2,5-dibromo-4,6-dimethylisophthalaldehyde

• 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: 2,5-dibromo-4,6-dimethylisophthalaldehyde
• 英文别名: 2,5-Dibromo-4,6-dimethylbenzene-1,3-dicarbaldehyde
• 化学式: C₁₀H₈Br₂O₂
• 分子量: 319.98
• InChiKey: DCXFCHZKQYFNRI-UHFFFAOYSA-N

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：

  2,5-dibromo-4,6-dimethylisophthalaldehyde 生成 (4R,10R)-2,7-dibromotricyclo[6.2.0.03,6]deca-1,3(6),7-triene-4,10-diol 、 (4R,10S)-2,7-dibromotricyclo[6.2.0.03,6]deca-1,3(6),7-triene-4,10-diol
  参考文献：
  名称：

  Self-Assembly of Conformationally Rigid Dialcohols (Bis-Benzocyclobutenols): Supramolecular Cyclophanes and Arrays

  摘要：

  Bis-benzocyclobutenols are synthetically important intermediates, and their structures have been established for the first time. These unique molecular systems allow investigation of the hydrogen bond-mediated aggregation of diols with rigid disposition of the hydroxyl groups on both sides of a flat arene core, namely bis-benzocyclobutene. The syn-diols la and 2a were found to assemble via O-H center dot center dot center dot O hydrogen bonds between the hydroxyl groups into dimers, which may be termed "supramolecular cyclophanes". However, the analogous diols that are sterically encumbered by ethyl and phenyl groups were found to aggregate via adoption of tetrameric (syn-2c) or water-expanded dimeric (syn-2b) supramolecular synthons. The sterically un-hindered anti diols were found to self-assemble via helical supramolecular synthon in contrast to the sterically encumbered ones; the latter were found to display preference to undergo cyclic tetrameric aggregation. The results thus point to intriguing possibilities in the adoption of supramolecular synthons when a given diol is constrained by the obligation to exploit two or more functional groups of the same kind.

  DOI：

  10.1021/cg400791a
• 作为产物：
  描述：

  1,2,4,5-四甲苯 、 alkaline earth salt of/the/ methylsulfuric acid 在 过氧化苯甲酰 1,3-二溴-5,5-二甲基海因 、 过氧化苯甲酰 作用下， 以 四氯化碳 为溶剂， 反应 25.0h， 生成 2,5-dibromo-4,6-dimethylisophthalaldehyde
  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.
• Self-Assembly of Conformationally Rigid Dialcohols (Bis-Benzocyclobutenols): Supramolecular Cyclophanes and Arrays
  作者：Alankriti Bajpai、Parthasarathy Venkatakrishnan、Susovan Mandal、Subhas Samanta、Paloth Venugopalan、Jarugu Narasimha Moorthy

  DOI：10.1021/cg400791a

  日期：2013.11.6

  Bis-benzocyclobutenols are synthetically important intermediates, and their structures have been established for the first time. These unique molecular systems allow investigation of the hydrogen bond-mediated aggregation of diols with rigid disposition of the hydroxyl groups on both sides of a flat arene core, namely bis-benzocyclobutene. The syn-diols la and 2a were found to assemble via O-H center dot center dot center dot O hydrogen bonds between the hydroxyl groups into dimers, which may be termed "supramolecular cyclophanes". However, the analogous diols that are sterically encumbered by ethyl and phenyl groups were found to aggregate via adoption of tetrameric (syn-2c) or water-expanded dimeric (syn-2b) supramolecular synthons. The sterically un-hindered anti diols were found to self-assemble via helical supramolecular synthon in contrast to the sterically encumbered ones; the latter were found to display preference to undergo cyclic tetrameric aggregation. The results thus point to intriguing possibilities in the adoption of supramolecular synthons when a given diol is constrained by the obligation to exploit two or more functional groups of the same kind.