2625-60-7

Usage

Uses

Used in Pharmaceutical Research and Development:
17-acetyl-10,13-dimethyl-1,2,6,7,8,9,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-one is used as a pharmaceutical research and development compound for its potential therapeutic properties. Its unique chemical structure and properties make it a valuable molecule for studying steroid chemistry and its biological effects, which can contribute to the discovery of new drugs and treatments.
Used in Steroid Chemistry Studies:
17-acetyl-10,13-dimethyl-1,2,6,7,8,9,14,15,16,17-decahydrocyclopenta[a ]phenanthren-3-one is used in the study of steroid chemistry due to its unique structure and properties. Understanding its chemical behavior and interactions can provide insights into the broader field of steroid chemistry, potentially leading to advancements in the development of new pharmaceuticals and therapeutic agents.
Used in Natural Product Research:
As a naturally occurring compound found in some plant species and fungi, 17-acetyl-10,13-dimethyl-1,2,6,7,8,9,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-one is used in natural product research. Studying its presence, distribution, and potential biological activities in these organisms can contribute to a better understanding of the role of natural products in various biological processes and their potential applications in medicine and other fields.

InChI:InChI=1/C21H28O2/c1-13(22)17-6-7-18-16-5-4-14-12-15(23)8-10-20(14,2)19(16)9-11-21(17,18)3/h9,11-12,16-19H,4-8,10H2,1-3H3

Upstream product

• 108-75-8 2,4,6-trimethyl-pyridine 
• 115758-63-9 12α-(toluene-4-sulfonyloxy)-pregn-4-ene-3,20-dione 
• 80-75-1 11-alpha-hydroxyprogesterone 
• 115759-02-9 11α-hydroxyprogesterone toluene-p-sulphonate 
• 96671-93-1 4β,11β,12α-Tribrom-5β-pregnandion-(3,20) 
• 106168-72-3 3-Ethylendioxy-5β-pregnen-(11)-on-(20) 
• 95949-16-9 11β,12α-Dibrom-5β-pregnandion-(3,20) 
• 1096-39-5 5β-H-11-pregnene-3,20-dione 
• 98-59-9 p-toluenesulfonyl chloride 
• 1109-03-1 12α-(toluene-sulfonyl-(4)-oxy)-5β-pregnanedione-(3,20) 
• 7726-95-6 bromine 
• 64-19-7 acetic acid 
• 96214-00-5 11β,12α-Dibrom-pregnen-(4)-dion-(3,20) 
• 10116-24-2 11α-methanesulfonyloxy-pregn-4-ene-3,20-dione 

Downstream Products

• 1242-47-3 12α-bromo-11β-hydroxy-pregn-4-ene-3,20-dione 
• 1099-20-3 11β,12β-Epoxy-pregn-4-en-3,20-dion 

Relevant academic research and scientific papers

Chloromethanesulfonate as an efficient leaving group: Rearrangement of the carbon-carbon bond and conversion of alcohols into azides and nitriles

The chloromethanesulfonate (monochlate) served as an efficient leaving group for rearrangement of the carbon-carbon bond and conversion of alcohols into azides and nitriles. The treatment of the monochlate 16a with zinc acetate in dioxane at 90 °C effected migration of the 4α-methyl group to give alkene 17a. Upon similar treatment of the monochlates 22a, 25a, 28a, and 31a with zinc acetate, the carbon-carbon bonds antiperiplanar to the hydroxyl groups efficiently migrated to afford the alkenes 23a, 26a-c, 29a,b, and 32a, respectively. In the case of the diol 40, the monochlate was converted into the ketone 41 via a rearrangement-ring expansion. The reaction of the monochlates 44a, 47a, 49a, 52a, and 57a with sodium azide or lithium azide in N,N-dimethylformamide efficiently afforded the azides with inversion of the configuration. The introduction of a nitrile group to the sterically hindered alcohol 59 was performed in high yield by the reaction of the monochlate 60a with sodium cyanide.

Ring-c Aromatic Steroids. Part 4. The c-Aromatic Analogue of Progesterone

The ring-c aromatic analogue of progesterone, 18-norpregna-4,8,11,13-tetraene-3,20-dione (2), was formed together with its 17-epimer (3) when 9α,11α-epoxy-20ξ-hydroxy-3-oxopregn-4-eno-18,20-lactone (14) was subjected to oxidative decarboxylation, and the resulting products treated with boron trifluoride.The precursor (14) was synthesised as follows. 11α-Hydroxyprogesterone (4) was dehydrated, and the product then selectively reduced (by two routes) to 20β-hydroxypregna-4,9(11)-dien-3-one (9).The latter was functionalised at C-18 to give 3-oxopregna-4,9(11)-dieno-18,20-lactone (10) which was oxidised, after opening of the lactone ring, to the corresponding lactol (12).The latter was converted into the required lactol epoxide (14).Internal displacement on the 9α,11α-epoxide occurred when the lactol epoxide (14) was treated with acid, yielding 9α-hydroxy-3,20-dioxopregn-4-eno-18,11β-lactone (16).