17214-44-7

Upstream product

• 5558-87-2 2-phenylpent-4-enenitrile 
• 34522-48-0 2-phenyl-4-pentenenamide 
• 31376-92-8 (1E,1Z)-2-bromo-N-methoxy-1-phenylethanimine 
• 100-47-0 benzonitrile 
• 140-29-4 phenylacetonitrile 
• 76403-12-8 2-Phenyl-4-pentenoyl chloride 
• 1575-70-8 2-phenyl-pent-4-enoic acid 
• 14815-73-7 methyl allylphenylacetate 

Downstream Products

• 13673-03-5 2-methyl-4-phenyl-1-pyrroline 
• 6947-14-4 2-methyl-4-phenyl-pyrrolidine 
• 916583-36-3 N-phenyl-N'-(2-phenyl-4-pentenyl)urea 
• 1073282-73-1 1-(2-phenylpent-4-enyl)-3-tosylurea 
• 70197-11-4 4-methyl-N-(2-phenylpent-4-en-1-yl)benzenesulfonamide 
• 1234715-19-5 C₁₃H₁₄F₃NO 
• 1370583-84-8 N-benzyl-2-phenylpent-4-en-1-amine 
• 1370583-88-2 1-benzyl-2-methyl-4-phenylpyrrolidine 
• 104177-99-3 2-Phenyl-pentylamine 

Relevant academic research and scientific papers

LOX ENZYME INHIBITING METHODS AND COMPOSITIONS

This invention relates to compounds, pharmaceutical compositions and their use for treating fibrotic disorders, proliferative disorders, cardiovascular diseases, acute and chronic inflammatory disorders, primary and metastatic cancer, pulmonary conditions, ocular diseases, or neurological and neuropsychiatric conditions. One particular aspect of the inventions relates to inhibitors of the family of lysyl oxidase enzymes and their use as therapeutics for fibrotic disorders.

Copper-Catalyzed Carbonylative Synthesis of β-Homoprolines from N-Fluoro-sulfonamides

A new methodology for the carbonylative transformation of N-fluoro-sulfonamides into N-sulfonyl-β-homoproline esters has been described. In the presence of a catalytic amount of Cu(OTf)2, a range of β-homoproline derivatives were prepared in moderate to good yield. The reaction proceeds via the intramolecular cyclization and intermolecular carbonylation of a free carbon radical. Notably, this procedure offers the possibility to build potential functionalized bioactive molecules.

Palladium(II)-Catalyzed Aminotrifluoromethoxylation of Alkenes: Mechanistic Insight into the Effect of N-Protecting Groups

An efficient palladium-catalyzed regioselective 5-exo aminotrifluoromethoxylation of alkenes has been established herein, which provides a practical route towards the synthesis of OCF3-containing pyrrolidines. tert-Butyloxycarbonyl (Boc) as an amino protecting group plays a significant role in both the chemo- and regioselectivities. In addition, preliminary mechanistic studies reveal that the amino protecting group of substrates and the counter anion of palladium catalyst play critical roles in reaction efficiency presumably due to an isomerization of alkyl- Pd(II) intermediates. Moreover, the asymmetric 5-exo aminotrifluoromethoxylation reaction has also been achieved by introducing a sterically bulky pyridinyl-oxazoline ligand.

Pd-Catalyzed Intramolecular Aminoalkylation of Unactivated Alkenes: Access to Diverse N-Heterocycles

A highly efficient palladium-catalyzed intramolecular aminoalkylation of unactivated alkenes in the absence of an external ligand and oxidant is described. New C-N and C(sp3)-C(sp3) bonds are formed simultaneously. This general transformation allows for construction of diverse N-heterocycles. Mechanistic studies show that the process may involve a four-membered Pd(alkyl)amido intermediate.

Enantioselective Palladium-Catalyzed Oxidative Cascade Cyclization of Aliphatic Alkenyl Amides

The catalyst system of Pd(TFA)2/(S,S)-diPh-pyrox is reported to promote the highly efficient enantioselective oxidative cascade cyclization of alkene-tethered aliphatic acrylamides under mild aerobic conditions. A series of pyrrolizidine derivatives have been synthesized in good yield and excellent enantioselectivity. Deuterium-labeling experiments have revealed that the reaction proceeded through an anti-aminopalladation (anti-AP) pathway with high selectivity. The transition states for the anti-AP step have been calculated to account for the observed enantioselectivity.

Green Organocatalytic Synthesis of Indolines and Pyrrolidines from Alkenes

Employing a green and efficient 2,2,2-trifluoroacetophenone-catalyzed oxidation of alkenes, which utilizes H2O2 as the green oxidant, a novel and sustainable synthesis of indolines and pyrrolidines was developed. This constitutes a cheap, general and environmentally-friendly protocol for the synthesis of substituted nitrogen-containing heterocycles. A variety of substitution patterns, both aromatic and aliphatic moieties, are well tolerated leading to the desired nitrogen heterocycles in good to excellent yields. (Figure presented.).

I2-Mediated oxidative bicyclization of 4-pentenamines to prolinol carbamates with CO2 incorporating oxyamination of the C=C bond

A metal-free oxyamination reaction of alkenes with ambient CO2 is reported. In the presence of I2 and DBU, CO2 is applied in situ as a protecting group to regulate the nucleophilicity of the amino group and facilitate the bicyclization of 4-pentenamines with high chemoselectivity. Moreover, this reaction provided a feasible approach to prepare prolinol carbamates with good tolerance of functional groups and high efficiency under mild conditions.

Palladium-catalyzed highly selective intramolecular bromoamination of alkenes: Efficient synthesis of substituted pyrrolidines

A new method has been developed for the preparation of substituted pyrrolidines by the palladium-catalyzed intramolecular bromoamination of substituted aminoalkenes. The catalytic system and reaction conditions used for this transformation have been fully optimized. Notably, this reaction exhibits excellent selectivity, affording the pyrrolidine products as single 5-exo-bromoalkylpyrrolidines in excellent yields. Furthermore, this reaction occurs at room temperature under mild conditions, reaching completion within 1?h.

Synthesis of allyl-aziridines from α-halo oxime ethers and allyl zinc bromides

A novel method for the preparation of substituted allyl aziridines by reaction of α-halo with allylic zinc reagents in mild conditions is reported in this paper. The present method complements the existing synthetic methods due to some advantages offered by the use of organozinc reagents, which are easily prepared, relatively stable and non-toxic, and more selective than Grignard reagents.

Copper(II)-catalyzed enantioselective intramolecular cyclization of N-alkenylureas

The first Cu(II)-catalyzed highly enantioselective intramolecular cyclization of N-alkenylureas was developed for the concise assembly of chiral vicinal diamino bicyclic heterocycles. Facile removal of carbonyl group of the carbamido moiety allowed for ready access to enantioenriched cyclic vicinal diamines.