Ethyl 6-cyclohexyl-6-oxohexanoate - ≥95% , CAS No.16076-62-3

CAS: 16076-62-3 Cat. No.: E1010128 Formula: C₁₄H₂₄O₃ Peso molecolare: 240.35 PubChem CID: 11770572

GRADE & PURITY ≥95%

Storage

Room temperature

Specifications

Specifiche e purezza

≥95%

Condizioni di conservazione di stoccaggio

Room temperature

Purezza

≥95%

Nomi e identificatori

• Sorrisi canonici: CCOC(=O)CCCCC(=O)C1CCCCC1
• IUPAC Name: ethyl 6-cyclohexyl-6-oxohexanoate
• InChIKey: YMTFBDCTGQKTQB-UHFFFAOYSA-N
• INCHI: 1S/C14H24O3/c1-2-17-14(16)11-7-6-10-13(15)12-8-4-3-5-9-12/h12H,2-11H2,1H3
• Isomeri SMILES: CCOC(=O)CCCCC(=O)C1CCCCC1
• PubChem CID: 11770572
• Peso molecolare: 240.35

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Lipids and lipid-like molecules
    • Classe Fatty Acyls
      • Subclass Fatty acid esters

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• Classe: Fatty Acyls
• Subclass: Fatty acid esters
• Intermediate Tree Nodes: Not available
• Direct Parent: Fatty acid esters
• Alternative Parents: Ketones Carboxylic acid esters Monocarboxylic acids and derivatives Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aliphatic homomonocyclic compounds
• Substituents: Fatty acid ester - Ketone - Carboxylic acid ester - Monocarboxylic acid or derivatives - Carboxylic acid derivative - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Carbonyl group - Aliphatic homomonocyclic compound
• Descrizione: This compound belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid.
• External Descriptors: Not available

Data sources

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.

DOI: 10.1186/s13321-016-0174-y

Proprietà chimiche e fisiche

• Peso molecolare: 240.340 g/mol
• XLogP3: 2.900
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 8
• Exact Mass: 240.173 Da
• Monoisotopic Mass: 240.173 Da
• Topological Polar Surface Area: 43.400 Ų
• Heavy Atom Count: 17
• Formal Charge: 0
• Complexity: 242.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

Application Protocols

Not applicable. No bioassay or immunoassay protocols (e.g., WB, IHC, IF, FC) are specified for this small‑molecule reagent. For synthetic use, refer to the Reaction Conditions and Synthetic Utility sections for practical guidance.

Biological Roles

This material is a synthetic aliphatic keto‑ester and is not known as a natural metabolite or cofactor.

• General commentary (no clinical claims)

  • No established biological role or pathway association has been reported for this exact structure in core metabolism. Its high hydrophobicity and lack of ionizable groups at neutral pH suggest poor aqueous bioavailability and limited interaction with typical aqueous enzymatic systems without formulation.
  • In biochemical method development, structurally related lipophilic esters sometimes serve as model substrates for esterase or ketone‑reducing enzyme studies; any such use should be validated empirically for this exact compound.

• Safety note

  • Use is restricted to research and laboratory applications only. Not intended for food, drug, household, or veterinary use.

Buffer Applications

Not typically applicable. Ethyl 6‑cyclohexyl‑6‑oxohexanoate is a neutral, hydrophobic organic reagent and does not function as a buffering agent. For experimental handling, dissolve in an appropriate organic co‑solvent before introducing into any buffered aqueous systems if required for assays.

Green Alternatives

• Product context: This is a target reagent, not a volatile solvent; “green alternative” considerations focus on transforming and processing it more sustainably rather than replacing it.

• Greener processing choices (general)

  • Solvents: Prefer 2‑MeTHF, CPME, EtOAc, or MeTHF/water biphasic systems over chlorinated solvents where reaction compatibility allows. For reductions, ethanol/isopropanol can sometimes replace MeOH or THF with suitable catalysts.
  • Reductions: Catalytic hydrogenation (H2, Pd/C or Raney Ni) in green solvents may replace stoichiometric metal hydrides for ketone→alcohol conversion, minimizing inorganic waste.
  • Oxidations: Choose greener oxidants (e.g., Oxone, H2O2 with suitable catalysts) rather than peracids, when compatible.
  • Workup: Use aqueous ethanol or brine‑assisted phase separations; avoid halogenated waste. Opt for heptane/EtOAc instead of hexane/DCM for chromatography when feasible.

• Trade‑offs

  • 2‑MeTHF and CPME form fewer peroxides than Et2O and are biomass‑derived (2‑MeTHF), but may alter enolate geometry/selectivity and can retain water; rigorous drying may be needed.
  • Replacing DCM with EtOAc or MeTHF can increase reaction times or change selectivity; pilot trials are recommended.

• Brief comparison (processing solvents)

  • DCM: excellent for extractions, poor EHS profile.
  • EtOAc: biodegradable, good eluotrope, higher polarity.
  • 2‑MeTHF: renewable source, good for organometallics, higher bp simplifies reflux but complicates removal.

Pharmaceutical Uses

• No excipient or pharmacopeial monograph is known for this specific compound. It is not used as a pharmaceutical buffer or additive.

• Potential roles in a pharmaceutical R&D context (general; no therapeutic claims)

  • Synthetic intermediate: The orthogonal ester/ketone functionality enables generation of analogs bearing secondary alcohols, diols, lactones, or extended esters for medicinal chemistry SAR campaigns.
  • Probing selectivity: May serve as a test substrate for chemoselective reduction protocols (ketone vs ester) or enzyme screening (esterases/ketoreductases) during process development.

• Compliance note

  • Any use in GMP or clinical manufacturing would require independent qualification of specifications and impurities; this listing is for research use only.

Physical Properties

• Item-specific specs for this SKU

  • Appearance: Not specified for this item; refer to CoA/Spec Sheet.
  • Grade/Purity: 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.

• Literature/computed expectations for this structure (non-authoritative)

  • Calculated molecular formula/MW (from name): C14H24O3; ~240.34 g/mol.
  • State at RT: typically a colorless to pale liquid for similar C14 aliphatic keto‑esters.
  • Density, refractive index: not located in authoritative literature for this exact CAS at time of writing; consult CoA/SDS.
  • Boiling point / melting point: not located in authoritative literature; consult CoA/SDS.
  • Solubility: expected to be practically insoluble in water; freely soluble in nonpolar and moderately polar organic solvents (hexanes, toluene, EtOAc, THF, DCM) due to a hydrophobic ring and limited polarity.
  • LogP: expected high (hydrophobic), typical of aliphatic C14 esters bearing one ketone; exact value not located.
  • UV: no strong chromophores; weak n→π* carbonyl absorption in near‑UV; no specified UV cutoff for this item.

• Notes

  • Use the Aladdin CoA for lot-specific constants (density, refractive index) when preparing calibrated solutions or performing quantitative methods.

Quality and Grades

• Item-specific grade/purity details

  • Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
  • Stabilizers/Inhibitors: Not specified for this item; refer to CoA/Spec Sheet.

• Guidance on grades relevant to this compound class (general)

  • Research grade: Suitable for most synthesis and discovery applications. Trace metal/UV absorbance specifications are typically not defined unless stated.
  • Purified/97–99%: Common for fine chemicals; supports most organic synthesis, analytics by NMR/GC/LC. Lower background in catalysis and polymerizations.
  • HPLC grade (for solvents): Not applicable here; this is a reagent, not a chromatographic solvent. If a low‑UV grade is offered, it indicates minimized absorbance for UV detection.

• Verification & QC tips

  • Confirm identity by 1H/13C NMR (diagnostic ester quartet/triplet for –CH2CH3, carbonyl signals ~170–175 ppm for ester and ~205–215 ppm for ketone), IR (two strong C=O bands), and HRMS.
  • Assess purity by GC‑MS or HPLC with ELSD/UV (weak UV response expected; use 210–220 nm if UV is used). Residual solvents and water content should be checked if critical to the intended application.
  • For specifications not listed above (water ppm, residual solvents, metals, UV cutoff): Not specified for this item; refer to CoA/Spec Sheet.

Reaction and Applications

As a cyclohexyl‑substituted aliphatic keto‑ester, this reagent is a versatile building block enabling orthogonal transformations at the ketone and ester.

• Chemoselective carbonyl chemistry (general/literature)

  • Reductions: NaBH4 or catalytic hydrogenation (Pd/C, H2) reduce the ketone preferentially to the secondary alcohol, leaving the ester intact. LiAlH4 reduces both to give diol or primary alcohol at the ester end.
  • Oxidations/Baeyer–Villiger: The ketone can undergo Baeyer–Villiger oxidation (mCPBA) to an ester; migration tendencies (cyclohexyl vs pentyl chain) can direct product distribution.
  • Acylation/derivatization: Convert the ketone to oximes/hydrazones (Beckmann/semicarbazone derivatives) for characterization or further rearrangements.

• Enolate and C–C bond formation

  • Site-selective deprotonation α‑to the ketone (C5) vs α‑to the ester (C2) with LDA/LHMDS allows directed alkylations, aldol, or Michael additions. HMPA or DMPU can increase reactivity/selectivity (use with caution; HMPA toxicity).
  • Claisen-type condensations from the ester end require appropriate enolate generation and trapping; crossed Claisen with simple esters can elaborate the chain length.

• Protecting-group orthogonality

  • The ester confers stability under many nucleophilic additions to the ketone; conversely, the ketone tolerates typical esterifications/transesterifications under acid catalysis.

• Applications (examples)

  • Synthesis of cyclohexyl‑substituted alcohol acids/esters via selective ketone reduction.
  • Precursor to lactones or diesters via oxidative rearrangements.
  • Scaffold for SAR libraries where lipophilic cyclohexyl and flexible linker are desired.

Reaction Conditions

General literature guidance for this class of keto‑esters (adjust to your substrate and scale):

• Chemoselective reductions

  • Ketone → alcohol: NaBH4 (1–2 equiv) in MeOH, EtOH, or THF/MeOH (0 to 25 °C, 0.5–2 h). Quench with NH4Cl. Typically leaves ester intact.
  • Global reduction: LiAlH4 (2–4 equiv) in dry THF or Et2O (0 °C to reflux, 1–3 h) converts ester and ketone to diol/primary alcohol; cautious quench.
  • DIBAL‑H (1.5–2 equiv) in toluene at −78 to −20 °C can reduce the ester to an aldehyde with minimal impact on the ketone if carefully controlled.

• Enolate chemistry

  • α‑to ketone: LDA (1.1–1.5 equiv) in THF at −78 °C, then electrophile (alkyl halide, aldehyde). Warm to 0 °C as needed.
  • α‑to ester: LDA or NaH with HMPA/DMPU (use with caution) to increase ester α‑acidity; trap with alkyl halides or perform Claisen‑type condensations.

• Oxidations and rearrangements

  • Baeyer–Villiger: mCPBA or peracetic acid (DCM, 0–25 °C) to convert the ketone to an ester; migration preference must be empirically determined (cyclohexyl often migratory).

• Hydrogenation

  • Pd/C (5–10 wt%) under H2 (1–5 bar) in EtOH or EtOAc can reduce the ketone to the alcohol; monitor for over‑reduction under forcing conditions.

Note: Temperatures, equivalents, and times are representative literature conditions for related substrates; optimize for this exact compound.

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/Pictograms: Not specified for this item; refer to SDS.

• General safety guidance for aliphatic keto‑esters (literature/practice)

  • Hazards: May cause skin/eye irritation; inhalation of vapors/mists may irritate respiratory tract. Combustible as an organic liquid.
  • PPE: Safety glasses or goggles, lab coat, and chemical‑resistant gloves (e.g., nitrile). Use in a fume hood to minimize inhalation exposure.
  • Handling: Avoid breathing vapors; prevent contact with oxidizers and strong bases/acids that may induce hydrolysis or transesterification. Minimize moisture exposure during moisture‑sensitive reactions.
  • Incompatibilities: Strong oxidizing agents (fire risk); strong bases/acids (ester cleavage or aldol side reactions at the ketone α‑positions).
  • First aid (overview; defer to SDS):
    • Eye/Skin: Rinse with water for at least 15 minutes; remove contaminated clothing; seek medical attention if irritation persists.
    • Inhalation: Move to fresh air; seek medical attention if symptoms occur.
    • Ingestion: Rinse mouth; do not induce vomiting unless directed by medical personnel; seek medical advice.
  • Fire: Use dry chemical, CO2, or alcohol‑resistant foam. Combustion may produce CO/CO2.

• Waste: Collect organic waste in compatible, closed containers; dispose per institutional and local regulations.

Solvent Selection

This product is a hydrophobic reagent (not a solvent). The following guidance concerns dissolving/processing it in reactions and purifications.

• Polarity/miscibility profile (literature expectations)

  • Practical water solubility: very low; avoid aqueous systems unless using emulsions, surfactants, or co‑solvents.
  • Organic solubility: high in nonpolar to moderately polar media (hexanes, toluene, MTBE, Et2O, CPME, EtOAc, DCM, THF, MeCN). THF/EtOAc often provide faster dissolution and support enolate chemistry.

• Selection by task

  • Nucleophilic additions to the ketone (e.g., NaBH4 reduction, organometallic additions): use protic alcohols (MeOH/EtOH) cautiously for NaBH4; for organometallics (RMgX/RLi), employ dry ether solvents (THF, Et2O) under inert gas to preserve the ester.
  • Selective ketone reduction over ester: NaBH4 in MeOH/THF; avoid LiAlH4 if ester must remain intact.
  • Enolate formation (α‑to ketone or ester): anhydrous THF, DME, or toluene with LDA/LHMDS at −78 to 0 °C; control temperature to bias site selectivity.
  • Purification: normal‑phase silica with hexanes/EtOAc (e.g., 8:2 → 6:4); ketone polarity aids elution control. For scale‑up, consider heptane/IPA gradients.

• Small comparison (general)

  • THF vs DCM: THF offers better solvation of bases/enolates; DCM is good for mild electrophilic reactions, but poor for strong bases.
  • EtOAc vs MTBE: EtOAc has higher polarity and better eluotropic strength; MTBE offers lower peroxide risk than Et2O and easy phase separations.

Storage and Reconstitution

• Item-specific storage

  • Storage Conditions (Product Data): Room temperature.
  • Shipped In: Not specified for this item; refer to CoA/Spec Sheet.

• General storage guidance for aliphatic keto‑esters

  • Keep tightly closed in the original container, protected from moisture and strong oxidizers/bases.
  • Store in a cool, dry, well‑ventilated area away from ignition sources. While room temperature is acceptable, prolonged exposure to heat or light should be avoided.
  • For long‑term storage, optional nitrogen/argon blanket minimizes oxidative degradation.

• Reconstitution/handling

  • Supplied neat; no reconstitution is required. For solution preparation, use dry, oxygen‑free solvents if performing moisture‑sensitive chemistry (e.g., enolate formation, organometallic additions).
  • If weighing viscous material, warm gently to ambient and use positive‑displacement pipettes or pre‑tared syringes for accuracy.

• Stability

  • Keto‑esters are generally stable at ambient conditions when dry. Hydrolysis may occur under strong acidic/basic conditions; avoid prolonged contact with aqueous media.

• Refer to the Aladdin CoA/SDS for any lot‑specific handling, stability, or impurity information.

Structure and Identity

Brief overview: Ethyl 6-cyclohexyl-6-oxohexanoate is a hydrophobic aliphatic keto‑ester featuring a terminal cyclohexyl‑substituted ketone and an ethyl ester at the opposite terminus; overall a 1,5‑dicarbonyl motif separated by a four‑carbon tether.

• Item-specific (Product Data)

  • Product Name: Ethyl 6-cyclohexyl-6-oxohexanoate
  • CAS: 16076-62-3
  • CID: 11770572
  • InChIKey: 441334 (as provided)
  • Storage Conditions: Room temperature
  • Research Use: For research use only

• Computed/literature identity (non-authoritative; derived from name)

  • Putative molecular formula: C14H24O3 (calculated)
  • Calculated molecular weight: ~240.34 g/mol (C=12.011, H=1.008, O=16.00)
  • Putative SMILES: CCOC(=O)CCCCC(=O)C1CCCCC1
  • Functional groups: one ethyl ester (–CO2Et), one aryl-free, aliphatic ketone (–CO–) bound to a cyclohexyl ring; saturated cyclohexyl ring; no heteroatoms beyond carbonyl oxygens; no stereocenters.
  • 2D structural description: An ethyl ester carbonyl at the left terminus connects through a four‑methylene chain (–CH2–)4 to a ketone carbonyl whose carbon is also bonded to a cyclohexyl ring (sp3), yielding an acyclic keto‑ester appended to a cyclohexane.

• Notes

  • Any registry identifiers not explicitly listed under Product Data should be verified against the CoA/SDS for this SKU prior to regulatory or QC use.

Synthetic Utility

• Functional group leverage

  • Ketone: amenable to nucleophilic addition (RMgX/RLi), selective NaBH4 reduction, oxime/hydrazone formation, and Baeyer–Villiger oxidation. α‑Functionalization (halogenation, alkylation) via enolate under basic conditions.
  • Ester: stable to many nucleophiles and bases used for ketone chemistry; can be hydrolyzed (saponified) to the acid, reduced (DIBAL to aldehyde at low T; LiAlH4 to alcohol), or transesterified (Fischer or basic conditions).

• Strategy and selectivity

  • Orthogonal reactivity enables stepwise derivatization: e.g., reduce ketone → secondary alcohol, then modify ester; or protect ketone as ketal before ester transformations.
  • Site‑selective enolate formation: LDA/LHMDS in THF at low temperature can favor deprotonation α‑to the ketone; stronger or warmer conditions may access the ester α‑position. Use of chelating additives (e.g., ZnCl2) can bias outcomes.

• Retrosynthetic value

  • Serves as a masked acyl/cyclohexyl synthon. Disconnection at the ketone suggests acylation of cyclohexylmetal species with a suitable acid chloride/anhydride followed by homologation to the ester; or conversely, acylation of a pentanoyl equivalent with cyclohexanecarbonyl equivalents.

• Purification/analysis tips

  • Two carbonyls provide strong IR bands; limited UV response necessitates ELSD, CAD, or low‑λ UV (210–220 nm) for HPLC.

Target Specificity

Not applicable. This product is a small‑molecule synthetic reagent and does not possess biological target specificity (no antigen/epitope/isotype attributes). No target-specific data are provided for this SKU.