5-[2,3,5,6-tetrafluoro-4-(2-propene-1-oxy)]-dipyrromethane

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 5-[2,3,5,6-tetrafluoro-4-(2-propene-1-oxy)]-dipyrromethane
• 英文别名: 5-{4-(prop-2-enyloxy)-2,3,5,6-tetrafluorophenyl}dipyrrane；2-[1H-pyrrol-2-yl-(2,3,5,6-tetrafluoro-4-prop-2-enoxyphenyl)methyl]-1H-pyrrole
• 化学式: C₁₈H₁₄F₄N₂O
• 分子量: 350.316
• InChiKey: XCBGEQZPBYWNJU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  40.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-[2,3,5,6-tetrafluoro-4-(2-propene-1-oxy)]-dipyrromethane 在 2,3-二氯-5,6-二氰基-1,4-苯醌 、 N,N-二异丙基乙胺 、 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 0.66h， 生成 8-[4-(2-propene-1-oxy)-2,3,5,6-tetrafluorophenyl]-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene
  参考文献：
  名称：

  探索用于抗菌光疗的BODIPY的结构与活性之间的关系

  摘要：

  提出了BODIPY染料的合成策略，可提供与抗菌光动力疗法（aPDT）相关的一系列新化合物。具有8-（4-氟-3-硝基苯基）和8-五氟苯基取代基的BODIPY用于合成新的单溴和二溴BODIPY。的对位在这些吸电子基团-氟原子促进功能修饰经由亲核芳族取代（S Ñ AR）与一些胺和硫代糖类。随后，已在细菌测定中评估了这些BODIPY的抗细菌光毒性活性，这些细菌对革兰氏阳性菌金黄色葡萄球菌以及革兰氏阴性菌铜绿假单胞菌。细菌测定允许鉴定不仅在磷酸盐缓冲盐水（PBS）中而且在血清存在下均确保抗菌活性的取代模式，从而更现实地模拟临床应用中存在的复杂生物环境。

  DOI：

  10.1039/d0ob00188k
• 作为产物：
  描述：

  五氟苯甲醛 在 三氟乙酸 、 potassium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 48.58h， 生成 5-[2,3,5,6-tetrafluoro-4-(2-propene-1-oxy)]-dipyrromethane
  参考文献：
  名称：

  Nucleophilic Substitution on (Pentafluorophenyl)dipyrromethane: A New Route to Building Blocks for Functionalized BODIPYs and Tetrapyrroles

  摘要：

  The reaction of alcohols with (pentafluorophenyl)dipyrromethane (PFP-DPM) under basic conditions has been studied, giving access to the corresponding alkoxy-substituted DPMs. This method represents the first high-yielding substitution of PFP-DPM carried out with oxygen nucleophiles. Condensation of these prefunctionalized DPMs with aldehydes led to the respective trans-A(2)B(2) porphyrins. This pathway allows a simple synthesis of multifunctionalized tetrapyrroles. Oxidation and boron complexation of these DPMs, on the other hand, led to meso-functionalized difluoroboraindacenes (BODIPYs). In addition, nucleophilic substitution of PFP-BODIPY with sodium azide led to a 4-azidophenyl derivative, thus further enhancing the scope of reactive sites suitable for subsequent transformations.

  DOI：

  10.1021/acs.orglett.5b00082

文献信息

• Pre-/post-functionalization in dipyrrin metal complexes – antitumor and antibacterial activity of their glycosylated derivatives
  作者：Claudia S. Gutsche、Susanna Gräfe、Burkhard Gitter、Keith J. Flanagan、Mathias O. Senge、Nora Kulak、Arno Wiehe

  DOI：10.1039/c8dt03059f

  日期：——

  post-functionalization route to tris(dipyrrinato) metal complexes is presented giving access to a range of new complexes relevant in the context of medicinal inorganic chemistry. A pentafluorophenyl group in the meso-position of the dipyrrin ligand serves as an anchor for the connection with alcohols and thiocarbohydrates. The photochemotherapeutic activity of the complexes has been assessed in cellular assays with

  提出了一种向三（dipyrrinato）金属配合物的后功能化途径，使人们可以使用与药用无机化学有关的一系列新配合物。在二吡啶配体的中间位置上的五氟苯基用作与醇和硫代碳水化合物连接的锚。在具有肿瘤细胞系和针对革兰氏阳性细菌金黄色葡萄球菌的细胞试验中已经评估了复合物的光化学治疗活性。最后，表明该后官能化也适用于其他二吡咯烷酮金属络合物。
• Nucleophilic Substitution on (Pentafluorophenyl)dipyrromethane: A New Route to Building Blocks for Functionalized BODIPYs and Tetrapyrroles
  作者：Hartwig R. A. Golf、Hans-Ulrich Reissig、Arno Wiehe

  DOI：10.1021/acs.orglett.5b00082

  日期：2015.2.20

  The reaction of alcohols with (pentafluorophenyl)dipyrromethane (PFP-DPM) under basic conditions has been studied, giving access to the corresponding alkoxy-substituted DPMs. This method represents the first high-yielding substitution of PFP-DPM carried out with oxygen nucleophiles. Condensation of these prefunctionalized DPMs with aldehydes led to the respective trans-A(2)B(2) porphyrins. This pathway allows a simple synthesis of multifunctionalized tetrapyrroles. Oxidation and boron complexation of these DPMs, on the other hand, led to meso-functionalized difluoroboraindacenes (BODIPYs). In addition, nucleophilic substitution of PFP-BODIPY with sodium azide led to a 4-azidophenyl derivative, thus further enhancing the scope of reactive sites suitable for subsequent transformations.
• Exploring the relationship between structure and activity in BODIPYs designed for antimicrobial phototherapy
  作者：Benjamin F. Hohlfeld、Burkhard Gitter、Keith J. Flanagan、Christopher J. Kingsbury、Nora Kulak、Mathias O. Senge、Arno Wiehe

  DOI：10.1039/d0ob00188k

  日期：——

  A synthetic strategy to BODIPY dyes is presented giving access to a range of new compounds relevant in the context of antimicrobial photodynamic therapy (aPDT). BODIPYs with the 8-(4-fluoro-3-nitrophenyl) and the 8-pentafluorophenyl substituents were used for the synthesis of new mono- and dibrominated BODIPYs. The para-fluorine atoms in these electron-withdrawing groups facilitate functional modification

  提出了BODIPY染料的合成策略，可提供与抗菌光动力疗法（aPDT）相关的一系列新化合物。具有8-（4-氟-3-硝基苯基）和8-五氟苯基取代基的BODIPY用于合成新的单溴和二溴BODIPY。的对位在这些吸电子基团-氟原子促进功能修饰经由亲核芳族取代（S Ñ AR）与一些胺和硫代糖类。随后，已在细菌测定中评估了这些BODIPY的抗细菌光毒性活性，这些细菌对革兰氏阳性菌金黄色葡萄球菌以及革兰氏阴性菌铜绿假单胞菌。细菌测定允许鉴定不仅在磷酸盐缓冲盐水（PBS）中而且在血清存在下均确保抗菌活性的取代模式，从而更现实地模拟临床应用中存在的复杂生物环境。