1,1'-dichloro-5-(4-hydroxyphenyl)dipyrromethane | 853073-92-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 1,1'-dichloro-5-(4-hydroxyphenyl)dipyrromethane
• 英文别名: 4-[bis(5-chloro-1H-pyrrol-2-yl)methyl]phenol
• CAS: 853073-92-4
• 化学式: C₁₅H₁₂Cl₂N₂O
• 分子量: 307.179
• InChiKey: LKOFEBCVUCSJBK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  51.8
• 氢给体数：
  3
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1,1'-dichloro-5-(4-hydroxyphenyl)dipyrromethane 在 四氯苯醌 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以83%的产率得到1,9-dichloro-5-(4-hydroxyphenyl)dipyrromethene
  参考文献：
  名称：

  BODIPY-Based Hydroxyaryl Derivatives as Fluorescent pH Probes

  摘要：

  Seven new 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY) dyes with phenolic or naphtholic subunits on position 8 and with substituents having different electron driving forces on positions 3 and 5 were synthesized. Their absorption and steady-state fluorescence properties were investigated as a function of solvent. The novel compounds, with the exception of 4,4-difluoro-8-(4-hydroxyphenyl)-3,5-bis-(4-methoxyphenyl)-4-bora-3a,4a-diaza-s-indacene, are characterized by absorption maxima in the range 493-515 nm and small (400-600 cm(-1)) Stokes shifts. The exceptional dye has absorption maxima in the 570-580 nm region and fluorescence emission maxima around 610-620 nm, depending on the solvent. In aqueous solution, the dyes show a large fluorescent enhancement upon increasing the acidity of the solution. They can be used in aqueous solution as fluorescent pH probes excitable with visible light, with pK(a) values ranging from 7.5 to 9.3, depending on the substitution pattern on positions 3, 5, and 8.

  DOI：

  10.1021/jo0503714
• 作为产物：
  描述：

  4-[双(1H-吡咯-2-基)甲基]苯酚 在 N-氯代丁二酰亚胺 作用下， 以 四氢呋喃 为溶剂， 生成 1,1'-dichloro-5-(4-hydroxyphenyl)dipyrromethane
  参考文献：
  名称：

  基于 BODIPY 固定化 MCM-41 的多分析物传感器：在检测和去除水介质中的三价（Al3+、Cr3+）和二价（Cu2+、Hg2+）金属离子中的应用

  摘要：

  合成对苯基羧酸BODIPY衍生物并固定在MCM-41上，制备固体介孔传感材料L-丙基甲硅烷基@MCM-41（MS4）。合成材料MS4用于检测和去除水性介质中的二价（Cu 2+、Hg 2+）和三价（Al 3+、Cr 3+ ）金属离子。BODIPY 固定化MS4在存在 Al 3+和 Cr 3+金属离子时显示开启荧光，在存在 Hg 2+和 Cu 2+金属离子时显示关闭荧光。

  DOI：

  10.1002/ejic.202200537

文献信息

• [EN] QUINONE-METHIDE PRECURSORS WITH BODIPY CHROMOPHORE, METHOD OF PREPARATION, BIOLOGICAL ACTIVITY AND APPLICATION IN FLUORESCENT LABELLING<br/>[FR] PRÉCURSEURS DE QUINONE-MÉTHIDE PRÉSENTANT UN GROUPE CHROMOPHORE DE TYPE BODIPY, PROCÉDÉ DE PRÉPARATION, ACTIVITÉ BIOLOGIQUE ET APPLICATION EN MARQUAGE FLUORESCENT
  申请人：RUDJER BOSKOVIC INST

  公开号：WO2017199056A1

  公开（公告）日：2017-11-23

  The invention relates to BODIPY derivatives of Formula (I) that bear one or more functional groups which in the photochemical reaction upon irradiation with visible light undergo deamination and deliver quinone methides. Furthermore, the invention relates to the antiproliferative activity of BODIPY derivatives and their use for pharmaceutical applications and for fluorescent labeling, particularly for labeling proteins.

  该发明涉及具有式（I）的BODIPY衍生物，其具有一个或多个功能基团，这些基团在受到可见光照射进行光化学反应时发生脱氨基作用，并释放醌亚甲基。此外，该发明涉及BODIPY衍生物的抗增殖活性以及它们在制药应用和荧光标记中的使用，特别是用于标记蛋白质。
• QUINONE-METHIDE PRECURSORS WITH BODIPY CHROMOPHORE, METHOD OF PREPARATION, BIOLOGICAL ACTIVITY AND APPLICATION IN FLUORESCENT LABELING
  申请人：Rudjer Boskovic Institute

  公开号：EP3246331A1

  公开（公告）日：2017-11-22

  The invention relates to BODIPY derivatives of Formula (I): that bear one or more functional groups which in the photochemical reaction upon irradiation with visible light undergo deamination and deliver quinone methides. Furthermore, the invention relates to the antiproliferative activity of BODIPY derivatives and their use for pharmaceutical applications and for fluorescent labeling, particularly for labeling proteins.

  本发明涉及式 (I) 的 BODIPY 衍生物： 这些衍生物带有一个或多个官能团，在可见光照射下发生光化学反应时，这些官能团发生脱氨反应，生成醌甲酰胺。此外，本发明还涉及 BODIPY 衍生物的抗增殖活性及其在制药和荧光标记（尤其是标记蛋白质）方面的用途。
• QUINONE-METHIDE PRECURSORS WITH BODIPY CHROMOPHORE, METHOD OF PREPARATION, BIOLOGICAL ACTIVITY AND APPLICATION IN FLUORESCENT LABELLING
  申请人：Rudjer Boskovic Institute

  公开号：EP3612538B1

  公开（公告）日：2021-01-13
• Quinone-methide precursors with bodipy chromophore, method of preparation, biological activity and application in fluorescent labelling
  申请人：Rudjer Boskovic Institute

  公开号：US20200197423A1

  公开（公告）日：2020-06-25

  The invention relates to BODIPY derivatives of Formula (I): that bear one or more functional groups which in the photochemical reaction upon irradiation with visible light undergo deamination and deliver quinone methides. Furthermore, the invention relates to the antiproliferative activity of BODIPY derivatives and their use for pharmaceutical applications and for fluorescent labeling, particularly for labeling proteins.
• BODIPY-Based Hydroxyaryl Derivatives as Fluorescent pH Probes
  作者：Mukulesh Baruah、Wenwu Qin、Nikola Basarić、Wim M. De Borggraeve、Noël Boens

  DOI：10.1021/jo0503714

  日期：2005.5.1

  Seven new 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY) dyes with phenolic or naphtholic subunits on position 8 and with substituents having different electron driving forces on positions 3 and 5 were synthesized. Their absorption and steady-state fluorescence properties were investigated as a function of solvent. The novel compounds, with the exception of 4,4-difluoro-8-(4-hydroxyphenyl)-3,5-bis-(4-methoxyphenyl)-4-bora-3a,4a-diaza-s-indacene, are characterized by absorption maxima in the range 493-515 nm and small (400-600 cm(-1)) Stokes shifts. The exceptional dye has absorption maxima in the 570-580 nm region and fluorescence emission maxima around 610-620 nm, depending on the solvent. In aqueous solution, the dyes show a large fluorescent enhancement upon increasing the acidity of the solution. They can be used in aqueous solution as fluorescent pH probes excitable with visible light, with pK(a) values ranging from 7.5 to 9.3, depending on the substitution pattern on positions 3, 5, and 8.