4588-81-2

Basic information

• Product Name: 17-bromoacetoxy-4-androsten-3-one
• Synonyms: 17-bromoacetoxy-4-androsten-3-one
• CAS NO: 4588-81-2
• Molecular Formula: C₂₁H₂₉BrO₃
• Molecular Weight: 409.3572
• Mol File: 4588-81-2.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 487.3°Cat760mmHg
• Flash Point: 248.5°C
• Appearance: /
• Density: 1.32g/cm³
• Vapor Pressure: 1.2E-09mmHg at 25°C
• Refractive Index: 1.565
• CAS DataBase Reference: 17-bromoacetoxy-4-androsten-3-one(CAS DataBase Reference)
• NIST Chemistry Reference: 17-bromoacetoxy-4-androsten-3-one(4588-81-2)
• EPA Substance Registry System: 17-bromoacetoxy-4-androsten-3-one(4588-81-2)

Safety Data

• Hazardous Substances Data: 4588-81-2(Hazardous Substances Data)

Usage

InChI:InChI=1/C21H29BrO3/c1-20-9-7-14(23)11-13(20)3-4-15-16-5-6-18(25-19(24)12-22)21(16,2)10-8-17(15)20/h11,15-18H,3-10,12H2,1-2H3/t15-,16-,17-,18?,20-,21-/m0/s1

Upstream product

• 22118-09-8 2-bromoacetyl chloride 
• 58-22-0 testosterone 
• 598-21-0 2-Bromoacetyl bromide 

Downstream Products

• 131447-69-3 testosterone triphenylphosphoranylideneacetate 
• 1255-49-8 testosterone 17β-phenylpropionate 

Relevant articles and documents

Selective Construction of C?C and C=C Bonds by Manganese Catalyzed Coupling of Alcohols with Phosphorus Ylides

Herein, we report the manganese catalyzed coupling of alcohols with phosphorus ylides. The selectivity in the coupling of primary alcohols with phosphorus ylides to form carbon-carbon single (C?C) and carbon-carbon double (C=C) bonds can be controlled by the ligands. In the conversion of more challenging secondary alcohols with phosphorus ylides the selectivity towards the formation of C?C vs. C=C bonds can be controlled by the reaction conditions, namely the amount of base. The scope and limitations of the coupling reactions were thoroughly evaluated by the conversion of 21 alcohols and 15 ylides. Notably, compared to existing methods, which are based on precious metal complexes as catalysts, the present catalytic system is based on earth abundant manganese catalysts. The reaction can also be performed in a sequential one-pot reaction generating the phosphorus ylide in situ followed manganese catalyzed C?C and C=C bond formation. Mechanistic studies suggest that the C?C bond was generated via a borrowing hydrogen pathway and the C=C bond formation followed an acceptorless dehydrogenative coupling pathway. (Figure presented.).

Long-acting contraceptive agents: testosterone esters of unsaturated acids

The synthesis of 13 new esters of testosterone is described, with the esterifying acids bearing acetylenic, olefinic, or polyunsaturated functions in the chain, for evaluation as long-acting androgens.

SYNTHESIS AND EVALUATION OF BROMOACETOXY 4-ANDROSTEN-3-ONES AS ACTIVE SITE-DIRECTED INHIBITORS OF HUMAN PLACENTAL AROMATASE

2α-Bromoacetoxy (II), 6-bromoacetoxy (VII and X), and 19-bromoacetoxy (XII) derivatives of androstenedione and 17β-bromoacetoxy compounds (III, IV, XIII-XVI) were synthesized as potential affinity-labeling reagents for aromatase. 6α-Bromoacetoxy derivative VII was the most potent inhibitor of human placental microsomal aromatase activity among this series.Its inhibitory activity was higher than that of the parent 6α-hydroxy compound V, although other bromoacetates showed weaker inhibition of aromatase than the corresponding alcohols.The bromoacetates (except the 6β-bromoacetate X) inhibited aromatase activity in a time-dependent manner in the absence of NADPH, and the enzyme inactivation was blocked by the addition of androstenedione to the incubates.Kinetic analysis of the time- and concentration-dependent inhibition by the 6β-bromo-17β-bromoacetoxy compound XV gave an apparent Ki of 25 μM and Kinact of 0.027 min-1.