8-(4-Bromophenyl)-2,2-difluoro-3-aza-1-azonia-2-boranuidatricyclo[7.3.0.03,7]dodeca-1(12),4,6,8,10-pentaene-5-carbaldehyde | 1341774-19-3

• 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: 8-(4-Bromophenyl)-2,2-difluoro-3-aza-1-azonia-2-boranuidatricyclo[7.3.0.03,7]dodeca-1(12),4,6,8,10-pentaene-5-carbaldehyde
• CAS: 1341774-19-3
• 化学式: C₁₆H₁₀BBrF₂N₂O
• 分子量: 374.98
• InChiKey: HDPZJTAFMKGKNS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.71
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  25
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  吡咯 、 8-(4-Bromophenyl)-2,2-difluoro-3-aza-1-azonia-2-boranuidatricyclo[7.3.0.03,7]dodeca-1(12),4,6,8,10-pentaene-5-carbaldehyde 在 三氟乙酸 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.16h， 以76%的产率得到
  参考文献：
  名称：

  Corrole-BODIPY Dyads: Synthesis, Structure, and Electrochemical and Photophysical Properties

  摘要：

  A free-base and its Cu(III) derivative of bichromophoric meso-beta linked corrole-BODIPY dyad were synthesized and structurally characterized by single crystal X-ray diffraction (XRD). Both corrole and BODIPY fragments maintained respective ground state electronic isolation despite their connection through a single bond due to a tilted orientation as observed by XRD. This was further supported by UV-vis and cyclic voltammetric studies. The Cu(III)-metalated dyad exhibits temperature-dependent paramagnetic behavior as observed in the variable temperature H-1 NMR due to the presence of a Cu(II)-corrole-pi-cation radical. Importantly, the free-base exhibits complete fluorescence quenching probably due to photoinduced electron transfer to a low lying charge separated state. Interestingly, emission was regained upon addition of 1,8-diazabicyclo [5.4.0]undec-7-ene (DBU) due to the deprotonation of corrole. The "turn on" fluorescence behavior and the presence of acidic NH protons were further exploited toward basic anion sensing utility.

  DOI：

  10.1021/ic502919s
• 作为产物：
  描述：

  5-(4-bromophenyl)dipyrromethane 在 三氟化硼乙醚 、 三乙胺 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 三氯氧磷 作用下， 以 二氯甲烷 为溶剂， 反应 12.17h， 生成 8-(4-Bromophenyl)-2,2-difluoro-3-aza-1-azonia-2-boranuidatricyclo[7.3.0.03,7]dodeca-1(12),4,6,8,10-pentaene-5-carbaldehyde
  参考文献：
  名称：

  α-/β-甲酰化硼二吡喃 (BODIPY) 染料：区域选择性合成和光物理特性

  摘要：

  基于 Vilsmeier-Haack 反应，已对吡咯未取代的二吡咯甲烷 1 和硼-二吡喃 (BODIPY) 染料 4 进行甲酰化。对于吡咯未取代的二吡咯甲烷 1 和 BODIPY 染料 4，它具有高度的区域选择性和互补性，分别仅出现在 α-和 β-位。这种区域选择性甲酰化可以合成各种 α- 和 β-取代的 BODIPY 染料。甲酰基的安装会影响 BODIPY 发色团的电子特性，导致 α- 和 β-甲酰化 BODIPY 3 和 5 的吸收和发射最大值分别发生红移和蓝移。

  DOI：

  10.1002/ejoc.201100736

文献信息

• FormylBODIPYs: Privileged Building Blocks for Multicomponent Reactions. The Case of the Passerini Reaction
  作者：Diana E. Ramírez-Ornelas、Enrique Alvarado-Martínez、Jorge Bañuelos、Iñigo López Arbeloa、Teresa Arbeloa、Héctor M. Mora-Montes、Luis A. Pérez-García、Eduardo Peña-Cabrera

  DOI：10.1021/acs.joc.5b02893

  日期：2016.4.1

  Eleven formyl-containing BODIPY dyes were prepared by means of either the Liebeskind-Srogl cross-coupling reaction or the Vilsmeier reaction. These dyes were used as components in the Passerini reaction to give highly substituted BODIPY dyes. A joined spectroscopic and theoretical characterization of the synthesized compounds was conducted to unravel the impact of the structural rigidity/flexibility on the photophysical signatures. These dyes were tested as fluorescent trackers for phagocytosis. Additionally, they proved to be useful to stain different blood cells with an intense and stable signal at a very low exposure time.