Preparation method for 22E-alkene-3a,5-ring-5a-cholest-6-ketone

Abstract

The invention belongs to the technical field of organic synthesis and relates to a preparation method for 22E-alkene-3a,5-ring-5a-cholest-6-ketone. The method comprises the following steps: placing 22E-alkene-3a,5-ring-5a-cholest-6-alcohol into an organic solvent, adding a catalyst under a certain temperature, performing oxidizing reaction under air or oxygen atmosphere and performing crystal suction filtration on the crude product, thereby obtaining an end product. According to the invention, any one of free radical catalyst, metal salt or free radical catalyst and metal salt is selected as the catalyst system of reaction; the 22E-alkene-3a,5-ring-5a-cholest-6-alcohol is directly oxidized into the 22E-alkene-3a,5-ring-5a-cholest-6-ketone under air or oxygen atmosphere; the yield thereof is above 90% and the content is above 98%; the raw materials are nontoxic or low-toxicity; the catalyst used in the reaction is low-cost and extensively sourced; the operation is safe, simple and convenient, the reaction condition is mild and the three wastes generated in the whole process are far less than those generated in the prior art; the production cost is low; no toxic three-waste emission exists; the total yield is high; the method is beneficial to industrialization.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and relates to a preparation method of 22E-ene-3α,5-cyclo-5α-cholestan-6-one. Background technique [0002] Brassinolide is a new type of green and environmentally friendly plant growth regulator. In 1970, American scientist Grove isolated it from rape pollen. Through the study of its crystal structure, it was found that it was a sterol compound, which was called brassinolide. Orcinolactone. This is one of the newly discovered plant growth regulators in nature, known as the sixth type of plant hormone, and its biological activity far exceeds the existing five major hormones. Most plant hormones only have physiological regulation effects on one or several periods of plants, such as: gibberellin can promote the division and elongation of plant cells; abscisic acid can inhibit plant growth and accelerate fruit shedding. However, brassinolide plays a great role in promoting crop productio...

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Problems solved by technology

[0003] The synthesis method reported in the literature mainly contains following four kinds: the first one utilizes chromium trioxide oxidation (J.AM.Chem.Soc., 1980,102,6580; J.Org.Chem.1993,58,2338; Pesticides 1996 ,35,8; J.Org.Chem.1979,44,5002; Synthesis Chem.1986,181; Chem.Pharm.Bull.1987,35,3006), this method uses highly toxic chromium trioxide, which pollutes a lot , there is a large potential safety hazard, and a large amount of Cr-containing wastewater is produced; the second is to oxidize with manganese dioxide (Agric.Biol.Chem.1980,44,1211). Waste water, easily causes environmental pollution; The 3rd kind of method adopts DMSO to carry out oxidation (CN1217227A), and this method produces a large amount of DMSO waste water and smell very big, causes environmental pollution; The 4th kind is to adopt periodate oxidation (OrganicChemistry Synthesis Division, National chemical Laboratory, pune-11008, India), there is also a large amount of iodine-containing wastewater, causing environmental pollution

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