74644-60-3

Basic information

• Product Name: (3S,8R,9S,10R,13S,16R)-16-Bromo-3-hydroxy-10,13-dimethyl-1,2,3,4,7,8,9,10,11,12,13,14,15,16-tetradecahydro-cyclopenta[a]phenanthren-17-one
• CAS NO: 74644-60-3
• Molecular Weight: 367.326
• Mol File: 74644-60-3.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: (3S,8R,9S,10R,13S,16R)-16-Bromo-3-hydroxy-10,13-dimethyl-1,2,3,4,7,8,9,10,11,12,13,14,15,16-tetradecahydro-cyclopenta[a]phenanthren-17-one(CAS DataBase Reference)
• NIST Chemistry Reference: (3S,8R,9S,10R,13S,16R)-16-Bromo-3-hydroxy-10,13-dimethyl-1,2,3,4,7,8,9,10,11,12,13,14,15,16-tetradecahydro-cyclopenta[a]phenanthren-17-one(74644-60-3)
• EPA Substance Registry System: (3S,8R,9S,10R,13S,16R)-16-Bromo-3-hydroxy-10,13-dimethyl-1,2,3,4,7,8,9,10,11,12,13,14,15,16-tetradecahydro-cyclopenta[a]phenanthren-17-one(74644-60-3)

Safety Data

• Hazardous Substances Data: 74644-60-3(Hazardous Substances Data)

Upstream product

• 1093-91-0 3β-hydroxy-16α-bromoandrost-5-ene-17-one 
• 50-00-0 formaldehyd 
• 24335-49-7 3β-acetoxy-16α-bromoandrost-5-en-17-one 
• 111293-55-1 3-acetoxy-16-bromo-androst-5-en-17-ol 
• 102813-25-2 3β-acetoxy-16β-bromo-17-hydroxy-pregn-5-en-20-one oxime 
• 53-43-0 dehydroepiandrosterone 
• 24335-50-0 3β-acetoxy-16β-bromo-androst-5-en-17-one 
• 53-43-0 dehydroepiandrosterone 

Downstream Products

• 1232-73-1 16α-hydroxy dehydroepiandrosterone 
• 1093-91-0 3β-hydroxy-16α-bromoandrost-5-ene-17-one 
• 1159-66-6 (R)-3,17-Dihydroxy-10,13-dimethyl-1,2,3,4,7,8,9,10,11,12,13,14,15,17-tetradecahydro-cyclopenta[a]phenanthren-16-one 
• 133522-45-9 14β-androst-5-ene-3β,17α-diyl 3-acetate 17-p-toluenesulfonate 
• 53-43-0 3β-hydroxy-14β-androst-5-en-17-one 

Relevant articles and documents

Synthesis and biological evaluation of 3β-androsta-5,8(14),15-trien-17-one derivatives as potential anticancer agents

A novel and operationally simple method for highly efficient synthesis of promising anti-cancer 3β-hydroxy-16-arylandrosta-5,8(14),15-trien-17-ones was reported. Compounds were tested for their cytotoxic activities against A549, SKOV3, MKN-45 and MDA-MB-4

Stereoselective hydrolysis of 16α-halo-17-keto steroids and long-range substitution effects on the hydrolysis of 16α-bromo-17-ketones and 2α-bromo-3-ketones

Epimerization of 16α-chloro- (1a), bromo- (1b), and iodo-3β-hydroxy-5-androsten-17-one (1c) by a brief treatment with 0.2 equiv NaOH in aqueous pyridine reached equilibrium between 16α- and 16β-halo ketones. 16α-/16β-Halo ketone ratios at equilibrium were 1.5 for Cl, 1.25 for Br, and 1.0 for I. Kinetic analysis showed that compounds 1a-c were stereoselectively converted to the corresponding 16α-hydroxy derivative 3 by an S(N)2 mechanism, in which the order of the apparent reactivity was Br > I > Cl. The hydrolysis of a number of 16α-bromo-17-ketones and 2α-bromo-3-ketones was carried out. The yields of the corresponding alcohols were found to depend on remote structural features in the steroids.

CONTROLLED ALKALINE HYDROLYSIS OF STEROIDAL α-BROMOKETONES: NEW CONDITIONS AND SYNTHESIS OF 2α-HYDROXY-3-ONES

Controlled alkaline hydrolysis of 16α-bromo-17-keto steroids 1, 5 and 7 with potassium carbonate and tetra-n-butylammonium hydroxide (n-Bu4NOH) and synthesis of 2α-hydroxy-3-ones 11, 13 and 16 by the controlled hydrolysis of the corresponding 2α-bromo-3-ones 9, 12 and 15 are described.Treatment of the bromoketones 1, 5 and 7 with potassium carbonate in aqueous acetone or with n-Bu4NOH in aqueous dimethylformamide (DMF) gave 16α-hydroxy-17-ones 3, 6 and 8 in 85-90percent yield, respectively. 2α-Hydroxy-3-ones 11, 13 and 16 were obtained by hydrolysis of the corresponding bromoketones 9, 12 and 15 in high yields using the above conditions or sodium hydroxide in pyridine or DMF, respectively.Deuterium labeling experiments suggested that equilibration between the 2α-bromoketone 9 and the 2β-bromo isomer 10 precedes the formation of the ketol 11 in which the true intermediate might be the 2β-isomer 10.However, rearranged androstane derivatives, 3β-hydroxy-2-ones 18 and 20, were stereoselectively obtained by treatment of the bromoketones 12 and 15 with an excess amount of sodium hydroxide.