2-[(Z)-(3,5-dimethyl-2H-pyrrol-2-ylidene)(4-iodophenyl)methyl]-3,5-dimethyl-1H-pyrrole | 945587-99-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 2-[(Z)-(3,5-dimethyl-2H-pyrrol-2-ylidene)(4-iodophenyl)methyl]-3,5-dimethyl-1H-pyrrole
• 英文别名: (2Z)-2-[(3,5-dimethyl-1H-pyrrol-2-yl)-(4-iodophenyl)methylidene]-3,5-dimethylpyrrole
• CAS: 945587-99-5
• 化学式: C₁₉H₁₉IN₂
• 分子量: 402.278
• InChiKey: JGOLURVRLSGOLB-ZPHPHTNESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.42
• 重原子数：
  22.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  28.15
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  2-[(Z)-(3,5-dimethyl-2H-pyrrol-2-ylidene)(4-iodophenyl)methyl]-3,5-dimethyl-1H-pyrrole 在 三氯化铝 、 三氟化硼乙醚 、 三乙胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 0.58h， 生成 2-[(Z)-(3,5-dimethyl-2H-pyrrol-2-ylidene)(4-iodophenyl)methyl]-3,5-dimethyl-1H-pyrrol-1yl boronic acid
  参考文献：
  名称：

  Convenient Method To Access New 4,4-Dialkoxy- and 4,4-Diaryloxy-diaza-s-indacene Dyes:  Synthesis and Spectroscopic Evaluation

  摘要：

  A straightforward method for the synthesis of original 4,4-dialkoxy- or 4,4-diaryloxy-diaza-s-indacenes (BODIPY) derivatives obtained by treatment of BODIPY 1 with various alcohols in the presence of AlCl3 is described. The novel compounds are characterized by spectroscopic properties similar to those of the parent BODIPY 1, absorption and emission spectra with similar band shapes, high molar absorption coefficients (epsilon(lambda max) approximate to 80 000 M-1 cm(-1)), and for most of them high fluorescence quantum yields (Phi(exp) from 0.52 to 0.71). Among all of the new compounds synthesized, the dye 2h exhibits higher fluorescence quantum yield (0.71) and lifetime (4.09 ns) than compound 1 and a good chemical stability toward conditions compatible with biological cell-based assays.

  DOI：

  10.1021/jo061567m
• 作为产物：
  描述：

  4-碘苯甲酰氯 在 甲基溴化镁 、 三氯氧磷 作用下， 以 乙醚 、 二氯甲烷 、 正戊烷 为溶剂， 反应 36.0h， 生成 2-[(Z)-(3,5-dimethyl-2H-pyrrol-2-ylidene)(4-iodophenyl)methyl]-3,5-dimethyl-1H-pyrrole
  参考文献：
  名称：

  Convenient Method To Access New 4,4-Dialkoxy- and 4,4-Diaryloxy-diaza-s-indacene Dyes:  Synthesis and Spectroscopic Evaluation

  摘要：

  A straightforward method for the synthesis of original 4,4-dialkoxy- or 4,4-diaryloxy-diaza-s-indacenes (BODIPY) derivatives obtained by treatment of BODIPY 1 with various alcohols in the presence of AlCl3 is described. The novel compounds are characterized by spectroscopic properties similar to those of the parent BODIPY 1, absorption and emission spectra with similar band shapes, high molar absorption coefficients (epsilon(lambda max) approximate to 80 000 M-1 cm(-1)), and for most of them high fluorescence quantum yields (Phi(exp) from 0.52 to 0.71). Among all of the new compounds synthesized, the dye 2h exhibits higher fluorescence quantum yield (0.71) and lifetime (4.09 ns) than compound 1 and a good chemical stability toward conditions compatible with biological cell-based assays.

  DOI：

  10.1021/jo061567m