68480-23-9

Usage

Uses

Used in Organic Synthesis:
Methyl 2-oxo-1-(2-pentynyl)cyclopentanecarboxylate is used as a building block for the synthesis of diverse molecules, including pharmaceuticals and natural products, due to its unique structure that allows for the incorporation of cyclopentane and alkynyl groups into various molecular scaffolds.
Used in Drug Discovery Research:
In the pharmaceutical industry, methyl 2-oxo-1-(2-pentynyl)cyclopentanecarboxylate is used as a key intermediate in the development of new drugs and materials, contributing to the production of biologically active compounds.

InChI:InChI=1/C12H16O3/c1-3-4-5-8-12(11(14)15-2)9-6-7-10(12)13/h3,6-9H2,1-2H3

Upstream product

• 16400-32-1 1-bromo-pent-2-yne 
• 10472-24-9 methyl 2-oxocyclopentane-1-carboxylate 
• 81159-43-5 methanesulfonic acid pent-2-ynyl ester 

Downstream Products

• 41031-88-3 (Z)-2-(2-pentenyl)-2-cyclopenten-1-one 
• 57026-62-7 2-(Pent-2-enyl)cyclopentan-1-one 
• 42537-02-0 2-<(Z)-2-pentenyl>cyclopentanone 

Relevant academic research and scientific papers

Route Scouting towards a Methyl Jasmonate Precursor

For the synthesis of methyl jasmonate (1), via the strategic intermediates 3, 4, and 6a, we constructed a synthetic network via the diverse intermediates 7-10, 13, 14, 17, and 18. This allowed us to compare the efficiency of more than 20 novel routes. The most productive pathway with a total yield of 38% is represented by the sequence→5a→5m→13b→13a→6a→4 and proceeds via sequential bromination, basic elimination, decarbomethoxylation, isomerization, and finally Lindlar hydrogenation. The shortest selective way, 2a→[(E,E)-12b]→3→4, is a two-pot sequence using a modification of Naef's method, based on an aldol condensation between inexpensive cyclopentanone (2a) and crotonaldehyde, with in situ Corey-Chaykovsky cyclopropanation under phase transfer conditions. The key intermediate 3 was then simply pyrolyzed to afford 4 in 27% total yield. The alternative isomerization method via the six-step deviation→5a→5c→8c→13a→6a→4 was longer, although more efficient, with a total yield of 32%. Alternatively, a yield of 34% was obtained via the five-step sequence→5a→5c→2h→2i→4. Another favored six-step pathway,→5a→5c→2h→17a→14a→4 afforded the target compound in 35% total yield.

Rhodium-catalyzed isomerization of unactivated alkynes to 1,3-dienes

A rhodium/binap complex has been found to effectively catalyze the isomerization of unactivated internal alkynes to the corresponding 1,3-dienes in the presence of an azomethine imine as the reaction promoter. The Royal Society of Chemistry 2006.