A kind of synthetic method of porphyrin

A synthesis method and technology of porphyrin, which are applied in the field of synthesis and purification of substituted porphyrin, can solve the problems of troublesome operation, low yield, difficult separation and the like

Inactive Publication Date: 2014-10-22
NORTHWEST UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, these methods generally can only obtain a kind of product, and there are many by-products, it is difficult to separate, and sometimes the yield is also very low.
With the deepening of people's research on porphyrin chemistry, it is often necessary to synthesize a series of porphyrin molecules with regular structural changes in order to study the influence of structure on properties. The existing synthetic methods are heavy workload and troublesome to operate.

Method used

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  • A kind of synthetic method of porphyrin
  • A kind of synthetic method of porphyrin
  • A kind of synthetic method of porphyrin

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Add 1.03g (4mmol) 2-(3-phenoxy) propoxybenzaldehyde, 0.89g (4mmol) dipyrrolidine and 600ml solvent chloroform in the 1000ml three-necked flask, stir at room temperature for 15 minutes under nitrogen protection , then 0.03 mL (0.25 mmol) of BF 3 ·Et 2 O dissolved in 10 mL CHCl 3 Slowly added dropwise to the reactor. After stirring for 24 hours, add 0.68 g (3 mmol) DDQ and stir for 30 hours. The reaction solution is decompressed and spin-dried to dry the solvent, and then the black viscous oily liquid is dissolved with a small amount of dichloromethane and passed through a silica gel column (silica gel: 200-300 mesh, column: 2.5cm in diameter, 40cm in length, 35cm in packing height), CH 2 Cl 2 As a developing agent, the first dark purple band is the mixed crude product. According to the actual situation, the column can be passed again under the same conditions. Then the mixture product was spin-dried, dissolved in 2mL of dichloromethane, and then passed through sili...

Embodiment 2

[0037] Add 1.03g (4mmol) 4-(3-phenoxy) propoxybenzaldehyde, 0.89g (4mmol) dipyrrolidine and 600ml solvent chloroform in the 1000ml three-necked flask, stir at room temperature for 15 minutes under nitrogen protection , then 0.03 mL (0.25 mmol) of BF 3 ·Et 2 O dissolved in 10 mL CHCl 3 Slowly added dropwise to the reactor. After stirring for 24 hours, add 0.68 g (3 mmol) DDQ and stir for 30 hours. The reaction solution is decompressed and spin-dried to dry the solvent, and then the black viscous oily liquid is dissolved with a small amount of dichloromethane and passed through a silica gel column (silica gel: 200-300 mesh, column: 2.5cm in diameter, 40cm in length, 35cm in packing height), CH 2 Cl 2 As a developing agent, the first dark purple band is the mixed crude product. According to the actual situation, the column can be passed again under the same conditions. Then the mixture product was spin-dried, dissolved in 2mL of dichloromethane, and then passed through sili...

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Abstract

The invention discloses a synthetic method for porphyrin. According to the synthetic method, 2-pyrrole benzaldehyde and R-substituted benzaldehyde which are used as raw material are subjected to one-step reaction under the action of a catalyst and an oxidant and are simultaneously synthesized to obtain substituted porphyrin of three kinds shown in a structure (I), wherein R is a fat-soluble substituent. By using a one-step reaction, porphyrin of at least three kinds containing different substituents is obtained. The total yield of the porphyrin obtained by the synthetic method disclosed by the invention is higher than the yield of mono-substituted or tri-substituted porphyrin by 15-30 percent by using a traditional Lindsey method.

Description

technical field [0001] The invention relates to a method for synthesizing and purifying substituted porphyrins, belonging to the technical field of organic synthesis. Background technique [0002] Porphyrin is a highly conjugated macrocyclic system. The discovery, synthesis and research of this special structural compound have greatly promoted the development of macrocyclic compounds. The field has been injected with new vitality. [0003] Porphyrin and its derivative compounds widely exist in animals and plants, especially in important organelles related to energy transfer. Such as heme (iron porphyrin) and hemocyanin (copper porphyrin) in animals, vitamin B in plants 12 (cobalt porphyrin) and chlorophyll (magnesium porphyrin), which play an extremely important role in the process of blood cell oxygen carrying for respiration and plant cells for light summing, respectively. Porphyrin chemistry is the simulation of porphyrin biochemical process and gradually developed in ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D487/22
Inventor 马晓迅王晨李珺徐龙
Owner NORTHWEST UNIV
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