Benzyl 4-oxocyclohexanecarboxylate

Base Information

• Chemical Name: Benzyl 4-oxocyclohexanecarboxylate
• CAS No.: 62596-26-3
• Molecular Formula: C14H16O3
• Molecular Weight: 232.279
• DSSTox Substance ID: DTXSID30572346
• Nikkaji Number: J994.490G
• Wikidata: Q82460654
• Mol file: 62596-26-3.mol

Synonyms:benzyl 4-oxocyclohexanecarboxylate;62596-26-3;BENZYL 4-OXOCYCLOHEXANE-1-CARBOXYLATE;Cyclohexanecarboxylic acid, 4-oxo-, phenylmethyl ester;SCHEMBL850782;benzyl4-oxocyclohexanecarboxylate;DTXSID30572346;AMDOCFYEPPIDNK-UHFFFAOYSA-N;benzyl 4-oxocyclohexane carboxylate;MFCD11113219;AB10002;4-oxo-cyclohexanecarboxylic acid benzyl ester;4-ketocyclohexane carboxylic acid phenylmethyl ester;A1-07820;Cyclohexanecarboxylic acid,4-oxo-,phenylmethyl ester

Chemical Property of Benzyl 4-oxocyclohexanecarboxylate

Chemical Property:

• PSA: 43.37000
• LogP: 2.48910
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 232.109944368
• Heavy Atom Count: 17
• Complexity: 269

Purity/Quality:

98%min ^*data from raw suppliers

Benzyl 4-oxocyclohexanecarboxylate 95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC(=O)CCC1C(=O)OCC2=CC=CC=C2

Technology Process of Benzyl 4-oxocyclohexanecarboxylate

There total 8 articles about Benzyl 4-oxocyclohexanecarboxylate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 92.0%

4-oxocyclohexanecarboxylic acid (874-61-3) + benzyl bromide (100-39-0) → benzyl 4-oxocyclohexane-1-carboxylate (62596-26-3)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 20 ℃; for 48h;

Reference yield: 83.0%

4-oxo-bicyclo[3.1.0]hexane-1-carboxylic acid benzyl ester (216106-48-8) → benzyl 4-oxocyclohexane-1-carboxylate (62596-26-3)

Guidance literature:

With samarium diiodide; In tetrahydrofuran; methanol; for 0.0333333h; Ambient temperature;

DOI:10.1016/S0040-4039(98)01749-3

Reference yield: 67.0%

benzyl 4-hydroxycyclohexane-1-carboxylate (123762-06-1) → benzyl 4-oxocyclohexane-1-carboxylate (62596-26-3)

Guidance literature:

With pyridinium chlorochromate; In dichloromethane; at 20 ℃;

DOI:10.2298/JSC150430063O

upstream raw materials:

(±)-benzyl cyclohex-3-ene-1-carboxylate

4-oxo-bicyclo[3.1.0]hexane-1-carboxylic acid benzyl ester

benzyl 4-hydroxycyclohexane-1-carboxylate

4-oxocyclohexanecarboxylic acid

Downstream raw materials:

benzyl 4-fluoro-cyclohex-3-ene-1-carboxylate

C₁₆H₂₃NO₂

C₁₇H₁₉Cl₂N₅O₄

C₂₄H₂₅Cl₂N₅O₄

Refernces

Tetraoxanes as inhibitors of apicomplexan parasites Plasmodium falciparum and Toxoplasma gondii growth and anti-cancer molecules

10.2298/JSC150430063O

The research presents the synthesis and evaluation of new cyclohexylidene 1,2,4,5-tetraoxanes with polar guanidine and urea-based groups for their potential as antimalarial agents against chloroquine-resistant and susceptible Plasmodium falciparum strains, and as anti-cancer molecules. The study involved the synthesis of derivatives using reactants such as gem-dihydroperoxide, benzyl 4-oxocyclohexanecarboxylate, and various coupling agents, followed by comprehensive analyses including NMR, IR, MS, and HPLC to characterize the compounds. The antimalarial activity was assessed using the Malaria SYBR Green I based fluorescence assay against different P. falciparum strains, while cytotoxicity was determined on human normal peripheral blood mononuclear cells (PBMC). Additionally, select compounds were tested for in vitro cytotoxic activity against various human cancer cell lines and in vivo activity against Toxoplasma gondii in a murine model. The experiments utilized techniques like MTT tests for cell survival, flow cytometry for cell cycle analysis, and microscopic examination for morphological assessment of cell death. The study identified derivative 24 as the most promising candidate with low nanomolar antimalarial activities, high selectivity indices, and significant in vivo potential against T. gondii.