69543-15-3

Usage

Uses

Used in Pharmaceutical Industry:
1-(Bromomethyl)cyclopentene is used as a chemical reagent for the preparation of Penicibilaenes, which are a class of natural products with potential pharmaceutical applications. These compounds exhibit a wide range of biological activities, including antimicrobial, anticancer, and immunosuppressive properties. The use of 1-(Bromomethyl)cyclopentene in the synthesis of Penicibilaenes allows for the development of new drugs and therapeutic agents to address various health challenges.
Used in Organic Synthesis:
1-(Bromomethyl)cyclopentene is used as a synthetic intermediate in the preparation of various organic compounds. Its unique structure allows for a range of chemical reactions, such as cross-coupling, substitution, and addition reactions, which can be employed to synthesize complex organic molecules. This makes it a valuable tool for chemists working in the field of organic synthesis, enabling the creation of new compounds with potential applications in various industries, including pharmaceuticals, agrochemicals, and materials science.
Used in Research and Development:
1-(Bromomethyl)cyclopentene is used as a research compound in academic and industrial laboratories. Its unique structure and reactivity make it an interesting subject for studying various aspects of organic chemistry, such as reaction mechanisms, stereochemistry, and the development of new synthetic methods. Additionally, it can be used to explore the properties and potential applications of Penicibilaenes and other related compounds, contributing to the advancement of scientific knowledge and the development of new technologies.

Upstream product

• 1120-80-5 cyclopent-1-ene-1-methanol 
• 6140-65-4 1-cyclopentene-1-carboxaldehyde 
• 1072-21-5 hexanedial 
• 10267-94-4 ethyl cyclopent-1-enecarboxylate 
• 1560-11-8 cyclopent-1-enecarboxylic acid 
• 120-92-3 cyclopentanone 
• 930-29-0 1-chlorocyclopent-1-ene 
• 5117-85-1 1-hydroxycyclopentanecarbonitrile 
• 3047-38-9 cyclopent-1-enecarbonitrile 
• 25662-28-6 1-(carboxymethoxy)cyclopentadiene 

Downstream Products

• 78258-55-6 ethyl 2-(cyclopent-1-enylmethyl)-3-methyl-4-oxocyclohex-2-enecarboxylate 
• 107616-22-8 2-(1-cyclopentenylmethoxy)-1-nitrobenzene 
• 150268-60-3 N-allyl-N-benzyl-1-(cyclopentenyl)methylamine 
• 205242-24-6 2,4-dibromo-6-tert-butylphenyl 1-cyclopent-1-enylmethyl ether 
• 340269-69-4 methyl (+/-)-3-(1-cyclopentenyl)-2-(2-nitrophenyl)-4-pentenoate 
• 477977-14-3 N-cyclopent-1-enylmethyl-4-methyl-N-prop-2-ynyl-benzenesulfonamide 
• 845252-80-4 N-(but-3-ynyl)-N-(cyclopent-1-enylmethyl)-p-toluenesulfonamide 
• 81769-23-5 N-benzyl-N-(cyclopent-1-en-1-ylmethyl)amine 

Relevant academic research and scientific papers

Total Synthesis of Penicibilaenes via C-C Activation-Enabled Skeleton Deconstruction and Desaturation Relay-Mediated C-H Functionalization

Herein, we describe the first total synthesis of sesquiterpene penicibilaenes A and B through a "C-C/C-H"approach. In the "C-C"stage, the Rh-catalyzed "cut-and-sew"transformation between trisubstituted alkene and cyclobutanone has been employed to constru

Synthesis of Seven-Membered Cross-Conjugated Cyclic Trienes by 8πElectrocyclic Reaction

A method for the synthesis of 3-methylene-1,4-cycloheptadiene derivatives via an 8πelectrocyclization reaction was developed. The triene substrate bearing a phosphate or carbamate group was prepared from γ,δ-unsaturated esters and α,β-unsaturated aldehydes in four steps. Upon treatment with NaHMDS or KHMDS, the substrate formed a heptatrienyl anion, which underwent electrocyclization and subsequent β-elimination of the leaving group. The product could be converted into a tropylium salt in two steps.

Alkyne Aminopalladation/Heck and Suzuki Cascades: An Approach to Tetrasubstituted Enamines

Alkyne aminopalladation reactions starting from tosylamides are reported. The emerging vinylic Pd species are converted either in an intramolecular Heck reaction with olefinic units or in an intermolecular Suzuki reaction by using boronic acids exhibiting broad functional group tolerance. Tetra(hetero)substituted tosylated enamines are obtained in a simple one-pot process.

FACTOR XIIA INHIBITORS

This invention relates to compoundsof formula (I)and methods of treatment using the compounds. The invention also relates to processes and methods for producing the compounds of the invention. The compounds of the invention are modulators of Factor XII (e.g. Factor XIIa). In particular, the compounds are inhibitors of Factor XIIa and may be useful as anticoagulants.

Lithium Chloride Catalyzed Asymmetric Domino Aza-Michael Addition/[3 + 2] Cycloaddition Reactions for the Synthesis of Spiro- and Bicyclic α,β,γ-Triamino Acid Derivatives

Angularly and peri-fused tricyclic pyrrolidinopyrazolines are efficiently prepared by LiCl-catalyzed domino aza-Michael addition-1,3-dipolar cycloaddition reactions. The absolute stereochemistry is controlled in the aza-Michael addition step, nonaflyl azide serves as effective diazo transfer reagent to the formed enolate and the resulting diazo dipole engages in the 1,3-dipolar cycloaddition step. The resulting tricyclic pyrrolidinopyrazolines can be easily transformed to enantiomerically enriched nonproteinogenic spirocyclic α,β,γ-triamino acids, angularly or peri-fused tricyclic β-prolines or pyrimidines. The activity of the tricyclic amino acid derivatives against the hepatitis C virus was determined.

Copper-Promoted Tandem Reaction of Azobenzenes with Allyl Bromides via N=N Bond Cleavage for the Regioselective Synthesis of Quinolines

A copper-promoted tandem reaction of a variety of azobenzenes and allyl bromides via N=N bond cleavage to regioselectively construct quinoline derivatives has been developed. The azobenzenes act as not only construction units but also an oxidant for quinoline formation.

Tandem ring-opening/ring-closing metathesis polymerization: Relationship between monomer structure and reactivity

Monomers containing either cycloalkenes with low ring strain or 1-alkynes are poor monomers for olefin metathesis polymerization. Ironically, keeping two inactive functional groups in proximity within one molecule can make it an excellent monomer for metathesis polymerization. Recently, we demonstrated that monomer 1 having cyclohexene and propargyl moieties underwent rapid tandem ring-opening/ring-closing metathesis (RO/RCM) polymerization via relay-type mechanism. Furthermore, living polymerization was achieved when a third-generation Grubbs catalyst was used. Here, we present a full account on this tandem polymerization by investigating how various structural modifications of the monomers affected the reactivity of the tandem polymerization. We observed that changing the ring size of the cycloalkene moieties, the length of the alkynes, and linker units influenced not only the polymerization rates but also the reactivities of Diels-Alder reaction, which is a post-modification reaction of the resulting polymers. Also, the mechanism of tandem polymerization was studied by conducting end-group analysis using 1H NMR analysis, thereby concluding that the polymerization occurred by the alkyne-first pathway. With this mechanistic conclusion, factors responsible for the dramatic structure-reactivity relationship were proposed. Lastly, tandem RO/RCM polymerization of monomers containing sterically challenging trisubstituted cycloalkenes was successfully carried out to give polymer repeat units having tetrasubstituted cycloalkenes.

Asymmetric lithiation-substitution sequences of substituted allylamines

(-)-Sparteine-mediated asymmetric lithiation-substitution sequences of 2- and 3-substituted N-(Boc)-N-(p-methoxyphenyl) allylic amines with electrophiles have been investigated. Asymmetric lithiation-substitutions of N-(Boc)-N-(p-methoxyphenyl) allylic am

ROM-RCM of cycloalkene-yne

Ring-opening metathesis and ring-closing metathesis (ROM-RCM) of cycloalkene-yne was demonstrated using a first- or second-generation ruthenium complex. When cycloalkenes bearing the alkyne part at the C-3 position were reacted with a first-generation ruthenium-carbene complex under an atmosphere of ethylene, ROM-RCM proceeded smoothly to give skeletal reorganized products in good yields. In this reaction, cycloalkene-ynes having terminal alkyne were suitable. On the other hand, when cycloalkenes bearing the alkyne part at the C-1 position were treated with a second-generation ruthenium-carbene complex, ROM-RCM proceeded smoothly to give bicyclic compounds and/or dimeric compounds in good yields.

A simple and efficient conversion of tertiary cyclopropanols to 2-substituted allyl halides

Readily available sulphonates of tertiary cyclopropanols are converted into 2-substituted allyl bromides in high yields under the action of magnesium bromide in diethyl ether. Magnesium chloride, aluminium chloride and titanium tetrachloride also induce effectively the transformation of cyclopropyl sulphonates into the corresponding allyl chlorides.