490-09-5

Usage

Uses

Used in Organic Synthesis:
(4R,4aR,7R,7aS)-4,7-Dimethyl-hexahydro-cyclopenta[c]pyran-1-one is used as a building block in organic synthesis for the creation of more complex molecules. Its unique structure and reactivity allow for the formation of various derivatives, making it a versatile component in the synthesis of a wide range of compounds.
Used in Pharmaceutical Research:
In the pharmaceutical industry, (4R,4aR,7R,7aS)-4,7-Dimethyl-hexahydro-cyclopenta[c]pyran-1-one is used as an intermediate in the production of pharmaceuticals and other fine chemicals. Its cyclic structure and functional groups make it a suitable candidate for the development of new drugs and therapeutic agents.
Used in Chemical Research:
(4R,4aR,7R,7aS)-4,7-Dimethyl-hexahydro-cyclopenta[c]pyran-1-one is also utilized in chemical research to study the properties and reactivity of cyclic ketones. This helps in understanding the fundamental principles of organic chemistry and contributes to the development of new synthetic methods and strategies.

Upstream product

• 490-10-8 nepetalactone 
• 15681-48-8 lithium dimethylcuprate 
• 123718-10-5 (4S*,4aS*)-4-Methyl-4,4a,5,6-tetrahydrocyclopentapyran-1(3H)-one 
• 82041-92-7 (1R*,2S*,5S*)-5-methyl-2-(methylethenyl)cyclopentane-carboxylic acid 
• 123718-07-0 (E,E)-2-methyl-octa-2,6-dienedioic acid diethyl ester 
• 123718-14-9 2-Benzylamino-5-(1-ethoxycarbonyl-ethyl)-cyclopentanecarboxylic acid ethyl ester 
• 123718-18-3 2-(Benzyl-methyl-amino)-5-(1-ethoxycarbonyl-ethyl)-cyclopentanecarboxylic acid ethyl ester 
• 81987-43-1 (Z)-8-hydroxy-3,7-dimethyl-6-octenoic acid 
• 81987-48-6 (Z)-3,7-dimethyl-8-hydroxy-6-octenoic acid lactone 
• 26505-44-2 dimethyl (E,E)-octa-2,6-diendioate 
• 141116-94-1 Methyl 2-(Methoxycarbonyl)-2-cyclopentene-1-acetate 
• 141045-81-0 Dimethyl (2E,6E)-2-Methyl-2,6-octadienedioate 
• 123718-16-1 2-(Hydroxymethyl)-β-methyl-2-cyclopentene-ethanol 
• 123718-19-4 2-Benzylamino-5-(1-methoxycarbonyl-ethyl)-cyclopentanecarboxylic acid methyl ester 

Downstream Products

• 21699-53-6 neomatatabiol 
• 34258-02-1 (1R,4R,4aR,7S,7aR)-dihydronepetalactol 
• 485-42-7 rac-(R)-2-[(1R,2R,3S)-2-(hydroxymethyl)-3-methylcyclopentyl]propan-1-ol 
• 485-43-8 (+/-)-Isoiridomyrmecin 

Relevant academic research and scientific papers

HYDROGENATION OF NEPETALACTONE

A process for the production of dihydronepetalactone including hydrogenating nepetalactone in the presence of a catalytic metal is provided. The catalytic metal may include nickel. The process may be performed in an aqueous medium.

Stereoselective synthesis of trans-fused iridoid lactones and their identification in the parasitoid wasp Alloxysta victrix, Part I: Dihydronepetalactones

Starting from the enantiomers of limonene, all eight stereoisomers of trans-fused dihydronepetalactones were synthesized. Key compounds were pure stereoisomers of 1-acetoxymethyl-2-methyl-5-(2-hydroxy-1-methylethyl)-1- cyclopentene. The stereogenic center of limonene was retained at position 4a of the target compounds and used to stereoselectively control the introduction of the other chiral centers during the synthesis. Basically, this approach could also be used for the synthesis of enantiomerically pure trans-fused iridomyrmecins. Using synthetic reference samples, the combination of enantioselective gas chromatography and mass spectrometry revealed that volatiles released by the endohyperparasitoid wasp Alloxysta victrix contain the enantiomerically pure trans-fused (4R,4aR,7R,7aS)-dihydronepetalactone as a minor component, showing an unusual (R)-configured stereogenic center at position 7.

Scope and applications of second generation palladium-catalyzed cycloalkenylation. Stereoselective total syntheses of isoiridomyrmecin, isodihydronepetalactone, and α-skytanthine

Functionalized bicyclo[3.2.1]octanes, -oxabicyclo-[4.3.0]nonanes, 3-azabicyclo[3.3.0]octanes, and 3-azabicyclo[4.3.0]nonanes were easily synthesized via a second generation palladium-catalyzed cycloalkenylation. Isoiridomyrmecin and isodihydronepetalactone, both of which feature a 3-oxabicyclo[4.3.0]nonane subunit, were stereoselectively synthesized via a second generation palladium-catalyzed cycloalkenylation as the key step. α-Skytanthine, a typical 3-azabicyclo[4.3.0]nonane alkaloid, was also constructed using the same catalytic cyclization protocol.

A divergent approach to the diastereoselective synthesis of several ant-associated Lridoids

(Figure Presented) The ant-associated iridoids nepetalactol, actinidine, dolichodial, isoiridomyrmecin and dihydronepetalactone were prepared from citronellal using a divergent approach. Key features include a three-step synthesis of the individual antipodes of actinidine by a novel tandem cycloaddition/ pyridine formation and a facile diastereoselective synthesis of both enantiomers of dolichodial.

HYDROGENATION OF CATMINT OIL

Disclosed are methods for treating catmint oil. The treated catmint oil can be used for the production of hydrogenated catmint oil, which is enriched in the insect repellent, dihydronepetalactone.

PRODUCTION OF DIHYDRONEPETALACTONE BY HYDROGENATION OF NEPETALACTONE

This invention provides a process for producing dihydronepetalactone using mixtures comprising both trans-cis nepetalactone and cis-trans nepetalactone. A reaction mixture comprising trans-cis nepetalactone and cis-trans nepetalactone is first contacted with hydrogen in the presence of at least one hydrogenation catalyst under conditions that optimize the preferential conversion of trans-cis nepetalactone to dihydronepetalactone. Cis-trans nepetalactone is subsequently converted to dihydronepetalactone by contact with hydrogen in the presence of at least one hydrogenation catalyst.

Efficient Oxidative Radical Cyclizations of Ester Enolates with Carbocation Desilylation as Termination: Synthesis of Cyclopentanoid Monoterpenes and Analogues

(Matrix presented) An efficient oxidative radical cyclization approach for the synthesis of 2-alkenyl cyclopentane or cyclohexane carboxylates from ω-silylallyl ester enolates induced by recyclable SET oxidant ferrocenium hexafluorophosphate has been deve

Production of dihydronepetalactone by hydrogenation of nepetalactone

This invention relates to a process for hydrogenating nepetalactone, utilizing a metal catalyst that is optionally supported, to yield dihydronepetalactone. A suite of supported catalytic metals lead to rapid hydrogenation and high selectivity for dihydronepetalactone.

Stereocontrol in organic synthesis using silicon-containing compounds. A synthesis of (±)-dihydronepetalactone using the SE2′ reaction of an allylsilane

A propargylic alcohol 24 with the propynyl group exo on the norbornene framework was used in a stereospecific synthesis of the mixture of allylsilanes 27 and 28. The stereospecific reaction of this mixture with peracid gave, with a high level of stereocon

New Type of Cyclization of α,β,χ,ψ-Unsaturated Dioic Acid Esters through Tandem Conjugate Additions by Using Lithium N-Benzyl-N-(trimethylsilyl)amide as a Nitrogen Nucleophile

Treatment of dimethyl (2E,6E)-2,6-octadienedioate with lithium N-benzyl-N-(trimethylsilyl)amide (LSA) gave 5-exo-trig ring closure products, methyl 3-(N-benzylamino)-2-(methoxycarbonyl)cyclopentane-1-acetates, through tandem conjugate additions.The relate