54089-45-1

Usage

Uses

Used in Pharmaceutical Research:
N-(3,4-METHYLENEDIOXYBENZYLIDENE)BENZYL& is used as a building block in organic synthesis for creating various types of compounds, particularly in the development of new drugs.
Used in Fragrance and Flavor Production:
Due to its aromatic nature, N-(3,4-METHYLENEDIOXYBENZYLIDENE)BENZYL& is used in the production of fragrances and flavors, adding unique scents and tastes to various products.
Used in Cosmetic Industry:
This versatile compound has potential applications in the cosmetic industry, where it can be utilized in the formulation of various cosmetic products.
Used in Food Industry:
N-(3,4-METHYLENEDIOXYBENZYLIDENE)BENZYL& also has potential applications in the food industry, where it can be used to enhance the flavor and aroma of food products.

InChI:InChI=1/C15H13NO2/c1-2-4-12(5-3-1)9-16-10-13-6-7-14-15(8-13)18-11-17-14/h1-8,10H,9,11H2/b16-10+

Upstream product

• 120-57-0 piperonal 
• 100-46-9 benzylamine 
• 495-76-1 piperonol 

Downstream Products

• 4720-73-4 1-(benzo[d][1,3]dioxol-5-yl)-N-benzylmethanamine 
• 1437799-09-1 2-(benzo[d][1,3]dioxol-5-yl)-N-benzyl-2-(N-benzylacetamido)acetamide 
• 6852-58-0 N-benzylidene tert-butylamine 
• 780-25-6 N-benzylidene benzylamine 
• 80985-00-8 3,4-methylenedioxybenzylideneethylamine 
• 396717-28-5 N-(benzo[1,3]dioxol-5-ylmethylene)-tert-butylamine 

Relevant academic research and scientific papers

Synthesis and anti-parasitic activity of N-benzylated phosphoramidate Mg2+-chelating ligands

A series of N-benzylated phosphoramidate esters, containing a 3,4-dihydroxyphenyl Mg2+-chelating group, has been synthesised in five steps as analogues of fosmidomycin, a Plasmodium falciparum 1-deoxy-1-D-xylulose-5-phosphate reductoisomerase (PfDXR) inhibitor. The 3,4-dihydroxyphenyl group effectively replaces the Mg2+-chelating hydroxamic acid group in fosmidomycin. The compounds showed very encouraging anti-parasitic activity with IC50 values of 5.6–16.4 μM against Plasmodium falciparum parasites and IC50 values of 5.2 – 10.2 μM against Trypanosoma brucei brucei (T.b.brucei). Data obtained from in silico docking of the ligands in the PfDXR receptor cavity (3AU9)5 support their potential as PfDXR inhibitors.

Substituted 4-Oxo-1,2,3,4-tetrahydroquinoline-3-carboxylic esters by a tandem imine addition-SNAr reaction

A tandem imine addition-SNAr annulation reaction has been developed as a new approach to the synthesis of 4-oxo-1,2,3,4- tetrahydroquinoline-3-carboxylic esters. A series of these structures has been generated by reacting selected imines with tert-butyl 2-fluoro-5- nitrobenzoylacetate. Structural variations in the final products are accomplished by changing the substituents on the imine and the alkyl group of the ester. The title compounds are isolated as their enols in 55-97% yield without the need for added base or catalysts. The synthesis of the starting materials as well as mechanistic studies and further synthetic conversions of the products are presented.

Ugi four-component reaction of alcohols: Stoichiometric and catalytic oxidation/MCR sequences

A new, simple, and efficient procedure for the one-pot Ugi four-component reaction of alcohols instead of aldehydes is described. Using a stoichiometric amount of IBX or only 1-2% of sodium 2-iodobenzenesulfonate in the presence of Oxone, a wide range of primary alcohols were oxidized to the aldehyde that were directly engaged in the Ugi four-component reaction to afford α-acetamidoamides in good to excellent yields.

Palladium-catalyzed aryl iodide carbonylation as a route to imidazoline synthesis: Design of a five-component coupling reaction

Take five: A new method employing aryl halide carbonylation to directly access heterocycles has been described (see scheme). In a single palladium-catalyzed reaction the catalyst mediates two consecutive carbonylation steps, thereby converting five components (aryl iodide, two units imine, and two units CO) into an imidazoline ring.

A highly diastereoselective synthesis of α-hydroxy-β-amino acid derivatives via a Lewis acid catalyzed three-component condensation reaction

A very efficient three-component synthesis of a series of syn α-hydroxy-β-amino esters, obtained in high diastereoselection and yield, was realized starting from an aldehyde, benzylamine, and the ketene silyl acetals derived from Ley's lactones. The synthetic protocol was optimized and the above compounds were obtained without the isolation of intermediates. The origin of the observed diastereoselection was investigated through a computational model of the key reaction step.

Sequential Cu(I)/Pd(0)-catalyzed multicomponent coupling and annulation Protocol for the synthesis of indenoisoquinolines

Copper-catalyzed coupling of imines, vinylstannanes, or alkynes and o-bromoaroyl chlorides followed by Pd(0)-catalyzed annulations afforded indenoisoquinolines. Protocols requiring minimal purifications were developed, providing new methods for the construction of combinatorial libraries.

Efficient microwave-assisted solvent-free synthesis of N-substituted aldimines

Neat non-volatile amines react with various aromatic aldehydes in the absence of any catalyst, solid support, or solvent, to give imines after a reaction time of eight minutes under microwave irradiation by a clean and very efficient process (yields: 75-100%). In the case of volatile amine, methylamine, 1,3-dimethylurea dispersed on montmorillonite K10 is used as an amine precursor to prepare the corresponding imines. Georg Thieme Verlag Stuttgart.

Preparation of benzolactams by Pd(OAC)2-catalyzed direct aromatic carbonylation

We developed a new method for Pd(II)-catalyzed direct aromatic carbonylation in a phosphine-free catalytic system using Pd(OAc)2 and Cu(OAc)2 in an atmosphere of CO gas containing air. The carbonylation proceeded with ortho-palladation, inducing a remarkable site selectivity to afford a variety of five- or six-membered benzolactams from secondary ω-arylalkylamines, such as N-alkylbenzylamines or N-alkylphenethylamines. Copyright

Synthesis of cytotoxic indenoisoquinoline topoisomerase I poisons

A number of indenoisoquinolines were prepared and evaluated for cytotoxicity in human cancer cell cultures and for activity vs topoisomerase 1 (top1). The two most cytotoxic indenoisoquinolines proved to be cis-6- ethyl-5,6,12,13-tetrahydro-2,3-dimethoxy-8,9-(methylenedioxy)-5,11-dioxo- 11H-indeno[1,2-c]isoquinoline (21) and cis-6-allyl-5,6,12,13-tetrahydro-2,3- dimethoxy-8,9-(methylenedioxy)-5,11-dioxo-11H-indeno[1,2-c]isoquinoline (22), both of which displayed submicromolar mean graph midpoints when tested in 55 human cancer cell cultures. Two of the most potent top i inhibitors were 6- (3-carboxy-1-propyl)-5,6-dihydro-5,11-dioxo-11H-indeno[1,2-c]isoquinoline (26) and 6-ethyl-2,3-dimethoxy-8,9-(methylenedioxy)-11H-indeno[1,2- c]isoquinolinium Chloride (27), both of which also inhibited top2, unwound DNA, and are assumed to be DNA intercalators. However, two additional potent top1 inhibitors, 6-allyl-5,6-dihydro-2,3-dimethoxy-8,9-(methylenedioxy)- 5,11-dioxo-11H-indeno[1,2-c]isoquinoline (13c) and 5,6-dihydro-6-(4- hydroxybut-1-yl)-2-3-dimethoxy-8,9-methylenedioxy-5,11-dioxo-11H-indeno[1,2- c]isoquinoline (19a), did not unwind DNA and did not affect top2. Some of the DNA cleavage sites detected in the presence of the indenoisoquinolines were different from those seen with the camptothecins. The cleavage sites induced by the indenoisoquinolines were reversed by salt treatment, which is consistent with the reversible trapping of top1 clearable complexes by the indenoisoquinolines. In general, the potencies of the indenoisoquinolines as top1 inhibitors did not correlate with their potencies as cytotoxic agents, as some of the most cytotoxic agents had little if any effect on top1. On the other hand, the most potent of the indenoisoquinolines vs top1 were not the most cytotoxic. In several cases, moderate activity was observed for both cytotoxicity and activity vs top1.

Synthesis of 7,12-dihydro-12-phenyl-5H-6,12-methanodibenz[cf]azocines via N,N-dibenzylphenacylamines

N,N-DibenzyIphenacylamines (1) were prepared in high yields by a onepot reaction and cyclized at room temperature to give 7,12-dihydro-12-phenyl-5H-6,12-methanodibenz[cf]azocines in high yields. 95% H2SO4 or 70% HClO4 was used as cyclization catalysts. The double-cyclization proceeds smoothly in the cases where electron-donating groups are present in both benzene ring. N-2,3-dimethoxybenzyl-N-benzylphenacylamine (If) gave the corresponding N-benzyl-1,2-dihydro-4-phenylisoquinoline on treatment with 95% H2SO4 while N-3,4-Dimethoxybenzyl-N-benzylphenacylamine (1a) at the same reaction conditions and reaction time cyclized to the corresponding dibenzazocine. However la gave the corresponding dihydroisoquinoline which disproportionates to give N-benzyl-1,2,3,4-tetrahydro-4-phenylisoquinoline and N-benzyl-4-phenylisoquinolinium when treated with 70% perchloric acid at room temperature.