甲酯 、 N,N-diethyl-N'-(2-ethynylphenyl)triazene 在 乙基溴化镁 作用下， 以 四氢呋喃 为溶剂， 以75%的产率得到Methyl 3-[2-(diethylaminodiazenyl)phenyl]prop-2-ynoate
  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.