98648-05-6

Basic information

• Product Name: Carbamic acid, (6-oxohexyl)-, phenylmethyl ester
• CAS NO: 98648-05-6
• Molecular Formula: C14H19NO3
• Molecular Weight: 249.31
• Mol File: 98648-05-6.mol
• Article Data: 10

Chemical Properties

• CAS DataBase Reference: Carbamic acid, (6-oxohexyl)-, phenylmethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Carbamic acid, (6-oxohexyl)-, phenylmethyl ester(98648-05-6)
• EPA Substance Registry System: Carbamic acid, (6-oxohexyl)-, phenylmethyl ester(98648-05-6)

Safety Data

• Hazardous Substances Data: 98648-05-6(Hazardous Substances Data)

Upstream product

• 1947-00-8 6-(benzyloxycarbonylamino)hexanoic acid 
• 25580-87-4 methyl 6-(((benzyloxy)carbonyl)amino)hexanoate 
• 60-32-2 6-aminohexanoic acid 
• 62252-26-0 JLK 6 
• 79-37-8 oxalyl dichloride 
• 17996-12-2 N-benzyloxycarbonyl-6-amino-1-hexanol 
• 7087-68-5 N-ethyl-N,N-diisopropylamine 
• 501-53-1 benzyl chloroformate 
• 4048-33-3 6-amino-1-hexanol 

Downstream Products

• 957829-63-9 10-(6-benzyloxycarbonylamino-hexyl)-1,4,7,10-tetraaza-cyclododecane-1,4,7-tricarboxylic acid tri-tert-butyl ester 
• 1318692-88-4 6-[6-(benzyloxycarbonylamino)hexylamino]-2-cyanobenzothiazole 
• 111497-08-6 7-(((benzyloxy)carbonyl)amino)-2-hydroxyheptanoic acid 
• 1290118-53-4 C₄₂H₆₆N₄O₁₂ 
• 1198782-08-9 1,15-bis[4,7,10-tris(t-butoxycarbonylmethyl)-1,4,7,10-tetraazacyclododec-1-yl]-6-{[N-cyclohexyl-1-(N-Cbz-5-aminopentyl)]carboxamidomethyl}-2,7,14-trioxo-3,6,13-triazapentadecane 
• 1015255-72-7 benzyl-7-(benzylamino)-6,7-dioxoheptylcarbamate 
• 1000886-00-9 methyl-N-[2-(1-[benzyl(4-hydroxybutyl)amino]-6-{[(benzyloxy)carbonyl]amino}hexyl)-3-oxa-1-azaspiro[4.5]dec-1-en-4-ylidene]glycinate 
• 179760-69-1 [6-(2-hydroxy-ethylamino)-hexyl]-carbamic acid benzyl ester 
• 929875-46-7 (benzyl-{2-[6-benzyloxycarbonylamino-1-({6-[(2-hydroxy-ethylcarbamoyl)-methyl]-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl}-amino)-hexyl]-oxazol-5-yl}-amino)-acetic acid methyl ester 

Relevant articles and documents

Enolesters as chain end-functionalizing agents for the living ring opening metathesis polymerization

Functional enolethers have previously been used to introduce functional end groups at the chain end of ruthenium carbene complex initiated living ring opening metathesis polymers. Here, we investigated whether the weaker π-donating enolesters could equally be used in regio selective reactions with ruthenium carbene complexes and thus as polymer end-functionalization reagents. Enolesters such as vinyl acetate, butenyl acetate, 3-(4-(tert-butoxy)phenyl)propenyl acetate and 6-(((benzyloxy)carbonyl)amino)hex-1-en-1-yl acetate were used as living ROMP terminating agents. All gave the expected end groups proving that enolesters are synthetically easily accessible targets for living ROMP end-functionalization.

Chloroperoxidase-catalyzed amino alcohol oxidation: Substrate specificity and novel strategy for the synthesis of N-Cbz-3-aminopropanal

The ability of chloroperoxidase (CPO) to catalyze amino alcohol oxidations was investigated. The oxidations of compounds with different configurations with respect to the amine position towards hydroxyl – using H2O2 and tert-butyl hydroperoxide (t-BuOOH) – were analyzed in terms of the initial reaction rate, substrate conversion, and CPO operational stability. It was observed that the further the amino group from the hydroxyl, the lower the initial reaction rate. The effect of the amino-protecting group and other substituents (i.e., methyl and hydroxyl) was also examined, revealing an increase in steric hindrance due to the effect of bulky substituents. The observed reaction rates were higher with t-BuOOH, whereas CPO was more stable with H2O2. Moreover, CPO stability had to be determined case by case as the enzyme activity was modulated by the substrate. The oxidation of N-Cbz-3-aminopropanol (Cbz, carboxybenzyl) to N-Cbz-3-aminopropanal was investigated. Main operational conditions such as the reaction medium, initial amino alcohol concentration, and peroxide nature were studied. The reaction kinetics was determined, and no substrate inhibition was observed. By-products from a chemical reaction between the formed amino aldehyde and the peroxide were identified, and a novel reaction mechanism was proposed. Finally, the biotransformation was achieved by reducing side reactions and identifying the key factors to be addressed to further optimize the product yield.

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.