2937-99-7

Usage

Uses

Used in Organic Synthesis:
5-Benzylamino-1-pentanol is used as a chiral building block for the synthesis of various organic compounds. Its chiral center allows for the creation of enantiomerically pure products, which are important in many applications, including pharmaceuticals and agrochemicals.
Used in Medicinal Chemistry:
5-Benzylamino-1-pentanol is used as a precursor for the synthesis of pharmaceuticals. Its unique structure can be incorporated into drug molecules to impart specific biological activities or improve pharmacokinetic properties, such as solubility, stability, or bioavailability.
Used in Specialty Chemicals Formulation:
5-Benzylamino-1-pentanol may have potential uses in the formulation of specialty chemicals, where its unique structure can contribute to the desired properties of the final product. This can include applications in areas such as fragrances, dyes, or coatings.
Used as a Reagent in Chemical Research:
5-Benzylamino-1-pentanol can be used as a reagent in chemical research to explore new reactions or synthetic pathways. Its unique structural features can provide insights into the reactivity and selectivity of various chemical transformations, contributing to the advancement of synthetic chemistry.

InChI:InChI=1/C12H19NO/c14-10-6-2-5-9-13-11-12-7-3-1-4-8-12/h1,3-4,7-8,13-14H,2,5-6,9-11H2

Upstream product

• 542-28-9 3,4,5,6-tetrahydro-2H-pyran-2-one 
• 42856-59-7 5-hydroxy-N-(phenylmethyl)-pentanamide 
• 100-46-9 benzylamine 
• 100-52-7 benzaldehyde 
• 5259-98-3 5-chloropentan-1-ol 
• 111-24-0 1,5-dibromo-pentane 
• 2508-29-4 5-hydroxypentylamine 
• 208244-48-8 5-{[1-Phenyl-meth-(E)-ylidene]-amino}-pentan-1-ol 
• 110-87-2 3,4-dihydro-2H-pyran 

Downstream Products

• 213771-60-9 tert-Butyl N-benzyl-5-hydroxypentylcarbamate 
• 357277-83-9 [(4-benzyl-2-{1-[benzyl-(5-hydroxy-pentyl)-amino]-heptyl}-oxazol-5-yl)-methyl-amino]-acetic acid methyl ester 
• 1426441-01-1 methyl 3-(4-((benzyl(5-hydroxypentyl)carbamoyloxy)methyl)phenyl)propanoate 
• 102666-89-7 N-benzyl-5-(1-benzylpiperidin-2-yl)-1,2,3,4-tetrahydropyridine 
• 6295-81-4 N-benzylpiperidine hydrochloride 
• 305351-57-9 N-(N'-benzyl-N'-tert-butoxycarbonyl-5-aminopentyl)-N-tert-butoxycarbonyl-6-aminopentanoyl-1-toluene-4-sulfonic acid 
• 213773-01-4 N-(N'-benzyl-N'-tert-butoxycarbonyl-5-aminopentyl)-N-tert-butoxycarbonyl-6-aminohexanoic acid 
• 213772-85-1 [5-(benzyl-tert-butoxycarbonyl-amino)-pentyl]-(6-hydroxy-hexyl)-carbamic acid tert-butyl ester 
• 213772-53-3 6-[5-(N-tert-Butoxycarbonyl-N-phenylmethylamino)-pentylamino]-hexan-1ol 
• 204773-56-8 Toluene-4-sulfonic acid 5-(benzyl-tert-butoxycarbonyl-amino)-pentyl ester 
• 2905-56-8 N-Benzylpiperidine 
• 60460-73-3 1-benzyl-1,2,3,4-tetrahydropyridine 

Relevant academic research and scientific papers

Hapten design and monoclonal antibody to fluoroacetamide, a small and highly toxic chemical

Fluoroacetamide (FAM) is a small (77 Da) and highly toxic chemical, formerly used as a rodenticide and potentially as a poison by terrorists. Poisoning with FAM has occurred in humans, but few reliably rapid detection methods and antidotes have been reported. Therefore, producing a specific antibody to FAM is not only critical for the development of a fast diagnostic but also a potential treatment. However, achieving this goal is a great challenge, mainly due to the very low molecular weight of FAM. Here, we design two groups of FAM haptens for the first time, maximally exposing the fluorine or amino groups, with the aid of linear aliphatic or phenyl-contained spacer arms. Interestingly, whereas the hapten with fluorine at the far end of the hapten did not induce an antibody response to FAM, the hapten with an amino group at the far end and phenyl-contained spacer arm triggered a significantly specific antibody response. Finally, a monoclonal antibody (mAb) named 5D11 was successfully obtained with an IC50 value of 97 μg mL?1 and negligible cross-reactivities to the other nine functional and structural analogs.

Design and synthesis of aminoester heterodimers containing flavone or chromone moieties as modulators of P-glycoprotein-based multidrug resistance (MDR)

In this study, a new series of heterodimers was synthesized. These derivatives are N,N-bis(alkanol)amine aryl esters or N,N-bis(ethoxyethanol)amine aryl esters carrying a methoxylated aryl residue combined with a flavone or chromone moiety. The new compounds were studied to evaluate their P-gp modulating activity on a multidrug-resistant leukemia cell line. Some of the new compounds show a good MDR reversing activity; interestingly this new series of compounds does not comply with the structure-activity relationships (SAR) outlined by previously synthesized analogs carrying different aromatic moieties. In the case of the compounds described in this paper, activity is linked to different features, in particular the characteristics of the spacer, which seem to be critical for the interaction with the pump. This fact indicates that the presence of a flavone or chromone residue influences the SAR of these series of products, and that flexible molecules can find different productive binding modes with the P-gp recognition site. These results support the synthesis of new compounds that might be useful leads for the development of drugs to control P-gp-dependent MDR.

Cyanopivaloyl Ester in the Automated Solid-Phase Synthesis of Oligorhamnans

The development of effective protecting group chemistry is an important driving force behind the progress in the synthesis of complex oligosaccharides. Automated solid-phase synthesis is an attractive technique for the rapid assembly of oligosaccharides, built up of repetitive elements. The fact that (harsh) reagents are used in excess in multiple reaction cycles makes this technique extra demanding on the protecting groups used. Here, the synthesis of a set of oligorhamnan fragments is reported using the cyanopivaloyl (PIVCN) ester to ensure effective neighboring group participation during the glycosylation events. The PIVCN group combines the favorable characteristics of the parent pivaloyl (PIV) ester, stability, minimal migratory aptitude, minimal orthoester formation, while it can be cleaved under mild conditions. We show that the remote CN group in the PIVCN renders the PIVCN carbonyl more electropositive and thus susceptible to nucleophilic cleavage. This feature is built upon in the automated solid-phase assembly of the oligorhamnan fragments. Where the use of a PIV-protected building block failed because of incomplete cleavage, PIVCN-protected synthons performed well and allowed the generation of oligorhamnans, up to 16 monosaccharides in length.

The scale-up of continuous biphasic liquid/liquid reactions under super-heating conditions: Methodology and reactor design

Biphasic liquid/liquid reactions are commonplace, however their scale-up under super-heating conditions is not. Even more challenging efforts have to be expected in the case of a large scale continuous production process, which also includes the development at a lab scale, the selection and design of the continuous reaction equipment. However, by running chemistry above the boiling point of the solvent, the solvent selection can be widened to include green solvents and continuous processing guarantees a limited and safe footprint. Herein is reported a systematic methodology for the development and scale-up of a biphasic reaction under super-heating conditions, as well as the design of a continuous reactor column suitable for handling such conditions. Taking the alkylation of benzylamine with 1,5-dibromopentane as a model reaction, kinetic determination and fluid dynamic characterization of the biphasic media have been instrumental for a successful scale-up concept which was proven in a custom-made hastelloy reactor column.

Broadening the chemical scope of laccases: Selective deprotection of N-benzyl groups

Laccase from Trametes versicolor together with TEMPO has been found to be a very efficient system to deprotect N-benzylated primary amines, differing from previously described methods since it uses oxygen as a mild oxidant in aqueous medium. Chemoselective removal of the benzyl group was achieved with excellent yields when secondary amines and alcohol moieties were also present.

Highly chemoselective aerobic oxidation of amino alcohols into amino carbonyl compounds

The direct oxidation of unprotected amino alcohols to their corresponding amino carbonyl compounds has often posed serious challenges in organic synthesis and has constrained chemists to adopting an indirect route, such as a protection/deprotection strategy, to attain their goal. Described herein is a highly chemoselective aerobic oxidation of unprotected amino alcohols to their amino carbonyl compounds in which 2-azaadamantane N-oxyl (AZADO)/copper catalysis is used. The catalytic system developed leads to the alcohol-selective oxidation of various unprotected amino alcohols, carrying a primary, secondary, or tertiary amino group, in good to high yield at ambient temperature with exposure to air, thus offering flexibility in the synthesis of nitrogen-containing compounds. Strong as an ox: The highly chemoselective aerobic oxidation of unprotected amino alcohols to their corresponding amino carbonyl compounds has been achieved by using 2-azaadamantane N-oxyl (AZADO)/copper catalysis. This catalytic system oxidizes not only alcohols with tertiary amino groups but also those with secondary and primary amines in good to high yield at ambient temperature in air. bpy=2,2-bipyridyl, DMAP=4-(N,N-dimethylamino)pyridine.

Acid promoted cyclodehydration of amino alcohols with amide acetal

A convenient acid-promoted cyclization protocol for the formation of azaheterocycles from amino alcohols is described. The reaction involves the use of N,N-dimethylacetamide dimethyl acetal (DMADA) as the activating reagent of the hydroxyl group. Using this protocol, pyrrolidines or piperidines with various substituents can be synthesized in good to high yields.

Acylsulfonamide safety-catch linker: Promise and limitations for solid-phase oligosaccharide synthesis

Safety-catch linkers are useful for solid-phase oligosaccharide synthesis as they are orthogonal to many common protective groups. A new acylsulfonamide safety-catch linker was designed, synthesized and employed during glycosylations using an automated carbohydrate synthesizer. The analysis of the cleavage products revealed shortcomings for oligosaccharide synthesis.

Reductive hydroxyalkylation/alkylation of amines with lactones/esters

We have developed a one-pot method for the direct intermolecular reductive hydroxyalkylation or alkylation of amines using lactones or esters as the hydroxyalkylating/alkylating reagents. The method is based on the in situ amidation of lactones/esters with DIBAL-H-amine complex (for primary amines) or DIBAL-H-amine hydrochloride salt complex (for secondary amines), followed by reduction of the amides with an excess of DIBAL-H. Different from the reduction of Weinreb amides with DIBAL-H where aldehydes are formed, the reduction of the in situ formed Weinreb amides yielded amines. Moreover, this method is not limited to Weinreb amides, instead, it also works for other amides in general. A plausible mechanism is suggested to account for the outcome of the reactions.

Benzo-21-crown-7/secondary dialkylammonium salt [2]pseudorotaxane- and [2]rotaxane-type threaded structures

We demonstrate that secondary dialkylammonium salts can thread through the cavity of benzo-21-crown-7 to form [2]pseudorotaxanes with binding constants (527-1062 M-1 in acetone) higher than the corresponding values (135-261 M-1 in acetone) of the analogous complexes with their traditionally used host, dibenzo-24-crown-8. Based on this new benzo-21-crown-7/secondary dialkylammonium salt recognition motif, a [2]rotaxane was successfully prepared. The formation of these threaded structures was confirmed by proton NMR spectroscopy, electrospray ionization mass spectrometry, and X-ray single crystal analysis.