117572-30-2

Basic information

• Product Name: 2,6-dibromospirost-4-ene-3-one
• Synonyms: 2,6-dibromospirost-4-ene-3-one
• CAS NO: 117572-30-2
• Molecular Formula: C27H38 Br2 O3
• Molecular Weight: 570.4
• Mol File: 117572-30-2.mol

Chemical Properties

• Boiling Point: 589.7°Cat760mmHg
• Flash Point: 310.5°C
• Appearance: /
• Density: 1.45g/cm³
• Vapor Pressure: 6.95E-14mmHg at 25°C
• Refractive Index: 1.593
• CAS DataBase Reference: 2,6-dibromospirost-4-ene-3-one(CAS DataBase Reference)
• NIST Chemistry Reference: 2,6-dibromospirost-4-ene-3-one(117572-30-2)
• EPA Substance Registry System: 2,6-dibromospirost-4-ene-3-one(117572-30-2)

Safety Data

• Hazardous Substances Data: 117572-30-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2,6-dibromospirost-4-ene-3-one is used as a pharmaceutical agent for its demonstrated biological activities, including its antitumor, antifungal, and antibacterial properties. The presence of bromine atoms may enhance its reactivity, potentially improving the compound's effectiveness in treating various conditions.
Used in Organic Synthesis:
In the field of organic synthesis, 2,6-dibromospirost-4-ene-3-one is utilized as a reactive intermediate due to the presence of bromine atoms, which can participate in a variety of chemical reactions, facilitating the creation of new compounds with potential applications in various industries.
Used in Research and Development:
2,6-dibromospirost-4-ene-3-one serves as a subject of study in research and development settings, where its unique structure and properties are explored for new applications and to understand its mechanisms of action, potentially leading to the discovery of novel therapeutic agents or synthetic pathways.

InChI:InChI=1/C27H38Br2O3/c1-14-5-8-27(31-13-14)15(2)24-23(32-27)11-18-16-9-20(28)19-10-22(30)21(29)12-26(19,4)17(16)6-7-25(18,24)3/h10,14-18,20-21,23-24H,5-9,11-13H2,1-4H3/t14-,15+,16-,17+,18+,20-,21-,23+,24+,25+,26-,27?/m1/s1

Upstream product

• 6870-79-7 (25R)-spirost-4-ene-3-one 

Relevant articles and documents

Conformational analysis of A and B rings in 2-, 4-, and 6-bromosubstituted steroidal 4-en-3-ones by nuclear magnetic resonance

The conformational preference of A and B rings in four differently functionalized bromosubstituted 4-en-3-ones steroids is studied by concerted application of high-resolution one- and two-dimensional nuclear magnetic resonance (NMR) techniques, such as homonuclear and heteronuclear correlated spectroscopy, transient and steady-state nOe spectroscopy, temperature-dependent chemical shift variation, and application of a modified Karplus equation.The steroids studied include 6β-bromocholest-4-en-3-one (3), 4,6β-dibromocholest-1,4-dien-3-one (2), 2α,4,6β-tribromocholest-4-en-3-one (1), and (25R)-2α,6β-dibromospirost-4-en-3-one.Steroids (1-4) were prepared by either acid-catalyzed or free-radical bromination from appropriate 4-en-3-one steroid.The study has yielded an insight into the factors responsible for conformational preferences of the A and B rings of these bromosubsituted steroids.Bromosubstitution at the 2α position is responsible for the inversion of the A ring to inverted 1β,2α-halfchair conformation.The electronic interaction between 4-bromine and carbonyl oxygen distorts the A-ring conformation further.Inversion of the A ring has a concomitant effect of distorsion in the chair form of the B ring.Conformational preferences of A and B rings are not found to be influenced by transmission effect of a side chain or oxygenated ring system.Temperature-dependent NMR studies indicate the reduced conformational flexibility of the A ring for 2α-bromosubstituted steroids.Complete assignment of the 13C and 1H resonances of two of the steroids studied (3 and 4) is presented.Keywords: 4-en-3-one steroids; two-dimensional nuclear magnetic resonance; bromosteroids; conformational analysis; total assignment; A and B rings

Steroids and Related Studies: Part 80 - 5-Pregneno-1',2',5'-oxadiazoles

5-Pregneno-1',2',5'-oxadiazol-20-one (1) and 17α-pregn-5-en-20-yno-1',2',5'-oxadiazol-17-ol (2) have been prepared and tested for their antifertility profiles.The key compound (25R)-5-spirosteno-1',2',5'-oxadiazole (7) has been prepared from (25R)-4-spirosten-3-one through a sequence of bromine treatment, reaction with potassium acetate, treatment with hydrochloric acid, oximation and refluxing with potassium hydroxide in ethylene glycol.The spirosteno-oxadiazole (7) has been degraded to 5,16-pregnadieno-1',2',5'-oxadiazol-20-one (8) and 5-androsteno-1',2',5'-oxadiazol-17-one (10) which have been used to prepare the compounds (1) and (2) respectively.None of the 5-ene steroidal oxadiazoles and the respective 5,6-saturated compounds prepared earlier have shown worthwhile activity in in vivo testing in hamster for post-coital contraceptive efficacy, and in in vitro testing against rabbit uterine cytosol for progesterone receptor binding affinity.