173948-26-0

Basic information

• Product Name: (E)-N,N-dibenzylbut-2-en-1-amine
• Synonyms: (E)-N,N-dibenzylbut-2-en-1-amine
• CAS NO: 173948-26-0
• Molecular Weight: 251.371
• Mol File: 173948-26-0.mol

Chemical Properties

• CAS DataBase Reference: (E)-N,N-dibenzylbut-2-en-1-amine(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-N,N-dibenzylbut-2-en-1-amine(173948-26-0)
• EPA Substance Registry System: (E)-N,N-dibenzylbut-2-en-1-amine(173948-26-0)

Safety Data

• Hazardous Substances Data: 173948-26-0(Hazardous Substances Data)

Upstream product

• 106-98-9 1-butylene 
• 103-49-1 dibenzylamine 
• 6117-91-5 (E/Z)-2-buten-1-ol 
• 504-61-0 (E)-but-2-enol 
• 598-32-3 2-hydroxy-3-butene 
• 68452-43-7 N,N-dibenzylbut-2-yn-1-amine 
• 103185-13-3 (E)-crotyl methyl carbonate 
• 4784-77-4 (E)-1-Bromo-2-butene 

Relevant articles and documents

One-Pot Synthesis of O-Allylhydroxylamines through the Organocatalytic Oxidation of Tertiary Allylic Amines Followed by a [2,3]-Meisenheimer Rearrangement

A cheap, green, and highly efficient one-pot method for the synthesis of O-protected allylic alcohols is described. By utilizing 2,2,2-trifluoroacetophenone as the organocatalyst and H2O2 as the oxidant, a variety of allylic amine N-

Electrochemical Synthesis of Allylic Amines from Terminal Alkenes and Secondary Amines

Allylic amines are valuable synthetic targets en route to diverse biologically active amine products. Current allylic C-H amination strategies remain limited with respect to the viable N-substituents. Herein, we disclose a new electrochemical process to p

Cobalt-Catalyzed Remote Hydroboration of Alkenyl Amines

We here present a generally applicable cobalt-catalyzed remote hydroboration of alkenyl amines, providing a practical strategy for the preparation of borylamines and aminoalcohols. This method shows broad substrate scope and good functional group tolerance, tolerating a series of alkenyl amines, including alkyl-alkyl amines, alkyl-aryl amines, aryl-aryl amines, and amides. Of note, this protocol is also compatible with a variety of natural products and drug derivatives. Preliminary mechanistic studies suggest that this transformation involves an iterative chain walking and hydroboration sequence.

C-N Bond Formation from Allylic Alcohols via Cooperative Nickel and Titanium Catalysis

Amination of allylic alcohols is facilitated via cooperative catalysis. Catalytic Ti(O-i-Pr)4 is shown to dramatically increase the rate of nickel-catalyzed allylic amination, and mechanistic experiments confirm activation of the allylic alcohol by titanium. Aminations of primary and secondary allylic alcohols are demonstrated with a variety of amine nucleophiles. Diene-containing substrates also cyclize onto the nickel allyl intermediate prior to amination, generating carbocyclic amine products. This tandem process is only achieved under our cooperative catalytic system.

Direct Allylic Amination of Allylic Alcohol Catalyzed by Palladium Complex Bearing Phosphine-Borane Ligand

The direct electrophilic, nucleophilic, and amphiphilic allylations of allylic alcohol by use of a palladium catalyst and organometallic reagents such as organoborane and organozinc has been developed. The phosphine-borane compound works as the effective ligand for palladium-catalyzed direct allylic amination of allylic alcohol. Thus, with secondary amines, the reaction was completed in only 1 h, even at room temperature.

Ligand-Controlled Cobalt-Catalyzed Transfer Hydrogenation of Alkynes: Stereodivergent Synthesis of Z- and E-Alkenes

Herein, we report a novel cobalt-catalyzed stereodivergent transfer hydrogenation of alkynes to Z- and E-alkenes. Effective selectivity control is achieved based on a rational catalyst design. Moreover, this mild system allows for the transfer hydrogenation of alkynes bearing a wide range of functional groups in good yields using catalyst loadings as low as 0.2 mol %. The general applicability of this procedure is highlighted by the synthesis of more than 50 alkenes with good chemo- and stereoselectivity. A preliminary mechanistic study revealed that E-alkene product was generated via sequential alkyne hydrogenation to give Z-alkene intermediate, followed by a Z to E alkene isomerization process.

Iridium-catalyzed asymmetric allylic substitutions with bulky amines/oxidative double bond cleavage - Entry into the reetz synthesis of amino alcohols

Branched allylic amines were prepared by Ir-catalyzed enantioselective allylic aminations with the bulky N-nucleophiles HN(Boc)2 and HNBn2. The products were transformed into N-protected amino aldehydes, which were either reduced or coupled diastereoselectively with organometallic compounds to give vicinal amino alcohols. A formal synthesis of the neurokinin receptor antagonist (+)-L-733060 was carried out as an application. Ir-catalyzed enantioselective allylic aminations with bulky N-nucleophiles HN(Boc)2 and HNBn2 gave N-protected allylic amines, which were transformed into N-protected chiral amino aldehydes. These are useful chiral building blocks as previously demonstrated by Reetz et al. A formal synthesis of the neurokinin receptor antagonist (+)-L-733060 was carried out as an application.

Pentacoordinated Carboxylate π-Allyl Nickel Complexes as Key Intermediates for the Ni-Catalyzed Direct Amination of Allylic Alcohols

Direct amination of allylic alcohols with primary and secondary amines catalyzed by a system made of [Ni(1,5-cyclooctadiene)2] and 1,1′-bis(diphenylphosphino)ferrocene was effectively enhanced by adding nBu4NOAc and molecular sieves, affording the corresponding allyl amines in high yield with high monoallylation selectivity for primary amines and high regioselectivity for monosubstituted allylic alcohols. Such remarkable additive effects of nBu4NOAc were elucidated by isolating and characterizing some nickel complexes, manifesting the key role of a charge neutral pentacoordinated η3-allyl acetate complex in the present system, in contrast to usual cationic tetracoordinated complexes earlier reported in allylic substitution reactions.

Amination of allylic alcohols in water at room temperature

The "trick" to carrying out regiocontrolled aminations of allylic alcohols in water as the only medium is use of a nanomicelle's interior as the organic reaction solvent. When HCO2Me is present, along with the proper base and source of catalytic Pd, allylic amines are cleanly formed at room temperature.