4075-12-1

Usage

InChI:InChI=1/C19H24O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h3-4,7,9,11,14-17,21H,5-6,8,10H2,1-2H3/t14-,15-,16-,17-,18-,19-/m0/s1

Upstream product

• 42224-78-2 17β-acetoxyandrost-1,4,6-trien-3-one 
• 633-35-2 1,4,6-androstatriene-3,17-dione 
• 58-22-0 testosterone 
• 135214-68-5 2α,6β-dibromo-17β-acetoxyandrost-3-en-3-one 
• 1458-93-1 6β-bromotestosterone acetate 
• 1045-69-8 testosterone acetate 
• 53-43-0 dehydroepiandrosterone 

Relevant academic research and scientific papers

Iodine, a Mild Reagent for the Aromatization of Terpenoids

Efficient procedures based on the use of iodine for the aromatization of a series of terpenoids possessing diene and homoallylic or allylic alcohol functionalities are described. Different examples are reported as a proof-of-concept study. Furthermore, iodine also proved to mediate the dehydrogenation of testosterone.

Chemoselective reduction of 1,4,6-cholestatrien-3-one and 1,4,6-androstatriene-3,17-dione by various hydride reagents

The chemoselectivity of rigid cyclic α,β-unsaturated carbonyl group on the reducing agents was influenced by the ring size and steric factor. Cholesterol (cholest-5-en-3β-ol) and dehydroepiandrosterone (DHEA) were oxidized with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone to form 1,4,6-cholestatrien-3-one and 1,4,6-androstatriene-3,17-dione. They were reduced with NaBH4, lithium tri-sec-butylborohydride (l-Selectride), LiAlH4, 9-borabicyclo[3.3.1]nonane (9-BBN), lithium triethylborohydride (Super-hydride), and BH3·(CH3)2S in various conditions, respectively. Reduction of 1,4,6-cholestatrien-3-one and 1,4,6-androstatriene-3,17-dione by NaBH4 (4 equiv.) produced 4,6-cholestadien-3β-ol and 4,6-androstadiene-3β,17β-diol, respectively. Reduction by l-Selectride (12 equiv.) afforded 4,6-cholestadien-3α-ol and 4,6-androstadiene-3α,17β-diol, chemoselectively. Reaction with Super-hydride (12 equiv.) produced 4,6-cholestadien-3-one and 3-oxo-4,6-androstadien-17β-ol. Reduction of 1,4,6-cholestatrien-3-one by 9-BBN (14 equiv.) produced 1,4,6-cholestatrien-3α-ol, but 1,4,6-androstatriene-3,17-dione was not reacted with 9-BBN in the reaction conditions. Reaction of LiAlH4 (6 equiv.) formed 4,6-cholestadien-3β-ol and 3-oxo-1,4,6-androstatrien-17β-ol. Reduction of 1,4,6-cholestatrien-3-one by BH3·(CH3)2S (11 equiv.) gave cholestane as major compound and unlike reactivity of cholesterol, 1,4,6-androstatriene-3,17-dione by 8 equiv. of BH3·(CH3)2S formed 3-oxo-1,4,6-androstatrien-17β-ol. LiAlH4 and BH3·(CH3)2S showed relatively low chemoselectivity.