566-91-6

Usage

Uses

Used in Pharmaceutical Industry:
(8S,9S,10S,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-one is used as a potential pharmaceutical agent for hormone regulation or anti-inflammatory effects, given the known activities of similar steroid compounds. Further studies are needed to fully understand its potential uses and biological effects in this industry.

InChI:InChI=1/C27H42O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h13,15,17-19,22-25H,6-12,14,16H2,1-5H3/t19-,22+,23-,24+,25+,26+,27-/m1/s1

Upstream product

• 566-88-1 dihydrocholesterone 
• 76748-84-0 2,4-dibromo-5α-cholestan-3-one 
• 78854-37-2 2α-iodocholest-4-en-3-one 
• 57-88-5 cholesterol 
• 108-75-8 2,4,6-trimethyl-pyridine 
• 2239-57-8 2α,4α-dibromo-5α-cholestan-3-one 

Downstream Products

• 1162-54-5 pregna-1,4-diene-3,20-dione 
• 68710-38-3 Cholesta-1,4-dien-3,24-dion 
• 108354-92-3 (8R,9S,10R,13R,14S,17R)-17-((R)-1,5-Dimethyl-hexyl)-10,13-dimethyl-7,8,9,10,11,12,13,14,16,17-decahydro-6H-cyclopenta[a]phenanthrene-3,15-dione 
• 601-57-0 Cholest-4-en-3-one 
• 566-88-1 dihydrocholesterone 
• 601-53-6 coprostanone 
• 19202-72-3 1-hydroxy-4-methyl-19-norcholesta-1,3,5⁽¹⁰⁾-triene 
• 17605-79-7 3-hydroxy-1-methyl-19-norcholesta-1,3,5(10)-triene 
• 33433-00-0 Trifluoro-acetic acid N-[(8S,9S,13R,14S,17R)-17-((R)-1,5-dimethyl-hexyl)-4,13-dimethyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-1-yl]-N'-(2,4-dinitro-phenyl)-hydrazide 
• 33432-93-8 4-Methyl-1-(p-methoxyphenyl)-19-nor-1,3,5⁽¹⁰⁾-cholestatrien 
• 116027-95-3 5α-cholest-1-en-3-one semicarbazone 
• 19202-76-7 cholestene-1 one-3 (5β) 
• 33432-99-4 N-[(8S,9S,10R,13R,14S,17R)-17-((R)-1,5-Dimethyl-hexyl)-10,13-dimethyl-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-cyclopenta[a]phenanthren-(3Z)-ylidene]-N'-(2,4-dinitro-phenyl)-hydrazine 
• 33432-92-7 3-(p-Methoxyphenyl)-1,3,5-cholestatrien 

Relevant academic research and scientific papers

Synthesis of α,β-unsaturated ketone from α-iodo ketone using photoirradiation

Irradiation of α-iodo ketone in hexane under a nitrogen atmosphere with a high-pressure mercury lamp (λ>300nm) at room temperature afforded the corresponding α,β-unsaturated ketones in good yield. This reaction affords a new, clean and convenient synthetic method for the α,β-unsaturated ketone.

Functionalisation of Saturated Hydrocarbons. Part 13. Futher Studies on the Gif Oxidation of Cholestane Derivatives

The oxidation of cholest-4-en-3-one by the GifIV system to give progesterone has been studied over the temperature range -40 to +80 deg C.The optimum temperature is ca. +20 deg C.Below 0 deg C the yield of progesterone diminishes and the formation of a new compound, 25-hydroxycholest-4-en-3-one, is observed.The latter has been synthesised from lithocholic acid.An unexpected major product of the oxidation was A-nor-5β-cholestan-3-one, identified by comparison with an authentic sample.

CHROMIUM(VI) BASED OXIDANTS-1. CHROMIUM PEROXIDE COMPLEXES AS VERSATILE, MILD, AND EFFICIENT OXIDANTS IN ORGANIC SYNTHESIS.

The preparation of 2,2'-bipyridylchromium peroxide, pyridinechromium peroxide, and chromium peroxide etherate is described. 2,2'-Bipyridylchromium peroxide converts different classes of alcohols to the carbonyl compounds.In 1,2-diols C-C bond cleavage occurs extensively. α-Hydroxy acids are decarboxylated quantitatively.Oximes are converted to their carbonyl compounds and thiols to their disulfides, dihydroxy phenolic compounds to quinones, benzyl amine to benzaldehyde, aromatic amines to their azo compounds, anthracene and phenanthrene to their quinones.Pyridinechromium peroxide converts different classes of alcohols efficiently to the carbonyl compounds, thiols to their disulfides, anthracene to anthraquinone.Mandelic and benzilic acids are decarboxylated very efficiently.Chromium peroxide etherate is an efficient reagent for the oxidation of different classes of alcohols to their carbonyl compounds.

A SYNTHESIS OF 11-HOMO-ALDOSTERONE

A synthesis of 11-homo-aldosterone acetate (1a) is described. 3β-Acetoxy-11-methylene-5α,25D-spirostan (3) was converted in 4 steps into 3β-acetoxy-11β-acetoxymethyl-5α-pregnan-20-one (9, Chart I), which was photocyclized to 20a, saponified regioselectively, and oxidized to 3-oxo-11β-acetoxymethyl-18,20-cyclopregnan-20α-ol-3-one (22, Chart II).Introduction of the 1,4-diene in 22 followed by a selective reduction of the 1-ene afforded 11β-acetoxymethyl-18,20-cyclopregn-4-en-20α-ol-3-one (26).Finally, the 18,20-cyclo ring of 26 was manipulated through 30, 31, 32, 33 to produce 1a.The bulky 11β-acetoxymethyl group distorted the steroid molecule to such an extent that the routine photochemical functionalization of the angular Me-18 via a nitrite or a hypoiodite became inoperative and routine procedures for introduction of a 4-ene into 5α-3-one via a 1,4-dien-3-one were unsuccessful.Two new methods for the introduction of a 4-ene into steroidal 5α-3-ones were investigated using 5α-cholestanone and 5α-dihydrotestosterone as models.The first route, which was applicable to the synthesis of 1a, was the stepwise introduction of a 1-ene and a 4-ene utilizing Sharpless's acidic phenylselenyl chloride procedure, followed by a selective reduction of the 1-ene.The second route, which appeared equally promising, was protection of the C-2 site with N-methylanilinomethylene followed by introduction of the 4-ene and subsequent deprotection of the C-2.