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Steroidal intermediate chemical as well as preparation method and application thereof

A chemical and steroid technology, applied in the field of steroid intermediate chemicals and their preparation, can solve the problems of limited industrial and social benefits, unreasonable selection of starting materials, and difficult recovery of solvents, and achieves low raw material prices, The effect of shortening the synthesis route, stable synthesis process and easy operation

Pending Publication Date: 2021-08-24
HENAN ACADEMY OF SCI CHEM RES INST CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] At present, there are many methods for synthesizing steroids, but most of them are limited by the selection of raw materials, the control of reaction conditions and safety, the convenience of post-processing, the amount of reagents, and environmental protection. The reaction conditions are harsh, the operation is cumbersome, and the post-treatment is complicated. The reagents and solvents used will cause physical injury to operators and serious environmental pollution, and the solvents are not easy to recycle, so the industrial and social benefits are limited.

Method used

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  • Steroidal intermediate chemical as well as preparation method and application thereof
  • Steroidal intermediate chemical as well as preparation method and application thereof
  • Steroidal intermediate chemical as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Dissolve 4g stigmasterol (9.7mmol) and 1.19g triethylamine (11.7mmol) in 40mL butanone. After the dissolution is complete, slowly add 2.38g p-toluenesulfonyl chloride (12.5mmol) dropwise. After the dropwise addition, Continue to react at room temperature for 4 hours under stirring, monitor the progress of the reaction with a TLC plate, and confirm the reaction end point with HPLC when it is close to the end point. The product does not need to be separated and purified for the next step reaction. After the end, it is distilled under reduced pressure to recover butanone.

[0028] Dissolve the product of the previous step in 120mL butanone, then add 40mL KHCO 3 (10mmol) solution, the temperature is controlled at 60-80°C, and the end point of the reaction is confirmed by TLC plate and HPLC. After the end, butanone is distilled off, and 20mL of petroleum ether is added to wash until neutral, and the organic phase is combined to enter the next step of reaction.

[0029] Slowl...

Embodiment 2

[0038] The difference between embodiment 2 and embodiment 1 is: after the rearrangement reaction, slowly add 1.27gMnO under stirring in the system 2 (14.6mmol), the temperature was controlled at 60°C, and the reaction was carried out for 3h. 2.80 g (yield: 70.6%) of high-purity steroidal intermediates were obtained.

Embodiment 3

[0040] The difference between embodiment 3 and embodiment 1 is: after the rearrangement reaction, slowly add 0.84gMnO under stirring in the system 2 (9.7mmol), control the temperature at 60°C, and react for 3h. Obtain high-purity steroidal intermediate chemical 2.58g (yield is 64.8%)

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Abstract

The invention belongs to the technical field of synthesis of steroidal intermediate chemicals, and particularly discloses a steroidal intermediate chemical and a preparation method and application thereof. The steroidal intermediate chemical can be used for synthesizing plant growth regulators, steroidal drugs and the like, stigmasterol serves as a raw material, and the steroidal intermediate chemical is obtained through three-step reactions of sulfonylation, rearrangement, manganese dioxide selective oxidation. The synthesis process is stable and easy to operate, and conditions are mild and easy to control; raw materials are rich in source and easy to obtain; purification is not needed in the intermediate process, the technological process is simplified, the solvent is easy to recover, and cost is reduced; and meanwhile, sewage and waste discharge is reduced, industrialization is facilitated, and high economic and social benefits can be brought.

Description

technical field [0001] The invention belongs to the technical field of synthesis of steroid intermediate chemicals, and in particular relates to a steroid intermediate chemical and its preparation method and application. Background technique [0002] Steroids have anti-oxidant, anti-inflammatory, anti-viral, anti-tumor, health care, beauty and other physiological activities, so they have attracted much attention and have been widely used in food, animal husbandry, daily chemicals, agriculture, and chemical industries. For example, related steroidal chemicals can be used as herbicides, insecticides, growth regulators, and as raw materials for the synthesis of steroidal hormones and other drugs that regulate metabolism. This is also an important source of steroidal drugs that are urgently needed in the world. [0003] Therefore, with the continuous discovery and understanding of steroid compounds and their functions, how to efficiently synthesize steroid compounds has become o...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J53/00
CPCC07J53/004
Inventor 陈世鹏樊燕鸽王红星曹长青王蜀江陈鹏丽薛宝玉朱朝印宁红龙李峥赵俊宏孔宏俊
Owner HENAN ACADEMY OF SCI CHEM RES INST CO LTD
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