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One-step synthesis method for novel water-soluble 8-hydroxy porphyrin

A synthesis method and water-soluble technology are applied in the field of one-step synthesis of novel water-soluble porphyrins, which can solve problems such as troublesome post-processing, and achieve the effects of simple post-processing, good water solubility, biocompatibility, and high reaction yield.

Active Publication Date: 2016-04-06
HUNAN UNIV OF SCI & TECH
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

If the hydroxyl group is obtained by cleavage from the methoxy group, BBr needs to be added 3 The target product can only be obtained by hydrolysis, and post-processing is also very troublesome

Method used

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  • One-step synthesis method for novel water-soluble 8-hydroxy porphyrin
  • One-step synthesis method for novel water-soluble 8-hydroxy porphyrin
  • One-step synthesis method for novel water-soluble 8-hydroxy porphyrin

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Embodiment

[0039] The name of the water-soluble porphyrin compound is 5,10,15,20-tetra-(3,5-dihydroxyphenyl)porphyrin, and the specific synthesis steps and characteristics are as follows:

[0040] figure 1 It is the synthetic route of this compound, using 40mL propionic acid / acetic acid (3:2; V / V) as the reaction solvent, heating to reflux to 120℃, and putting 1.4 g of 3,5-dihydroxybenzaldehyde into the mixed acid under vigorous stirring Dissolve in the medium, about 0.68mL (0.68g) of freshly steamed pyrrole is added dropwise within 2min, reflux is continued for 45min, and then the mixed acid is removed by distillation under reduced pressure. Dissolve the crude product with 30 mL methanol, add 10 mL silica gel (100-150 mesh) to adsorb the product, and distill off the methanol solvent. The adsorbed product is separated by column chromatography with the same silica gel, and the sample is loaded by dry method. 2 Cl 2 And CH 2 Cl 2 / Methanol mixed solvent (10:1; V / V) was used as eluent for grad...

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Abstract

The invention relates to a synthesis method for a compound 5,10,15,20-tetra-(3,5-dihydroxy phenyl) porphyrin of water-soluble porphyrin shown in the formula I. The synthesis method includes the following steps that mixed acid of propionic acid / acetic acid is used as a reaction solvent, 3,5-dihydroxy benzaldehyde reacts with pyrrole (for example, 30 min or above, preferably, 40 min or above, such as 30 min-3 h, and preferably, 40 min-1 h) under heating reflux (for example, 115-125 DEG C, and for example, about 120 DEG C), reduced pressure distillation is conducted after the reaction, the mixed acid is removed, separation is conducted through a column chromatography method, recrystallization purifying is conducted, and 5,10,15,20-tetra-(3,5-dihydroxy phenyl) porphyrin is obtained. The formula I is shown in the description.

Description

Technical field [0001] The invention relates to a one-step synthesis method of a novel water-soluble porphyrin, in particular to a method for preparing a meso-position 5,10,15,20-tetra-(3,5-dihydroxyphenyl)porphyrin. Background technique [0002] Porphyrin is a kind of compound that plays an important role in the living body. It is closely related to life science and is the core structure of natural materials such as heme and chlorophyll. Porphyrins can be divided into water-insoluble porphyrins and water-soluble porphyrins according to their water solubility. Water-soluble porphyrins are hydrophilic and have greater advantages than non-water-soluble porphyrins. They are widely used in analytical chemistry, medicine, catalysis and supramolecular chemistry. Obtaining water-soluble porphyrin from natural environment has low yield, unstable structure and extremely high cost; artificial synthesis of water-soluble porphyrin is currently a more common method. [0003] According to the ...

Claims

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Application Information

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IPC IPC(8): C07D487/22
CPCC07D487/22
Inventor 刘秋华唐敏周再春
Owner HUNAN UNIV OF SCI & TECH
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