77881-13-1

Basic information

• Product Name: (17alpha)-17-hydroxy-3-oxoandrost-4-ene-17-carbonitrile
• Synonyms: (17alpha)-17-hydroxy-3-oxoandrost-4-ene-17-carbonitrile;(17R)-17α-Hydroxy-3-oxoandrost-4-ene-17-carbonitrile;(8R,9S,10R,13S,14S,17S)-17-Hydroxy-10,13-diMethyl-3-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-17-carbonitrile;17alpha-Hydroxy-17beta-cyanoandrost-4-en-3-one;Androstenedione cyanohydrin;Cyanohydrin matter;17β-Cyano-17α-hydroxyandrost-4- en-3-one;17alpha-Hydroxy-17β-cyanoandrost-4-en-3-on
• CAS NO: 77881-13-1
• Molecular Formula: C₂₀H₂₇NO₂
• Molecular Weight: 313.43388
• EINECS: 278-780-9
• Mol File: 77881-13-1.mol

Chemical Properties

• Melting Point: 222-226℃
• Boiling Point: 498.457°C at 760 mmHg
• Flash Point: 255.258°C
• Appearance: /
• Density: 1.176g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.572
• PKA: 11.20±0.60(Predicted)
• Water Solubility: 10mg/L at 25℃
• CAS DataBase Reference: (17alpha)-17-hydroxy-3-oxoandrost-4-ene-17-carbonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: (17alpha)-17-hydroxy-3-oxoandrost-4-ene-17-carbonitrile(77881-13-1)
• EPA Substance Registry System: (17alpha)-17-hydroxy-3-oxoandrost-4-ene-17-carbonitrile(77881-13-1)

Safety Data

• Hazardous Substances Data: 77881-13-1(Hazardous Substances Data)

Usage

Flammability and Explosibility

Nonflammable

InChI:InChI=1/C20H27NO2/c1-18-8-5-14(22)11-13(18)3-4-15-16(18)6-9-19(2)17(15)7-10-20(19,23)12-21/h11,15-17,23H,3-10H2,1-2H3/t15-,16+,17+,18+,19+,20+/m1/s1

Upstream product

• 63-05-8 Androstenedione 
• 75-86-5 2-hydroxy-2-methylpropanenitrile 
• 74-90-8 hydrogen cyanide 
• 38394-98-8 17α-cyano-17β-hydroxyandrost-4-en-3-one 
• 151-50-8 potassium cyanide 

Downstream Products

• 34184-82-2 pregna-4,9⁽¹¹⁾-diene-3,20-dione-17-hydroxy-21-methyl 
• 846-46-8 androstanedione 
• 94291-96-0 17α-hydroxy-3,3-(2,2-dimethyltrimethylenedioxy)-17β-cyanoandrost-5-ene 
• 57-83-0 Progesterone 
• 481-29-8 Epiandrosterone 
• 53-42-9 Etiocholanolone 
• 640-87-9 cortexolone 21-acetate 
• 68-96-2 17-hydroxyprogesterone 
• 2477-61-4 17α-hydroxypregna-1,4-diene-3,20-dione 
• 206351-46-4 3-[(3R,3aS,5aS,6R,9aS,9bS)-3-Hydroxy-3a,6-dimethyl-3-(4-nitro-3-trifluoromethyl-phenylcarbamoyl)-7-oxo-dodecahydro-cyclopenta[a]naphthalen-6-yl]-propionic acid 
• 206351-47-5 N-(3'-trifluoromethyl-4'-nitrophenyl)-17α-hydroxy-3-oxo-4-azaandrost-5-ene-17β-carboxamide 
• 206351-45-3 N-(3'-trifluoromethyl-4'-nitrophenyl)-17α-hydroxy-3-oxoandrost-4-ene-17β-carboxamide 
• 633-29-4 17α-hydroxyandrost-4-en-3-one-17β-carboxylic acid 
• 132639-68-0 17α-ethoxycarbonyloxy-3-oxoandrost-4-ene-17-carbonitrile 

Relevant articles and documents

Highly efficient synthesis of steroid-17-spiro-5'-oxazolidine-2',4'-diones from 17-keto steroids

Spiro-2',3,4'-trione 8a and spiro-2',3,4',11-tetraone 8b, two potentially bioactive spiranes, were prepared from the parent 17-ketones in four steps (64percent and 49.5percent yield, respectively).The key intermediates were the hydroxyimidates 5a and 5b, which easily underwent cyclization to the corresponding spirooxazolinone 4'-enol ethers when treated with alkylchlorocarbonates.The respective N-amyl derivatives of the spiranes 8a and 8b were obtained with n-pentyl bromide in the presence of KF.A new method for the synthesis of steroid 17α-hydroxy-17carboxyesters and 17α-hydroxy-17-carboxamides is described.Attempts to synthesize the title compounds from these products were unsuccessful.

Synthesis method of 17[beta]-cyano-17[alpha]-hydroxyandrost-4-ene-3-one

The invention relates to a synthesis method of 17[beta]-cyano-17[alpha]-hydroxyandrost-4-ene-3-one, wherein the synthesis method comprises the steps: S1, dispersing 4-androstenedione in a solvent of which the mass is 4-6 times that of the 4-androstenedione, adding a catalyst accounting for 4-8% of the molar weight of the 4-androstenedione, and uniformly mixing to obtain a mixed system, wherein the solvent is a mixed solvent of water and one or more of a mixture of liquid chlorinated hydrocarbon, ester, ketone, aromatic hydrocarbon or alcohol, and the mass fraction of the water in the mixed solvent is 30-50%; S2, adding a hydrocyanic acid liquid into the mixed system, and enabling the molar ratio of the hydrocyanic acid liquid to the 4-androstenedione to be (1.1-4):1, so as to obtain a reaction system; and maintaining the temperature of the reaction system at 20-60 DEG C, and reacting for 5-20 hours; and S3, adding acid to carry out acidification, concentration, crystallization, suction filtration, soaking and washing and drying on the reaction system, so as to obtain 17[beta]-cyano-17[alpha]-hydroxyandrost-4-ene-3-one, wherein the solvent recovered through concentration and suction filtration is applied to the step S1. By optimizing the composition and dosage of the reaction solvent, the catalyst and dosage, the molar ratio of the reaction materials, the reaction temperature and the like, the yield exceeds 99.0%, the content reaches 99.0% or above, and the stable product quality is obtained.

Preparation method 5α- androstane -3,17- diketone (by machine translation)

The preparation method 5α - of, androstane - 333317-dione comprises the following steps: (4 -) preparing the compound, androstanone through 17-hydroxycyanidation, 3-hydroxycyanidation- 17-hydroxycyanidation of, 5,6-hydroxycyanidation to, 3-position ketal acid hydrolysis as the raw material 5α - and the method has the advantages. of low production cost, product purity. (by machine translation)

Preparation method of progesterone and progesterone intermediate

The invention relates to a method for preparing progesterone and a progesterone intermediate. According to the method, a cyano compound 2 is used as a substrate; reaction is carried out in an aproticorganic solvent at a temperature of -20 DEG C to 5 DEG C by taking trimethylhalosilane as a hydroxyl-removing reagent, so that a progesterone intermediate 3 is obtained; and a methylation reaction isconducted on the progesterone intermediate 3, so that progesterone is obtained. The reaction route is shown in the specification.

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.

A high yield of 17 α - hydroxy progesterone of simple preparation method

The invention relates to a high-yield simple preparation method of 17alpha-hydroxy progesterone. With 4-androstenedione as an initial raw material, the method comprises the following steps: performing a cyanogen alcoholization addition reaction between the 17-site carbonyl of 4-androstenedione and acetone hydrogen alcohol to obtain 17-alpha hydroxyl-17-beta cyanoandrostane-4-ene-3-one; performing a ketal protection reaction of the C3-site carbonyl to obtain a ketal product; and performing a direct methylation reaction between the ketal product and zinc chloride methane, and hydrolyzing to obtain 17alpha-hydroxy progesterone. The method provided by the invention has the advantages of short process, high yield, high product purity, mild reaction conditions, low cost and low energy consumption and is particularly suitable for industrial production.

Preparation method of steroidal compound with multiple olefin groups

The invention relates to a preparation method of a steroid medicine intermediate body, in particular to a method for preparing a steroid carrying medicine intermediate body, namely steroid carrying-1,4,9(11),16(17)-tetraterpene-3,20-diketone and steroid carrying-4,9(11)-diene-3,20-diketone-17 alpha-hydroxyl, by taking androstane-4-alkene-3,17-diketone as a substrate.

Method for preparing progesterone

The invention discloses a method for preparing progesterone. 4-androstenedione (I) is taken as a raw material, a 17-position branch chain is introduced through cyanation and other reactions, and progesterone (VI) is prepared. The reaction formula is shown in the specification. The invention discloses a novel process for preparing progesterone. 4-androstenedione (I) with low price is initially taken as a starting raw material, progesterone with the total yield as high as 80% or higher by weight is obtained after five steps of reactions, the cost is low, and the method is suitable for industrial production.

Transformation of androstenedione into 17α-hydroxy-16β-methylpregn-4-ene-3,20-dione

An efficient synthesis of 17α-hydroxy-16β-methylpregn-4-ene-3,20-dione from androstenedione has been studied. Structure of the product and its intermediates has been examined by spectral methods such as IR, MS, 1D and 2D NMR.

The regio- and stereo-selective reduction of steroidal 4-en-3-ones using Na2S2O4/NaHCO3 and CuCl/NaBH 4

This paper describes the regio- and stereoselective reduction of a.