92610-10-1

Basic information

• Product Name: 1-Naphthalenemethanamine, N-[(2E)-3-phenyl-2-propenyl]-
• CAS NO: 92610-10-1
• Molecular Formula: C20H19N
• Molecular Weight: 273.378
• Mol File: 92610-10-1.mol

Chemical Properties

• CAS DataBase Reference: 1-Naphthalenemethanamine, N-[(2E)-3-phenyl-2-propenyl]-(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Naphthalenemethanamine, N-[(2E)-3-phenyl-2-propenyl]-(92610-10-1)
• EPA Substance Registry System: 1-Naphthalenemethanamine, N-[(2E)-3-phenyl-2-propenyl]-(92610-10-1)

Safety Data

• Hazardous Substances Data: 92610-10-1(Hazardous Substances Data)

Upstream product

• 98977-78-7 N-(3-phenyl-2-propenylidene)-1-naphthalenemethanamine 
• 14371-10-9 (E)-3-phenylpropenal 
• 118-31-0 (naphth-1-yl)methylamine 
• 4407-36-7 (2E)-3-phenyl-2-propen-1-ol 
• 106625-69-8 ethyl (E)-3-phenyl-2-propenyl carbonate 

Downstream Products

• 98977-83-4 (E)-N-benzyl-N-(3-phenyl-2-propenyl)-1-naphthalenemethanamine 
• 65472-88-0 naftifine 
• 79416-78-7 (E)-N-(3-phenyl-2-propenyl)-N-2-propenyl-1-naphthalenemethanamine 
• 98977-86-7 (E)-N-acetyl-N-(3-phenyl-2-propenyl)-1-naphthalenemethanamine 
• 98977-80-1 (E)-N,N-bis(3-phenyl-2-propenyl)-1-naphthalenemethanamine 
• 65472-96-0 (E)-N-isopropyl-N-(3-phenyl-2-propenyl)-1-naphthalenemethanamine 

Relevant articles and documents

Efficient Synthesis of Trifluoromethyl Amines through a Formal Umpolung Strategy from the Bench-Stable Precursor (Me4N)SCF3

Reported herein is the one-pot synthesis of trifluoromethylated amines at room temperature using the bench-stable (Me4N)SCF3reagent and AgF. The method is rapid, operationally simple and highly selective. It proceeds via a formal umpolung reaction of the SCF3with the amine, giving quantitative formation of thiocarbamoyl fluoride intermediates within minutes that can readily be transformed to N-CF3. The mildness and high functional group tolerance render the method highly attractive for the late-stage introduction of trifluoromethyl groups on amines, as demonstrated herein for a range of pharmaceutically relevant drug molecules.

Efficient ruthenium-catalyzed N-methylation of amines using methanol

An in situ-generated complex from [RuCpCl2]2 and dpePhos ligand is reported as an efficient catalyst in the presence of 5 mol % of LiOtBu for the N-methylation of amines using methanol as the methylating agent at moderate conditions, following hydrogen borrowing strategy. This simple catalyst system provides selective N-monomethylation of substituted primary anilines and sulfonamides as well as N,N dimethylation of primary aliphatic amines in excellent yields at 40-100 °C with good tolerance to reducible functional groups. The catalytic intermediate CpRu(dpePhos)H was isolated and was shown to be active for methylation in the absence of base.

Metal-free catalyst for the chemoselective methylation of amines using carbon dioxide as a carbon source

N-methylation of amines is an important step in the synthesis of many pharmaceuticals and has been widely applied in the preparation of other key intermediates and chemicals. Therefore, the development of efficient methylation methods has attracted considerable attention. In this respect, carbon dioxide is an attractive C1 building block because it is an abundant, renewable, and nontoxic carbon source. Consequently, we developed a highly chemoselective, metal-free catalytic system that operates under ambient conditions for the N-methylation of amines. The methylation of amines with CO2 as C1 source and Ph2SiH2 as reducing agent was achieved with an N-heterocyclic carbene (NHC) as the catalyst. The catalyst is tolerant toward a variety of functional groups (including esters and ethers, nitro, nitrile, and carbonyl groups, and unsaturated C-C bonds); the reaction uses commercially available reagents and can be performed on a gram scale.

N-heterocyclic carbene C,S palladium(II) π-allyl complexes: Synthesis, characterization, and catalytic application in allylic amination reactions

A series of five-membered N-heterocyclic carbene C,S palladium(II) π-allyl complexes were successfully developed and characterized. Structural analyses of these complexes revealed that the organopalladium chelates adopt a skew-envelope conformation with a

An efficient and convenient palladium catalyst system for the synthesis of amines from allylic alcohols

A novel catalyst system for efficient amination of allylic alcohols with aryl and alkyl amines is presented. By applying a convenient combination consisting of Pd(OAc)2/1,10-phenanthroline, a variety of allylic alcohols reacted smoothly to give the corresponding secondary and tertiary amines in good to excellent yields with high regioselectivity. The usefulness of our protocol is demonstrated in the one-step synthesis of the antifungal drug naftifine and the calcium channel blocker flunarizine. One pot is all it takes: By applying a convenient combination consisting of Pd(OAc)2/1,10- phenanthroline, a variety of allylic alcohols reacts smoothly to give the corresponding secondary and tertiary amines in good to excellent yields with high regioselectivity (see picture).

Direct use of allylic alcohols for platinum-catalyzed monoallylation of amines

A new direct catalytic amination of allylic alcohols promoted by the combination of platinum and a large bite-angle ligand DPEphos was developed in which the allylic alcohol was effectively converted to a π-allylplatinum intermediate without the use of an activating reagent. The use of the DPEphos ligand was essential for obtaining high catalyst activity and high monoallylation selectivity of primary amines, allowing the formation of a variety of monoallylation products in good to excellent yield.

A one-pot oxidation-imine formation-reduction route from alcohols to amines using manganese dioxide-sodium borohydride: The synthesis of naftifine

A new procedure for the one-pot conversion of alcohols into amines is described which utilises manganese dioxide in the presence of sodium borohydride; the scope of this process is outlined, as is its application to the preparation of the topical antifungal agent, naftifine.

Synthesis and Structure-Activity Relationships of Naftifine-Related Allylamine Antimycotics

Naftifine (1) is the first representative of the new antifungal allylamine derivatives.Its biological activity is strictly bound to specific structural requirements that are unrelated to those of known antifungals.A tertiary allylamine function seems to be a prerequisite for activity against fungi.By systematic variation of the individual structural elements in 1, detailed structure-activity relationships are defined in which the phenyl ring is the structural feature permitting the widest variations.Versatile synthetic routes to allylamine derivatives and comparative biological data are presented.

REDUKTIVE METHYLIERUNG PRIMAERER UND SEKUNDAERER AMINE MIT HILFE VON FORMALDEHYD UND SALZEN DER PHOSPHORIGEN SAEURE

Salts of phophorous acid were found to be useful alternative reducing agents for the reductive methylation of amines.