4,6-Dibromo-2,5-dimethylbenzene-1,3-dicarbaldehyde | 499154-42-6

• 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: 4,6-Dibromo-2,5-dimethylbenzene-1,3-dicarbaldehyde
• CAS: 499154-42-6
• 化学式: C₁₀H₈Br₂O₂
• 分子量: 319.98
• InChiKey: NEUGHKBZWCHUNZ-UHFFFAOYSA-N

物化性质

• 沸点：
  383.2±42.0 °C(Predicted)
• 密度：
  1.800±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4,6-Dibromo-2,5-dimethylbenzene-1,3-dicarbaldehyde 反应 24.0h， 以33%的产率得到3,5-Dibromo-7-hydroxy-4-methylbicyclo[4.2.0]octa-1,3,5-triene-2-carbaldehyde
  参考文献：
  名称：

  Solid-State Diphotocyclization of Iso- and Terephthalaldehydes via Dihalogen Substitution

  摘要：

  The supramolecular nonbonded C-H...X interactions between formyl hydrogens and ortho-halogen atoms (Br/Cl) have been exploited to achieve conformational control in the solid state of dimethyl-substituted iso- and terephthaladehydes (1-3) for unprecedented diphotocyclization. It is shown that the dihalogen substitution also contributes to the stability of the benzocyclobutenols relative to their precursor photoenols, so that the solid-state photolysis of dialdehydes 2b, 2c, and 3b leads to diphotocyclization to afford respectable yields of bis-benzocyclobutenols.

  DOI：

  10.1021/jo026055w
• 作为产物：
  描述：

  3,5-二氰基甲基甲苯 在 N-溴代丁二酰亚胺(NBS) 、 二异丁基氢化铝 作用下， 以 二氯甲烷 、 甲苯 、 三氟乙酸 为溶剂， 反应 10.5h， 生成 4,6-Dibromo-2,5-dimethylbenzene-1,3-dicarbaldehyde
  参考文献：
  名称：

  Solid-State Diphotocyclization of Iso- and Terephthalaldehydes via Dihalogen Substitution

  摘要：

  The supramolecular nonbonded C-H...X interactions between formyl hydrogens and ortho-halogen atoms (Br/Cl) have been exploited to achieve conformational control in the solid state of dimethyl-substituted iso- and terephthaladehydes (1-3) for unprecedented diphotocyclization. It is shown that the dihalogen substitution also contributes to the stability of the benzocyclobutenols relative to their precursor photoenols, so that the solid-state photolysis of dialdehydes 2b, 2c, and 3b leads to diphotocyclization to afford respectable yields of bis-benzocyclobutenols.

  DOI：

  10.1021/jo026055w

文献信息

• Solid-State Diphotocyclization of Iso- and Terephthalaldehydes via Dihalogen Substitution
  作者：J. Narasimha Moorthy、P. Venkatakrishnan、Prasenjit Mal、P. Venugopalan

  DOI：10.1021/jo026055w

  日期：2003.1.1

  The supramolecular nonbonded C-H...X interactions between formyl hydrogens and ortho-halogen atoms (Br/Cl) have been exploited to achieve conformational control in the solid state of dimethyl-substituted iso- and terephthaladehydes (1-3) for unprecedented diphotocyclization. It is shown that the dihalogen substitution also contributes to the stability of the benzocyclobutenols relative to their precursor photoenols, so that the solid-state photolysis of dialdehydes 2b, 2c, and 3b leads to diphotocyclization to afford respectable yields of bis-benzocyclobutenols.