21800-83-9

Usage

Uses

Used in Pharmaceutical Industry:
D-Ethylgonendione is used as a chemical intermediate for the synthesis of Norgestrel, a progestin hormone. It is essential in the production process of various hormonal medications, including contraceptives and hormone replacement therapies, due to its role in facilitating the synthesis of the active pharmaceutical ingredient.
Used in Contraceptive Applications:
As a precursor to Norgestrel, D-Ethylgonendione indirectly contributes to the development of contraceptive products, such as birth control pills and patches. These contraceptives help in preventing unintended pregnancies by regulating hormonal levels in the body.
Used in Hormone Replacement Therapy:
D-Ethylgonendione, through its role in the synthesis of Norgestrel, is also utilized in hormone replacement therapy (HRT) for conditions like menopause. HRT helps in alleviating symptoms associated with hormonal imbalances and maintaining overall health and well-being in individuals undergoing hormonal changes.

InChI:InChI=1/C19H26O2/c1-2-19-10-9-15-14-6-4-13(20)11-12(14)3-5-16(15)17(19)7-8-18(19)21/h11,14-17H,2-10H2,1H3/t14-,15+,16+,17-,19-/m0/s1

Upstream product

• 53662-97-8 (3S,3aS,5aS,6R,9aR,9bS)-3-tert-Butoxy-3a-ethyl-6-[2-(2-methyl-[1,3]dioxolan-2-yl)-ethyl]-dodecahydro-cyclopenta[a]naphthalen-7-one 
• 23759-68-4 (3aS,5aS,6R,9aR,9bS)-3a-Ethyl-6-(3-oxo-butyl)-decahydro-cyclopenta[a]naphthalene-3,7-dione 
• 23855-42-7 (5R,8R,9S,10R,13S,14S)-13-Ethyl-5-hydroxy-3-methyl-tetradecahydro-4-oxa-cyclopenta[a]phenanthren-17-one 
• 29371-39-9 C₂₃H₃₆O₅ 
• 14507-49-4 D-13β-ethyl-17β-hydroxy-3-methoxy-gona-2,5(10)-diene 
• 7443-72-3 18-methyl-3-methoxy-1,3,5(10),8-estratetraen-17β-ol 
• 3625-82-9 (+)-17β-hydroxy-13β-ethyl-3-methoxygona-1,3,5(10)-triene 
• 2322-77-2 13β-ethyl-3-methoxygona-2,5(10)-diene-17-one 
• 144-55-8 sodium hydrogencarbonate 
• 76739-55-4 13β-ethyl-3-methoxy-17,17-ethylenedioxy-gona-2,5(10)-diene 
• 160683-92-1 18a-homo-estr-4-ene-11α,17β-diol 
• 797-63-7 levonorgestrel 
• 793-55-5 17beta-hydroxy-18-methyl-4-estren-3-one 

Downstream Products

• 6544-68-9 13β-ethyl-3-hydroxygona-1,3,5(10)-trien-17-one 
• 793-55-5 17beta-hydroxy-18-methyl-4-estren-3-one 
• 808-89-9 13β-Ethyl-17β-(3-phenylpropionoxy)-gon-4-en-3-one 
• 797-63-7 levonorgestrel 
• 176254-10-7 C₂₂H₃₀O₂ 
• 170901-07-2 13-ethyl-11-hydroxygon-4-ene-3,17-dione 
• 848-04-4 dl-13-ethyl-3-methoxygona-1,3,5⁽¹⁰⁾-trien-17-one 
• 3625-82-9 (+)-17β-hydroxy-13β-ethyl-3-methoxygona-1,3,5(10)-triene 
• 192722-02-4 16-phenylsulfinylmethyl-18-methyl-19-norpregna-4,16-diene-3,20-dione 
• 60282-87-3 gestodene 
• 53067-82-6 13β-ethyl-11α-hydroxygon-5-ene-3,17-dione 
• 19882-75-8 13-Ethyl-3-methoxygona-1,3,5⁽¹⁰⁾,9⁽¹¹⁾-tetraen-17-one 
• 60919-46-2 15α-Hydroxy-18-methyl-4-estren-3,17-dion 
• 797-63-7 norgestrel 

Relevant academic research and scientific papers

Steroid intermediate products and method of their production

The invention is directed to novel steroid intermediate products of general formula I STR1 The steroid intermediate products which can be isolated according to the invention are suitable for the synthesis of 13-ethyl-11-methylene-18,19-bisnor-17α-pregn-4-en-20-in-17-ol (desogestrel). Further, processes for producing the steroid intermediate products of general formula I are described. The olefination of the 11-oxo steroids is carried out under the influence of ultrasound.

Preparative chemical methods for aromatization of 19-nor-Δ4-3-oxosteroids

Two preparative chemical methods for aromatization of 19-nor-Δ4-3-oxosteroids are described.The first method consists of an oxidative aromatization of 19-nor-Δ4-3-oxosteroids with iodine-ceric ammonium nitrate in methanol to give a mixture of 3-methoxy ring-A aromatized derivatives consisting of the desired product, the Δ9,11 derivative, the 6-oxo derivative as well as some ring-A iodinated material.Conversion of this material to a mixture of the 3-methoxy ring-A aromatized derivative and its 6-oxo derivative was achieved by catalytic hydrogenation.Finally, reduction of the 6-oxo function with triethylsilane in trifluoroacetic acid gave the 3-methoxy-17-trifluoroacetate ring-A aromatized derivative as a single product.In the second method, reaction of 19-nor-Δ4-3-oxosteroids with copper(II) bromide in acetonitrile at room temperature resulted in aromatic steroids in a single step in excellent yields.The second method was used in the first practical chemical synthesis of a 6-dehydroestrogen from a 19-nor-Δ4,6-3-oxosteroid. - Keywords: copper(II) bromide; ceric ammonium nitrate; iodine; aromatization; 19-nor-Δ4-3-oxosteroids

Synthesis of gon-4-enes

1. A therapeutic composition having progestational activity comprising as active ingredient a 17-aliphatic carboxylic acid ester of 17α-ethynyl-18-methyl-19-nortestosterone and a pharmaceutical carrier for said compound.

Synthesis of 13-alkyl-gon-4-ones

The preparation of 13-methylgon-4-enes and novel 13-polycarbonalkylgon-4-enes by a new total synthesis is described. 13-Alkylgon-4-enes having progestational, anabolic and androgenic activities are prepared by forming a tetracylic gonane structure unsaturated in the 1,3,5(10),9(11) and 14-positions, selectively reducing in the B- and C-rings, and converting the aromatic A-ring compounds so-produced to gon-4-enes by Birch reduction and hydrolysis.

Tetrahydropyran-2-ols

Stereo-specific total synthesis of steroidal materials. 7-Substituted 3-oxo-1-heptenes or variants thereof are reacted with 2-alkylcycloalkane-1,3-diones yielding 3-substituted 6a β-alkyl-cyclopenta [f] [1] benzopyrans or naphtho [2,1-b] pyrans. These are then subjected to a selective catalytic hydrogenation followed by an introduction of a hydroxy, alkoxy or acyloxy group at the 4a-position to produce a 3-substituted 6a β,4a-hydroxy, alkoxy or acyloxy perhydrocyclopenta [f] [1] benzopyran or perhydro-naphtho [2,1-b] pyran. These latter compounds are then converted into 4- or 5-(3-oxoalkyl)perhydroindene-5-ones or perhydronaphthalene-6-ones which in turn can be converted to known steroidal materials by known methods.

Aryl ketals of 1-chloro-4-oxo-pentane

The intermediates and processes of this disclosure provide a new stereo-specific total synthesis of steroidal materials having known valuable pharmacological properties. A fundamental feature of this disclosure is the utilization of aryl ketals, preferably phenylenedioxy ketals derived from catechol as protective groups for oxo moieties in the polycyclic intermediates used in the aforesaid total snythesis.