110775-38-7

Basic information

• Product Name: Benzenemethanamine, a-4-pentenyl-
• CAS NO: 110775-38-7
• Molecular Formula: C12H17N
• Molecular Weight: 175.274
• Mol File: 110775-38-7.mol

Chemical Properties

• CAS DataBase Reference: Benzenemethanamine, a-4-pentenyl-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzenemethanamine, a-4-pentenyl-(110775-38-7)
• EPA Substance Registry System: Benzenemethanamine, a-4-pentenyl-(110775-38-7)

Safety Data

• Hazardous Substances Data: 110775-38-7(Hazardous Substances Data)

Upstream product

• 19679-59-5 propiophenone N,N-dimethylhydrazone 
• 110775-31-0 3-methyl-2-pent-4-enyl-2-phenyl-2H-azirine 
• 17247-58-4 (Bromomethyl)cyclobutane 
• 100-47-0 benzonitrile 
• 22524-25-0 1-phenylhex-5-en-1-one 
• 1334324-92-3 1-azido-1-phenyl-hex-5-ene 
• 144121-60-8 1-phenylhex-5-en-1-ol 
• 34164-50-6 4-penten-1-ylmagnesium bromide 
• 100-52-7 benzaldehyde 
• 1119-51-3 bromopentene 
• 764-59-0 hex-5-en-1-al 
• 821-41-0 5-Hexen-1-ol 

Downstream Products

• 1334324-93-4 C₂₀H₂₃NO₂ 
• 1221972-17-3 4-methyl-N-(1-phenylhex-5-en-1-yl)benzenesulfonamide 

Relevant articles and documents

Visible-Light Photoredox-Catalyzed Remote Difunctionalizing Carboxylation of Unactivated Alkenes with CO2

Remote difunctionalization of unactivated alkenes is challenging but a highly attractive tactic to install two functional groups across long distances. Reported herein is the first remote difunctionalization of alkenes with CO2. This visible-light photoredox catalysis strategy provides a facile method to synthesize a series of carboxylic acids bearing valuable fluorine- or phosphorus-containing functional groups. Moreover, this versatile protocol shows mild reaction conditions, broad substrate scope, and good functional-group tolerance. Based on DFT calculations, a radical adds to an unactivated alkene to smoothly form a new carbon radical, followed by a 1,5-hydrogen atom-transfer process, the rate-limiting step, generating a more stable benzylic radical. The reduction of the benzylic radicals by an IrII species generates the corresponding benzylic carbanions as the key intermediates, which further undergo nucleophilic attack with CO2 to generate carboxylates.

Iron-Catalyzed Synthesis of α-Dienyl Five- and Six-Membered N-Heterocycles

The iron-catalyzed synthesis of α-dienyl N-heterocycles is reported. The method is cost-effective, atom-economic, and led to a range of substituted α-dienyl heterocycles in moderate to good yields and diastereoselectivities. The α-dienyl piperidines are key synthetic intermediates as demonstrated by the preparation of a panel of α-polyenyl N-heterocycles.

ERK INHIBITORS

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Diastereoselective control of intramolecular aza-Michael reactions using achiral catalysts

An intramolecular aza-Michael reaction with a Cbz carbamate and an enone is reported to result in 3,5-disubstituted nitrogen-containing heterocycles. Either cis or trans isomers were obtained selectively using chiral substrates and an achiral Pd (II) comp

FeCl3-catalyzed highly diastereoselective synthesis of substituted piperidines and tetrahydropyrans

The eco-friendly and highly diastereoselective synthesis of substituted cis-2,6-piperidines and cis-2,6-tetrahydropyrans is described. The key step of this method is the iron-catalyzed thermodynamic equilibration of 2-alkenyl 6-substituted piperidines and 2-alkenyl 6-substituted tetrahydropyrans allowing the isolation of enriched mixtures of the most stable cis-isomers.

Broadening the scope of group 4 hydroamination catalysis using a tethered ureate ligand

(Chemical Equation Presented) A broadly applicable group-4-based precatalyst for the hydroamination of primary and secondary amines was developed. Screening experiments involving a series of amide and urea proligands led to the discovery of a tethered bis(ureate) zirconium complex with unprecedented reactivity in the intermolecular hydroamination of alkynes and the intramolecular hydroamination of alkenes. This catalyst system is effective with primary and secondary amines, 1,2-disubstituted alkenes, and heteroatom-containing functional groups, including ethers, silanes, amines, and heteroaromatics. The gem-disubstituent effect is not required for cyclization. The catalyst is generally regioselective for the anti-Markovnikov product of intermolecular alkyne hydroamination, and chemoselective for hydroamination over C-alkylation when forming 6- and 7-membered rings from aminoalkenes.

Kinetic resolution of aminoalkenes by asymmetric hydroamination: A mechanistic study

The kinetic resolution of chiral aminoalkenes by hydroamination-cyclization was studied by using 3,3'-bis(triarylsilyl)-substituted binaphtholate rare-earth-metal complexes. The resolution of 1-arylaminopentenes proceeds with high efficiency and high irans-diastereoselectivity, whereas the resolution process of 1-alkylaminopentenes suffers from decreasing resolution efficiency with increasing steric demand of the aliphatic substituent. Kinetic studies of the matching and mismatching substrate-catalyst pair by using enantiopure substrates and either the (R)- or (S)-binaphtholate catalysts revealed that the difference in resolution efficiency stems from a shift of the Curtin-Hammett pre-equilibrium. Al-though 1-arylaminopentenes favor the matching substrate-catalyst complex, preference for the mismatching substrate-catalyst complex for 1-alkylaminopentenes diminishes resolution efficiency. Nevertheless, the relative cyclization rate for the two diastereomeric substrate-catalyst complexes remains in a typical range of 7-10:1. Plausible attractive π interactions between the aryl substituent and either the metal center or the aromatic system of the bis(triarylsilyl)-substituted binaphtholate ligand may explain increased sta-bility of the matching substrate-catalyst complex. Incidentally, the methoxymethyl (MOM)-substituted aminopentene 3g also exhibited a strong preference for the matching substrate-catalyst complex, possibly due to the chelating nature of the MOM substituent. The proximity of the stereocenter to the amino group in the aminoalkene substrate was crucial to achieve good kinetic resolution efficiency. The more remote β-phenyl substituent in 2-phenylpent-4-en-l-amine (5) resulted in diminished discrimination of the substrate enantiomers with respect to the relative rate of cyclization of the two substrate-catalyst complexes and a Curtin-Hammett preequilibrium close to unity.

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Intramolecular Diels-Alder Reactions of 3H-Pyrroles Resulting from the Thermal Rearrangements of 2H-Pyrroles

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