This compound belongs to the class of organic compounds known as methyl esters. These are organic compounds containing a carboxyl group that is esterified with a methyl group. They have the general structure RC(=O)OR', where R=H or organyl group and R'=methyl group.
External Descriptors
Not available
1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.
Certificados (CoA, COO, BSE/TSE y tabla de análisis)
C of A & Other Certificates(BSE/TSE, COO):
Analytical Chart:
Propiedades químicas y físicas
Peso molecular
184.230 g/mol
XLogP3
1.100
Hydrogen Bond Donor Count
0
Hydrogen Bond Acceptor Count
3
Rotatable Bond Count
2
Exact Mass
184.11 Da
Monoisotopic Mass
184.11 Da
Topological Polar Surface Area
43.400 Ų
Heavy Atom Count
13
Formal Charge
0
Complexity
230.000
Isotope Atom Count
0
Defined Atom Stereocenter Count
0
Undefined Atom Stereocenter Count
1
Defined Bond Stereocenter Count
0
Undefined Bond Stereocenter Count
0
The total count of all stereochemical bonds
0
Covalently-Bonded Unit Count
1
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Application Protocols
Not applicable. No tested bioassay protocols (e.g., WB, IHC, IF, FC) are associated with this small-molecule building block. For practical laboratory use, refer instead to the Reaction Conditions, Synthetic Utility, and Solvent Selection sections for stepwise chemistry guidance.
Biological Roles
This compound is a synthetic organic intermediate (ester/ketone on a cyclohexyl core) and is not a known metabolite or cofactor.
Known biological occurrence: none reported for the exact structure (literature survey context). The features (alicyclic ketone, aliphatic methyl ester) are common in small molecules but this substituted scaffold is man-made.
Potential interactions (general chemistry perspective, not clinical): neutral, hydrophobic core with limited hydrogen-bonding capability (acceptors at the two carbonyls). May partition into lipid phases due to cycloaliphatic framework and gem-dimethyl substitution.
Biotransformations (literature trends for esters/ketones): esters are typically susceptible to hydrolysis by esterases; ketones can undergo reductive metabolism by carbonyl reductases. These comments are general for the functional groups and not specific to in vivo use.
Research-use context: Use as a building block for probe or ligand synthesis where a rigid, hydrophobic cyclohexyl 1,4-dicarbonyl topology is desired. No claims are made regarding biological activity, safety, or suitability for clinical applications.
Note: For any work involving biological systems, ensure appropriate compatibility testing and safety approvals; this product is supplied strictly for research use only (per Product Data).
Buffer Applications
Not typically applicable. This material is a neutral, poorly water-soluble organic building block (ester/ketone) and is not used to prepare aqueous buffer systems. For experimental design, focus instead on the Solvent Selection, Reaction & Applications, and Synthetic Utility sections for guidance on handling and use in organic-phase chemistry.
Green Alternatives
This product is a specific building block rather than a solvent; “greener alternatives” typically refer to process choices when using it.
Greener process considerations (literature/industry guidance):
Solvent selection: prefer ethyl acetate, 2-MeTHF, CPME, toluene, or propylene carbonate over chlorinated solvents when feasible. Replace DCM with EtOAc or toluene for extractions/chromatography.
Coupling chemistry: employ carbodiimide alternatives with better EHS profiles (e.g., EDC·HCl in aqueous-organic media) or enzyme-catalyzed amidation/esterification when compatible.
Reductions/oxidations: choose chemoselective reagents with benign workups (e.g., NaBH(OAc)3 for reductive amination in EtOAc; H2/Pd for hydrogenations) instead of pyrophoric hydrides when possible.
Bases: use carbonate or tert-amine bases (DBU, DIPEA) in greener solvents for transesterification/aminolysis rather than strong alkoxides in MeOH when not required.
Small comparison table (illustrative, not product specs):
DCM vs EtOAc: EtOAc is biodegradable, lower toxicity; may require longer times for phase separation but avoids halogenated waste.
THF vs 2-MeTHF: 2-MeTHF is biorenewable, forms fewer peroxides, and enables aqueous biphasic separations; similar solubilizing power.
LiAlH4 vs DIBAL-H/NaBH4 variants: safer handling and simpler quench with DIBAL-H/NaBH4 when compatible; avoid over-reduction by controlling temperature.
Implement life-cycle thinking: minimize protecting-group manipulations, run at higher concentrations, and recycle solvents where validated.
Pharmaceutical Uses
Formulation/excipient status: none specified for this item; not a standard pharmacopeial excipient.
Context (general, non-clinical):
Role in drug discovery/manufacturing: building block for medicinal chemistry synthesis, enabling installation of a cycloaliphatic, sterically demanding scaffold with dual carbonyl functionality.
Process considerations: if used in GMP routes, material specifications (assay, residual solvents, elemental impurities) must be established per ICH guidelines. This listing provides research-use material only; no GMP status is implied.
Derivatization potential in API analog development: amidation of the ester, reduction to alcohols, or reductive amination at the ketone can rapidly generate analog series.
No therapeutic or clinical claims are made. If an excipient or GMP-grade version is required, consult regulatory resources and request a customized quality package with detailed CoA and change control.
Physical Properties
Item-specific specs (from Product Data):
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Literature/computed values for the named structure (for guidance only; not product specifications):
Empirical formula (computed from name): approximately C10H16O3.
Approximate molecular weight (calculated from C10H16O3): ~184.23 g/mol.
Expected physical state: low-melting solid or high-boiling liquid depending on exact stereochemistry and purity (literature expectation for similar cyclohexanone esters).
Volatility: lower than small esters; likely moderate vapor pressure.
Solubility (qualitative, literature expectation):
Good solubility in common organic solvents (EtOAc, CH2Cl2, THF, toluene, acetonitrile).
Low solubility in water due to hydrophobic cyclohexyl and dimethyl substitution.
Partitioning (qualitative): logP expected in the 1.5–2.5 range (typical for C10 esters/ketones), favoring organic phases.
Spectroscopic handles (general): strong IR C=O bands near ~1735 cm−1 (ester) and ~1715 cm−1 (cyclohexanone; literature), 1H NMR: distinct OMe singlet (~3.6–3.8 ppm), gem-dimethyl singlets/overlapping signals (~0.9–1.2 ppm), ring methylenes (1.2–2.5 ppm), 13C NMR: carbonyls ~170–210 ppm.
Note: No authoritative BP/MP, density, refractive index, or UV cutoff data were located for this exact CAS. For critical parameters, consult the product CoA/SDS.
Quality and Grades
Item-specific quality: Not specified for this item; refer to CoA/Spec Sheet.
Guidance on typical grades for small-molecule building blocks (general):
Research/technical grade: suitable for routine synthesis and method development; impurity profiles may include low-level solvents or closely related isomers.
High-purity or >95–98% assay material: preferred for structure–activity studies, mechanistic work, or when spectral clarity is essential.
Stabilizers: none are typically needed for neutral esters/ketones; if any stabilizer is used (e.g., acid traces to suppress transesterification), it will be disclosed on the CoA.
UV/LC suitability: For LC/UV work, low-UV-absorbing solvents and high assay are advantageous; if “HPLC grade” is specified, it refers to solvent quality, not reagents.
What to check on receipt:
CoA assay by 1H NMR/GC/LC and residual solvent profile.
Identity confirmation (IR: dual C=O bands; NMR: OMe singlet; HRMS consistent with calculated MW ~184.23 g/mol — literature guidance).
Water content if moisture sensitivity is a concern for your application (Karl Fischer), although esters/ketones are generally robust.
Note: In the absence of an explicit grade on this listing, treat as standard research-use material and verify fitness for purpose with small-scale trials.
Reaction and Applications
This compound is a ring-constrained 1,4-dicarbonyl equivalent (ketone at C4 and methyl ester at C1) with a gem-dimethyl at C2. Its bifunctionality enables diverse synthetic manipulations.
Transformations at the ester (literature/general):
Hydrolysis to the corresponding acid (acidic or basic conditions; control to avoid ketone aldolization under base).
Transesterification (acid or base catalysis) to tune protecting-group strategy.
Amidation via activation (DCC/EDC, mixed anhydrides, or thionyl chloride to acid chloride followed by amine coupling).
Reduction: selective ester reduction (e.g., DIBAL-H to aldehyde at low T; LiAlH4 to primary alcohol) with chemoselectivity considerations vs the ketone.
Transformations at the ketone:
Oxime/hydrazone formation; reductive amination (NaBH3CN, NaBH(OAc)3) to install amines on the ring.
Nucleophilic addition (organometallics); protect the ester or use cuprates for 1,2-addition control.
Baeyer–Villiger oxidation to give a lactone (ring expansion) — the gem-dimethyl can influence migratory aptitude.
Alpha-functionalization/enolate chemistry:
Enolization alpha to the ketone enables aldol, Michael additions, or halogenation; control base strength to avoid ester cleavage.
The gem-dimethyl (Thorpe–Ingold effect) can bias ring conformations, sometimes facilitating intramolecular cyclizations or dictating diastereofacial approach.
Strategic use:
As a masked, conformationally constrained 1,4-dicarbonyl synthon in heterocycle formation (e.g., Paal–Knorr-type accesses after appropriate elaboration).
Scaffold for SAR libraries where hydrophobic, sterically demanding cycloaliphatic cores are desired.
Note: The above are literature-informed applications; adjust for your selectivity needs and confirm with small-scale trials.
Reaction Conditions
General literature guidance for common transformations on this scaffold (not product specifications):
Ester hydrolysis:
Basic: NaOH or K2CO3 in MeOH/H2O or THF/H2O, 0–25 °C; monitor to suppress ketone aldolization. Acidify to isolate the acid.
Acidic: HCl or H2SO4 in MeOH/H2O or aqueous dioxane, reflux as needed; minimizes enolate formation.
Amidation:
Via acid chloride: SOCl2 (cat. DMF) in DCM or toluene, 0–25 °C; then amine coupling with base (Et3N). Alternatively EDC·HCl/HOBt or HOAt in DCM/DMF at 0–25 °C.
Transesterification:
Cat. acid (p-TsOH) or base (NaOMe) in corresponding alcohol, 0–65 °C; remove MeOH by azeotrope to drive equilibrium.
Reductive amination at ketone:
Amine + NaBH(OAc)3 in DCE/EtOAc/MeOH, 0–25 °C; or NaBH3CN in MeOH with AcOH buffer. Protect ester if stronger hydrides are required.
Ketone reduction:
NaBH4 in MeOH/EtOH at 0–25 °C (ester inert); for stereocontrol, use Luche conditions (NaBH4/CeCl3) in MeOH at 0 °C.
Baeyer–Villiger oxidation:
mCPBA (1.2–2.0 equiv) in DCM at 0–25 °C; buffer acid byproducts. Alternatively, H2O2/AcOH with catalytic acids.
Enolate alkylation (at ketone alpha):
LDA (1.1–1.5 equiv) in THF at −78 to −40 °C, then electrophile (R–X). Quench carefully to avoid ester saponification.
Yields/times: strongly substrate- and condition-dependent; typical reactions reach 60–90% under optimized conditions. Always run pilot experiments and monitor by TLC/GC/LC.
Safety and Handling
Item-specific hazard info (from Product Data):
Signal word: Not specified for this item; refer to SDS.
H-statements: Not specified for this item; refer to SDS.
GHS classification: Not specified for this item; refer to SDS.
Pictograms: Not specified for this item; refer to SDS.
General safety guidance for cyclohexanone/ester derivatives (literature/industry practice; defer to SDS for this item):
Likely hazards: combustible liquid; may cause skin/eye irritation; may cause respiratory irritation if aerosolized; harmful if swallowed. Avoid inhalation of vapors/mists.
Peroxide formation: not typically peroxide-forming (unlike ethers), but avoid prolonged exposure to air/heat which can lead to oxidation.
Incompatibilities: strong oxidizers, strong bases (can saponify the ester), strong acids (acid-catalyzed transesterification/ketalization possible). Avoid reactive reducing agents near the ester unless intended.
Recommended PPE: lab coat, safety glasses, appropriate chemically resistant gloves (e.g., nitrile); use in fume hood.
Handling tips: keep containers tightly closed; minimize headspace to limit hydrolysis/oxidation; purge with inert gas if storing long term.
First-aid (overview):
Skin: wash with soap and water; remove contaminated clothing.
Eyes: rinse cautiously with water for several minutes; seek medical attention if irritation persists.
Inhalation: move to fresh air; seek medical attention if symptoms occur.
Ingestion: rinse mouth; do not induce vomiting; seek medical attention.
Always consult the product-specific SDS for authoritative hazard, exposure limits, and emergency procedures.
Solvent Selection
Relevance: This product is a neutral organic building block (ester/ketone). Solvent selection pertains to its handling, purification, and reactions employing it as substrate.
Polarity class: moderately polar, dipolar aprotic functionality; overall hydrophobic due to cyclohexyl and gem-dimethyl groups.
Limited: lower alcohols (MeOH, EtOH) — soluble but may engage in transesterification under acidic/basic conditions.
Poor: water.
Selection guidelines by task:
Chromatography: hexanes/EtOAc or toluene/EtOAc gradients separate from polar byproducts; dual carbonyl stretches aid TLC visualization (UV/anisaldehyde).
NMR: CDCl3 recommended; DMSO-d6 for less volatile handling; note potential keto–enol traces under basic impurities.
Reactions affecting the ester (aminolysis, transesterification): use aprotic solvents (THF, toluene, MeCN) to control chemoselectivity; exclude alcohols unless used as nucleophile.
Enolate chemistry at the ketone: THF, DME, or toluene under inert atmosphere; ensure anhydrous conditions.
Comparison (literature-based):
THF vs 2-MeTHF: similar solubility; 2-MeTHF offers greener profile and easier phase separation.
DCM vs EtOAc: DCM gives faster mixing and lower viscosity; EtOAc is greener and compatible with aqueous workups.
Storage and Reconstitution
Item-specific storage and shipping (from Product Data):
Storage conditions: Room temperature.
Shipped in: Normal.
Research use note: For research use only.
General handling guidance (literature/industry practice for esters/ketones):
Store in a tightly closed container, protected from moisture and direct sunlight. If long-term storage is planned, consider inert gas backfill (N2/Ar) and desiccation to minimize hydrolysis/oxidation.
Avoid prolonged exposure to strong acids/bases which can induce transesterification or saponification.
If crystallinity is observed, gentle warming or use of a compatible solvent (e.g., EtOAc, DCM) can aid dissolution for weighing/transfer.
No reconstitution is required; this is supplied as a neat compound. For solution prep, use anhydrous solvents and document concentrations. Common stock solutions: 0.1–1.0 M in DCM, THF, toluene, or EtOAc (as appropriate to planned reaction).
Freeze–thaw: not generally relevant; if stored as a solution, aliquot to avoid repeated warming cycles.
Always consult the container label and CoA/SDS for any product-specific instructions or stability notes.
Structure and Identity
Brief description: A cyclohexane scaffold bearing a methyl ester at the carboxylic position and a 4-keto group, with a gem-dimethyl substitution at C2; overall a 1,4-dicarbonyl motif on a substituted cyclohexane.
SMILES: Not specified for this item; refer to CoA/Spec Sheet.
Molecular formula: Not specified for this item; refer to CoA/Spec Sheet.
Molecular weight: Not specified for this item; refer to CoA/Spec Sheet.
Structural features (general/literature-based description of the named structure):
Ring system: six-membered cyclohexane ring.
Functional groups: one ketone (4-oxo on the ring) and one methyl ester (carboxylate methyl ester at the ring carbon), making a ring-constrained 1,4-dicarbonyl motif.
Substitution: geminal dimethyl at C2 (Thorpe–Ingold effect potential), increasing steric bulk and conformational bias.
2D description in words: A cyclohexanone (C4 carbonyl) in which the C1 ring carbon bears a carboxylate carbonyl connected to a methoxy group (–CO2Me). C2 carries two methyl substituents. No defined stereocenters are implied by the name (racemic/conformational mixture expected).
Closely related identifiers (literature/computed, for context only):
Putative empirical formula from name parsing (literature/computed): ~C10H16O3 (see Physical Properties).
Synthetic Utility
Functional group set and reactivity (literature/general):
Ester (–CO2Me at ring carbon): platform for hydrolysis, transesterification, amidation, and acyl activation. The alpha-position (ring C1) can, under strong base, participate in enolization though ring substitution may limit acidity.
Ketone (4-oxo): enolization enables alpha-functionalization (alkylation, halogenation), aldol reactions, and reductive amination. Carbonyl serves as a handle for oxime/hydrazone formation and selective reductions.
Gem-dimethyl (C2): increases steric hindrance, alters conformational preferences (chair bias), and can enhance intramolecular reaction rates (Thorpe–Ingold effect) or block undesired side reactions at adjacent positions.
Named/related reactions (as applicable to motifs):
Baeyer–Villiger oxidation of cyclohexanone motifs to lactones (migration selectivity impacted by substitution).
DIBAL-H partial reduction of esters to aldehydes at cryogenic temperatures; Luche or NaBH(OAc)3 conditions for chemoselective ketone reduction/reductive amination in presence of esters.
Claisen-type condensations are generally on acyclic esters; here, ring attachment alters acidity—prefer reactions at the ketone alpha positions for predictable outcomes.
Retrosynthetic value:
Serves as a masked 1,4-dicarbonyl synthon on a saturated ring, allowing access to substituted lactams/lactones or annulated systems after appropriate functional group interconversions.
Practical tip: Control base strength and temperature to preserve ester integrity during enolate chemistry on the ketone; protect or sequence transformations to achieve chemoselectivity.
Target Specificity
Not applicable. This product is a small-molecule building block and not a biological targeting reagent (e.g., antibody, inhibitor with defined biological target, or probe with validated specificity). No antigen/epitope, species reactivity, clone, or isotype information applies.
Preguntas frecuentes
How is this product shipped?
This product ships under standard ambient conditions. No temperature-controlled packaging is required.
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