17243-87-7

Basic information

• Product Name: (16E)-3-hydroxy-16-(phenylmethylidene)androst-5-en-17-one
• CAS NO: 17243-87-7
• Molecular Formula: C₂₆H₃₂O₂
• Molecular Weight: 376.5311
• Mol File: 17243-87-7.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 543.1°C at 760 mmHg
• Flash Point: 228.8°C
• Density: 1.15g/cm³
• Vapor Pressure: 1.26E-12mmHg at 25°C
• Refractive Index: 1.605
• CAS DataBase Reference: (16E)-3-hydroxy-16-(phenylmethylidene)androst-5-en-17-one(CAS DataBase Reference)
• NIST Chemistry Reference: (16E)-3-hydroxy-16-(phenylmethylidene)androst-5-en-17-one(17243-87-7)
• EPA Substance Registry System: (16E)-3-hydroxy-16-(phenylmethylidene)androst-5-en-17-one(17243-87-7)

Safety Data

• Hazardous Substances Data: 17243-87-7(Hazardous Substances Data)

Usage

General Description

"(16E)-3-hydroxy-16-(phenylmethylidene)androst-5-en-17-one" is a chemical compound that belongs to the class of androstenediones. It is a steroid compound with a hydroxy group at the 3-position and a phenylmethylidene group at the 16-position. (16E)-3-hydroxy-16-(phenylmethylidene)androst-5-en-17-one is a derivative of androstenedione, which is a hormone and intermediate in the biosynthesis of testosterone and estrone. It may have potential biological activities and applications in the field of steroid chemistry and pharmacology. However, further research is needed to fully understand its properties and potential uses.

Upstream product

• 17243-84-4 3β,17α-Dihydroxy-16β,17β-(1-phenyl-2-hydroxymethylen-3-oxo-trimethylen)-androst-5-en 
• 17243-79-7 3β-Acetoxy-17α-hydroxy-16β.17β-(1-phenyl-3-oxo-trimethylen)-androsten-(5) 
• 853-23-6 prasterone acetate 
• 100-52-7 benzaldehyde 
• 53-43-0 dehydroepiandrosterone 
• 17243-85-5 α-<3β-Acetoxy-17-oxo-Δ⁵-androsten-16ξ-yl>-phenylessigsaeure-methylester 

Downstream Products

• 1428382-38-0 C₄₁H₄₃NO₃S 
• 1369581-64-5 3β-hydroxy-5-en-7'-phenyl-androstano[17,16-d][1,2,4]triazolo[1,5-a]pyrimidine 
• 129908-91-4 16-benzylidene-17-oxo-5-androsten-3β-yl acetate 

Relevant articles and documents

Androsterone-based gels enable diastereospecific reductions and diastereoselective epoxidations of gelators

Eleven new androsterone-based gelators were synthesized, and their gelation properties and gel-mediated reactions were investigated. The relationships between the structures, gelation and self-assembly processes of the gelators are discussed. By using granular PTFE (polytetrafluoroethylene) as costirrers, quantitative and diastereospecific reductions of the gelator carbonyl groups mediated by water were achieved in the gels of seven gelators. This reduction did not occur in the control experiment which used organic solvent-mediated conventional conditions. The diastereospecific and quantitative reductions possibly occur via a hydrogen-bonded-activated carbonyl mechanism. Five of the gelators underwent gel-mediated epoxidation and the products were more diastereoselective than those obtained using conventional epoxidation reactions. This can be attributed to the ordered arrangements in the gels.

Neighboring heteroatom effect unique to aqueous aldol reactions of water-insoluble substrates

The reactions of ketones and aldehydes in the presence of Li+ and in the presence or absence of PTC mediated by water were performed to produce aldol products. Several advantages of the aqueous reactions over organic solvent-mediated ones have been demonstrated including higher yields, shorter reaction times, simpler purifications, and better functional group tolerance. Some reactions that do not take place in organic solvents have been realized in water. The successes are attributed to the neighboring heteroatom effect. In the aqueous aldol condensations, Li2CO3 was an efficient catalyst, and therefore base-liable groups such as epoxides, esters, and silyl groups could survive. For heteroaromatic ethanones, the aqueous aldol reactions were accomplished without PTC to give β-hydroxyketones in good yields. The water-mediated condensations of aldosyl hemiacetals with aromatic ketones led to a new carbohydrate-derived skeleton in quantitative yields. To some extent, this research has expanded the applicablities of aldol condensations and reactions.

Synthesis of novel 16-spiro steroids: Spiro-7′-(aryl)tetrahydro-1H- pyrrolo[1,2-c][1,3]thiazolo-trans-androsterone hybrid heterocycles

The 1,3-dipolar cycloaddition of azomethine ylide derived in situ from the reaction of acenaphthylene-1,2-dione and 1,3-thiazolane-4-carboxylic acid to various exocyclic dipolarophiles synthesized from trans-androsterone and trans-dehydroandrosterone afforded a library of novel spiro[5′.2″] acenaphthylene-1″-one-spiro[16.6′]-(7′-aryl) -tetrahydro-1H-pyrrolo [1,2-c][1,3]thiazolo-trans-androsterone/ dehydroandrosterone hybrid heterocycles respectively. These reactions proceeded stereo-specifically affording a single isomer of the 16-spiro steroids in excellent yields.