59253-90-6

Usage

Uses

Used in Pharmaceutical Industry:
1-Cyclopentene-1-carbonyl chloride is used as a reactant for the synthesis of N-(pheneethylcarbamothioyl)cyclopent-1-enecarboxamide, a compound with potential applications in cancer treatments. Its role in the synthesis process is crucial, as it contributes to the formation of the final product's structure, which is believed to have structural bioactivity against cancer cells.

Upstream product

• 1560-11-8 cyclopent-1-enecarboxylic acid 
• 25662-28-6 1-(carboxymethoxy)cyclopentadiene 
• 10472-24-9 methyl 2-oxocyclopentane-1-carboxylate 
• 90085-05-5 (R)-Trans-2-Methoxycarbonylcyclopentanol 

Downstream Products

• 16112-10-0 1-(cyclopent-1-en-1-yl)ethanone 
• 5434-85-5 1-cyclopentene-1-carboxamide 
• 100797-46-4 cyclopentenyl(4-methoxyphenyl)methanone 
• 21573-70-6 (cyclopent-1-en-1-yl)(phenyl)methanone 
• 59253-94-0 Propargyl-1-cyclopentencarboxylat 
• 59253-91-7 allyl 1-cyclopentene-1-carboxylate 
• 82494-85-7 (6aR*,3aS*)-3-phenylthio-4,5,6,6a-tetrahydro-3aH-pentalen-1-one 
• 141753-26-6 (1'R,2'R)-2'-Hydroxycyclohexyl cyclopentene-1-carboxylate 
• 133386-63-7 N-(Cyclopent-1-enoyl)-N-isopropylthiobenzamide 
• 130267-90-2 (Z)-1-Cyclopent-1-enyl-3-phenylselanyl-propenone 
• 135631-26-4 Phenyl cyclopent-1-ene-1-carboselenoate 
• 135631-19-5 4-(Phenylseleno)bicyclo<3.3.0>oct-3-en-2-one 
• 135631-13-9 1-(Cyclopent-1'-enyl)-3-(phenylseleno)-3-(trimethylsilyl)prop-2-en-1-one 
• 82494-88-0 4-<(4-chlorophenyl)thio>-cis-bicyclo<3.3.0>oct-3-en-2-one 

Relevant academic research and scientific papers

Photoredox Cyclization of N-Arylacrylamides for Synthesis of Dihydroquinolinones

Metal- and additive-free photoredox cyclization of N-arylacrylamides is herein reported that provides a concise access to the formation of dihydroquinolinones. In this protocol, sustainable visible light was used as the energy source, and the organic light-emitting molecule 4CzIPN served as the efficient photocatalyst. This reaction system features exclusive 6-endo-trig cyclization selectivity with a generally good yield of a range of functionalized dihydroquinolinones and dihydrobenzoquinolinones. Mechanistical studies reveal the feasibility of both 1,3-H shift and intersystem crossing of the diradical intermediate.

RhIII-Catalyzed C-H (Het)arylation/Vinylation of N-2,6-Difluoroaryl Acrylamides

RhIII-catalyzed sp2 C-H cross-coupling of acrylamides with organoboron reactants has been accomplished using a commercially available N-2,6-difluoroaryl acrylamide auxiliary. A broad range of aryl and vinyl boronates as well as a variety of heterocyclic boronates with strong coordinating ability can serve as the coupling partners. This transformation proceeds under moderate reaction conditions with excellent functional group tolerance and high regioselectivity.

Novel monocyclic amide-linked phenol derivatives without mitochondrial toxicity have potent uric acid-lowering activity

Although benzbromarone (BBR) is a conventional, highly potent uricosuric drug, it is not a standard medicine because it causes rare but fatal fulminant hepatitis. We transformed the bis-aryl ketone structure of BBR to generate novel monocyclic amide-linked phenol derivatives that should possess uric acid excretion activity without adverse properties associated with BBR. The derivatives were synthesized and tested for uric acid uptake inhibition (UUI) in two assays using either urate transporter 1-expressing cells or primary human renal proximal tubule epithelial cells. We also evaluated their inhibitory activity against mitochondrial respiration as a critical mitochondrial toxicity parameter. Some derivatives with UUI activity had no mitochondrial toxicity, including compound 3f, which effectively lowered the plasma uric acid level in Cebus apella. Thus, 3f is a promising candidate for further development as a uricosuric agent.

Synthesis of Succinimides via Intramolecular Alder-Ene Reaction of 1,6-Enynes

A novel and convenient method has been developed for the facile synthesis of functionalized succinimide derivatives via intramolecular Alder-ene reaction of 1,6-enynes. This reaction features mild and metal-free reaction conditions, which offers a green and efficient entry to synthetically important succinimide scaffolds. Preliminary mechanistic studies suggest that a diradical intermediate might be involved in this transformation.

Synthesis of Forms of a Chiral Ruthenium Complex Containing a Ru-Colefin(sp2) Bond and Their Application to Catalytic Asymmetric Cyclopropanation Reactions

Organometallic complexes [Ru-Colefin(sp2)-Ru(II)-Pheox 2a-2d] containing a Ru-Colefin(sp2) bond have been prepared from unsaturated chiral oxazoline derivatives and evaluated for asymmetric cyclopropanation reactions. The corresponding optically active cyclopropanes were obtained with high yields and high stereoselectivities (≥99/2) bond. In particular, Ru(II)-Prox catalyst 2c, in which there was no geminal substituent on the metal, was shown to have the highest enantioselectivities.

Photoredox-Controlled β-Regioselective Radical Hydroboration of Activated Alkenes with NHC-Boranes

In this Communication, we report an unprecedented β-regioselective radical inverse hydroboration (compared with ionic hydroboration) of α,β-unsaturated amides with NHC-BH3 enabled by photoredox catalysis. Density functional theory (DFT) calculations show that the unique photoredox cycle is a key factor to control the β-regioselective radical hydroboration, by lowering the energy barrier in comparison with other pathways. This protocol provides a general and convenient route to construct a wide range of structurally diverse β-borylated amides in synthetically useful yields under mild conditions.

Macrolactam Synthesis via Ring-Closing Alkene-Alkene Cross-Coupling Reactions

Reported herein is a practical method for macrolactam synthesis via a Rh(III)-catalyzed ring closing alkene-alkene cross-coupling reaction. The reaction proceeded via a Rh-catalyzed alkenyl sp2 C-H activation process, which allows access to macrocyclic molecules of different ring sizes. Macrolactams containing a conjugated diene framework could be easily prepared in high chemoselectivities and Z,E stereoselectivities.

Design, synthesis and biological study of potent and covalent HER-2 tyrosine kinase inhibitors with low cytotoxicity in vitro

The discovery and development of a novel HER-2 tyrosine kinase inhibitor for the treatment of HER2-positive breast cancer are presented in this article. EGFR family has been recognized as a crucial meditator in the cancer progression; HER-2 tyrosine kinase was one of the members among them. In the effort to explore potent HER-2 inhibitors, a novel series of 4-anilino-3-cyanoquinoline derivatives have been designed, synthesized and evaluated. Most compounds possessed modest proliferation inhibition on SK-BR-3 cell line and HER-2 kinase. Compound 16 appeared to be the most potent compound (HER-2 kinase IC50: 19.4?nM, SK-BR-3 IC50: 94?nM). In the experiment of cellular cytotoxicity assay, compound 16 shows a much lower cytotoxicity than neratinib on Beas-2b cell line (Human bronchial epithelial cells). In conclusion, compound 16 would be a promising lead compound for further anti-breast cancer drug discovery.

A tethering directing group strategy for ruthenium-catalyzed intramolecular alkene hydroarylation

We report a new catalyst design for N-heterocycle synthesis that utilizes an alkene-tethered amide moiety as a directing group for aromatic C-H activation. This tethering directing group strategy is demonstrated in a ruthenium-catalyzed intramolecular alk

Macrolide Synthesis through Intramolecular Oxidative Cross-Coupling of Alkenes

A RhIII-catalyzed intramolecular oxidative cross-coupling between double bonds for the synthesis of macrolides is described. Under the optimized reaction conditions, macrocycles containing a diene moiety can be formed in reasonable yields and with excellent chemo- and stereoselectivity. This method provides an efficient approach to synthesize macrocyclic compounds containing a 1,3-conjugated diene structure.