1,4-dipyridin-2-ylphthalazine | 1147699-40-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 1,4-dipyridin-2-ylphthalazine
• 英文别名: 1,4-di-pyridin-2-yl-phthalazine；1,4-Dipyridin-2-ylphthalazine
• CAS: 1147699-40-8
• 化学式: C₁₈H₁₂N₄
• 分子量: 284.32
• InChiKey: QDQJLMHXFKZRQS-UHFFFAOYSA-N

物化性质

• 熔点：
  163-165 °C(Solvent: Ethyl acetate)
• 沸点：
  521.7±45.0 °C(predicted)
• 密度：
  1.252±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  51.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,4-dipyridin-2-ylphthalazine 、 1,4-dihydro-9,10-dimethoxy-1,4-methanoanthracene 在 对苯醌 作用下， 以 二氯甲烷 为溶剂， 100.0 ℃ 、1000.01 MPa 条件下， 反应 48.0h， 以46%的产率得到(6β,6aα,7α,7aα,8β,15β,15aα,16α,16aα,17β)-6,6a,7,7a,8,15,15a,16,16a,17-decahydro-5,9,14,18-tetramethoxy-7,16-dipyridin-2-yl-7,16[1',2']-benzeno-6,17:8,15-dimethanoheptacene
  参考文献：
  名称：

  刚性双环[2.2.1]庚-2-烯（= 8,9,10-三降冰片烯）和1,4-二吡啶-2-基邻苯二甲腈作为立体选择性偶联剂的脂环族分子。

  摘要：

  Abstractmagnified imageFor the preparation of rigid polycyclic molecules from 8,9,10‐trinorbornenes (=bicyclo[2.2.1]hept‐2‐enes), 1,4‐dipyridin‐2‐ylphthalazines were used. Cycloaddition reactions with trinorbornenes gave coupled products in a stereoselective manner. In these reactions, the phthalazines delivered a new bicyclo[2.2.2] moiety at the junction of two trinorbornene units, which could bear appropriate functional groups (Schemes 4and5). The crystal structure of a key cycloadduct,i.e., of18was also determined (Fig. 2). Relative reactivities for a series of phthalazines (Fig. 3) were estimated by density‐functional‐theory (DFT) calculations at the B3LYP/6‐31G* level (Table). The calculations indicated an increase of reactivity when the aromaticity of the phthalazine moiety is decreased. Finally, experimentally observed stereoselectivities of the phthalazine reactions with trinorbornenes were readily predicted by DFT calculations (Fig. 4).

  DOI：

  10.1002/hlca.200800205
• 作为产物：
  描述：

  3,6-二-2-吡啶基-1,2,4,5-四嗪 、 邻氨基苯甲酸 在 亚硝酸异戊酯 作用下， 以 1,4-二氧六环 为溶剂， 反应 3.0h， 以29%的产率得到1,4-dipyridin-2-ylphthalazine
  参考文献：
  名称：

  刚性双环[2.2.1]庚-2-烯（= 8,9,10-三降冰片烯）和1,4-二吡啶-2-基邻苯二甲腈作为立体选择性偶联剂的脂环族分子。

  摘要：

  Abstractmagnified imageFor the preparation of rigid polycyclic molecules from 8,9,10‐trinorbornenes (=bicyclo[2.2.1]hept‐2‐enes), 1,4‐dipyridin‐2‐ylphthalazines were used. Cycloaddition reactions with trinorbornenes gave coupled products in a stereoselective manner. In these reactions, the phthalazines delivered a new bicyclo[2.2.2] moiety at the junction of two trinorbornene units, which could bear appropriate functional groups (Schemes 4and5). The crystal structure of a key cycloadduct,i.e., of18was also determined (Fig. 2). Relative reactivities for a series of phthalazines (Fig. 3) were estimated by density‐functional‐theory (DFT) calculations at the B3LYP/6‐31G* level (Table). The calculations indicated an increase of reactivity when the aromaticity of the phthalazine moiety is decreased. Finally, experimentally observed stereoselectivities of the phthalazine reactions with trinorbornenes were readily predicted by DFT calculations (Fig. 4).

  DOI：

  10.1002/hlca.200800205