19099-93-5

Basic information

• Product Name: 1-Cbz-4-Piperidone
• Synonyms: 1-(Benzyloxycarbonyl)-4-piperidinone, 1-Cbz-4-Piperidone, Benzyl 4-oxo-1-piperidinecarboxylate;1-(Benzyloxycarbonyl)piperidine-4-one;1-Cbz-Piperidin-4-one;N-Cbz-piperidone;Piperidin-4-one, N-CBZ protected;benzyl 4-o×opiperidine-1-carbo×ylate;1-Carbobenzoxy-4-piperidone 1-Cbz-4-piperidone 4-Oxo-1-piperidinecarboxylic Acid Benzyl Ester 1-Benzyloxycarbonyl-4-piperidine;1-CBZ-4-piperidinone
• CAS NO: 19099-93-5
• Molecular Formula: C₁₃H₁₅NO₃
• Molecular Weight: 233.26
• EINECS: 1312995-182-4
• Product Categories: Building Blocks;Chemical Synthesis;Heterocyclic Building Blocks;Piperidones;Piperidine Series;Miscellaneous Biochemicals;Pyrans, Piperidines &Piperazines;API intermediates;Piperidines;Aromatics;Heterocycles;Pyrans, Piperidines & Piperazines
• Mol File: 19099-93-5.mol

Chemical Properties

• Melting Point: 38-41°C
• Boiling Point: 114-140 °C0.25 mm Hg(lit.)
• Flash Point: >110 °C
• Appearance: White to pale yellow or clear/Solid or Lliquid
• Density: 1.172 g/mL at 25 °C(lit.)
• Vapor Pressure: 4.18E-06mmHg at 25°C
• Refractive Index: n20/D 1.542(lit.)
• Storage Temp.: Refrigerator
• Solubility: Chloroform, Dichloromethane, Ethyl Acetate, Methanol
• PKA: -1.63±0.20(Predicted)
• BRN: 1533716
• CAS DataBase Reference: 1-Cbz-4-Piperidone(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Cbz-4-Piperidone(19099-93-5)
• EPA Substance Registry System: 1-Cbz-4-Piperidone(19099-93-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 23-24/25-36-26-37/39
• WGK Germany: 3
• Hazardous Substances Data: 19099-93-5(Hazardous Substances Data)

Usage

Chemical Properties

Colourless Oil

Uses

Protected piperidinone that can undergo interesting synthetic transformations including the Knoevenagel reaction,1 hetero-Diels-Alder reactions,2 and reactions to form N-(4-piperidinyl)oxindoles.3

General Description

1-Z-4-Piperidone is the starting material in biheteroaromatic diphosphine oxides-catalyzed stereoselective direct aldol condensation reactions.

InChI:InChI=1/C13H15NO3/c15-12-6-8-14(9-7-12)13(16)17-10-11-4-2-1-3-5-11/h1-5H,6-10H2

Upstream product

• 41661-47-6 piperidin-4-one 
• 42116-21-2 2-benzyloxycarbonylsulfanyl-4,6-dimethyl-pyrimidine 
• 13139-17-8 N-(Benzyloxycarbonyloxy)succinimide 
• 40064-34-4 piperidine-4,4-diol hydrochloride 
• 553672-12-1 benzyl 4-methoxypiperidine-1-carboxylate 
• 95798-23-5 1-(benzyloxycarbonyl)-4-hydroxypiperidine 
• 41979-39-9 4-piperidone hydrochloride 
• 138163-08-3 N-(benzyloxycarbonyl)piperidine-4-carboxaldehyde 
• 79099-07-3 N-tert-butyloxycarbonylpiperidin-4-one 
• 286961-24-8 benzyl 1,2,3,6-tetrahydro-4-(trifluoromethylsulphonyloxy)-pyridine-1-carboxylate 
• 6099-86-1 cyclohexylmethyl chlorocarbonate 
• 501-53-1 benzyl chloroformate 
• 5382-16-1 4-HYDROXYPIPERIDINE 
• 3612-20-2 1-phenylmethyl-4-piperidone 

Downstream Products

• 82244-11-9 ethyl-1-carbobenzoxy-Δ^4,α-piperidine-4-acetate 
• 382150-71-2 2-[2-(1-benzyloxycarbonyl-piperidin-4-ylamino)-phenyl]-malonic acid di-tert-butyl ester 
• 382150-80-3 2-[2-(1-benzyloxycarbonyl-piperidin-4-ylamino)-4-fluoro-phenyl]-malonic acid di-tert-butyl ester 
• 255050-44-3 4-hydroxy-4-(4-methoxy-2-methylthiophenyl)-N-Cbz-piperidine 
• 853784-41-5 3-trifluoromethyl-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-b]pyridine 
• 174184-13-5 benzyl 3-bromo-4-oxo-piperidine-1-carboxylate 
• 377730-05-7 4-hydroxy-4-[4-(2-methoxy-ethoxy)-phenyl]-piperidine-1-carboxylic acid benzyl ester 
• 494792-24-4 6-amino-2,1'-bis(benzyloxycarbonyl)-5,7,7-tricyanospiro[3,7,8,8a-tetrahydro-1H-isoquinoline-8,4'-piperidine] 
• 439942-28-6 4-(4-fluoro-2-methylsulfanyl-phenyl)-4-hydroxy-piperidine-1-carboxylic acid benzyl ester 
• 465536-02-1 4-hydroxy-4-[2,4-bis(methylthio)phenyl]-N-Cbz-piperidine 
• 945843-07-2 benzyl 3,3-bis-(hydroxymethyl)-1,5-dioxa-9-azaspiro[5.5]undecane-9-carboxylate 
• 475095-03-5 4-(cyano-ethoxycarbonyl-methylene)-piperidine-1-carboxylic acid benzyl ester 
• 91157-41-4 benzyl 4-pyrrolidin-1-yl-3,6-dihydro-2H-pyridine-1-carboxylate 
• 138163-12-9 benzyl 4-methylene-1-piperidinecarboxylate 

Relevant articles and documents

Chemo-Enzymatic Synthesis of Poly(4-piperidine lactone- b-ω-pentadecalactone) Block Copolymers as Biomaterials with Antibacterial Properties

With increasing troubles in bacterial contamination and antibiotic-resistance, new materials possessing both biocompatibility and antimicrobial efficacy are supposed to be developed for future biomedical application. Herein, we demonstrated a chemo-enzymatic ring opening polymerization (ROP) approach for block copolyester, that is, poly(4-benzyl formate piperidine lactone-b-ω-pentadecalactone) (PNPIL-b-PPDL), in a one-pot two-step process. Afterward, cationic poly(4-piperidine lactone-b-ω-pentadecalactone) (PPIL-b-PPDL) with pendent secondary amino groups was obtained via acidic hydrolysis of PNPIL-b-PPDL. The resulting cationic block copolyester exhibited high antibacterial activity against Gram negative E. coli and Gram positive S. aureus, while showed low toxicity toward NIH-3T3 cells. Moreover, the antibacterial property, cytotoxicity and degradation behavior could be tuned simply by variation of PPIL content. Therefore, we anticipate that such cationic block copolymers could potentially be applied as biomaterials for medicine or implants.

Unconventional Synthetic Process of Fasudil Hydrochloride: Costly Homopiperazine Was Avoided

An efficient, robust, and cost-effective synthetic process of fasudil hydrochloride 1 was developed. Starting from readily available ethylenediamine and 5-isoquinoline sulfonyl chloride, the target product 1 was prepared through a six-step reaction, including sulfonamidation, protection, nucleophilic substitution, deprotection, cyclization, and salification. The process afforded 1 in 67.1% overall yield (based on 5-isoquinoline sulfonyl chloride) with 99.94% purity. Compared to the earlier published methodologies, the use of homopiperazine or its derivatives as intermediates was avoided. The salient features of this environmentally friendly synthetic route include easily available starting materials and operational simplicity, which could be suitable for large-scale industrial production.

Cobalt-Catalyzed Aerobic Oxidative Cleavage of Alkyl Aldehydes: Synthesis of Ketones, Esters, Amides, and α-Ketoamides

A widely applicable approach was developed to synthesize ketones, esters, amides via the oxidative C?C bond cleavage of readily available alkyl aldehydes. Green and abundant molecular oxygen (O2) was used as the oxidant, and base metals (cobalt and copper) were used as the catalysts. This strategy can be extended to the one-pot synthesis of ketones from primary alcohols and α-ketoamides from aldehydes.

HPK1 ANTAGONISTS AND USES THEREOF

The present invention provides compounds, compositions thereof, and methods of using the same for the inhibition of HPK1, and the treatment of HPK1-mediated disorders.

Oxidation of Secondary Methyl Ethers to Ketones

We present a mild way of converting secondary methyl ethers into ketones using calcium hypochlorite in aqueous acetonitrile with acetic acid as activator. The reaction is compatible with various oxygen- and nitrogen-containing functional groups and afforded the corresponding ketones in up to 98% yield. The use of this methodology could expand the application of the methyl group as a useful protecting group.

Synthesis of Ketones and Esters from Heteroatom-Functionalized Alkenes by Cobalt-Mediated Hydrogen Atom Transfer

Cobalt bis(acetylacetonate) is shown to mediate hydrogen atom transfer to a broad range of functionalized alkenes; in situ oxidation of the resulting alkylradical intermediates, followed by hydrolysis, provides expedient access to ketones and esters. By modification of the alcohol solvent, different alkyl ester products may be obtained. The method is compatible with a number of functional groups including alkenyl halides, sulfides, triflates, and phosphonates and provides a mild and practical alternative to the Tamao-Fleming oxidation of vinylsilanes and the Arndt-Eistert homologation.

COMPOUNDS AS CRTH2 ANTAGONIST AND USES THEREOF

The compounds of Formula (I) which can be used as CRTH2 receptor antagonists are provided. The compounds of Formula (I) can be used in the treatment and prevention of asthma, allergic rhinitis and atopic dermatitis, as well as other diseases mediated by prostaglandin D2 (PGD2) at the CRTH2 receptor.

INHIBITORS OF RENAL OUTER MEDULLARY POTASSIUM CHANNEL

Disclosed are compounds of Formula I and the pharmaceutically acceptable salts thereof, which are inhibitors of the ROMK (Kir1.1) channel. The compounds may be used as diuretic and/or natriuretic agents and for the therapy and prophylaxis of medical conditions including cardiovascular diseases such as hypertension, heart failure and chronic kidney disease and conditions associated with excessive salt and water retention.

Remote Oxidation of Aliphatic C-H Bonds in Nitrogen-Containing Molecules

Nitrogen heterocycles are ubiquitous in natural products and pharmaceuticals. Herein, we disclose a nitrogen complexation strategy that employs a strong Bronsted acid (HBF4) or an azaphilic Lewis acid (BF3) to enable remote, non-directed C(sp3)-H oxidations of tertiary, secondary, and primary amine- and pyridine-containing molecules with tunable iron catalysts. Imides resist oxidation and promote remote functionalization.

Highly efficient aerobic oxidation of alcohols by using less-hindered nitroxyl-radical/copper catalysis: Optimum catalyst combinations and their substrate scope

The oxidation of alcohols into their corresponding carbonyl compounds is one of the most fundamental transformations in organic chemistry. In our recent report, 2-azaadamantane N-oxyl (AZADO)/copper catalysis promoted the highly chemoselective aerobic oxidation of unprotected amino alcohols into amino carbonyl compounds. Herein, we investigated the extension of the promising AZADO/copper-catalyzed aerobic oxidation of alcohols to other types of alcohol. During close optimization of the reaction conditions by using various alcohols, we found that the optimum combination of nitroxyl radical, copper salt, and solution concentration was dependent on the type of substrate. Various alcohols, including highly hindered and heteroatom-rich ones, were efficiently oxidized into their corresponding carbonyl compounds under mild conditions with lower amounts of the catalysts.