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Preparation method of [2,7,12,18-tetramethyl-3,8-diethyl-13,17-dicarboxyethyl]-porphyrin
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A 17-, dicarboxylic technology, applied in the field of organic synthesis, can solve unreasonable problems, achieve simple steps, avoid additional steps, and facilitate post-processing
Active Publication Date: 2016-01-20
NANJING UNIV OF SCI & TECH
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Problems solved by technology
However, it is obviously unreasonable to prepare diethyl hypoporphyrin with diethyl hypoporphyrin dimethyl ester
Method used
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Embodiment 1
[0024] Example 1: In a three-necked flask, add 1 g of hemin and 30 mL of formic acid respectively, heat to 100° C. in an oil bath, add 0.909 g of reduced iron powder in 3 times within 15 min, and react for 4 h. Cool after the reaction, filter, wash with formic acid 3 times, collect the filtrate, slowly add 6mol / L sodium hydroxide solution dropwise to the filtrate to adjust the pH of the system to 4~5, let it stand for several hours, filter and collect the precipitate, and distilled water Washing and drying in an oven, the product was recrystallized with acetone to obtain [2,7,12,18-tetramethyl-3,8-diethyl-13,17-dicarboxyethyl]-porphyrin, The yield was 53.3%. Its NMR characterization data are as follows: 1 HNMR(500MHz,DMSO-d6),δ:12.24(s,2H,13-,17-COOH),10.29(s,1H,20-H),10.22(s,1H,5-H),10.20(s ,1H,15-H),10.19(s,1H,10-H),4.36(t,4H,J HH =7.5Hz,13-,17-β-CH 2 , αtocarbonyl), 4.12, 4.10 (2q, 4H, J HH =7.5Hz,3,8-CH 2 CH 3 ),3.65,3.64,3.63(3s,12H,2-,7-,12-,18-CH 3 ),3.20(t,4H,J...
Embodiment 2
[0025] Example 2: In a three-necked flask, add 1g hemin and 30mL acetic acid respectively, heat to 100°C in an oil bath, add 0.909g reduced iron powder in 3 times within 15min, and react for 4h. Cool after the reaction, filter, wash with acetic acid for 3 times, collect the filtrate, slowly add 6mol / L sodium hydroxide solution dropwise to the filtrate to adjust the pH of the system to 4~5, let it stand for several hours, filter to collect the precipitate, and distilled water Washing and drying in an oven, the product was recrystallized with acetone to obtain [2,7,12,18-tetramethyl-3,8-diethyl-13,17-dicarboxyethyl]-porphyrin, The yield was 31.9%.
Embodiment 3
[0026] Example 3: In a three-necked flask, add 1 g of hemin and 30 mL of dilute sulfuric acid respectively, heat to 100° C. in an oil bath, add 0.909 g of reduced iron powder in 3 times within 15 min, and react for 4 h. Cool after the reaction, filter, wash with dilute sulfuric acid for 3 times, collect the filtrate, slowly add 6 mol / L sodium hydroxide solution dropwise to the filtrate to adjust the pH of the system to 4-5, let it stand for several hours, collect the precipitate by filtration, and use Wash with distilled water, dry in an oven, and recrystallize the product with acetone to obtain [2,7,12,18-tetramethyl-3,8-diethyl-13,17-dicarboxyethyl]-porphyrin , and the yield was 11.6%.
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Abstract
The invention relates to a method for preparing (2,7,12,18-tetramethyl-3,8-diethyl-13,17-dicarboxyethyl)-porphyrin, and the product can be synthesized according to the following synthetic method: dissolving hemin in the acid solvent; in the 90-140 DEG C. condition, adding reduction metal of equal mass in batches for reaction; after reaction, cooling, filtering, washing, collecting filtrate, adjusting pH, standing for hours, filtering and collecting deposition, washing, drying, recrystallizing the crude product, and obtaining the (2,7,12,18-tetramethyl-3,8-diethyl-13,17-dicarboxyethyl)-porphyrin. Compared with the prior art, the significant advantages include: (1) according to the invention, the raw material of the scheme is cheap and easily available, thereby avoiding usage of noble metal catalyst, and substantially reducing the preparation cost; (2) the steps of the scheme method are simple, and only one step is needed for synthesizing the object product, thereby effectively avoiding the product loss caused by increase of steps, and substantially improving the yield of the object product; (3) the experiment scheme has the advantages of safe preparation and simple post-treatment, and is suitable for multiple batches and large batch of production.
Description
technical field [0001] The invention belongs to the field of organic synthesis, in particular to [2,7,12,18-tetramethyl-3,8-diethyl-13,17-dicarboxyethyl]-porphyrin (also known as m-porphyrin) Preparation. Background technique [0002] The chemical structural formula of [2,7,12,18-tetramethyl-3,8-diethyl-13,17-dicarboxyethyl]-porphyrin is as follows: [0003] [0004] Porphyrin is an important class of organic compounds with 18π conjugated structure. As a common biomimetic enzyme model, it has been widely used in many fields such as medicine, biochemistry, materials chemistry and medicine. Due to its stable physical and chemical properties, diethylporphyrin is closer to the active center of natural biomimetic enzyme models, so it has become the first choice for metalloporphyrin biomimetic catalysis application research centers, and has attracted extensive attention from chemists in recent years. [0005] In 1934, Fischer first proposed the synthesis method of diethyl hyp...
Claims
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