57734-99-3

Usage

Uses

Used in Pharmaceutical Industry:
N-Benzylidene-2-propynylamine is used as a key intermediate for the synthesis of various drugs. Its chemical properties make it a valuable component in the development of new medications, contributing to the advancement of pharmaceutical research and drug discovery.
Used in Pesticide Industry:
In the pesticide industry, N-Benzylidene-2-propynylamine is utilized as an essential intermediate in the production of different types of pesticides. Its incorporation into these chemical formulations helps enhance the effectiveness of pest control solutions, promoting agricultural productivity and food security.

InChI:InChI=1/C10H9N/c1-2-8-11-9-10-6-4-3-5-7-10/h1,3-7,9H,8H2/b11-9+

Upstream product

• 100-52-7 benzaldehyde 
• 2450-71-7 Propargylamine 
• 100-51-6 benzyl alcohol 

Downstream Products

• 57790-32-6 1-trimethylsilyl-N-benzylidene-3-aminoprop-1-yne 
• 1197-51-9 N-propargylbenzylamine 
• 183963-69-1 diethyl phenyl(prop-2-yn-1-ylamino)methanephosphonate 
• 145126-88-1 1-butyl-2-(ethoxycarbonyl)-N-benzyl-N-propynylaziridine-2-carboxamide 
• 57735-01-0 (1-Methyl-3-trimethylsilanyl-prop-2-ynyl)-[1-phenyl-meth-(E)-ylidene]-amine 
• 57790-33-7 [1-Phenyl-meth-(E)-ylidene]-(1-trimethylsilanylethynyl-but-3-ynyl)-amine 
• 57735-02-1 [1-Phenyl-meth-(E)-ylidene]-(1-trimethylsilanylethynyl-pentyl)-amine 
• 57735-00-9 methyl 4-(benzylideneamino)-6-(trimethylsilyl)-5-hexynoate 
• 1198108-86-9 ethyl N-(ethoxyphenylmethyl)-N-propargylcarbamate 
• 1007389-70-9 3-benzyl-6-methyl-3,4-dihydro-2H-1,3-oxazin-2-one 
• 1041425-04-0 N-benzyl-N-(2-propynyl)-2-chloroacetamide 
• 111493-11-9 (E)-3-benzyl-5-(iodomethylene)-1,3-oxazolidin-2-one 

Relevant academic research and scientific papers

Reductive Amination Revisited: Reduction of Aldimines with Trichlorosilane Catalyzed by Dimethylformamide─Functional Group Tolerance, Scope, and Limitations

Aldimines, generated in situ from aliphatic, aromatic, and heteroaromatic aldehydes and aliphatic, aromatic, and heteroaromatic primary or secondary amines, can be reduced with trichlorosilane in the presence of dimethylformamide (DMF) as an organocatalys

Biocatalytic N-Alkylation of Amines Using Either Primary Alcohols or Carboxylic Acids via Reductive Aminase Cascades

The alkylation of amines with either alcohols or carboxylic acids represents a mild and safe alternative to the use of genotoxic alkyl halides and sulfonate esters. Here we report two complementary one-pot systems in which the reductive aminase (RedAm) from Aspergillus oryzae is combined with either (i) a 1° alcohol/alcohol oxidase (AO) or (ii) carboxylic acid/carboxylic acid reductase (CAR) to affect N-alkylation reactions. The application of both approaches has been exemplified with respect to substrate scope and also preparative scale synthesis. These new biocatalytic methods address issues facing alternative traditional synthetic protocols such as harsh conditions, overalkylation and complicated workup procedures.

Iodocarbamation of N-Homopropargyl Carbamates: Mild and Stereoselective Entry to Functionalized Oxazinan-2-ones

An efficient and general iodocarbamation of benzyl N-homopropargylcarbamates has been developed by using iodine as the electrophilic agent. This regio- and stereoselective cyclization yielded (E)-6-iodomethyleneoxazinan-2-ones, which can be further transformed through palladium cross-coupling reactions followed by hydrogenation to produce 1,3-oxazinan-2-ones.

Diastereoselective synthesis of γ- And δ-lactams from imines and sulfone-substituted anhydrides

Sulfone-substituted γ- and δ-lactams have been prepared in a single step with high diastereoselectivity. Sulfonylglutaric anhydrides produce intermediates that readily decarboxylate to provide δ-lactams with high diastereoselectivity. Substituents at the 3- or 4-position of the glutaric anhydride induce high levels of stereocontrol. Sulfonylsuccinic anhydrides produce intermediate carboxylic acids that can be trapped as methyl esters or allowed to decarboxylate under mild conditions. This method has been applied to a short synthesis of the pyrrolizidine alkaloid (±)-isoretronecanol.

An expeditious and atom-economic synthesis of lead-like, medicinally important 4,5-dihydropyrazolo[1,5-a]pyrazin-6-ones

We have developed an expeditious and atom-economic synthesis of lead-like, privileged 4,5-dihydropyrazolo[1,5-a]pyrazin-6-ones, which is based on Sonogashira coupling and a two-step condensation with hydrazine hydrate leading to two ring-forming events, with full control over the two elements of diversity present.

Gold-catalyzed oxycyclization of allenic carbamates: Expeditious synthesis of 1,3-oxazin-2-ones

A combined experimental and computational study on regioselective gold-catalyzed synthetic routes to 1,3-oxazinan-2-ones (kinetically controlled products) and 1,3-oxazin-2-one derivatives (thermodynamically favored) from easily accessible allenic carbamates has been carried out.

Synthesis of a γ-lactam library via formal cycloaddition of imines and substituted succinic anhydrides

Formal cycloaddition reactions between imines and cyclic anhydrides serve as starting point for the synthesis of diverse libraries of small molecules. The synthesis of succinic anhydrides substituted with electron-withdrawing groups is facilitated by new mild conditions for alkylation of aryl-substituted acetyl esters with ethyl bromoacetate. These anhydrides are then used in formal cycloaddition reactions with imines to produce γ-lactams. 2-Fluoro-5-nitrophenylsuccinic anhydride reacts efficiently with imines to provide lactams that are further diversified by conversion of the nitro group to either an aniline and an azide for subsequent reactions with acylating agents and alkynes, respectively. The synthesis of cyanosuccinic anhydride is reported for the first time, and the use of this compound in reactions with imines and subsequent functionalization of the resultant lactams is demonstrated.

Monoamine oxidase inhibitors: Benzylidene-prop-2-ynyl-amines analogues

A new series of benzylidene-prop-2-ynyl-amines analogues have been synthesized and evaluated for their monoamine oxidase A and B inhibitory activity by determination of IC50 and selectivity index (SI). Among these inhibitors, benzhydrylidene-prop-2-ynyl-amine (2, IC50 32nM) and (3, 4-dimethoxy-benzylidene)-prop-2-ynylamine (10, IC50 14nM) provide the highest inhibitory potency toward monoamine oxidase (MAO) A and B respectively. (3,5-Dimethyl-1H-pyrrol-2-ylmethylene)-prop-2-ynyl-amine (1, SI=58.96) and compound (2, SI=0.34) were proved to be the superior selective inhibitors toward MAO-A and MAO-B respectively. Docking studies show that the imine moiety is located in hydrophobic pocket, bringing the propargyl group close to FAD which indicates that the different inhibitory potency toward MAO-A may be ascribable to both the distance between alkynyl group and N5 of FAD, and hydrogen bonding interactions between inhibitors and enzymes.

Phosphatase inhibitors. III. Benzylaminophosphonic acids as potent inhibitors of human prostatic acid phosphatase

Further investigation of the structural requirements of a series of benzylphosphonic acid inhibitors of human prostatic acid phosphatase has led to the highly potent series of α-aminobenzylphosphonic acids. The α-benzylaminobenzylphosphonic acid, with an IC50 = 4 nM, exhibited a 3500-fold improvement in potency over the carbon analogue, α-phenylethyl. The enhanced potency may be due to a combination of four favorable interactions including those with the phosphate binding region, the presence the hydrophobic moieties of the benzylamino and phenylphosphonic acid, and a rigid conformer produced by an internal salt bridge between the phosphonate and the α-amino group. Replacement of the phosphonic acid moiety with a phosphinic or carboxylic acid as well as deletion of the benzyl substitution on the α-amino group led to great reductions in potency.

Intramolecular 1,3-Dipolar Cycloaddition of Stabilized Azomethine Ylides to Unactivated Dipolarophiles

The scope and limitations of the intramolecular 1,3-dipolar cycloaddition of doubly-stabilized azomethine ylides to unactivated olefinic, acetylenic, and aromatic dipolarophiles is reported.The azomethine ylides studied were generated by flash vacuum pyrolysis of their corresponding aziridines and were found to add stereospecifically in good to excellent yields to a variety of unactivated dipolarophiles.Generation of the diazabicyclooctane (e.g., 15a,b), diazabicyclononane (e.g., 4, 13), and diazabicyclodecane (e.g., 15c) ring systems are possible using this technology.In addition, the first examples of cycloaddition of a stabilized azomethine ylide to benzene dipolarophiles are reported.Cycloadditions of this type generate highly functionalized tricyclic systems with complete relative stereocontrol at the newly formed stereocenters (e.g., 24-26).Finally, it has been shown that cycloadducts 31 and 32 are in equilibrium, presumably by way of the intermediate azomethine ylide 33, under conditions of flash vacuum pyrolysis.