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A kind of synthetic method of β-hydroxy selenide compound

A synthesis method and compound technology, applied in the direction of organic chemistry, etc., can solve the problem of unsatisfactory atom utilization and other problems

Active Publication Date: 2016-04-13
WENZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0022] As mentioned above, a variety of methods for preparing aryl selenides have been disclosed in the prior art, but there are certain defects in these methods, for example, the utilization rate of atoms is not ideal enough, sometimes it is necessary to use toxic and environmentally harmful halogenated reagents ( Such as chlorine, SO 2 Cl 2 , liquid bromine, etc.)

Method used

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  • A kind of synthetic method of β-hydroxy selenide compound
  • A kind of synthetic method of β-hydroxy selenide compound
  • A kind of synthetic method of β-hydroxy selenide compound

Examples

Experimental program
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Effect test

Embodiment 1

[0071]

[0072] At room temperature, in the organic solvent DMSO in the reaction vessel, add above formula (II) compound, above formula (III) compound, elemental Se, CuCl and K 3 PO 4 . Wherein, the molar ratio of formula (II) and formula (III) compound is 1:1, the molar ratio of formula (II) compound and elemental Se is 1:1, and the molar dosage of CuCl is 10 of the molar dosage of formula (II) compound %, formula (II) compound and K 3 PO 4 The molar ratio of the mixture was 1:0.8, and then filled with nitrogen, and replaced twice, so that the reaction environment was a nitrogen atmosphere; the temperature was raised to 100° C. under stirring, and the reaction was kept for 30 hours.

[0073] After post-treatment, the product (I) of the above formula was obtained with a yield of 84.5% and a purity of 98.7% (HPLC).

[0074] NMR: 1 HNMR (500MHZ, CDCl 3 )δ7.50(d, J=8.7HZ, 2H), 6.82(d, J=8.7HZ, 2H), 3.81(s, 3H), 3.27-3.23(m, 1H), 2.98(s, 1H), 2.79-2.73 (m, 1H), 2.13-2.10...

Embodiment 2

[0077]

[0078] At room temperature, in the organic solvent DMSO in the reaction vessel, add above formula (II) compound, above formula (III) compound, elemental Se, CuCl and K 3 PO 4 . Wherein, the molar ratio of the compound of formula (II) to the compound of formula (III) is 1:2, the molar ratio of the compound of formula (II) to elemental Se is 1:2, and the molar dosage of CuCl is 20% of the molar dosage of the compound of formula (II). %, formula (II) compound and K 3 PO 4 The molar ratio of the mixture was 1:1.2, and then filled with nitrogen, and replaced twice, so that the reaction environment was a nitrogen atmosphere; the temperature was raised to 140° C. under stirring, and the reaction was kept for 20 hours.

[0079] After post-treatment, the product (I) of the above formula was obtained with a yield of 86.7% and a purity of 98.9% (HPLC).

[0080] NMR: 1 HNMR (500MHZ, CDCl 3 )δ7.60 (d, J = 6.95HZ, 2H), 7.34-7.27 (m, 3H), 3.33 (s, 1H), 2.92-2.87 (m, 2H), 2....

Embodiment 3

[0083]

[0084] At room temperature, in the organic solvent DMSO in the reaction vessel, add above formula (II) compound, above formula (III) compound, elemental Se, CuCl and K 3 PO 4 . Wherein, the molar ratio of the compound of formula (II) to the compound of formula (III) is 1:3, the molar ratio of the compound of formula (II) to elemental Se is 1:3, and the molar dosage of CuCl is 30% of the molar dosage of the compound of formula (II). %, formula (II) compound and K 3 PO 4 The molar ratio of the mixture was 1:1.5, then filled with nitrogen, and replaced twice, so that the reaction environment was a nitrogen atmosphere; the temperature was raised to 180° C. under stirring, and the reaction was kept for 15 hours.

[0085] After post-treatment, the product (I) of the above formula was obtained with a yield of 89.6% and a purity of 99.4% (HPLC).

[0086] NMR: 1 HNMR (CDCl 3 ,500MHz): δ7.47(d,J=7.9Hz,2H), 7.09(d,J=7.9Hz,2H), 3.29(td,J 1 =4.1Hz,J 2 =10.1Hz,J 3 =20.1...

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Abstract

The invention relates to a synthetic method of Beta-hydroxyl selenide compound. The method includes: in organic solvent, in the presence of catalyst and alkali, allowing halogenated compound to react with elemental Se and epoxy compound to obtain Beta-hydroxyl selenide compound. The synthetic method has the advantages that reaction is simple, operating is simple, yield is high, the method is a novel one, a novel synthetic route is provided for the synthesis of the Beta-hydroxyl selenide compounds, and the method has good scientific research value and industrial potential.

Description

technical field [0001] The invention relates to a synthesis method of selenide compounds, in particular to a synthesis method of β-hydroxy selenide compounds, belonging to the field of organic chemical synthesis. Background technique [0002] Selenium is an important trace element that can maintain a variety of metabolic and physiological activities in organisms, so it is often used in drug synthesis. A large number of scientific studies have shown that many organic selenium compounds not only have anti-virus, anti-tumor and therapeutic effects on nervous system diseases, but also have biochemical and pharmacological effects such as anti-inflammation, anti-aging, prevention and treatment of cardiovascular diseases and liver diseases. . For example, Ebselen (Ebselen) and Selenazofurin (Selenazofurin) are two representative drugs that are undergoing clinical research. [0003] In addition, organic selenium compounds can also be used as important intermediates, chiral ligands...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C391/02C07D333/30C07D307/20
Inventor 陈久喜吴华悦闵林刘妙昌高文霞黄小波
Owner WENZHOU UNIV