40032-55-1

Usage

Uses

Used in Pharmaceutical Industry:
BENZYL-((E)-3-PHENYL-ALLYL)-AMINE is used as a building block for the preparation of various pharmaceuticals due to its ability to contribute to the synthesis of a broad spectrum of medicinal compounds.
Used in Chemical Industry:
In the chemical industry, BENZYL-((E)-3-PHENYL-ALLYL)-AMINE is utilized in the production of polymers, dyes, and pharmaceutical intermediates, highlighting its importance in the synthesis of a variety of chemical products.
Used in Agrochemical Production:
BENZYL-((E)-3-PHENYL-ALLYL)-AMINE is used as a starting material for the synthesis of bioactive compounds, making it an essential intermediate in the development of agrochemicals.
Used in Fine Chemicals Synthesis:
BENZYL-((E)-3-PHENYL-ALLYL)-AMINE also plays a crucial role in the production of fine chemicals, where its unique structure and functional groups are leveraged to create high-value specialty products.

Upstream product

• 60293-41-6 N-((E)-3-phenylallylidene)benzylamine 
• 106-95-6 allyl bromide 
• 2687-12-9 cinnamyl chloride 
• 100-46-9 benzylamine 
• 14371-10-9 (E)-3-phenylpropenal 
• 17101-77-8 Benzyl-(α-bromvinyl)-sulfon 
• 21040-45-9 Cinnamyl acetate 
• 87802-71-9 (E)-methyl cinnamyl carbonate 
• 106625-70-1 ethyl (1-phenylallyl) carbonate 
• 4407-36-7 (2E)-3-phenyl-2-propen-1-ol 
• 24074-26-8 ethyl (diisopropylphosphoryl)acetate 
• 511286-64-9 (+/-) 3,5-dibenzyl[1,2,3]oxathiazolidine-2,2-dioxide 
• 141-97-9 ethyl acetoacetate 
• 36457-58-6 N-benzyl-1,1,1-trifluoromethanesulfonamide 

Downstream Products

• 154417-80-8 4--3-formyl-2(2H)-chromenone 
• 107175-77-9 3-Benzyl-5-(iodo-phenyl-methyl)-oxazolidin-2-one 
• 173548-43-1 (Z)-3-[Benzyl-((E)-3-phenyl-allyl)-carbamoyl]-2,3-dichloro-acrylic acid methyl ester 
• 221873-11-6 3--2,2-dimethylpropionaldehyde 
• 221873-24-1 1-cyclohexanecarbaldehyde 
• 265658-95-5 3-{N-benzyl[(E)-cinnamyl]amino}-2-(methoxycarbonyl)acrolein 
• 691409-22-0 benzaldehyde O-(N-cinnamyl-benzylaminooxalyl)oxime 
• 697287-01-7 (E)-N-benzyl-N-(3-phenyl-2-propenyl)glycine methyl ester 
• 282524-07-6 (E)-3-{benzyl[(E)-cinnamyl]amino}-2-cyanoacrolein 
• 887235-24-7 S-(4-pentynyl) N-benzyl-N-[(E)-3-phenyl-2-propenyl]carbamothioate 
• 552321-84-3 1-[((E)-N-benzyl-N-(3-phenyl-2-propenyl)amino)acetyl]pyrrolidine 

Relevant academic research and scientific papers

Intramolecular Cyclization of 3,3-Diarylpropenylamides of Electron-Deficient Alkenes: Stereoselective Synthesis of Functionalized Hexahydrobenzo[f]isoindoles

Intramolecular Diels–Alder reactions of various 3,3-diarylpropenylamides of electron-deficient alkenes to give hexahydrobenzo[f]isoindoles were investigated. Reaction of 1,1,2-ethenetricarboxylic acid 1,1-diethyl ester with 3,3-diaryl-2-propen-1-amines under the amide formation conditions gave the tricyclic compounds in sequential processes involving intramolecular Diels–Alder reaction. The reaction gave cis- and trans-fused tricyclic compounds selectively, depending on the substituents on the benzene ring, reaction temperature and solvent. In the reaction with dissymmetrically substituted 3,3-diaryl-2-propen-1-amines, trans-substituted aryl group reacted mainly as a styrene component. Amides of electron-deficient alkenic carboxylic acids such as fumarate do not undergo cyclization at room temperature sequentially and the reaction on heating gave trans-fused hexahydrobenzo[f]isoindoles. The origin of the observed stereoselectivity has been examined by the DFT calculations.

Stereoselective synthesis of cis-2,6-disubstituted piperidines from 1,2-cyclic sulfamidates

Diastereoselective synthesis of cis-2,6-disubstituted piperidines from 1,2-cyclic sulfamidates is described. Regioselective ring-opening reactions of 1,2-cyclic sulfamidates derived from L-phenylalanine, alanine, valine, norvaline with the ketal protected acetylide with a phenyl substituent proceed smoothly to form the N-sulfamate intermediates which on acidic hydrolysis give alkynylated amines with the ketal group intact. Hydrogenation of the alkynylated amines, debenzylation, ketal deprotection, subsequent cyclization (of aminoketones) and stereoselective hydrogenation of the cyclic iminium ion intermediates afford the corresponding cis-2,6-disubstituted piperidines in high diastereoselectivity (98% ≥ d.e.) with good chemical yields (68–86%). The present approach provides a novel route for the stereoselective synthesis of cis-2,6-disubstituted piperidines.

Lanthanide-Catalyzed Tandem Addition of Amines to Cyanoalkenes: Synthesis of Cyclic Amidines

A tandem insertion of aliphatic nitriles and unactivated alkenes to the N-H bond of secondary aliphatic amines catalyzed by simple trialkyl rare-earth metal complexes was disclosed. This reaction provides a highly atom-economic and stereoselective way to a range of cyclic amidines under mild reaction conditions.

Visible Light-Mediated Synthesis of Enantiopure γ-Cyclobutane Amino and 3-(Aminomethyl)-5-phenylpentanoic Acids

A visible light-mediated [2+2] photocycloaddition of amide-linked dienes using [Ir(dtb-bpy)(dF(CF3)ppy)2]PF6 as triplet sensitizer was applied to generate a variety of N-tert-butyl, N-benzyl- and N-tert-butoxycarbonyl-protected 3-azabicyclo[3.2.0]heptan-2-ones in good yields and with good diastereoselectivity. Density functional theory calculations shed light on the conformational prerequisites for the [2+2] photocycloaddition. The bicyclic key structures could be readily transformed into γ-cyclobutane amino acids. For the obtained racemic 3-phenyl-2-aminocyclobutane-1-carboxylic acid the resolution with chiral oxazolidin-2-one is demonstrated to allow access to both enantiomers. Alternatively, a chiral auxiliary approach led as well to the enantiomerically pure target compound. Finally, the synthesis of either enantiomer of 3-(aminomethyl)-5-phenylpentanoic acid, the racemate being described as an anticonvulsant, is described.

Visible Light-Mediated Synthesis of Enantiopure g-Cyclobutane Amino and 3-(Aminomethyl)-5-phenylpentanoic Acids

A visible light-mediated [2+2] photocycloaddition of amide-linked dienes using [Ir(dtb-bpy)(dF(CF3)ppy)2]PF6 as triplet sensitizer was applied to generate a variety of N-tert-butyl, N-benzyl- and N-tert-butoxycarbonyl-protected 3-aza-bicyclo[3.2.0]heptan-2-ones in good yields and with good diastereoselectivity. Density functional theory calculations shed light on the conformational prerequisites for the [2+2] photocycloaddition. The bicyclic key structures could be readily transformed into g-cyclobutane amino acids. For the obtained racemic 3-phenyl-2-aminocyclobu-tane-1-carboxylic acid the resolution with chiral oxazolidin-2-one is demonstrated to allow access to both enantiomers. Alternatively, a chiral auxiliary approach led as well to the enantiomerically pure target compound. Finally, the synthesis of either enantiomer of 3-(aminomethyl)-5-phenylpentanoic acid, the racemate being described as an anticonvulsant is described.

Unexpected Rearrangement of N-Allyl-2-phenyl-4,5-Dihydrooxazole-4-Carboxamides to Construct Aza-Quaternary Carbon Centers

The unexpected rearrangement of N-allyl-2-phenyl-4,5-dihydrooxazole-4-carboxamides in the presence of LiHMDS has been found. The key features are: (1) the net reaction consisted of 1,3-migration of the N-allyl group, (2) the rearrangement produced a congested aza-quaternary carbon center, (3) both cyclic and acyclic substrates underwent the unexpected rearrangement to afford products in moderate to high yields, and (4) the reaction seemed to be highly stereoselective. In addition, a plausible mechanism has been discussed.

Expanding the Boundaries of Water-Tolerant Frustrated Lewis Pair Hydrogenation: Enhanced Back Strain in the Lewis Acid Enables the Reductive Amination of Carbonyls

The development of a boron/nitrogen-centered frustrated Lewis pair (FLP) with remarkably high water tolerance is presented. As systematic steric tuning of the boron-based Lewis acid (LA) component revealed, the enhanced back-strain makes water binding increasingly reversible in the presence of relatively strong base. This advance allows the limits of FLP's hydrogenation to be expanded, as demonstrated by the FLP reductive amination of carbonyls. This metal-free catalytic variant displays a notably broad chemoselectivity and generality.

Direct use of allylic alcohols and allylic amines in palladium-catalyzed allylic amination

Allylic alcohols and allylic amines were directly utilized in a Pd-catalyzed hydrogen-bond-activated allylic amination under mild reaction conditions in the absence of any additives. The cooperative action of a Pd-catalyst and a hydrogen-bonding solvent is most likely responsible for its high reactivity. The catalytic system is compatible with a variety of functional groups and can be used to prepare a wide range of linear allylic amines in good to excellent yields. Furthermore, this methodology can be easily applied to the one-step synthesis of two drugs, cinnarizine and naftifine, on a gram scale.

Synthesis of Cyclic Guanidines Bearing N-Arylsulfonyl and N-Cyano Protecting Groups via Pd-Catalyzed Alkene Carboamination Reactions

Palladium-catalyzed carboamination reactions of N-allylguanidines bearing cleavable N-cyano or N-arylsulfonyl protecting groups are described. The reactions afford cyclic guanidine products in good yield, and transformations of substrates bearing internal alkenes proceed with high diastereoselectivity. Deuterium labeling studies indicate these transformations proceed via anti-aminopalladation pathways.

Simple Metal-Free Direct Reductive Amination Using Hydrosilatrane to Form Secondary and Tertiary Amines

This work describes the use of cheap, safe, and easy-to-handle hydrosilatrane as the reductant in direct reductive amination reactions. This efficient method enables a facile, metal-free access to secondary and tertiary amines from a wide range of aldehydes and ketones, with the synthesis of tertiary amines requiring no additives at all. This reaction demonstrates excellent functional group tolerance, chemoselectivity, and scalability. (Figure presented.).