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
• Article Data: 2

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

General Description

2,6-dibromospirost-4-ene-3-one is a chemical compound classified under the category of spirosteroids, which are naturally occurring steroids with a spiro (bridged) ring. This particular compound contains two bromine atoms and a 3-one functional group on the spirost-4-ene skeleton. Spirosteroids have been shown to possess various biological activities, including antitumor, antifungal, and antibacterial properties. The bromine atoms present in 2,6-dibromospirost-4-ene-3-one may contribute to its reactivity and potential use in organic synthesis. Additionally, the presence of the 3-one group suggests that it may have potential pharmaceutical applications. Overall, 2,6-dibromospirost-4-ene-3-one is a chemically interesting compound with potential for further study and application in various fields.

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.