68480-23-9

Basic information

• Product Name: methyl 2-oxo-1-(2-pentynyl)cyclopentanecarboxylate
• Synonyms: methyl 2-oxo-1-(2-pentynyl)cyclopentanecarboxylate;2-Oxo-1-(2-pentynyl)cyclopentanecarboxylic acid methyl ester;Cyclopentanecarboxylic acid, 2-oxo-1-(2-pentyn-1-yl)-, methyl ester;Cyclopentanecarboxylic acid, 2-oxo-1-(2-pentynyl)-, methyl ester;Einecs 270-900-8
• CAS NO: 68480-23-9
• Molecular Formula: C₁₂H₁₆O₃
• Molecular Weight: 208.25364
• EINECS: 270-900-8
• Mol File: 68480-23-9.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 300.9°Cat760mmHg
• Flash Point: 129.2°C
• Appearance: /
• Density: 1.086g/cm³
• Vapor Pressure: 0.00109mmHg at 25°C
• Refractive Index: 1.488
• CAS DataBase Reference: methyl 2-oxo-1-(2-pentynyl)cyclopentanecarboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 2-oxo-1-(2-pentynyl)cyclopentanecarboxylate(68480-23-9)
• EPA Substance Registry System: methyl 2-oxo-1-(2-pentynyl)cyclopentanecarboxylate(68480-23-9)

Safety Data

• Hazardous Substances Data: 68480-23-9(Hazardous Substances Data)

Usage

General Description

Methyl 2-oxo-1-(2-pentynyl)cyclopentanecarboxylate is a chemical compound with the molecular formula C11H14O3. It is a cyclopentane derivative containing a methyl ester group, a ketone group, and a 2-pentynyl substituent. methyl 2-oxo-1-(2-pentynyl)cyclopentanecarboxylate is commonly used in organic synthesis and drug discovery research as a building block for the synthesis of diverse molecules, including pharmaceuticals and natural products. Its unique structure allows for the incorporation of the cyclopentane and alkynyl groups into various molecular scaffolds, making it a valuable intermediate in the production of biologically active compounds. Methyl 2-oxo-1-(2-pentynyl)cyclopentanecarboxylate is a versatile and important chemical for the development of new drugs and materials.

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

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

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 articles and documents

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.