dimethyl rose bengal | 115546-28-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: dimethyl rose bengal
• 英文别名: DMRB；2,3,4,5-Tetrachloro-6-(2,4,5,7-tetraiodo-6-methoxy-3-oxo-3H-xanthen-9-yl)-benzoic acid methyl ester；Methyl 2,3,4,5-tetrachloro-6-(2,4,5,7-tetraiodo-3-methoxy-6-oxoxanthen-9-yl)benzoate
• CAS: 115546-28-6
• 化学式: C₂₂H₈Cl₄I₄O₅
• 分子量: 1001.73
• InChiKey: VQQZVJDIDAEPHC-UHFFFAOYSA-N

物化性质

• 沸点：
  821.0±65.0 °C(Predicted)
• 密度：
  2.58±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.2
• 重原子数：
  35
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  dimethyl rose bengal 在 锌 作用下， 以 溶剂黄146 为溶剂， 反应 0.5h， 生成 2,3,4,5-Tetrachloro-6-(3-hydroxy-2,7-diiodo-6-methoxy-9H-xanthen-9-yl)-benzoic acid methyl ester
  参考文献：
  名称：

  Bleaching products of rose bengal under reducing conditions

  摘要：

  DOI：

  10.1016/s0040-4020(01)86891-5
• 作为产物：
  描述：

  rose bengal 、 硫酸二甲酯 在 15-冠醚-5 作用下， 以 乙腈 为溶剂， 以280 mg的产率得到dimethyl rose bengal
  参考文献：
  名称：

  Hydrogen‐Bond‐Modulated Nucleofugality of Se ^III Species to Enable Photoredox‐Catalytic Semipinacol Manifolds

  摘要：

  AbstractChemical bond activations mediated by H‐bond interactions involving highly electronegative elements such as nitrogen and oxygen are powerful tactics in modern catalysis research. On the contrary, kindred catalytic regimes in which heavier, less electronegative elements such as selenium engage in H‐bond interactions to co‐activate C−Se σ‐bonds under oxidative conditions are elusive. Traditional strategies to enhance the nucleofugality of selenium residues predicate on the oxidative addition of electrophiles onto SeII‐centers, which entails the elimination of the resulting SeIV moieties. Catalytic procedures in which SeIV nucleofuges are substituted rather than eliminated are very rare and, so far, not applicable to carbon‐carbon bond formations. In this study, we introduce an unprecedented combination of O−H⋅⋅⋅Se H‐bond interactions and single electron oxidation to catalytically generate SeIII nucleofuges that allow for the formation of new C−C σ‐bonds by means of a type I semipinacol process in high yields and excellent selectivity.

  DOI：

  10.1002/anie.202208611