54201-84-2

Basic information

• Product Name: 3,20-Bis(ethylenedioxy)-19-norpregna-5(10)9(11)dien-17-ol
• Synonyms: 3,20-Bis(ethylenedioxy)-19-norpregna-5(10)9(11)dien-17-ol;17-Hydroxy-19-norpregna-5(10),9(11)-diene-3,20-dione cyclic bis(1,2-ethanediyl acetal);3,3,20,20-Bis(ethylene-dioxy)-17α-hydroxy-19-norpregna-5(10),9(11)-diene;3,3,20,20-bis(ehtylene-dioxy)-17a-hydroxy-19-norpregna-5(10),9(11)-diene;19-Norpregna-5(10),9(11)-diene-3,20-dione,17-hydroxy-, cyclic 3,20-bis(1,2-ethanediyl acetal), (5a,10a)-;3,3,20,20-Bis(ethylene-dioxy)-17α-hydroxy-19/;17-hydroxy-19-norpregna-5(10),9(11)-diene-3,20-dione 3,20-bis(ethylene acetal);3,20-BIS(ETHYLENEDIOXY)-19-NORPREGNA-5(10),9(11)-DIENE-17-OL
• CAS NO: 54201-84-2
• Molecular Formula: C₂₄H₃₄O₅
• Molecular Weight: 402.52376
• EINECS: 1308068-626-2
• Product Categories: API
• Mol File: 54201-84-2.mol

Chemical Properties

• Boiling Point: 568 °C at 760 mmHg
• Flash Point: 297.3 °C
• Appearance: /
• Density: 1.25
• PKA: 14.95±0.40(Predicted)
• CAS DataBase Reference: 3,20-Bis(ethylenedioxy)-19-norpregna-5(10)9(11)dien-17-ol(CAS DataBase Reference)
• NIST Chemistry Reference: 3,20-Bis(ethylenedioxy)-19-norpregna-5(10)9(11)dien-17-ol(54201-84-2)
• EPA Substance Registry System: 3,20-Bis(ethylenedioxy)-19-norpregna-5(10)9(11)dien-17-ol(54201-84-2)

Safety Data

• Hazardous Substances Data: 54201-84-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Research:
3,20-Bis(ethylenedioxy)-19-norpregna-5(10)9(11)dien-17-ol is used as a research compound for exploring its interactions with hormone receptors and related pathways. Its potential applications include the development of new drugs for hormone-related conditions and diseases.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, 3,20-Bis(ethylenedioxy)-19-norpregna-5(10)9(11)dien-17-ol is utilized as a starting material or a structural template for the synthesis of novel steroidal compounds with potential therapeutic properties. Its unique structural features may contribute to the discovery of innovative treatments for various medical conditions.

Upstream product

• 107-21-1 ethylene glycol 
• 596-61-2 17α-19-Dihydroxy-progesteron 
• 5251-19-4 17α-Hydroxy-19-nor-pregnen-(5(10))-dion-(3,20) 
• 510-64-5 3,17-Dioxo-13-methyl-10-hydroxymethyl-1,2,3,6,7,8,9,10,11,12,13,14,15,16-tetradekahydro-17H-cyclopentaphenanthren 
• 42982-49-0 3,3-[1,2-ethanediylbis(oxy)]-17α-hydroxy-19-norpregna-5(10),9(11)-diene-20-one 
• 290825-36-4 3,3-ethylenedioxy-17β-cyano-17α-chloromethyl(dimethyl)siloxy estren-5(10),9(11)diene 
• 5571-36-8 ethylene deltenone 
• 14340-01-3 17α-hydroxy-19-norpregna-4(5),9(10)-diene-3,20-dione 

Downstream Products

• 54201-83-1 C₂₄H₃₄O₆ 
• 25092-42-6 (11β,17α)-17-hydroxy-11-methyl-norpregna-4-en-3,20-dione 
• 14340-01-3 17α-hydroxy-19-norpregna-4(5),9(10)-diene-3,20-dione 
• 244206-54-0 C₃₄H₅₁NO₆Si 
• 244206-51-7 3,20-bis-ethylenedioxy-5α,17α-dihydroxy-11β-(4-aminophenyl)-19-norpregn-9-ene 
• 244206-53-9 11β-(4-N-trifluoroacetamidophenyl)-17α-acetoxy-19-norpregna-4,9-diene-3,20-dione 
• 244206-56-2 17α-acetoxy-11β-(4-N-acetyl-N-methylaminophenyl)-19-norpregna-4,9-diene-3,20-dione 
• 244206-52-8 11β-(4-aminophenyl)-17α-hydroxy-19-norpregna-4,9-diene-3,20-dione 
• 159681-67-1 11β-(4-N-methylaminophenyl)-17α-hydroxy-19-norpregna-4,9-diene-3,20-dione 
• 126690-41-3 3,3,20,20-bis(ethylene-dioxy)-5α-17α-dihydroxy-11β-[4-(N,N-dimethylamino)-phenyl-]-19-norpregna-9(11)-ene 
• 159811-51-5 CDB-3236 
• 54201-83-1 5α,10α-epoxy-17α-hydroxy-19-norpregn-9(11)-ene-3,20-dione 3,20-bis(ethylene acetal) 

Relevant articles and documents

Synthesis method of ulipristal acetate intermediate

The invention provides a synthesis method of a ulipristal acetate intermediate. The synthesis method of the ulipristal acetate intermediate comprises the following steps: 1) a cyano reaction: dissolving a 3-ketal compound (I) in ethyl acetate, adding acetone cyanohydrin and triethylamine, and carrying out reacting to obtain a 17-cyanohydrin compound (II); 2) a protective reaction: adding dichloromethane, imidazole and a silanization reagent into a wet product of the 17-cyanohydrin compound (II), keeping the above raw materials at a temperature of 20-25 DEG C until the raw materials react completely so as to obtain a protected compound (III); 3) a methylation reaction: adding an ether solvent into a wet product of the protected compound (III), controlling a temperature to be -10 DEG C to 5DEG C, dropwise adding a lithium methide solution, carrying out a reaction with a temperature controlled to be -40 DEG C to 5 DEG C until the raw materials are completely reacted so as to obtain a methide (IV-1) solution; and 4) a ketalation reaction: adding ethylene glycol, triethyl orthoformate and p-toluenesulfonic acid (PTS) into the methide (IV-1) solution, and carrying out a heat-preserved reaction at a temperature of 20-25 DEG C until the raw materials are completely reacted so as to obtain a diketal (V).

Environmentally-friendly synthesis method of ulipristal acetate intermediate and ulipristal acetate

The invention provides a method for environmentally-friendly synthesis of an ulipristal acetate intermediate and ulipristal acetate. According to the invention, a compound 2 is used as a starting rawmaterial, and reacts with acetylene in a solvent to form an alkynyl alcohol compound intermediate 3, a hydration reaction is performed with water under the catalysis of an ionic liquid and CO2 to obtain an intermediate 4, the intermediate 4 is subjected to carbonyl protection to obtain an intermediate 5, and the intermediate 5 is subjected to double bond epoxidation, a Grignard reaction, decarbonylation protection and acetylation to obtain the high-purity ulipristal acetate. The method is environment-friendly, convenient in steps, mild in conditions, low in cost, easy to amplify and suitable for industrial production, and the solvent can be recycled.

Method for preparing di-ketal

The invention discloses a method for preparing di-ketal. An open-loop substance 1 used as a raw material is subjected to cyanide reaction, ketalation, etherifying reaction, oxidization, decarboxylic reaction, diene reaction and di-ketal reaction to obtain di-ketal 9, and reaction formulas are as follows: as shown in the description.

Preparation method of ulipristal acetate diketal

The invention discloses a preparation method of ulipristal acetate diketal. Dihydroxyprogesterone dehydrogenate 1 is used as the raw material to prepare an important intermediate of sterides, namely ulipristal acetate diketal 8; a reaction formula is shown in the attached figure. The preparation method has the advantages that the dihydroxyprogesterone dehydrogenate 1 is used as a starting raw material, seven steps are performed, and the ulipristal acetate diketal with weight total yield rate of 65% or above can be obtained; the reaction is simple, the selectivity is good, and the preparation method is suitable for industrialization production.

Synthesis method of ulipristal acetate

The invention discloses a synthesis method of ulipristal acetate. The synthesis method comprises the following steps: 1), producing a compound VI from gestadienol under the action of ethylene glycol,p-toluenesulfonic acid and trimethyl orthoformate; 2), oxidizing the compound VI by using hydrogen peroxide to obtain a compound VII; 3), preforming a reaction on the compound VII and a 4-(N, N-dimethylamino) phenylmagnesium bromide Grignard reagent to obtain a compound VIII; 4), hydrolyzing a compound VIII to obtain a compound XI; 5), preforming a reaction on the compound XI, glacial acetic acidand acetic anhydride under the catalytic action of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, 4-dimethylaminopyridine and iron perchlorate to obtain the ulipristal acetate. In the synthesis method, reaction conditions for obtaining the ulipristal acetate from ulipristal are relatively mild, demethylated ulipristal or ulipristal oxynitride is unlikely to produce, and the production process is more controllable.

Cyclic utilization method of sterides epoxy isomer

The invention provides a cyclic utilization method of sterides epoxy isomer. Biphenyl organic solvent is reacted with active metal lithium, sodium, and potassium, and others, and reduced to be conjugated double bond; under the alkali environment, the ketal protection radical group is not influenced, and 17- hydroxyl is also not influenced, thus the position of double bond is not changed and doublebonds are directly transformed to be raw material of the last step, and the raw materials are recycled. The method adopts one-step reduction, and solves the existing common technique of opening loopof epoxy bond firstly and then dewatering to be double bonds, and avoids that the ketal protection radical can be damaged by directly reducing epoxy bond to be double bonds by metal in the alkali environment; the epoxy isomer beta and a part of alpha isomer are directly reduced to be the raw material containing conjugated double bond in last step, thus a simple cycle is realized.

Acetic acid wu lisi he intermediate and its preparation method

The invention relates to an ulipristal acetate intermediate product and a preparation method thereof. In particular, the invention discloses multiple intermediate products for preparing 3,3,20,20-bis (ethylene dioxy)-17 alpha-hydroxy-19-norpregna-5(10),9(11)-diene (namely, a compound represented as formula VII), and a preparation method thereof, wherein structures of the intermediate products are represented as formula I, formula II, formula III, formula IV or formula V. Furthermore, the invention discloses a method for preparing the compound represented as formula VII. The method disclosed by the invention is easily available in raw material, mild in reaction condition, high in yield, relatively low in cost, low in byproduct content in reaction process, high in target product purity and applicable to industrial production.

ACOH wu Lisi he key intermediate 3,20-bis-(ethylenedioxy) - 19-norpregna -5,9-diene -17-ol synthesis method

The invention discloses a novel synthetic method of ulipristal acetate key intermediate 3, 20-bis (ethylenedioxy)-19-norpregna-5, 9-dien-17-ol. According to the novel synthetic method, estradiene dione-3-keta17 carbonyl which can be easily obtained from markets reacts with trimethylsilycyanide to directly form stable 17 cyanohydrin silicon ether compound; hydrolysis is conducted on substrate formed from reaction of methyl Grignard reagent and cyanogroup with hydrochloric acid to produce the key intermediate, gestadienol, and the target molecule is obtained through reaction of the gestadienol and ethanediol. The novel synthetic method is simple in process, high in reaction yield and little in environment pollution, and reaction conditions can be controlled easily.

17-Alpha-substituted-11-beta-substituted-4-aryl and 21-substituted 19-norpregnadienediones as antiprogestational agents

The invention provides 17-alpha-substituted-11-beta-substituted-4-aryl and 21-substituted 19-norpregnadienediones as antiprogestational agents.

Method for preparing ulipristal acetate and key intermediate thereof

A method as well as new intermediates for preparing Ulipristal acetate (a compound I) and a method for preparing the new intermediates are provided. The intermediate in a constitutional formula IV is conductive to reacting with methyl lithium or methyl Grignard reagent, a protective group is easy to be removed after a reaction, side reactions are few, a mid-term treatment is simple, the reagents used are cheap, costs are low and a yield is high, if a compound in a constitutional formula V is obtained by the reaction of a compound in a constitutional formula III and the intermediate in the constitutional formula IV, the yield of a two-step reaction is 75%, a purity is above 98%. wherein R is defined in the specification.