75265-67-7

Usage

Uses

Used in Fragrance Industry:
Allyl 2-oxocyclopentanecarboxylate is used as a key ingredient in the production of perfumes, flavors, and other fragrance products, leveraging its unique scent profile to enhance the sensory experience of these products.
Used in Pharmaceutical Industry:
As a chemical intermediate, Allyl 2-oxocyclopentanecarboxylate plays a crucial role in the synthesis of various pharmaceuticals. Its versatility in chemical reactions allows for the creation of a wide range of medicinal compounds.
Used in Agrochemical Industry:
Similarly, in the agrochemical sector, Allyl 2-oxocyclopentanecarboxylate is utilized as an intermediate in the synthesis of different agrochemicals, contributing to the development of products that aid in crop protection and enhancement of agricultural yields.

InChI:InChI=1/C9H12O3/c1-2-6-12-9(11)7-4-3-5-8(7)10/h2,7H,1,3-6H2

Upstream product

• 2998-04-1 diallyl adipate 
• 611-10-9 2-ethoxycarbonyl-1-cyclopentanone 
• 106-95-6 allyl bromide 
• 1460-08-8 2-diazocyclohexane-1,3-dione 
• 107-18-6 allyl alcohol 
• 10472-24-9 methyl 2-oxocyclopentane-1-carboxylate 
• 124-04-9 Adipic acid 
• 936-52-7 1-(N-morpholino)cyclopent-1-ene 
• 2937-50-0 Allyl chloroformate 

Downstream Products

• 30079-93-7 2-allylcyclopentanone 
• 106020-61-5 2-(1-Hydroxyhexyl)cyclopentanone 
• 161394-50-9 bicyclo<3.3.0>-2-oxa-5-(2-propenyl)-1-octene 
• 121720-85-2 allyl 2-(phenylazo)cyclopentene-1-carboxylate 
• 121721-07-1 5-phenyl-3,3a,4,5,7,8-hexahydrocyclopentafuro<3,4-d>pyridazin-1(9H)-one 
• 121721-06-0 5-t-butoxycarbonyl-3,3a,4,5,7,8-hexahydrocyclopentafuro<3,4-d>pyridazin-1(9H)-one 
• 121720-96-5 allyl 2-(2,4-dinitrophenylazo)cyclopent-1-ene-1-carboxylate 
• 121720-97-6 1-Chloro-2-[(2,4-dinitro-phenyl)-hydrazono]-cyclopentanecarboxylic acid allyl ester 
• 121721-12-8 5-(2,4-dinitrophenyl)-3,3a,4,5,7,8-hexahydrocyclopentafuro<3,4-d>pyridazin-1(9H)-one 
• 1352662-68-0 allyl 1-(2-ethoxy-1-(4-methoxyphenylamino)-2-oxoethyl)-2-oxocyclopentanecarboxylate 
• 1362387-31-2 allyl 1-(4-methylbenzyl)-2-oxocyclopentanecarboxylate 
• 1362388-13-3 (S)-2-allyl-2-(4-methylbenzyl)cyclopentanone 
• 1362387-29-8 allyl 1-(4-methoxybenzyl)-2-oxocyclopentanecarboxylate 
• 1362388-11-1 (S)-2-allyl-2-(4-methoxybenzyl)cyclopentanone 

Relevant academic research and scientific papers

Discovery of N-Substituted 3-Amino-4-(3-boronopropyl)pyrrolidine-3-carboxylic Acids as Highly Potent Third-Generation Inhibitors of Human Arginase i and II

Recent efforts to identify new highly potent arginase inhibitors have resulted in the discovery of a novel family of (3R,4S)-3-amino-4-(3-boronopropyl)pyrrolidine-3-carboxylic acid analogues with up to a 1000-fold increase in potency relative to the current standards, 2-amino-6-boronohexanoic acid (ABH) and N-hydroxy-nor-l-arginine (nor-NOHA). The lead candidate, with an N-2-amino-3-phenylpropyl substituent (NED-3238), example 43, inhibits arginase I and II with IC50 values of 1.3 and 8.1 nM, respectively. Herein, we report the design, synthesis, and structure-activity relationships for this novel series of inhibitors, along with X-ray crystallographic data for selected examples bound to human arginase II.

Enantioselective Total Syntheses of (-)-Rhazinilam, (-)-Leucomidine B, and (+)-Leuconodine F

A divergent total synthesis of three structurally distinct natural products from imine 9 was accomplished through an approach featuring: 1) a Pd-catalyzed decarboxylative cross-coupling, and 2) heteroannulation of 9 with bromoacetaldehyde and oxalyl chloride to give tetrahydroindolizine 6 and dioxopyrrole 7, respectively. The former was converted into (-)-rhazinilam, while the latter was converted into (-)-leucomidine B and (+)-leuconodine F. A substrate-directed highly diastereoselective reduction of a sterically unbiased double bond by using a homogeneous palladium catalyst was developed. A self-induced diastereomeric anisochronism (SIDA) phenomenon was observed for leucomidine B. Be divergent: Concise total syntheses of (-)-rhazinilam, (-)-leucomidine B, and (+)-leuconodine F were accomplished from the common intermediate A. A homogeneous palladium catalyst was exploited for the first time to accomplish a substrate-directed highly diastereoselective hydrogenation of a sterically unbiased double bond. A self-induced diastereomeric anisochronism (SIDA) phenomenon was observed for leucomidine B.

An enantioselective total synthesis of (-)-isoschizogamine

A concise enantioselective total synthesis of (-)-isoschizogamine, a complex bridged polycyclic monoterpene indole alkaloid, was accomplished. N-Alkylation of an enantio-enriched imine with an alkyl iodide afforded an iminium salt, which, upon heating by microwave irradiation in the presence of pivalic acid, was converted into the hexacyclic structure of natural product by a complex but ordered domino sequence. The one-pot process leading to the formation of one C-C bond and three C-N bonds created three rings and three contiguous stereogenic centers with complete control of both the relative and absolute stereochemistry. Mix and go: Simply heating the alkyl iodide 1 and imine 2 afforded the hexacyclic compound 3, which was subsequently converted, in one step, into (-)-isoschizogamine. Pivalic acid is the only reagent needed to promote this complex yet ordered domino sequence creating three rings and three contiguous stereogenic centers with complete control of both the relative and absolute stereochemistry.

Catalytic asymmetric synthesis of sterically hindered tertiary α-aryl ketones

The catalytic asymmetric synthesis of a series of tertiary α-aryl cyclopentanones and cyclohexanones has been accomplished via a Pd-catalyzed decarboxylative protonation of the corresponding α-aryl-β-keto allyl esters. Enantioselectivities of up to 92% ee and 74% ee were achieved for cyclopentanone and cyclohexanone substrates, respectively. The route described gives access to these important structural motifs in moderate to high levels of enantioselectivity. In particular, this is only the second direct approach for the preparation of tertiary α-aryl cyclopentanones. The synthetic approach allows for simple modification of the aryl group. Significantly, substrates containing sterically hindered aryl groups gave the highest levels of enantioselectivity, and these aryl groups were readily installed by a Pb-mediated arylation of a β-keto allyl ester.

RING CONSTRAINED ANALOGS AS ARGINASE INHIBITORS

The inventive boronic acid analogs are potent inhibitors of Arginase I and II activity. These compounds are candidate therapeutics for treating a disease or disorder associated with an imbalance in the activity or concentration of cellular arginase I and

Formal synthesis of aspidospermidine via the intramolecular cascade transannular cyclization

A formal synthesis of aspidospermidine is reported through a novel preparation of Stork's penultimate tricyclic ketone intermediate. The key steps of the synthesis consist of an intramolecular cascade transannular cyclization, triggered by the removal of Boc group, which simultaneously forms the C, D, and E rings of aspidospermidine and conveniently setting up the quaternary stereocenter via decarboxylative alkylation reaction of the β-keto ester. Georg Thieme Verlag Stuttgart. New York.

BORONATES AS ARGINASE INHIBITORS

Compounds according to Formula I are potent inhibitors of Arginase I and II activity: (I) where R1, R2, R3, R4, D, W, X, Y, and Z are defined in the specification. The invention also provides pharmaceutical compositions of the compounds and methods of their use in treating or preventing a disease or a condition associated with arginase activity.

Combination of rearrangement with metallic and organic catalyses - A step- and atom-economical approach to α-spiroactones and -lactams

A general synthetic route to α-spirolactones and -lactams from 2-diazo-1,3-dicarbonyl compounds, (homo)allylic alcohols or amines and acrylic derivatives, involving a single consecutive reaction consisting of a Wolff rearrangement/α-oxo ketene trapping/cr

Niobium(V) oxide: A new and efficient catalyst for the transesterification of β-keto esters

Niobium(V) oxide is an efficient catalyst for the transesterification of β-keto esters with several kinds of alcohols, leading to good conversions. Moderate to good isolated product yields have been obtained at faster rates than those recently reported for various catalysts.

Synthesis of tricyclic β-methylene spiro lactones related to bakkenolides by successive radical cyclization-high pressure Diels-Alder reactions

The synthesis of some novel bakkenolides and their epi-spiro analogues was achieved by a new approach. Photolysis of allyl 1-(phenylseleno)-2-oxocyclopentanecarboxylates 7-9 afforded the corresponding spiro lactones 10-12 by radical cyclization via group transfer of the phenylseleno group. Selenoxide elimination of 11 and 12 produced the corresponding β-methylene lactones 14 and 15. Diels-Alder cycloaddition of lactone 11 with piperylene failed at ambient pressure, but proceeded in generally good yield in the presence of various Lewis acids at pressures of ca. 16 kbar, to give mixtures of β-exo, α-endo, and β-endo cycloadducts 19, 21, and 23, respectively. The preponderance of endo products 21 and 23, formed via highly hindered, but more compact, transition states was attributed to the high pressure and resulted in trans-dimethyl configurations of the products. The facial selectivity was dependent upon the Lewis acids, and the greatest α:β ratio was observed with catalysts of the type TiCl2(OR)2. Epimerization of the C-4 methyl group in 21 and 23 to furnish the corresponding cis-dimethyl analogues was achieved via exo-epoxidation, regioselective reduction, oxidation to the corresponding 3-keto derivatives, and base-catalyzed equilibration, thereby affording (±)-3,6-dioxobakkenolide-A (39) and its epi-spiro derivative 28, respectively. When the radical cyclization step was performed subsequent to the Diels-Alder cycloaddition by photolysis of perhydrindane 43, only the epi-spiro product 44 was obtained.