34184-82-2

Basic information

• Product Name: 17-hydroxypregna-4,9(11)-diene-3,20-dione
• Synonyms: 17-hydroxypregna-4,9(11)-diene-3,20-dione;17-Hydroxypregna-4,9(11)-diene-3,20-dione Pregna-4,9(11)-dien-17-ol-3,20-dione
• CAS NO: 34184-82-2
• Molecular Formula: C₂₁H₂₈O₃
• Molecular Weight: 328.44522
• EINECS: 251-868-4
• Mol File: 34184-82-2.mol

Chemical Properties

• Boiling Point: 497.5°Cat760mmHg
• Flash Point: 268.8°C
• Appearance: /
• Density: 1.17g/cm³
• Vapor Pressure: 5.52E-12mmHg at 25°C
• Refractive Index: 1.576
• CAS DataBase Reference: 17-hydroxypregna-4,9(11)-diene-3,20-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 17-hydroxypregna-4,9(11)-diene-3,20-dione(34184-82-2)
• EPA Substance Registry System: 17-hydroxypregna-4,9(11)-diene-3,20-dione(34184-82-2)

Safety Data

• Hazardous Substances Data: 34184-82-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
17-Hydroxypregna-4,9(11)-diene-3,20-dione is used as an intermediate in the synthesis of various steroidal drugs for the treatment of different medical conditions. Its unique structural features make it a valuable compound for the development of new therapeutic agents.
Used in Ophthalmic Applications:
In the ophthalmic industry, 17-hydroxypregna-4,9(11)-diene-3,20-dione has been used in the synthesis of the drug fluorometholone, which is an effective anti-inflammatory agent used for the treatment of various eye conditions, such as uveitis and postoperative inflammation.
Used in Hormone Replacement Therapy:
17-Hydroxypregna-4,9(11)-diene-3,20-dione is also used as a precursor in the synthesis of hormone replacement therapy (HRT) drugs, particularly for the treatment of menopausal symptoms and osteoporosis in women.
Used in Contraceptive Development:
This steroidal compound has been explored for its potential use in the development of new contraceptive agents, due to its ability to modulate hormonal levels and interfere with the reproductive cycle.

InChI:InChI=1/C21H28O3/c1-13(22)21(24)11-8-18-16-5-4-14-12-15(23)6-9-19(14,2)17(16)7-10-20(18,21)3/h7,12,16,18,24H,4-6,8-11H2,1-3H3/t16-,18+,19+,20+,21+/m1/s1

Upstream product

• 113752-83-3 17-hydroxy-11α,21-bis-methanesulfonyloxy-pregn-4-ene-3,20-dione 
• 144490-18-6 C₂₂H₂₈O₄ 
• 144396-26-9 C₂₇H₃₆O₆ 
• 1035-69-4 androst-4,9⁽¹¹⁾-dien-3,17-dione 
• 917-54-4 methyllithium 
• 560-62-3 9-alpha-hydroxyandrost-4-ene-3,17-dione 
• 75868-48-3 21-chloro-17-hydroxy-pregna-4,9⁽¹¹⁾-diene-3,20-dione 
• 33767-06-5 11β,17α-dihydroxy-21-iodopregn-4-ene-3,20-dione 
• 641-77-0 21-deoxycortisol 
• 603-98-5 11α,17α-dihydroxypregn-4-ene-3,20-dione 
• 68-96-2 17-hydroxyprogesterone 
• 77881-13-1 17β-cyano-17α-hydroxy-4-androsten-3-one 
• 63-05-8 Androstenedione 
• 83196-56-9 17β-Cyano-17α-hydroxyandrosta-4,9(11)-dien-3-one 

Downstream Products

• 5106-48-9 17-acetoxy-pregna-4,9⁽¹¹⁾-diene-3,20-dione 
• 641-77-0 21-deoxycortisol 
• 1882-82-2 17-hydroxy-pregn-4-ene-3,11,20-trione 
• 7780-63-4 pregna-4,9(11)-diene-17α,21-diol-3,20-dione 17,21-diacetate 
• 23460-76-6 21-acetoxy-pregna-4,9⁽¹¹⁾,16-triene-3,20-dinone 
• 37413-91-5 2-((10S,13S,14S)-10,13-dimethyl-3-oxo-6,7,8,10,12,13,14,15-octahydro-3H-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl acetate 
• 2529-45-5 fluorogestone acetate 
• 5106-48-9 17α-acetoxy-Δ9(11)-progesterone 

Relevant articles and documents

Synthesis of 17α-Hydroxy-20-oxo-pregnanes from 17(20)-Dehydro-23,24-dinorcholan-22-oic Acids

Title transformation involving catalytic epoxidation, Curtius rearrangement and acidic hydrolysis has been accomplished.This synthetic sequence offers a novel route from a partial microbial side chain degradation product of natural sterols into useful precursors of antiinflammatory, antiandrogen and gestagen pharmaceuticals.

Method for preparing 17alpha-hydroxy androstane-4,9-diene-3,20-dione

The invention discloses a method for preparing 17alpha-hydroxyl androstane-4,9-diene-3,20-diketone, and the method comprises the following steps: (1) dispersing a ketal protector (I) in an organic solvent, and carrying out Grignard reaction in a tubular reactor filled with a catalyst; (2) carrying out a deprotection reaction on the obtained Grignard reaction raw material solution in a tubular reactor filled with strongly acidic ion exchange resin to prepare an intermediate ketone (II); (3) carrying out post-treatment on the feed liquid subjected to the deprotection reaction to obtain 17alpha-hydroxyl androstane-4,9-diene-3,20-diketone (III). According to the invention, the continuous tubular reaction technology is used for replacing the existing interval kettle type reaction to prepare 17alpha-hydroxyl androstane-4,9-diene-3,20-diketone, so the automatic control of the process is easy to realize, the continuous production is convenient, and the process stability is improved.

An efficient procedure for the synthesis of 21-acetoxypregna-1,4,9(11),16-tetraene-3,20-dione

Background: Halogenated corticosteroids are widely used in medicine, and the global need of these steroidal APIs is estimated to be 40 - 70 tons, annually. Vietnam currently imports the pharmaceutical compounds up to 90%, in particular 100% of steroidal drugs. Currently, industrial production is based on the chemical syntheses of corticosteroids from either 16-dehydropregnenolone acetate (obtained from diosgenin) or androstenedione (obtained from phytosterol). The development of shorter synthetic schemes and more economically feasible technologies is of great significance. Introduction of 1(2)-double bond at the final stages of the corticosteroids synthesis results inpoor yield. 21-Acetoxypregna-1,4,9(11),16-tetraene-3,20-dione (tetraene acetate) is a key intermediate in the synthesis of highly active halogenated corticosteroids such as dexamethasone and other halogenated corticosteroids. 21-acetoxypregna-1,4,9(11),16-tetraene-3,20-dione is a key intermediate in the synthesis of dexamethasone from the readily available and cheap 9α-hydroxyandrost-4-ene-3,17-dione. Objective: The purpose of this study was the development of an efficient and shorter procedure for the synthesis of 21-acetoxypregna-1,4,9(11),16-tetraene-3,20-dione from 9α-hydroxyan-drostenedione, which is a product of a bio-oxidative degradation of the side chain of phytosterols. Methods: Pregnane side chain was constructed using cyanohydrin method. For 1(2)-dehydrogenation, selene dioxide was applied for the introduction of Δ1(2)-double bond. Other stages of the synthesis were epimerization, Stork’s iodination procedure and dehydration. Result: 21-Acetoxypregna-1,4,9(11),16-tetraene-3,20-dione was prepared from 9α-hydroxyandrostenedione in yield more than 46%. Conclusion: An efficient and practically feasible procedure for the synthesis of 21-acetoxypregna-1,4,9(11),16-tetraene-3,20-dione from 9α-hydroxyandrostenedione, a key intermediate for the synthesis of 9-haloidated corticoids, has been developed. The procedure can be applied for the production of value-added 9-haloidated corticoids.

Methylprednisolone intermediate debrominated product and preparation method thereof

The invention discloses a methylprednisolone intermediate debrominated product and a preparation method thereof. According to the preparation method, a compound shown as a formula I is used as a raw material, and a dechlorination reaction, a bromination reaction, a debromination reaction and an oxidation reaction are sequentially performed to prepare a compound (debrominated substance) shown as aformula V. The preparation method has the advantages of short synthetic route, high yield, low cost and easily available raw materials, is suitable for industrial production, and has very high industrial value.

Fluorometholone, fluorometholone acetate, and preparation method thereof

The invention discloses fluorometholone, fluorometholone acetate, and a preparation method thereof. According to the preparation method, a compound represented by a formula (II) is taken as a raw material, the compound carries out de-chlorination reaction, esterification reaction, methenylation reaction, hydrogenation reaction, fermentation de-hydrogenation reaction, epoxidation reaction, and ring-opening reaction in sequence to obtain derivatives of fluorometholone; and fluorometholone derivatives carry out hydrolysis to obtain fluorometholone. The preparation method has the advantages of short synthesis route, high yield, low raw material cost, easily available raw materials, simple and convenient purification, high product purity, and strong technological operability, is suitable for industrial production, and has a high industrialization value.

Synthetic method of Delta-9,11-hydroxyl progesterone

The invention discloses a synthetic method of Delta-9,11-hydroxyl progesterone. The synthetic method comprises the following steps: (1) a siloxane reaction: carrying out the siloxane on a 17-beta-cyano substance, chloromethyl chlorosilane and a catalyst in a solvent to obtain a siloxane substance; (2) a chloromethylation reaction: carrying out the reaction on the siloxane, LDA and concentrated hydrochloric acid and adjusting the pH of the system after the reaction to obtain a chloromethyl substance; and (3) a reduction reaction: carrying out the reaction on the chloromethyl substance, a reducer and concentrated hydrochloric acid, and concentrating and separating out crystals to obtain the Delta-9,11-hydroxyl progesterone. The initial raw material 17-beta-cyano is originated from a biofermented product 9-OH AD, the production links are green and environment-friendly, and no heavy metal chromium is generated. The cost of the synthetic method is reduced greatly compared with that of conventional processes. In addition, the product quality is improved greatly compared with that of conventional processes. The product yield can reach 90-95%, and the HPLC purity reaches over 99.5%.

Metal-Free Iodine-Mediated Deoxygenation of Alcohols in the Position α to Electron-Withdrawing Groups

The use of a substoichiometric amount of molecular iodine in the presence of PPh3 and pyridine effects a direct deoxygenation of primary and secondary alcohols in positions α to a variety of activating electron-withdrawing groups, including ketones, esters, amides, imides and nitrile groups.

Preparation method of 17alpha-acetoxy-(8, 13)-ene-11alpha-hydroxyprogesterone

The invention relates to the field of compound preparation, in particular to a preparation method of 17alpha-acetoxy-(8, 13)-ene-11alpha-hydroxyprogesterone. The method includes: taking 11alpha, 17alpha-dihydroxyprogesterone as the raw material, carrying out elimination reaction, esterification reaction, bromination epoxy reaction and fluorination reaction to synthesize a 17alpha-acetoxy-(8, 13)-ene-11alpha-hydroxyprogesterone crude product; and finally performing column chromatography to obtain the high purity target object 17alpha-acetoxy-(8, 13)-ene-11alpha-hydroxyprogesterone refined product. The invention mainly solves the problem that the existing technology is short of synthesis method of the product, the product can be used as a reference substance for quality control of flurogestone acetate, is more beneficial to control of the flurogestone acetate quality and improvement of the drug safety.

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.

Preparation method of dexamethasone intermediate

The invention discloses a preparation method of a dexamethasone intermediate. According to the preparation method of the dexamethasone intermediate, a compound 17beta-cyano-17alpha-hydroxyandrost-4,9-diene-3-one is taken as a starting material and has a 3-site keto-carbonyl protective reaction, a 17-site hydroxyl protective reaction, a Grignard reaction, a 3-site keto-carbonyl deprotection reaction, a dehydration reaction and a dehydrogenation reaction, and 5ST tetraene methyl is obtained. The starting material 17beta-cyano-17alpha-hydroxyandrost-4,9-diene-3-one has abundant sources and is low in cost, further, the process route design is novel, the production process has small influence on the environment, the overall yield is high, and the preparation method of the dexamethasone intermediate has higher competitiveness and is suitable for industrial production.