Ethyl 5-cyclopentyl-5-oxovalerate , CAS No.24071-97-4

CAS: 24071-97-4 Cat. No.: E975072 Formula: C₁₂H₂₀O₃ Peso molecolare: 212.29 PubChem CID: 24727432

Storage

Room temperature

Specifications

Condizioni di conservazione di stoccaggio

Room temperature

Nomi e identificatori

Sorrisi canonici

CCOC(=O)CCCC(=O)C1CCCC1

IUPAC Name

ethyl 5-cyclopentyl-5-oxopentanoate

InChIKey

NRMVAQXDOTYGBH-UHFFFAOYSA-N

INCHI

1S/C12H20O3/c1-2-15-12(14)9-5-8-11(13)10-6-3-4-7-10/h10H,2-9H2,1H3

Isomeri SMILES

CCOC(=O)CCCC(=O)C1CCCC1

PubChem CID

24727432

Peso molecolare

212.29

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: 212.280 g/mol
• XLogP3: 2.000
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 7
• Exact Mass: 212.141 Da
• Monoisotopic Mass: 212.141 Da
• Topological Polar Surface Area: 43.400 Ų
• Heavy Atom Count: 15
• Formal Charge: 0
• Complexity: 217.000
• 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

No assay/application protocols are specified for this item. As a synthetic intermediate, its use depends on the intended transformation.

• General lab protocol pointers (informational):
  • For enolate chemistry: dry glassware and solvents, inert atmosphere, low-temperature control, titrated base (e.g., LDA from n‑BuLi/diisopropylamine).
  • For ketone reduction: choose selective hydride/catalyst; monitor by TLC/GC; quench carefully to avoid exotherms.
  • For workup: favor EtOAc or MTBE extractions; wash with saturated bicarbonate if acidic catalysts were used, or dilute acid if basic catalysts were used.

Consult primary literature or internal SOPs tailored to your synthesis goals.

Biological Roles

This product is a synthetic organic building block without a known intrinsic biological role.

• Not typically a metabolite, cofactor, or biomacromolecule component.
• Use in life-science contexts would generally be as a chemical intermediate, probe precursor, or hydrophobic fragment in library synthesis rather than a functional biological agent.
• Any biochemical testing should be performed strictly in research settings. No clinical or diagnostic use is intended or implied.

For biological safety, handling should follow general organic compound precautions; consult the SDS for exposure and toxicity details specific to this item.

Buffer Applications

Not typically applicable. Ethyl 5-cyclopentyl-5-oxovalerate is a neutral, water-insoluble keto ester and is not used to prepare aqueous buffer systems. For experimental planning, focus instead on the Synthetic Utility, Reaction Conditions, and Solvent Selection sections.

Green Alternatives

While the substrate itself is fixed, greener choices can be made in the solvents and reagents used with Ethyl 5-cyclopentyl-5-oxovalerate.

• Greener solvent swaps (general guidance):

  • Replace THF with 2-MeTHF where feasible (biomass-derived, better phase separation, higher boiling point) for enolate chemistry and carbonyl additions.
  • Prefer ethyl acetate or dimethyl carbonate over DCM/chloroform for extractions and some reactions when compatible.
  • Use toluene or cyclopentyl methyl ether (CPME) instead of chlorinated solvents for reductions or metal-catalyzed steps if reactivity allows.

• Reagent considerations:

  • Opt for catalytic hydrogenation or transfer hydrogenation (e.g., isopropanol/Ru or Mn catalysts) over stoichiometric hydrides when reducing selectively, provided chemoselectivity can be maintained.
  • For base-mediated steps, consider carbonate bases or organic superbases under solvent-minimized conditions instead of strong mineral bases when compatible.

• Comparison snapshot (general):

  • THF vs 2-MeTHF: similar enolate performance; 2-MeTHF offers lower peroxide formation rate and improved life-cycle metrics but can retain more water—dry thoroughly.
  • DCM vs EtOAc: DCM gives low-temperature handling; EtOAc is biodegradable with lower toxicity but has narrower solubility window for some substrates.

Balance green choices against chemoselectivity (ketone vs ester) and safety; verify with small-scale trials.

Pharmaceutical Uses

No pharmacopeial status or excipient role is specified for this item; refer to CoA/Spec Sheet.

• General context (non-clinical):

  • Compounds of this class are used as intermediates in medicinal chemistry campaigns to access ketone- and ester-containing scaffolds. The cyclopentyl group can modulate lipophilicity and metabolic stability in small-molecule leads.
  • The bifunctional carbonyl pattern enables rapid analog generation by selective modification of either the ketone or ester.

• Manufacturing/formulation notes:

  • If used as a process intermediate, typical quality controls include assay by GC/HPLC, residual solvent profile, identity by NMR/IR/MS, and water content when moisture-sensitive steps follow.

No therapeutic claims are made. This product is provided strictly for research and development use.

Physical Properties

• Item-specific specifications:

  • Boiling point, melting point, density, refractive index, water/peroxide/metal limits, and UV cutoff: Not specified for this item; refer to CoA/Spec Sheet.

• Literature/computed properties (for planning only; not product specifications):

  • Molecular formula: C12H20O3 (computed from structure)
  • Molecular weight: ~212.29 g/mol (computed)
  • Polarity/character: moderately lipophilic bifunctional carbonyl compound; expected good solubility in common organic solvents (e.g., ethers, chlorinated solvents, aromatics) and low solubility in water (general expectation for aliphatic keto esters).
  • Acid–base: No strongly ionizable groups; forms enol/enolate at the ketone alpha position under basic conditions (general carbonyl chemistry).

• Practical implications (general):

  • As an aliphatic keto ester, the material is typically a low- to medium-viscosity liquid at ambient temperature; however, exact appearance for this SKU is not specified.
  • Dry, oxygen-free handling improves stability during strong-base enolate chemistry, though routine storage at room temperature is generally acceptable for neutral esters.

Always consult the product’s CoA/Spec Sheet for definitive specifications relevant to your lot.

Quality and Grades

• Item-specific grade/purity: Not specified for this item; refer to CoA/Spec Sheet.

• Guidance on typical grades (general information):

  • Synthetic/building-block grade: Suitable for routine organic synthesis; purity typically reported by GC/HPLC and NMR on CoA.
  • Higher-purity grades (e.g., ≥98–99% by GC/HPLC) are often preferred for enolate chemistry or asymmetric catalysis to minimize side reactions.
  • Low-UV or HPLC grades (when applicable) focus on minimizing UV-absorbing impurities and peroxides; not specified for this SKU.

• Stabilizers/antioxidants:

  • None specified for this item. If stabilizers are present in a related grade, they will be declared on the label/CoA, as they can influence catalytic hydrogenations or metal-catalyzed reactions.

• What to check on receipt:

  • Confirm appearance and purity on the CoA match process needs.
  • Review residual solvents, assay method, and any water/peroxide content if your reaction is moisture- or redox-sensitive.

For definitive grade definitions and acceptance criteria, rely on the lot-specific CoA/Spec Sheet.

Reaction and Applications

Ethyl 5-cyclopentyl-5-oxovalerate is a versatile δ‑keto ester that provides orthogonal reactivity at a secondary ketone and an aliphatic ethyl ester.

• Strategic uses (general chemistry):

  • Ketone enolate chemistry: The methylene alpha to the ketone undergoes deprotonation with LDA/LiHMDS, enabling C–C bond formation via alkylation, aldol additions, or conjugate additions to Michael acceptors.
  • Chemoselective carbonyl transformations: Ketone can be reduced (e.g., NaBH4) to give a secondary alcohol while retaining the ester. Alternatively, ester manipulations (e.g., transesterification under acidic/basic catalysis) can proceed without affecting the ketone if conditions are controlled.
  • Carbonyl protection: Transient ketal formation on the ketone allows independent modification of the ester (e.g., reductions or conversions to acid chlorides/amide couplings), followed by deprotection.
  • Cyclization strategies: Enolate alkylation with dihalides followed by intramolecular aldol can build carbocyclic frameworks where the cyclopentyl group imparts steric bias.

• Synthesis planning:

  • The 1,5‑dicarbonyl relationship is useful for stepwise fragment assembly where spacing of three methylenes is desired between ester and ketone handles.
  • The cyclopentyl substituent behaves as a saturated, conformationally restricted hydrophobic group, often improving partitioning and enabling test substrates for C–H functionalization screening on alicyclic systems.

• Practical tips:

  • Exclude moisture during strong-base steps to avoid ester saponification.
  • Control temperature carefully during hydride reductions to maintain chemoselectivity (ketone vs ester).

Reaction Conditions

General literature-guidance for transformations of δ‑keto esters like Ethyl 5‑cyclopentyl‑5‑oxovalerate (not product specifications):

• Enolate formation and alkylation:

  • Base: LDA (1.1–1.5 equiv) or LiHMDS in dry THF/2‑MeTHF.
  • Temperature: −78 °C to −20 °C for deprotonation; warm to −40–0 °C for electrophile addition.
  • Electrophiles: primary alkyl halides, acyl chlorides (for acylation), Michael acceptors (for conjugate additions) with typical yields ranging from moderate to high depending on electrophile and sterics.

• Ketone-selective reduction:

  • NaBH4 (1–2 equiv) in MeOH, EtOH, or i‑PrOH at 0–25 °C; monitor to avoid ester transesterification. Alternatively, catalytic hydrogenation (Pd/C, 1–10 mol %) in EtOAc/EtOH at rt–40 °C and 1–3 bar H2.

• Ester transformations:

  • Transesterification: catalytic acid (p‑TsOH) or base (NaOMe) in corresponding alcohol, reflux as needed.
  • Amidation: activate ester via acid chloride formation (SOCl2 or oxalyl chloride after hydrolysis) or use coupling reagents after converting to the acid.

• Carbonyl protection:

  • Ketone → ketal with ethylene glycol or diols under acid catalysis (Dean–Stark in toluene) to shield during aggressive ester chemistry.

• Workup/purification:

  • Quench bases at low temperature, extract with EtOAc/MTBE, wash with brine, dry (Na2SO4/MgSO4), and concentrate under reduced pressure. Purify by silica gel chromatography; hexanes/EtOAc gradients are commonly effective.

Verify all conditions on small scale and adjust to your specific substrate and equipment.

Safety and Handling

• Item-specific GHS information:

  • Signal word, hazard statements, pictograms, and classification: Not specified for this item; refer to SDS.

• General safety guidance for aliphatic keto esters (informational; defer to SDS):

  • Likely to cause irritation upon contact with skin/eyes or if inhaled as vapors/aerosols. Avoid breathing vapors/mists; use in a fume hood.
  • Personal protective equipment: lab coat, safety goggles, and compatible chemical-resistant gloves (e.g., nitrile). For bulk handling, consider splash protection.
  • Incompatibilities: strong bases (can induce saponification or enolate formation), strong acids (acid-catalyzed hydrolysis), strong oxidizers (may react with the aliphatic framework), and strong reducing agents (reduce carbonyls).
  • First aid overview: rinse eyes/skin with water for at least 15 minutes upon exposure; remove contaminated clothing; seek medical attention if symptoms persist. If inhaled, move to fresh air; if ingested, do not induce vomiting—seek medical attention.
  • Fire safety: treat as combustible organic liquid; use CO2, dry chemical, or foam. Cool containers with water spray if involved in a fire.
  • Waste: collect organic waste according to institutional and local regulations; segregate from aqueous corrosives and oxidizers.

Always consult the Aladdin SDS for authoritative hazard, exposure control, and first-aid information for this specific item.

Solvent Selection

This product is a synthetic building block, not a bulk solvent. Solvent selection pertains to using Ethyl 5-cyclopentyl-5-oxovalerate in reactions or sample preparation.

• Polarity and miscibility (general expectations for aliphatic keto esters):

  • Miscible with nonpolar to moderately polar organic solvents (e.g., hexanes to toluene, Et2O, MTBE, THF, DCM, chloroform, ethyl acetate). Poorly soluble in water.
  • Dielectric environment: Enolate formation and carbonyl additions are typically conducted in ethereal solvents (THF, MTBE) or polar aprotics (DMF, DMSO, MeCN) depending on base/nucleophile.

• Choosing a medium by transformation type:

  • Enolate chemistry (LDA, LiHMDS): anhydrous THF or 2-MeTHF at −78 to 0 °C, under inert gas.
  • Nucleophilic additions to the ketone: Et2O, THF, or toluene with controlled temperature.
  • Selective reductions: DCM or toluene for hydrosilane/catalyst systems; THF/MeOH for borohydride (if compatible).
  • Workup/extraction: ethyl acetate or MTBE often give efficient phase separation; brine aids drying.

• Comparison notes (general):

  • THF versus 2-MeTHF: 2-MeTHF offers greener profile and higher hydrophobicity, aiding separations; THF offers broader literature precedent and lower viscosity.
  • DCM versus toluene: DCM provides high solubility and low reaction temperatures; toluene is less volatile and more environmentally preferred in some settings.

Storage and Reconstitution

• Item-specific storage: Room temperature (per Product Data).

• Shipped in: Not specified for this item; refer to CoA/Spec Sheet.

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

• General guidance for keto esters (informational):

  • Store tightly closed in a dry, well-ventilated place away from strong acids/bases and oxidizers.
  • Protect from moisture to minimize slow hydrolysis; consider using inert gas blanket for long-term storage after opening.
  • No reconstitution is required; the compound is used as supplied. If solidification occurs at low temperature, gently warm to ambient and mix thoroughly before use.
  • For analytical consistency, record opening date and consider retesting purity (GC/HPLC) after extended storage.

Always defer to the product label and SDS for authoritative storage and handling instructions.

Structure and Identity

Ethyl 5-cyclopentyl-5-oxovalerate is a bifunctional aliphatic building block bearing an ethyl ester and a distal ketone on a five‑carbon tether, with a cyclopentyl substituent at the ketone carbon.

• Item-specific (Product Data):
  • CAS: 24071-97-4
  • CID: 24727432
  • InChIKey: 246088 (as provided)
  • Storage conditions: Room temperature
  • Research Use: For research use only
• Literature/computed identifiers (not specifications):
  • Suggested 2D description: an ethyl ester (EtO–C(=O)–) linked via –CH2–CH2–CH2– to a ketone carbonyl C(=O) bearing a cyclopentyl group (–C5H9)
  • Functional groups: secondary ketone (acyclic), ethyl ester (aliphatic), saturated cyclopentyl ring
  • Molecular formula (computed from structure): C12H20O3
  • Molecular weight (computed): ~212.29 g/mol
  • Representative SMILES (literature, for reference only): CCOC(=O)CCC(=O)C1CCCC1
• Structural features and reactivity-relevant notes (general chemistry):
  • The molecule is a 1,5‑dicarbonyl equivalent (ester and ketone separated by three methylenes).
  • The methylene alpha to the ketone is the most acidic site and forms enolates readily; the ester carbonyl can be addressed orthogonally under stronger or selective conditions.
  • No stereocenters are present; the compound is achiral in its parent form.

Synthetic Utility

Key functional elements: a secondary aliphatic ketone and an ethyl ester separated by a three‑carbon spacer, with a cyclopentyl substituent at the ketone carbon.

• Enolate-driven C–C formation:

  • The site alpha to the ketone is the most acidic; deprotonation with LDA or LiHMDS in THF/2‑MeTHF enables alkylation (primary halides), aldol additions (to aldehydes), and Michael additions (to acrylates/enones). Control temperature (−78 to 0 °C) to minimize ester involvement.

• Chemoselective reductions/oxidations:

  • Ketone → alcohol via NaBH4 or catalytic hydrogenation conditions, often leaving the ester intact. Subsequent acylations can furnish β‑hydroxy esters.
  • Ester transformations (transesterification, aminolysis) can be performed under conditions that avoid ketone reduction; protect the ketone as a ketal/acetal if necessary for strongly reducing conditions.

• Fragment coupling and diversification:

  • Convert the ester to an acid chloride, then couple to amines/alcohols (after ketone protection) to access amides/diesters.
  • Use the ketone for oxime/hydrazone formation, enabling traceless reductive unveiling or as handles for further cyclizations.

• Stereocontrol and ring effects:

  • The cyclopentyl group introduces steric bias that can influence enolate geometry and facial selectivity in additions, offering a handle for diastereocontrol in downstream steps.

Overall, the molecule serves as a robust linchpin for building hydrophobic, cycloalkyl-bearing frameworks with orthogonal carbonyl reactivity.

Target Specificity

Not applicable. This product is a small-molecule chemical building block and is not an antibody, enzyme, or targeted biological reagent. No target, epitope, or isotype information applies.