This compound belongs to the class of organic compounds known as indolines. These are compounds containing an indole moiety, which consists of pyrrolidine ring fused to benzene to form 2,3-dihydroindole.
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.
Certificati (CoA, COO, BSE/TSE e tabella di analisi)
C of A & Other Certificates(BSE/TSE, COO):
Analytical Chart:
Proprietà chimiche e fisiche
Peso molecolare
201.260 g/mol
XLogP3
2.700
Hydrogen Bond Donor Count
1
Hydrogen Bond Acceptor Count
1
Rotatable Bond Count
0
Exact Mass
201.115 Da
Monoisotopic Mass
201.115 Da
Topological Polar Surface Area
29.100 Ų
Heavy Atom Count
15
Formal Charge
0
Complexity
268.000
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
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Recensioni
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Application Protocols
No validated biological assay protocols are provided for this catalog item. As a small-molecule building block, usage protocols depend on the intended synthetic or screening application.
General guidance (literature)
Stock solutions: prepare in DMSO at 10–100 mM for screening; filter (0.22 µm PTFE) if needed. Verify stability over the assay timeframe.
Analytical QC: record 1H/13C NMR, LC-MS, and HPLC purity before biological screening to ensure data quality.
Crystallization: for solid form studies, attempt slow evaporation from EtOAc/hexanes or toluene/hexanes.
For specific synthetic procedures (e.g., N-alkylation, halogenation), follow standard organic synthesis protocols and optimize conditions for your substrate and scale.
Biological Roles
Item-specific biological data: Not specified for this item; refer to CoA/Spec Sheet. For research use only (per Product Data).
General chemistry/chemical biology context (literature)
Spirooxindoles constitute a privileged scaffold in chemical biology due to their rigid 3D architecture, presenting vectors orthogonal to the oxindole plane. This geometry enables exploration of protein pockets with enhanced shape complementarity in screening libraries.
The oxindole core (indolin-2-one) is a common heteroaromatic-derived lactam with hydrogen-bond donor (N–H) and acceptor (C=O) features, often used to probe H-bonding motifs in enzyme active sites and protein–protein interfaces.
Physicochemical profile: neutral lactam with moderate polarity; tunable lipophilicity via N-alkylation or ring substitution allows SAR around permeability/solubility balance in probe development.
Derivatization handles: N–H for H-bonding or functionalization; aromatic ring for EAS or cross-coupling after halogenation; cyclohexane ring for C–H functionalization to introduce additional substituents and stereocenters.
No medical or clinical claims are made here. Any biological evaluation should be conducted under appropriate ethical and safety frameworks, and conclusions must not be inferred to this catalog item without experimental verification.
Buffer Applications
This compound is a neutral organic solid and not a buffering reagent. It does not form a defined conjugate acid/base pair suitable for maintaining solution pH in typical laboratory buffers.
Practical note
If dissolution in aqueous systems is required for assays, use co-solvents (DMSO, MeCN, ethanol) and, if appropriate, mild basification to deprotonate the N–H for temporary solubilization. Validate that such treatments do not alter assay outcomes.
For buffer preparation guidance, please refer to dedicated buffering agents (e.g., phosphate, HEPES, Tris).
Green Alternatives
As a solid building block, the principal environmental lever is solvent and reagent choice rather than replacing the compound itself.
Greener solvent choices (general guidance)
Prefer EtOAc, MeTHF, CPME, or 2-propanol over DCM/chloroform when solubility allows.
Use acetonitrile or ethanol as more benign polar solvents instead of DMF/DMSO for certain transformations, balancing solubility and reaction rate.
Reagent considerations
For N-alkylation, use greener bases (K2CO3, Cs2CO3) in alcohols/acetone/MeTHF rather than NaH in DMF, when compatible with the electrophile.
Employ catalytic hydrogenation (H2/Pd) for reductions rather than stoichiometric metal hydrides when chemoselectivity permits.
Mini comparison (illustrative; not item-specific)
DCM vs EtOAc: EtOAc has better environmental, health, and safety profile; DCM offers superior solubility and chromatographic handling.
DMF vs MeCN: DMF offers higher solubility but is reproductive toxin–classified and high-boiling; MeCN is more volatile, easier to remove, and greener by several metrics.
Waste minimization
Plan telescoped sequences (e.g., N-alkylation → EAS halogenation without isolation) to reduce solvent consumption.
Favor crystallization-induced purifications from greener binary systems (EtOAc/hexanes, IPA/water) to minimize silica gel use.
Pharmaceutical Uses
Item-specific pharmacopeia/excipient status: Not specified for this item; refer to CoA/Spec Sheet. For research use only.
General formulation/manufacturing context (literature)
Spirooxindole building blocks like this are used in discovery chemistry to assemble screening libraries and probe molecules; they are not typical excipients.
In pre-formulation studies for chemical probes, N-alkylation and ring substitution can modulate solubility and solid-state properties, aiding salt/salt-free form screening. Lactam N can form salts when quaternized or when converted to more basic derivatives, but the parent lactam is generally non-ionizable at neutral pH.
Solid form considerations: polymorphism and cocrystal formation with hydrogen-bond donors/acceptors (e.g., carboxylic acids, phenols) are avenues to tune material properties for research-scale crystallization or purification.
No therapeutic or clinical claims are made for this catalog item; it is intended solely for R&D use in laboratory settings.
Physical Properties
Item-specific properties (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.
Storage Conditions: Room temperature (per Product Data)
Shipped In: Not specified for this item; refer to CoA/Spec Sheet.
Literature or computed (general references; not item specifications)
Physical state: typically a crystalline solid for spirooxindoles of this size (literature trend).
Molecular formula and mass: often reported as C14H15NO; Mr ≈ 213.28 g/mol (literature; verify by CoA/MS for this SKU).
Solubility: expected low solubility in water; good solubility in polar aprotic organic solvents (DMF, DMSO, NMP) and moderate in chlorinated/aromatic solvents (DCM, chloroform, toluene) (literature expectations for neutral oxindole lactams).
Acid/base behavior: weakly acidic N–H (anilide-type); pKa of oxindole N–H typically ~15–18 in DMSO (literature class value); far less acidic in water. The lactam carbonyl is non-basic.
Partitioning: logP for unsubstituted spirooxindoles of this size commonly in the 1.5–2.5 range (literature class estimate); increases with N-alkylation.
Thermal behavior: many oxindole solids melt in the 150–250 °C range; specific melting point for this exact compound should be confirmed from CoA/Spec Sheet.
Note: Do not treat literature values as product specifications; consult the lot-specific CoA for definitive properties.
Quality and Grades
Item-specific grade/purity: Not specified for this item; refer to CoA/Spec Sheet.
How to interpret grades for this scaffold (general guidance)
Research grade: suitable for most synthetic and screening work; typical control of residual solvents and major impurities. Verify chromatographic purity and identity (1H/13C NMR, LC-MS) for critical studies.
High-purity (>98% or >99%) material: preferred for structure–activity relationship (SAR) or crystallographic studies where minor isomers could confound results.
Stabilizers: none are typically required for this neutral lactam; product is generally stable at ambient conditions. If any stabilizer is present, it will be stated on the label/CoA.
Spectroscopic quality: for photophysical studies, low UV-absorbing impurities and defined water content may be important; check the CoA for UV cutoffs or Karl Fischer values where relevant.
Verification recommendations
Identity confirmation: 1H/13C NMR (diagnostic lactam carbonyl ~δ 170–180 ppm in 13C), IR (amide C=O ~1680–1730 cm−1), and HRMS consistent with the empirical formula.
Purity assessment: HPLC or GC (if derivatized) with a suitable detection wavelength (oxindoles absorb in UV, ~230–280 nm). Document any enantiomeric excess only if a chiral variant is purchased.
Reaction and Applications
Spiro[cyclohexane-1,3'-indolin]-2'-one is a versatile spirooxindole building block. The rigid spiro-quaternary carbon and lactam motif make it valuable in complexity-generating synthesis and scaffold diversification.
Typical transformations (literature/general)
N-Functionalization: the anilide N–H can be deprotonated (e.g., NaH, K2CO3, Cs2CO3) and alkylated (alkyl halides, Michael acceptors) or acylated (acyl chlorides, anhydrides) to access N-substituted analogs.
Carbonyl chemistry: reduction (NaBH4 with Lewis acid, BH3·THF, or catalytic hydrogenation) affords the corresponding indolinol (lactam to hemiaminal/alcohol) or, under stronger conditions, ring-opened products. Oxidation to imide-like derivatives is possible via electrophilic activation.
Aromatic substitution: electrophilic aromatic substitution on the benzene ring (nitration, halogenation, Friedel–Crafts acylation) proceeds with directing effects of the lactam.
Cross-coupling via prefunctionalization: install aryl halides (e.g., via directed ortho-lithiation and quench with electrophiles) followed by Suzuki/Miyaura, Buchwald–Hartwig (on N-aryl derivatives), or Kumada couplings.
Alpha-functionalization to the lactam is limited because C-3 is a quaternary center; tactics rely on radical or photoredox C–H functionalization of the cyclohexane ring.
Application domains
Library synthesis: generation of 3D-rich fragment or lead-like libraries exploiting the spiro center.
Conformational constraint: incorporation into peptidomimetics or PROTAC linkers where a rigid hinge is advantageous.
Chiral chemistry: when resolved, enantioenriched forms enable stereodefined probe molecules; organocatalytic desymmetrization of the cyclohexane ring can create additional stereocenters.
Practical tips
Ensure dry, oxygen-free conditions for strong-base N-alkylations. Monitor by LC-MS; N-alkylation often shifts retention and m/z by +alkyl mass.
For aromatic substitutions, control temperature to avoid overreaction and preserve the spiro junction integrity.
Reaction Conditions
The following conditions are general literature guidance for oxindole scaffolds and should be optimized for this substrate. They are not product specifications.
N-Alkylation (typical)
Base/solvent: K2CO3 or Cs2CO3 in DMF, MeCN, or acetone; or NaH in THF/DMF for less reactive electrophiles.
Electrophiles: primary alkyl bromides/iodides, benzylic halides, or Michael acceptors (e.g., acrylates) under phase-transfer or polar aprotic conditions.
Temperature/time: 20–60 °C, 2–16 h; monitor by LC-MS/HPLC.
Aromatic halogenation
Reagents: NBS/NCS with catalytic acid (AcOH) or halogenation under electrophilic conditions (Br2/FeBr3) at 0–25 °C to control regioselectivity.
Follow-up: install boron (e.g., via lithium–halogen exchange then B(OMe)3) for Suzuki couplings.
Carbonyl reduction
Hydride: NaBH4 with Lewis acid (e.g., BF3·Et2O) in THF/MeOH at 0–25 °C to access indolinols; or BH3·THF for deeper reduction.
Catalytic hydrogenation: H2 (1–5 bar) with Pd/C or Pt at 25–60 °C in EtOAc/EtOH; monitor to avoid over-reduction of the aromatic ring.
Radical C–H functionalization (cyclohexane ring)
Photoredox: Ir(ppy)3 or [Ru(bpy)3]2+ with HAT catalysts (e.g., quinuclidine derivatives) in MeCN/MeOH or DCE under blue LEDs; 20–40 °C, 2–12 h.
Workup/purification
Quench strong bases with saturated NH4Cl; extract into DCM/EtOAc; dry (Na2SO4); purify by flash chromatography (hexanes/EtOAc or DCM/MeOH).
Expected yields vary widely (40–90%) depending on substitution and conditions; confirm experimentally.
Safety and Handling
Item-specific hazard data (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 oxindole spirocycles (literature/ best practice; not a substitute for SDS)
Likely low volatility solid; handle powders to minimize dust generation and inhalation.
PPE: lab coat, safety glasses or goggles, and appropriate chemically resistant gloves (e.g., nitrile). Use a fume hood for weighing, charging, and any reactions.
First aid overview: after skin contact, wash with soap and water; after eye contact, rinse cautiously with water for several minutes and seek medical attention if irritation persists; after inhalation of dust, move to fresh air; after ingestion, rinse mouth and seek medical advice. Always follow your institutional SOPs.
Incompatibilities: strong oxidizers and strong reducing agents may react; strong bases can deprotonate the N–H and enable N-alkylation; strong acids may cause protonation and potentially ring-opening under forcing conditions. Avoid sodium hydride contact in protic media.
Thermal hazards: as with many organic solids, avoid excessive heating and open flames. Combustible; use standard fire-fighting measures for organic materials (CO2, dry chemical, foam) per SDS.
Always defer to the Aladdin SDS for authoritative hazard classifications, exposure limits, and spill/fire-fighting procedures.
Solvent Selection
This product is a neutral, moderately polar organic solid rather than a solvent. Solvent selection is typically about dissolving it for reaction or formulation.
Polarity and dissolution (literature guidance)
Good solubility: polar aprotic solvents (DMSO, DMF, NMP, acetonitrile at elevated temperature), halogenated solvents (DCM, chloroform) and aromatic solvents (chlorobenzene, toluene when heated).
Limited solubility: alcohols (MeOH, EtOH) may dissolve upon heating; water is generally poor unless co-solvents or pH adjustments are used (N-deprotonation increases solubility in basic aqueous-organic mixtures).
Practical choices by task
Reaction medium: DMF/DMSO for N-alkylation or coupling chemistry; DCM or THF for electrophilic aromatic substitutions or reductions; toluene/xylene for high-temperature transformations.
Purification: normal-phase silica gel chromatography using hexanes/EtOAc or DCM/MeOH gradients; reverse-phase HPLC with ACN/H2O + 0.1% acid for analytical purity checks.
Small comparison (general, not item-specific)
DCM vs EtOAc: DCM often gives better solubility but is less green; EtOAc is a greener alternative when solubility allows.
DMF/DMSO vs MeCN: DMF/DMSO maximize solubility; MeCN is more volatile and easier to remove but may dissolve less.
Always confirm solubility at your working temperature and scale; seed crystallization from EtOAc/hexanes or toluene/hexanes is common for spirooxindoles.
Storage and Reconstitution
Item-specific storage/shipping
Storage Conditions: Room temperature (per Product Data). Store tightly closed in a dry, well-ventilated place, away from strong acids/bases and oxidizers.
Shipped In: Not specified for this item; refer to CoA/Spec Sheet.
Stability (general guidance)
The oxindole lactam is typically stable at ambient conditions. Protect from prolonged light and moisture to maintain solid-state integrity and prevent hydrolysis of any sensitive derivatives.
Reconstitution/handling
For stock solutions, dissolve in dry DMSO, DMF, MeCN, or DCM to the desired concentration. Filter through a 0.22 µm PTFE membrane if particulate is present.
If aqueous compatibility is needed, prepare DMSO concentrates (e.g., 10–50 mM) and dilute into buffered media with vigorous mixing; final DMSO content commonly kept ≤1–2% v/v in assays.
Avoid repeated freeze–thaw of solutions; aliquot and store at −20 °C (for DMSO/DMF stocks) if multi-week use is anticipated. Assess solution stability by LC-MS/HPLC periodically.
Always consult the Aladdin CoA/SDS for lot-specific guidance on stability, storage, and safe handling. For research use only.
Structure and Identity
Spiro[cyclohexane-1,3'-indolin]-2'-one is a spiro-fused oxindole scaffold in which the C-3 position of an indolin-2-one (oxindole) is the spiro-junction carbon to the C-1 of a cyclohexane ring. This generates a rigid, three-dimensional, quaternary center.
Core framework: oxindole (indolin-2-one) spiro-fused to cyclohexane at C-3 of the oxindole.
Functional groups: lactam (amide) carbonyl at the 2-position, an anilide-type N–H (secondary amide), aromatic benzene ring, saturated cyclohexane ring, spiro-quaternary carbon at C-3.
Stereochemistry: the spiro center is a quaternary stereogenic center; commercial material may be racemic unless specified. No additional defined stereocenters in the parent scaffold.
Typical literature identifiers: Commonly reported empirical formula C14H15NO and formula mass ~213.28 g/mol (literature; verify against CoA for this lot).
2D structure (described): a benzene ring fused to a five-membered lactam (oxindole). The carbon at the 3-position of the five-membered ring is a spiro junction to a cyclohexane ring; the 2-position bears the carbonyl; the ring nitrogen is adjacent to the carbonyl (indolin-2-one).
Synthetic Utility
The scaffold offers multiple orthogonal vectors for diversification, making it a valuable synthon in complexity-oriented synthesis and library design.
Functional handles and reactivity (literature/general)
N–H lactam: deprotonate for N-alkylation (alkyl halides, Michael acceptors) or N-acylation/carbamoylation. Mitsunobu N-alkylation is also possible with appropriate alcohol partners.
Aromatic ring: electrophilic substitution (halogenation, nitration, sulfonylation); directed metalation strategies can introduce halogens or boron for subsequent cross-coupling.
Carbonyl: reductions to indolinols; activation (e.g., via Vilsmeier–Haack type reagents) for further functionalization; formation of imines/enamines after derivatization is limited by lactam stability but possible via O-activation.
Cyclohexane ring: radical C–H functionalization (photoredox HAT, Minisci-type after suitable activation) to append alkyl/heteroatom substituents and install new stereocenters.
Strategic roles
3D-rich fragment: enhances Fsp3 content of libraries, improving coverage of 3D chemical space.
Chiral pool proxy: resolution of the spiro center (e.g., chiral HPLC or salt formation after N-functionalization) furnishes enantioenriched scaffolds for asymmetric synthesis.
Linker platform: N-functionalization enables attachment to tags, handles (biotin, fluorophores), or linkers for target engagement studies.
Practical notes
Maintain mild conditions to preserve the spiro junction; avoid harsh acidic/basic conditions that could promote ring opening.
LC-MS monitoring is effective; the lactam typically gives a strong [M+H]+ signal in ESI(+).
Target Specificity
Not applicable. This product is a small-molecule building block and not a biological macromolecule or affinity reagent. No antigen/epitope/clone/isotype information applies. If used in target engagement studies, any observed specificity arises from user-designed derivatives and must be empirically determined.
Domande frequenti
What is the purity of this product?
This product is supplied at ≥95% purity (chemical assay). Lot-specific values are stated on the Certificate of Analysis.
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