34027-33-3

Basic information

• Product Name: Cyclopentaneacetic acid, 3-hydroxy-2-(2-pentenyl)-
• CAS NO: 34027-33-3
• Molecular Formula: C12H20O3
• Molecular Weight: 212.289
• Mol File: 34027-33-3.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: Cyclopentaneacetic acid, 3-hydroxy-2-(2-pentenyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Cyclopentaneacetic acid, 3-hydroxy-2-(2-pentenyl)-(34027-33-3)
• EPA Substance Registry System: Cyclopentaneacetic acid, 3-hydroxy-2-(2-pentenyl)-(34027-33-3)

Safety Data

• Hazardous Substances Data: 34027-33-3(Hazardous Substances Data)

Upstream product

• 53320-18-6 ((3aR,4S,6aS)-2-Hydroxy-hexahydro-cyclopenta[b]furan-4-yl)-acetic acid methyl ester 
• 53403-88-6 (1S,5S,8R)-((Z)-8-Pent-2-enyl)-2-oxa-bicyclo[3.2.1]octan-3-one 
• 131447-75-1 [(1R,2S,3S)-3-Acetoxy-2-((Z)-pent-2-enyl)-cyclopentyl]-acetic acid methyl ester 
• 129971-57-9 (1α,2α(Z),3α)-(+/-)-3-<(2-methoxyethoxy)methoxy>-2-(2-pentenyl)cyclopentaneacetonitrile 
• 129971-55-7 <1R*,2S*,3S*>-1-methoxyethoxymethoxy-2-<(3Z)-pentenyl>-3-hydroxymethylcyclopentane 
• 134826-73-6 <1S*,2R*,5S*>-2-methoxyethoxymethoxy-8-ethoxy-7-oxabicyclo<4.3.0>nonane 
• 134826-71-4 3-(2-bromo-1-ethoxyethoxymethyl)cyclopentanone 
• 134826-72-5 <1S*,5S*>-8-ethoxy-7-oxabicyclo<4.3.0>nonane-2-one 
• 134826-74-7 (4aS,5R,7aS)-3-Ethoxy-octahydro-cyclopenta[c]pyran-5-ol 
• 1027275-03-1 Benzoic acid (3aR,4R,5R,6aS)-4-((E)-2-ethoxycarbonyl-vinyl)-2-oxo-hexahydro-cyclopenta[b]furan-5-yl ester 
• 1028281-47-1 (1S,5R)-6-(2'-carbethoxyethyl)-2-oxabicyclo[3.3.0]-oct-3-one 
• 1026628-14-7 (1S,5R)-6-(2'-carbethoxy-1'-ethenyl)-2-oxabicyclo[3.3.0]-oct-6-en-3-one 
• 194141-91-8 (1S,5R)-6-(2'-carboxyethyl)-2-oxabicyclo[3.3.0]-oct-3-one 
• 194141-95-2 ((3aR,4S,6aS)-2-Oxo-hexahydro-cyclopenta[b]furan-4-yl)-acetic acid 

Downstream Products

• 1211-29-6 methyl (2-(2-pent-2Z-enyl)-3-oxocyclopentyl)acetate 
• 34027-33-3 (+/-)-Cucurbic acid 
• 2570-03-8 (+/-)-methyl trans-dihydrojasmonate 
• 2570-03-8 (+/-)-methyl dihydroepijasmonate 

Relevant articles and documents

A convenient synthesis of (-)-methyl epijasmonate

A short, enantioselective synthesis of (-)-methyl epi-jasmonate, ent-1, has been achieved starting from readily available Corey lactone aldehyde 9. The key features include the stereoselective installation of 2,3-cis- disubstituted side-chains by hydrogen

Synthesis of 12-Oxophytodienoic Acid (12-OxoPDA) and the Compounds of its Enzymic Degradation Cascade in Plants, OPC-8:0, -6:0, -4:0 and -2:0 (epi-Jasmonic Acid), as their Methyl Esters

The synthesis of 12-Oxophytodienoic acid, and the compounds of its enzymatic degradation sequence, OPC-8:0, -6:0, -4:0 and -2:0, important plant metabolites derived from linolenic acid, is reported.The syntheses use the known cyclopent-3-ene-1,2-diacetic acid as an early intermediate, and this is derived from the Cope rearrangement of 5-vinyltrinorborn-2-ene via bicyclonona-3,7-diene.Iodolactonisation and tributyltin hydride reduction provides the key intermediate (3-oxo-2-oxabicyclooctan-6-yl)acetic acid for the OPC series, whilstphenylselenolactonisation and elimination provides the necessary unsaturated lactone (7-oxo-8-oxabicyclooct-2-en-4-yl)acetic acid for 12-oxoPDA.Members of the OPC-series were made by chain extending the saturated oxabicyclooctane acid: that for the OPC-4:0 involved double Arndt-Eistert reaction, whilst the intermediates for OPC-6:0 and -8:0 were made by Kolbe anodic crossed coupling.The lactones were than converted via their lactols, Wittig reaction, esterfication and oxidation, into the compounds of the OPC ester series, including OPC-2:0 (methyl epi-jasmonate).The unsaturate lactone 8-(7-oxo-8-oxabicyclooct-2-en-4-yl)octanoic acid required for 12-oxoPDA synthesis could also be prepared by anodic synthesis either from (7-oxo-8-oxa-bicyclooct-2-en-4-yl)acetic acid, or from its 2-phenylseleno-2,3-dihydro precursor as elimination occurred concomitantly during the reaction.Since yields were low, the unsaturated acid lactone was converted into its lactol and the (Z)-pent-2-enyl side-chain was inserted first.After TBDMS blocking of the cyclopentene hydroxy group, the side-chain was elaborated to give5-(pent-2-enyl)cyclopent-2-enylacetaldehyde and chain extension carried out by a Grignard-demesylation procedure.Sequential desilylation and depyranylation, followed by oxidation of the diol, gave 12-oxoPDA, isolated as its methyl ester.