5-(4-bromophenyl)-1,9-diformyldipyrrylmethane | 892872-12-7

• 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: 5-(4-bromophenyl)-1,9-diformyldipyrrylmethane
• 英文别名: 1,9-diformyl-meso-(4-bromophenyl) dipyrromethane；5-(4-bromophenyl)-1,9-diformyldipyrromethane；5-[(4-bromophenyl)-(5-formyl-1H-pyrrol-2-yl)methyl]-1H-pyrrole-2-carbaldehyde
• CAS: 892872-12-7
• 化学式: C₁₇H₁₃BrN₂O₂
• 分子量: 357.206
• InChiKey: XKGHACVIGUEBEC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  65.7
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-(4-bromophenyl)-1,9-diformyldipyrrylmethane 在 2,3-二氯-5,6-二氰基-1,4-苯醌 、 三氟化硼乙醚 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以9%的产率得到3,5-diformyl-8-(4-bromophenyl)-4-bora-3a,4a-diaza-s-indacene
  参考文献：
  名称：

  3,5-Diformylboron Dipyrromethenes as Fluorescent pH Sensors

  摘要：

  A series of boron dipyrromethene (BODIPY) dyes containing two aldehyde functional groups at the 3 and 5 positions have been synthesized in low-to-decent yields in two steps. In the first step, the meso-aryl dipyrromethanes were treated with POCl(3) in N,N-dimethylformamide to afford 1,9-diformylated dipyrromethanes. In the second step, the diformylated dipyrromethanes were first in situ oxidized with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone and then reacted with BF(3)center dot OEt(2) to afford 3,5-diformylboron dipyrromethenes. The X-ray structural analysis indicated that the aldehyde groups are involved in intramolecular hydrogen bonding with fluoride atoms, which may be responsible for the stability of the diformylated BODIPY compounds. The presence of two formyl groups significantly alters the electronic properties, which is clearly evident in downfield shifts in the (1)H and (19)F NMR spectra, bathochromic shifts in the absorption and fluorescence spectra, better quantum yields, and increased lifetimes compared to 3,5-unsubstituted BODIPYs. Furthermore, 3,5-diformylboron dipyrromethenes are highly electron-deficient and undergo facile reductions compared to unsubstituted BODIPYs. These compounds exhibit pH-dependent on/off fluorescence and thus act as fluorescent pH sensors.

  DOI：

  10.1021/ic102499h
• 作为产物：
  描述：

  对溴苯甲醛 在 三氟乙酸 、 三氯氧磷 作用下， 以 1,2-二氯乙烷 为溶剂， 生成 5-(4-bromophenyl)-1,9-diformyldipyrrylmethane
  参考文献：
  名称：

  3,5-Diformylboron Dipyrromethenes as Fluorescent pH Sensors

  摘要：

  A series of boron dipyrromethene (BODIPY) dyes containing two aldehyde functional groups at the 3 and 5 positions have been synthesized in low-to-decent yields in two steps. In the first step, the meso-aryl dipyrromethanes were treated with POCl(3) in N,N-dimethylformamide to afford 1,9-diformylated dipyrromethanes. In the second step, the diformylated dipyrromethanes were first in situ oxidized with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone and then reacted with BF(3)center dot OEt(2) to afford 3,5-diformylboron dipyrromethenes. The X-ray structural analysis indicated that the aldehyde groups are involved in intramolecular hydrogen bonding with fluoride atoms, which may be responsible for the stability of the diformylated BODIPY compounds. The presence of two formyl groups significantly alters the electronic properties, which is clearly evident in downfield shifts in the (1)H and (19)F NMR spectra, bathochromic shifts in the absorption and fluorescence spectra, better quantum yields, and increased lifetimes compared to 3,5-unsubstituted BODIPYs. Furthermore, 3,5-diformylboron dipyrromethenes are highly electron-deficient and undergo facile reductions compared to unsubstituted BODIPYs. These compounds exhibit pH-dependent on/off fluorescence and thus act as fluorescent pH sensors.

  DOI：

  10.1021/ic102499h

文献信息

• Synthetic porphyrins bearing β-propionate chains as photosensitizers for photodynamic therapy
  作者：Nelson Pereira、Arménio C. Serra、Marta Pineiro、António M. d'A. Rocha Gonsalves、Margarida Abrantes、Mafalda Laranjo、Filomena Botelho

  DOI：10.1142/s1088424610002227

  日期：2010.5

  Porphyrins with different numbers of β-propionate chains mimicking natural porphyrins were prepared via the 2+2 MacDonald type approach. Photodynamic activity against WiDr colon adenocarcinoma cells showed that activity is related to the number of β-propionate chains, with the derivatives with two carboxylic groups showing higher activity.

  通过 2+2 MacDonald 型方法，制备了模仿天然卟啉的具有不同数量 β 丙酸链的卟啉。对 WiDr 结肠腺癌细胞的光动力活性表明，活性与 β-丙酸链的数量有关，带有两个羧基的衍生物具有更高的活性。
• SWALLOWTAIL MOTIFS FOR IMPARTING WATER SOLUBILITY TO PORPHYRINIC COMPOUNDS
  申请人：North Carolina State University

  公开号：US20140106367A1

  公开（公告）日：2014-04-17

  Porphyrinic compounds that contain solubilizing groups are described, along with methods of making and using the same and compositions comprising such compounds. Examples of such compounds include compounds of Formula I: wherein: Z is a porphyrinic macrocycle, Alk 1 and Alk 2 are each independently an alkylidene chain; L is a linking group or is absent; R 1 is preferably an ionic group or polar group; R 2 is an ionic group, polar group, bioconjugatable group, or targeting group; R 3 is present or absent and when present is a halo group, bioconjugatable group, or targeting group, n is O or 1 (that is, the CH group is present, or Alk 1 and Alk 2 are bonded directly to a carbon of the porphyrinic macrocycle Z); or a salt thereof.

  本文介绍了含有溶解基团的卟啉化合物，以及制备和使用这些化合物的方法和包含这些化合物的组合物。这些化合物的示例包括式I的化合物：其中：Z是卟啉宏环，Alk1和Alk2各自独立地是烷基链；L是连接基团或不存在；R1首选为离子基团或极性基团；R2是离子基团、极性基团、生物共轭基团或靶向基团；R3存在或不存在，当存在时是卤素基团、生物共轭基团或靶向基团，n为O或1（即，CH基团存在，或Alk1和Alk2直接连接到卟啉宏环Z的碳原子）；或其盐。
• WO2007/47925
  申请人：——

  公开号：——

  公开（公告）日：——
• Dye-sensitized solar cells and methods of making same
  申请人：Honeywell Romania S.R.L.

  公开号：EP2730623B1

  公开（公告）日：2016-12-14
• 3,5-Diformylboron Dipyrromethenes as Fluorescent pH Sensors
  作者：Sheri Madhu、Malakalapalli Rajeswara Rao、Mushtaque S. Shaikh、Mangalampalli Ravikanth

  DOI：10.1021/ic102499h

  日期：2011.5.16

  A series of boron dipyrromethene (BODIPY) dyes containing two aldehyde functional groups at the 3 and 5 positions have been synthesized in low-to-decent yields in two steps. In the first step, the meso-aryl dipyrromethanes were treated with POCl(3) in N,N-dimethylformamide to afford 1,9-diformylated dipyrromethanes. In the second step, the diformylated dipyrromethanes were first in situ oxidized with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone and then reacted with BF(3)center dot OEt(2) to afford 3,5-diformylboron dipyrromethenes. The X-ray structural analysis indicated that the aldehyde groups are involved in intramolecular hydrogen bonding with fluoride atoms, which may be responsible for the stability of the diformylated BODIPY compounds. The presence of two formyl groups significantly alters the electronic properties, which is clearly evident in downfield shifts in the (1)H and (19)F NMR spectra, bathochromic shifts in the absorption and fluorescence spectra, better quantum yields, and increased lifetimes compared to 3,5-unsubstituted BODIPYs. Furthermore, 3,5-diformylboron dipyrromethenes are highly electron-deficient and undergo facile reductions compared to unsubstituted BODIPYs. These compounds exhibit pH-dependent on/off fluorescence and thus act as fluorescent pH sensors.