7-(2,2-Dimethyl-1-phenyl-propylidene)-2,3-diaza-bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid dimethyl ester | 153620-28-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 7-(2,2-Dimethyl-1-phenyl-propylidene)-2,3-diaza-bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid dimethyl ester
• CAS: 153620-28-1
• 化学式: C₂₀H₂₄N₂O₄
• 分子量: 356.422
• InChiKey: AYSBAMTZMIMODO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.86
• 重原子数：
  26.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  59.08
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  7-(2,2-Dimethyl-1-phenyl-propylidene)-2,3-diaza-bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid dimethyl ester 在 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 以98%的产率得到7-(2,2-Dimethyl-1-phenyl-propylidene)-2,3-diaza-bicyclo[2.2.1]heptane-2,3-dicarboxylic acid dimethyl ester
  参考文献：
  名称：

  Conformational effects on high-spin organic molecules

  摘要：

  The ability of m-phenylene to ferromagnetically couple spin-containing substituents that are substantially twisted out of conjugation is investigated. The ''bis(TMM)'' strategy is employed, in which two triplet TMM biradicals am linked through m-phenylene to produce relatively stable, organic tetraradicals that are characterized by EPR spectroscopy. Under conditions of moderate twisting (4), ferromagnetic coupling is seen, and the tetraradical has a quintet ground state. Severely twisting both TMMs as in 13 disrupts spin communication, and two noninteracting triplets are produced. This is in contrast to other highly twisted m-phenylene derivatives, in which antiferromagnetic coupling has been observed. Surprisingly, severely twisting only one TMM (14) still produces ferromagnetic coupling and a quintet ground state through a spin polarization mechanism analogous to that proposed for 90-degrees twisted ethylene. Several ring-constrained TMMs (17-19) are investigated as models for mom nearly planar systems.

  DOI：

  10.1021/j100152a035
• 作为产物：
  描述：

  2,2,2-三甲基苯乙酮 以 二氯甲烷 为溶剂， 反应 2.5h， 生成 7-(2,2-Dimethyl-1-phenyl-propylidene)-2,3-diaza-bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid dimethyl ester
  参考文献：
  名称：

  Conformational effects on high-spin organic molecules

  摘要：

  The ability of m-phenylene to ferromagnetically couple spin-containing substituents that are substantially twisted out of conjugation is investigated. The ''bis(TMM)'' strategy is employed, in which two triplet TMM biradicals am linked through m-phenylene to produce relatively stable, organic tetraradicals that are characterized by EPR spectroscopy. Under conditions of moderate twisting (4), ferromagnetic coupling is seen, and the tetraradical has a quintet ground state. Severely twisting both TMMs as in 13 disrupts spin communication, and two noninteracting triplets are produced. This is in contrast to other highly twisted m-phenylene derivatives, in which antiferromagnetic coupling has been observed. Surprisingly, severely twisting only one TMM (14) still produces ferromagnetic coupling and a quintet ground state through a spin polarization mechanism analogous to that proposed for 90-degrees twisted ethylene. Several ring-constrained TMMs (17-19) are investigated as models for mom nearly planar systems.

  DOI：

  10.1021/j100152a035