116256-35-0

Basic information

• Product Name: 17-cyano-9,17-dihydroxyandrost-4-ene-3-one
• Synonyms: 17-cyano-9,17-dihydroxyandrost-4-ene-3-one
• CAS NO: 116256-35-0
• Molecular Formula: C20H27 N O3
• Molecular Weight: 329.43
• Mol File: 116256-35-0.mol

Chemical Properties

• Boiling Point: 537.1°Cat760mmHg
• Flash Point: 278.6°C
• Appearance: /
• Density: 1.24g/cm³
• Vapor Pressure: 8.9E-14mmHg at 25°C
• Refractive Index: 1.592
• CAS DataBase Reference: 17-cyano-9,17-dihydroxyandrost-4-ene-3-one(CAS DataBase Reference)
• NIST Chemistry Reference: 17-cyano-9,17-dihydroxyandrost-4-ene-3-one(116256-35-0)
• EPA Substance Registry System: 17-cyano-9,17-dihydroxyandrost-4-ene-3-one(116256-35-0)

Safety Data

• Hazardous Substances Data: 116256-35-0(Hazardous Substances Data)

Usage

InChI:InChI=1/C20H27NO3/c1-17-7-5-14(22)11-13(17)3-4-16-15-6-8-19(23,12-21)18(15,2)9-10-20(16,17)24/h11,15-16,23-24H,3-10H2,1-2H3/t15-,16-,17-,18-,19?,20?/m0/s1

Upstream product

• 560-62-3 9-alpha-hydroxyandrost-4-ene-3,17-dione 
• 151-50-8 potassium cyanide 
• 75-86-5 2-hydroxy-2-methylpropanenitrile 
• 116256-44-1 9α-hydroxyandrost-4-ene-3-one-17β-hydroxynitrile 
• 116256-30-5 9α-hydroxy-3-methoxy-3,5-androstenedione-17-one 
• 131077-37-7 17α-cyano-3-methoxy-17β-trimethyl-silyloxyandrosta-3,5-dien-9α-ol 

Relevant articles and documents

Synthesis method of hydrocortisone intermediate 17beta-cyan steroid compound

The invention discloses a synthesis method of a hydrocortisone intermediate 17-beta cyan steroid compound. The method includes the steps: performing cyanation reaction on 9-OH AD and acetone cyanohydrin to obtain cyanides; removing oxhydryl of the cyanides to obtain a target product-17-beta cyan steroid compound. A synthetic route of the method is as shown in the specification. According to the method, side reaction of cyanation reaction of a traditional route can be completely avoided in cyanation reaction process, the yield and the quality of products are greatly improved, the total yield is95% or more, and the purity of the products is 98% or more.

Preparation method of 17-alpha hydroxynitrile steroid derivative

The invention relates to a preparation method of a steroid derivative, in particular to a preparation method of a 17-alpha hydroxynitrile steroid derivative, comprising: using 3,17-dione steroid compound (I) as a material, allowing it to react with acetone cyanohydrin in a solution of weak organic base to obtain 17-beta hydroxynitrile steroid derivative (II) as an intermediate (II), and allowing the intermediate (II) to react with hydroxynitrile in a strong base solution to obtain the 17-alpha hydroxynitrile steroid derivative (III). The materials for the preparation method are easy to obtain,the preparation method is simple to perform, side reactions can be effectively controlled, and reaction yield and weight can be increased; the preparation method does not involve high-danger reactions, and the preparation method is easy to industrialize, and is free of high-pollution reactions so that environmental treatment burden is relieved.

Preparation method of betamethasone intermediate

The invention relates to a preparation method of a steroid drug intermediate, and concretely relates to a preparation method of a betamethasone intermediate which is 16beta-methyl-17alpha-hydroxypregna-4,9-diene-3,20-dione. The method comprises the following steps: carrying out a cyanidation reaction on 9alpha-hydroxy-4-ene-pregna-3,17-dione, carrying out a ketal protection reaction, carrying out a double elimination reaction, carrying out an epoxy reaction, and carrying out a Grignard addition hydrolysis reaction to prepare the target product. The method is a brand preparation technology for producing the betamethasone intermediate, and has the characteristics of cheap and easily available initial raw material, simple operations of all above reactions, high yield, suitableness for industrial massive production, and realization of the yield and the quality reaching satisfactory levels.

The chemistry of 9α-hydroxysteroids. 3. Methods for selective formation and dehydrations of 17β-cyano-9α,17α-dihydroxyandrost-4-en-3-one

Two methods to produce the 17-cyanohydrin, using potassium cyanide in acetic acid/methanol or acetone cyanohydrin with aqueous sodium hydroxide, were followed with 9α-hydroxyandrost-4-ene-3,17-dione, both providing 17β-cyano-9α,17α-dihydroxyandrost-4-en-3-one.The selectivity of one of these methods, that which uses acetone cyanohydrin, is not in agreement with a comparable reaction with the 9α-unsubstituted androst-4-ene-13,17-dione to give the 17α-cyano-17β-hydroxy product, as reported in the literature and confirmed by us.The 9α-hydroxy and 17α-hydroxy groups were used for the regioselective introduction of 9(11)- and 16(17)-double bonds by dehydrating 17β-cyano-9α,17α-dihydroxyandrost-4-en-3-one under different conditions.

17β-cyano-9α,17α-dihydroxyandrost-4-en-3-one

The invention is the compound 17β-cyano-9α, 17α-dihydroxyandrost-4-en-3-one (I) which is particularly useful as an intermediate in the production of the 17α-halo silyl ethers (II).