62756-20-1

Basic information

• Product Name: spiro[2H-1-benzopyran-2,1'-cyclohexan]-4(3H)-one
• Synonyms: spiro[2H-1-benzopyran-2,1'-cyclohexan]-4(3H)-one;Spiro[chroMan-2,1'-cyclohexan]-4-one;3,4-dihydrospiro[1-benzopyran-2,1-cyclohexan]-4-one
• CAS NO: 62756-20-1
• Molecular Formula: C₁₄H₁₆O₂
• Molecular Weight: 216.27564
• Mol File: 62756-20-1.mol

Chemical Properties

• Boiling Point: 361.3±22.0 °C(Predicted)
• Appearance: /
• Density: 1.15±0.1 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• CAS DataBase Reference: spiro[2H-1-benzopyran-2,1'-cyclohexan]-4(3H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: spiro[2H-1-benzopyran-2,1'-cyclohexan]-4(3H)-one(62756-20-1)
• EPA Substance Registry System: spiro[2H-1-benzopyran-2,1'-cyclohexan]-4(3H)-one(62756-20-1)

Safety Data

• Hazardous Substances Data: 62756-20-1(Hazardous Substances Data)

Usage

Uses

Used in Flavoring and Fragrance Industry:
Coumarin is used as a flavoring agent for its sweet, vanilla-like fragrance in food and beverages, enhancing the sensory experience of these products.
Used in Traditional Medicine:
Coumarin has been utilized in traditional medicine as an anticoagulant for the treatment of edema and venous insufficiency, due to its ability to improve blood circulation and reduce swelling.
Used in Pharmaceutical Synthesis:
Coumarin serves as a key component in the synthesis of various pharmaceuticals, contributing to the development of new medications with diverse therapeutic applications.
Used in Fragrance Creation:
In the fragrance industry, coumarin is employed to create unique and appealing scents for perfumes and other scented products, capitalizing on its distinctive aroma.

Upstream product

• 108-94-1 cyclohexanone 
• 118-93-4 o-hydroxyacetophenone 
• 130984-35-9 2-(1-hydroxycyclohexyl)-1-(2-hydroxyphenyl)ethanone 
• 86769-52-0 C₁₄H₁₅BrO₂ 
• 70577-31-0 3,4-dihydro-spiro[2H-1-benzopyran-2,1'-cyclohexan]-4-ol 
• 123-75-1 pyrrolidine 
• 582-24-1 1-phenyl-2-hydroxyethanone 
• 2981-10-4 1-(cyclohex-1-en-1-yl)piperidine 

Downstream Products

• 1190962-22-1 tert-butyl 4-(4-(spiro[chromeno[3,4-d]pyrimidine-5,1'-cyclohexane]-3-ylamino)phenyl)-piperazine-1-carboxylate 
• 1190961-31-9 N-(4-(1-piperazinyl)phenyl)-spiro[chromeno[3,4-d]pyrimidine-5,1'-cyclohexane]-3-amine 
• 1630952-63-4 1-phenyl-8-(spiro[chroman-2,1'-cyclohexan]-4-yl)-1,3,8-triazaspiro[4.5]decan-4-one 
• 97207-15-3 3-Cyclohex-1-enyl-chromen-4-one 
• 173469-28-8 C₂₂H₂₁N₃O₄ 
• 586956-86-7 (3aRS) 3a-chloro-2-(4-nitrophenyl)spirochromane(4,1')cyclohexane[4,3-d]-Δ^1,9b-[1,2,3]thiadiazoline 
• 586956-81-2 spirochroman(2,1')cyclohexane-4-one (4-nitrophenyl)hydrazone 

Relevant articles and documents

CYCLIC CYANOENONE DERIVATIVES AS MODULATORS OF KEAP1

The present invention relates to cyclic cyanoenone derivatives of Formula (I) or pharmaceutically acceptable salts or solvates thereof, wherein R1, R2, R3, R4 and m are as defined herein. The present invention also relates to pharmaceutical compositions comprising the cyclic cyanoenone derivatives of Formula (I) and to their use in therapy.

New 1-(Spiro[chroman-2,1′-cycloalkan]-4-yl)-1H-1,2,3-Triazoles: Synthesis, QTAIM/MEP analyses, and DNA/HSA-binding assays

This study synthesized and characterized the DNA/HSA properties of a new series of 12 examples of 4-(alkyl/aryl)-1-(spiro[chroman-2,1′-cycloalkan]-4-yl)-1H-1,2,3-triazoles (SCTz), in which alkyl = CH3(CH2)5 and aryl = C6H5, 4-NH2C6H4, 3-OCH3C6H4 (47–95% yield) by regioselective Copper-Catalyzed Azide–Alkyne Cycloaddition (CuAAC) reaction. Additioanally, single crystal X-ray diffraction (SC-XRD) analysis was carried out and the SC-XRD data enabled a broad molecular analysis using QTAIM and MEP analysis. Absorption UV–Vis properties of SCTz series were investigated and all derivatives absorb in the UV region and no are observed emission fluorescence in solution. The DNA-binding assays (UV–Vis analysis) showed that the all spiroderivatives demonstrated strong binding forces to CT-DNA. The Stern-Volmer quenching constants (KSV) of SCTz were calculated and derivatives containing the OCH3 group competed more strongly with DNA minor grooves, followed by the increasing general order of (KSV): EB-DNA q) indicated a static interaction between spiroderivatives and DNA in all cases. Finally, the HSA-binding experiments and molecular docking studies for the new spiroderivatives were determined and quenching (KSV) and quenching rate (kq) constants values obtained for the SCTz suggest good interaction between HSA and derivatives, probably by static mechanism, forming HSA:compound adduct in the ground state.

Design, synthesis and anticancer evaluation of novel spirobenzo[h]chromene and spirochromane derivatives with dual EGFR and B-RAF inhibitory activities

A novel series of spirobenzo[h]chromene and spirochromane derivatives was designed, synthesized and evaluated as potential anticancer agents against MCF-7 (human breast carcinoma), HT-29 (human colorectal adenocarcinoma) and A549 (human lung carcinoma) cell lines using MTT assay. Eight compounds 7, 8e, 13a-e and 16 showed a better anticancer activity than that of sorafenib, the multi-kinase inhibitor with IC50 values between 1.78 and 5.47 μM or erlotinib with IC50 values over 20 μM. Representative compounds 8e, 13c and 16 were selected for further mechanistic investigation via EGFR, B-RAF and tubulin polymerization assays. Compound 16 was the most potent EGFR inhibitor (IC50 = 1.2 μM), yet compounds 8e, 13c and 16 displayed moderate tubulin polymerization inhibition effects. Molecular docking studies of those compounds revealed their possible binding modes into the active sites of both EGFR and B-RAF kinases. The newly developed compounds represent a therapeutically promising approach for the treatment of different types of cancer.

An Efficient Synthesis of 6-oxa-spiro[3.4]octan-1-one Derivates Through 3-diazochroman-4-one and Alkene

Spiro[2,2-dimethyl-benzofuran,bicyclo [4.2.0]octane]-7′-one with fused and spirocyclic oxygen-containing rigid skeleton structure is obtained via Wolff rearrangement and cycloaddition with good yields. Then Spiro[2,2-dimethyl-benzofuran,hexahydro-isobenzofuran]-7′-one is synthesized by further Baeyer-Villiger oxidation. These two kinds of products have a special fused and spirocyclic oxygen-containing rigid skeleton structure and are reported by our group. (Figure presented.).

Synthesis of novel trifluoromethyl-substituted spiro-[chromeno[4,3-d]pyrimidine-5,1′-cycloalkanes], and evaluation of their analgesic effects in a mouse pain model

Herein we report the synthesis of twelve 2,5-substituted 4-(trifluoromethyl)-spirochromeno[4,3-d]pyrimidines (7–10), as well as an evaluation of their analgesic effect in a mouse pain model. The nine new chromeno[4,3-d]pyrimidines (7–9) were synthesized f

Efficient approach for regioselective synthesis of new trifluoromethyl-substituted spirotetracyclic isoxazolines and isoxazoles

This paper describes firstly an effective protocol for the synthesis of a new series of five examples of 3-(trifluoromethyl)-3,3a-dihydrospiro[chromeno[4,3-c]isoxazole-4,1′-cycloalkan]-3-ols (4), in which the cycloalkanes — cyclopentane, cyclohexane, cycloheptane, and 4′-methyl- and 4′-t-butyl-cyclohexane — were isolated at yields of 65–84%. The dihydro-isoxazolinols 4 were obtained regioselectively from the reactions of 2,2,2-trifluoro-1-[4-methoxy-spiro(2H-chromen-2,1′-cycloalkane)-3-yl]ethanones (3) with hydroxylamine hydrochloride, in the presence of sodium bicarbonate and methanol as solvent, for 24?h at 60?°C. The ethanone precursors 3 were synthesized by trifluoroacetylation reaction, employing trifluoroacetic anhydride and mixtures of enolethers and/or acetals derived from spiro[chroman-2,1′-cycloalkan]-4-ones (2) (Kabbe's adducts), which were obtained beforehand from the reaction of cycloalkanones 1 with 2-hydroxyacetophenone and pyrrolidine. Subsequently, dehydration reactions of isoxazolinols 4, employing thionyl chloride and pyridine, enabled the isolation of another series of five novel spiro-isoxazoles 5 (76–95% yield). The structural features of the two series of new spiro heterocycles (4 and 5) were unequivocally determined with the aid of: one-dimensional1H,13C, and19F NMR spectroscopy; two-dimensional1H and13C NMR spectroscopy (NOESY, gHMBC, and gHMQC); single crystal X-ray diffraction; and GC–MS.

Synthesis, biological evaluation and molecular docking study of 7-amine-spiro[chromeno[4,3-b]quinoline-6,1′-cycloalkanes] as new tacrine hybrids

This Letter reports the first series of seven examples of novel 7-amine-spiro[chromeno[4,3-b]quinoline- 6,1′-cycloalkanes], where cycloalkane is cyclopentane, cyclohexane, cycloheptane, 2-methyl-, 3-methyl-, 4-methyl-, and 4-t-butyl-cyclohexane. These new compounds were synthesized at yields of 30-65% by a one-pot cyclocondensation reaction of 2-aminobenzonitrile and seven examples of spiro[chroman-2,1′-cycloalkan]-4-ones, using AlCl3 as the catalyst, without solvent and under conventional thermal heating. Subsequently, these spirochromeno-quinolines were subjected to AChE and cytotoxicity activity, and molecular docking studies. Both results for these new tacrine analogues were correlated with the structural features and showed the best results for the tacrine hybrid that possesses the spirocyclopentane moiety.

Regioselective synthesis and through-space 13C-19F spin-spin coupling NMR of new tetracyclic 3-(trifluoromethyl)-spiro(chromen[4,3-c]pyrazole-4,1′-cycloalkanes)

This paper firstly describes an efficient and regioselective method for the synthesis of a new series of 2,2,2-trifluoro-1-[4-methoxy-spiro(2H-chromen-2,1′-cycloalkane)-3-yl]ethanones from spiro[chroman-2,1′-cycloalkan]-4-ones (Kabbe's adduct). Yields of 38-61% were obtained when trifluoroacetylation reactions of mixtures of enolethers and/or acetals derived from four spiro ketones (Kabbe's adduct) were performed at a temperature of 45 °C, employing anhydrous chloroform as the solvent. Subsequently, when the respective trifluoroacetylated Kabbe adducts reacted with phenylhydrazine and methylhydrazine at a 1:1 molar ratio in refluxing ethanol for 24 h, a new series of seven examples of a new spiro-condensed heterocyclic system, namely 1(2)-methyl(phenyl)-3-(trifluoromethyl)-1,4(2,4)-dihydro-spiro(chromen[4,3-c]pyrazole-4,n′-cycloalkanes) - where cycloalkanes are cyclopentane, cyclohexane, and cycloheptane for n = 1; and tetrahydro-2H-pyran for n = 2 - were isolated at yields of between 35% and 51%. Finally, the structures of new spiro heterocycles were determined with the aid and simultaneous application of 1H, 13C and 19F one-dimensional and gHMBC NMR experiments, X-ray monocrystal diffraction, and mass spectrometry techniques.

Synthesis, enantiomeric separation and docking studies of spiropiperidine analogues as ligands of the nociceptin/orphanin FQ receptor

A series of triazospirodecanone derivatives were synthesized as potential NOP ligands. 8-(Chroman-4-yl)-1-phenyl-1,3,8-triazaspiro[4.5]decan-4-one (4) and its 5-fluoro analogue (18) proved to be active as agonists with EC50 values in the submicromolar range. Single enantiomers of compound 4 were separated and tested as NOP agonists; the eutomer R-(+)-4 showed a pEC 50 of 7.34. Finally docking studies were performed on the NOP receptor to identify the most significant stereospecific interactions.

Regioselective synthesis and through-space 13C-19F spin-spin coupling NMR of new tetracyclic 3-(trifluoromethyl)-spiro(chromen[4,3- c]pyrazole-4,1′-cycloalkanes)

This paper firstly describes an efficient and regioselective method for the synthesis of a new series of 2,2,2-trifluoro-1-[4-methoxy-spiro(2H-chromen-2, 1′-cycloalkane)-3-yl]ethanones from spiro[chroman-2,1′-cycloalkan]- 4-ones (Kabbe's adduct). Yields o