39191-12-3

Usage

Uses

Used in Organic Synthesis:
N-(2-furylmethyl)-N-propylamine is used as a reagent in organic synthesis for the preparation of various types of organic compounds. Its unique structure allows it to participate in a range of chemical reactions, making it a versatile component in the synthesis of complex organic molecules.
Used in Pharmaceutical Production:
N-(2-furylmethyl)-N-propylamine is used as a building block in the production of pharmaceuticals. Its incorporation into drug molecules can contribute to the development of new medications with specific therapeutic properties.
Used in Agrochemical Production:
N-(2-furylmethyl)-N-propylamine is also utilized in the production of agrochemicals, where it can be a key component in the synthesis of pesticides, herbicides, and other agricultural chemicals designed to protect crops and enhance agricultural productivity.
Safety Considerations:
N-(2-furylmethyl)-N-propylamine is considered to be a hazardous chemical. It should be handled with care and used in a well-ventilated area with appropriate personal protective equipment to ensure the safety of those working with the compound.

InChI:InChI=1/C8H13NO/c1-2-5-9-7-8-4-3-6-10-8/h3-4,6,9H,2,5,7H2,1H3

Upstream product

• 4437-18-7 2-bromomethylfuran 
• 98-00-0 (2-furyl)methyl alcohol 
• 107-12-0 propiononitrile 
• 87869-92-9 [1-Furan-2-yl-meth-(E)-ylidene]-((E)-propenyl)-amine 
• 34756-44-0 furfural-propylimine 
• 34756-44-0 N-(2-furanylmethylene)-1-propanamine 
• 98-01-1 furfural 
• 107-10-8 propylamine 

Relevant academic research and scientific papers

Cucurbit[7]uril as a Supramolecular Artificial Enzyme for Diels–Alder Reactions

The ability to mimic the activity of natural enzymes using supramolecular constructs (artificial enzymes) is a vibrant scientific research field. Herein, we demonstrate that cucurbit[7]uril (CB[7]) can catalyse Diels–Alder reactions for a number of substituted and unreactive N-allyl-2-furfurylamines under biomimetic conditions, without the need for protecting groups, yielding powerful synthons in previously unreported mild conditions. CB[7] rearranges the substrate in a highly reactive conformation and shields it from the aqueous environment, thereby mimicking the mode of action of a natural Diels–Alderase. These findings can be directly applied to the phenomenon of product inhibition observed in natural Diels–Alderase enzymes, and pave the way toward the development of novel, supramolecular-based green catalysts.

Synthesis and Characterization of Diimine Adducts of BIS(N-Alkyl-N-Furfuryldithiocarbamato-S,S′)Cadmium(II): Crystal Structure of BIS(N-Furfuryl-N-Propyldithiocarbamato-S,S′)(1,10-Phenanthroline)Cadmium(II)

A series of homoleptic and heteroleptic complexes: [Cd(fprdtc)2] (1), [Cd(fprdtc)2(1,10-phen)] (2), [Cd(fprdtc)2(2,2′-bipy)] (3), [Cd(bufdtc)2] (4), [Cd(bufdtc)2(1,10-phen)] (5), and [Cd(bufdtc)2(2,2′-bipy)] (6)(where fprdtc = N-furfuryl-N-propyldithiocarbamate; bufdtc = N-butyl-N-furfuryldithiocarbamate) have been prepared and characterized. A single crystal X-ray structural analysis was carried out for 2. Reduction in C-N (thioureide) for the heteroleptic complexes (2, 3, 5, and 6) compared to that of homoleptic complexes (1 and 4) is attributed to the change in coordination number from four to six and steric effect exerted by 1,10-phenanthroline and 2,2′-bipyridine. The downfield shift of N13CS2 carbon signal for heteroleptic complexes from the chemical shift value of homoleptic complexes is also attributed to the increase in coordination number. Single crystal X-ray structure of 2 indicates that the mononuclear structure of 2 shows symmetric coordination of the dithiocarbamate ligands and a distorted octahedral geometry for cadmium, defined by an N2S4 donor set, results. In this crystal structure, most significant π-π interaction is also observed.

Synthesis, characterization, cytotoxicity and antimicrobial studies on Bi(III) dithiocarbamate complexes containing furfuryl group and their use for the preparation of Bi2O3nanoparticles

Bismuth(III) dithiocarbamate complexes, tris(N-furfuryl-N-propyldithiocarbamato-S,S')bismuth(III) (1), tris(N-furfuryl-N-butyldithiocarbamato-S,S')bismuth(III) (2) and tris(N-furfuryl-N-benzyldithiocarbamato-S,S')bismuth(III) (3), have been prepared and characterized by microanalysis, and spectroscopy (IR and NMR). Structure of 3 has been obtained by single crystal X-ray diffraction. This complex contains distorted pentagonal pyramidal Bi(III) centres which attain an overall distorted pentagonal bipyramidal coordination via long range intermolecular Bi?S interactions. DFT quantum mechanical studies of 3 were carried out, supporting the partial double bond character of C–N (thioureide) and C–S bonds in dithiocarbamate ligands. All the compounds have been screened against a panel of microbes viz. Vibrio cholerae, Bacillus subtilis, Klebsiella pneumoniae, Escherichia coli, Staphylococcus aureus, Aspergillus niger and Candida albicans. Complexes 1 and 3 were found to have better activity against K. pneumoniae, V. cholerae, A. niger and C. albicans than the complex 2. Complexes 1–3 have been evaluated for their in vitro cytotoxic activity against KB cells. Complexes 1 and 3 showed higher activity than 2. Bi2O3obtained from thermal decomposition of 3 has been characterized by PXRD, HRTEM, EDAX, UV–Vis and Fluorescence spectroscopy. PXRD study showed that the sample is composed of monoclinic phase of α-Bi2O3. Photocatalytic activity of as-prepared α-Bi2O3was determined by decolourization of rhodamine-B in aqueous solution under ultra violet irradiation.

Efficient Synthesis, Spectral, Characterization, Antimicrobial and DFT Studies of Antimony(III) Dithiocarbamates

The synthesis and characterization of novel antimony(III) dithiocarbamate complexes tris(N-furfuryl-N-propyldithiocarbamatoS,S′)antimony(III) (1) and tris(N-furfuryl-N-butyldithiocarbamato-S,S′)antimony(III) (2) have been characterized by elemental analysis, FT-IR, NMR (1H and 13C) spectra and antimicrobial studies. The characteristic thioureide (νC-N) bands occur at 1462 and 1475 cm-1 for complex 1 and 2, respectively. The theoretical calculations of the complexes have been carried out by density functional theory (DFT). The FMOs, MEP, Mulliken charge distribution and chemical activity parameters of the optimized structure have been calculated at the same level of theory. The MEP structure indicated that the positive and negative potential sites are around hydrogen atoms and electronegative atoms of the studied complexes, respectively. The Agar-well diffusion method were used to study the antimicrobial activity of the complexes against two Gram-positive bacteria (Klebsiella pneumoniae and Staphylococcus aureus), two Gram-negative bacteria (Escherichia coli and Vibrio cholera) and two fungal organisms (Candida albicans and Aspergillus Niger).

Direct Reductive Amination of Biobased Furans to N-Substituted Furfurylamines by Engineered Reductive Aminase

Furfurylamines are important building blocks for the synthesis of many pharmacologically active compounds and polymers. In this work, direct reductive amination of biobased furans to N-substituted furfurylamines by reductive aminase from Aspergillus oryzae (AspRedAm) was reported. Besides the reductive aminase activity, AspRedAm also showed a promiscuous, yet low alcohol dehydrogenase activity. The variant W210F proved to be a good catalyst for the synthesis of N-substituted furfurylamines. Furans were transformed to the target products with the conversions up to >99% and selectivities up to >99%. In addition, N-substituted furfurylamines were synthesized in the total turnover number (TTN) up to 3200 on a preparative scale, indicating the applicability of this biocatalytic route in synthetic chemistry. (Figure presented.).

Methyl-triflate-mediated dearylmethylation of: N -(arylmethyl)carboxamides via the retro-Mannich reaction induced by electrophilic dearomatization/rearomatization in an aqueous medium at room temperature

We have developed a protocol for the dearylmethylation of N-(arylmethyl)carboxamides under metal-free conditions in an aqueous medium at room temperature. This protocol involves methyl triflate-mediated successive C-C and C-N bond cleavages (retro-Mannich reaction) induced by electrophilic dearomatization/rearomatization. The dearomatization/rearomatization strategy can be expected to inspire the development of novel transformations based on the C-C bond cleavage in an environmentally benign manner.

Access to Densely Functionalized Chalcone Derivatives with a 2-Pyridone Subunit via Pd/Cu-Catalyzed Oxidative Furan-Yne Cyclization of N -(2-Furanylmethyl) Alkynamides under Air

A protocol for synthesis of chalcone derivatives with a 2-pyridone subunit from N-(2-furanylmethyl) alkynamides is reported. This synthesis involves Pd/Cu-catalyzed oxidative furan-yne cyclization at room temperature in air and may proceed via nucleopalladation of the alkyne to form a vinylpalladium intermediate, with a furan ring acting as the nucleophile.

Discovery of 2-[1-(4,4-Difluorocyclohexyl)piperidin-4-yl]-6-fluoro-3-oxo-2,3-dihydro-1H-isoindole-4-carboxamide (NMS-P118): A Potent, Orally Available, and Highly Selective PARP-1 Inhibitor for Cancer Therapy

The nuclear protein poly(ADP-ribose) polymerase-1 (PARP-1) has a well-established role in the signaling and repair of DNA and is a prominent target in oncology, as testified by the number of candidates in clinical testing that unselectively target both PARP-1 and its closest isoform PARP-2. The goal of our program was to find a PARP-1 selective inhibitor that would potentially mitigate toxicities arising from cross-inhibition of PARP-2. Thus, an HTS campaign on the proprietary Nerviano Medical Sciences (NMS) chemical collection, followed by SAR optimization, allowed us to discover 2-[1-(4,4-difluorocyclohexyl)piperidin-4-yl]-6-fluoro-3-oxo-2,3-dihydro-1H-isoindole-4-carboxamide (NMS-P118, 20by). NMS-P118 proved to be a potent, orally available, and highly selective PARP-1 inhibitor endowed with excellent ADME and pharmacokinetic profiles and high efficacy in vivo both as a single agent and in combination with Temozolomide in MDA-MB-436 and Capan-1 xenograft models, respectively. Cocrystal structures of 20by with both PARP-1 and PARP-2 catalytic domain proteins allowed rationalization of the observed selectivity.

Synthesis, spectral and X-ray structural studies on Hg(II) dithiocarbamate complexes: A new precursor for HgS nanoparticles

Bis(N-furfuryl-N-(2-phenylethyl)dithiocarbamato-S,S′)mercury(II) (1), bis((furan-2-yl)methyl(2-(thiophen-2-yl)ethyl)dithiocarbamato-S,S′)mercury(II) (2), bis(N-benzyl-N-(2-(thiophen-2-yl)ethyl)dithiocarbamato-S,S′)mercury(II) (3) and bis(N-furfuryl-N-prop

Reduction of imines via titanium-catalyzed hydromagnesation

We have recently discovered that imines can be reduced to amines via a titanium catalyzed hydromagnesation reaction. These reactions employ n-BuMgCl (1.2 eq) as the stoichiometric reducing agent and Cp2TiCl2 (3-5 mol%) as a catalyst. Reactions are run under nitrogen at ambient temperature and pressure. For most aldimine and cyclic ketimine substrates amine products are obtained in yields ranging from 69-94%. The reaction is not tolerant of bulky nitrogen substituents or primary enolizable protons on the imine substrate.