37435-88-4

Basic information

• Product Name: 3-Oxo-2-(2-pentynyl)cyclopentylacetic acid methyl ester
• Synonyms: 3-Oxo-2-(2-pentynyl)cyclopentylacetic acid methyl ester
• CAS NO: 37435-88-4
• Molecular Formula: C₁₃H₁₈O₃
• Molecular Weight: 0
• Mol File: 37435-88-4.mol
• Article Data: 9

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3-Oxo-2-(2-pentynyl)cyclopentylacetic acid methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Oxo-2-(2-pentynyl)cyclopentylacetic acid methyl ester(37435-88-4)
• EPA Substance Registry System: 3-Oxo-2-(2-pentynyl)cyclopentylacetic acid methyl ester(37435-88-4)

Safety Data

• Hazardous Substances Data: 37435-88-4(Hazardous Substances Data)

Upstream product

• 37435-86-2 2-(3-Oxo-2-pent-2-ynyl-cyclopentyl)-malonic acid dimethyl ester 
• 186581-53-3 diazomethane 
• 37435-87-3 2-(pent-2-ynyl)-3-oxo-cyclopentyl acetic acid 
• 29119-44-6 2-(pent-2-ynyl)-cyclopent-2-enone 
• 63072-97-9 trans-3-Allyl-2-(2-pentin-1-yl)-cyclopentanon 
• 16400-32-1 1-bromo-pent-2-yne 
• 34130-51-3 methylester of 3-oxo-cyclopentylacetic acid 
• 68931-54-4 ((1S,2S)-3-Oxo-2-pent-2-ynyl-cyclopentyl)-thioacetic acid S-methyl ester 
• 82423-67-4 methyl (3-dimethyl-t-butylsiloxycyclopent-2-enyl)acetate 
• 92775-78-5 (3-oxo-2-(pent-2-yn-1-yl)cyclopentyl)trimethylsilylacetic acid methyl ester 
• 113949-05-6 (1R,5S)-1-Pent-2-ynyl-bicyclo[3.2.0]heptane-2,7-dione 
• 29119-46-8 (2R*,3S*)-3-carboxymethyl-2-(2-pentynyl)cyclopentanone 
• 74-88-4 methyl iodide 
• 73205-94-4 Methyl 6-oxo-2(E)-dodecen-9-ynoate 

Downstream Products

• 2570-03-8 (+/-)-methyl trans-dihydrojasmonate 
• 1211-29-6 methyl jasmonate 
• 183948-77-8 methyl (+/-)-2-(2,3-2H2)jasmonate 
• 1211-29-6 methyl (2-(2-pent-2Z-enyl)-3-oxocyclopentyl)acetate 
• 183948-71-2 (+/-)-2-(2,3-2H2)jasmonic acid 

Relevant articles and documents

Behaviour of monocomplexed 1,4-diynes in the Khand reaction and use of ethylene equivalent techniques in a convenient route to tritium-labelled methyl jasmonate

1,2-Complexed hexacarbonyl(hepta-1,4-diyne)dicobalt, obtained from hexacarbonyl(propargyl acetate)dicobalt with tri-1-butynylaluminium, has been converted, by selective Khand annulation of the complexed triple bond with vinyl benzoate, to 2-pent-2-yn-1-ylcyclopent-2-en-1-one. By use of standard procedures this alkynyl cyclopentenone has been transformed into methyl jasmonate, allowing replacement of the final hydrogenation step by tritiation to produce the labelled analogue. Two alternative approaches to the intermediate pentynylcyclopentenone were examined and shown to be unsuccessful.

Structural separation of biological activities of jasmonates and related compounds

A wide range of compounds derived from the basic structure of jasmonic acid, when tested for biological activity in different bioassays (Eschscholzia californica elicitation, Bryonia dioica tendril coiling, tomato transpiration and senescence and barley senescence assays) display, in each of the assays, an activity profile that is distinctly characteristic and different between assays. While differences in uptake, metabolism and/or sequestration of the compounds may account for some of the effects observed, the data allow the conclusion that structural requirements are also different for different physiological responses regulated by jasmonates. While jasmonic acid itself is active in all assays employed, some of the compounds tested in our study display a much narrower range of biological effects. Thus, tailoring of jasmonate analogues for specific applications and lacking undesirable side effects should be possible.

Type II Intramolecular Cycloadditions of Alkenes with Alkylvinylketenes. Synthesis of Methyl Jasmonate

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