19090-04-1

Basic information

• Product Name: 3-Chromanone
• Synonyms: 3-Chromanone;ChroMan-3-one
• CAS NO: 19090-04-1
• Molecular Formula: C₉H₈O₂
• Molecular Weight: 148.16
• Mol File: 19090-04-1.mol

Chemical Properties

• Boiling Point: 281.452 °C at 760 mmHg
• Flash Point: 136.065 °C
• Appearance: /
• Density: 1.197 g/cm³
• Vapor Pressure: 0.004mmHg at 25°C
• Refractive Index: 1.562
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 3-Chromanone(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Chromanone(19090-04-1)
• EPA Substance Registry System: 3-Chromanone(19090-04-1)

Safety Data

• Hazardous Substances Data: 19090-04-1(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Synthesis, p. 268, 1984 DOI: 10.1055/s-1984-30805

InChI:InChI=1/C9H8O2/c10-8-5-7-3-1-2-4-9(7)11-6-8/h1-4H,5-6H2

Upstream product

• 6538-94-9 3,4-epoxy-chroman 
• 122-97-4 3-Phenyl-1-propanol 
• 21443-40-3 1-Diazo-3-phenoxy-2-propanone 
• 124067-29-4 3-(2-anisyl)-α-diazo-2-propanone 
• 80379-31-3 ethyl 3-hydroxy-2H-<1>benzopyran-4-carboxylate 
• 22649-28-1 2H-chromene-3-carboxylic acid 
• 57543-66-5 2H-chromene-3-carbonitrile 
• 90-02-8 salicylaldehyde 
• 121985-99-7 2-hydroxy-2-(2-methoxyphenyl)acetonitrile 
• 701-99-5 Phenoxyacetyl chloride 
• 13610-02-1 1-phenoxy-2-propyne 
• 108-95-2 phenol 
• 41051-18-7 4-Phenoxyacetessigsaeure-ethylester 
• 14650-51-2 ethyl 2-diazo-3-oxo-4-phenoxy-butanoate 

Downstream Products

• 83823-50-1 3-Piperidinochroman 
• 83823-51-2 4-Chroman-3-yl-morpholine 
• 83823-52-3 1-Chroman-3-yl-4-phenyl-piperazine 
• 83823-54-5 1-Chroman-3-yl-4-(4-methoxy-phenyl)-piperazine 
• 83823-53-4 1-Chroman-3-yl-4-(2-methoxy-phenyl)-piperazine 
• 83953-71-3 Chroman-3-yl-[2-(3,4-dimethoxy-phenyl)-ethyl]-amine 
• 83823-55-6 1-Chroman-3-yl-4-(4-fluoro-phenyl)-piperazine 
• 54445-15-7 Benzyl-chroman-3-yl-amine 
• 539857-50-6 N-(2H-benzo[b]pyran-3-yl)-benzamide 
• 59108-54-2 (S)-chroman-3-amine 
• 59108-53-1 (R)-3-aminochromane 
• 60575-19-1 3,4-dihydro-3-amino-2H-benzopyran 
• 21834-59-3 chroman-3-one-(2,4-dinitro-phenylhydrazone) 

Relevant articles and documents

HETEROCYCLIC COMPOUNDS AND USES THEREOF

Provided herein are novel heterocyclic compounds, for example, compounds having Formula I, I-P, II, lI-P, or III. Also provided herein are pharmaceutical compositions comprising the compounds and methods of using the same, for example, in inhibiting aldehyde dehydrogenases and/or for treating various cancers, cancer metastasis, type 2 diabetes, pulmonary arterial hypertension (PAH) or neointimal hyperplasia (NIH).

Synthesis of Pharmaceutically Relevant 2-Aminotetralin and 3-Aminochroman Derivatives via Enzymatic Reductive Amination

2-Aminotetralin and 3-aminochroman derivatives are key structural motifs present in a wide range of pharmaceutically important molecules. Herein, we report an effective biocatalytic approach towards these molecules through the enantioselective reductive coupling of 2-tetralones and 3-chromanones with a diverse range of primary amine partners. Metagenomic imine reductases (IREDs) were employed as the biocatalysts, obtaining high yields and enantiocomplementary selectivity for >15 examples at preparative scale, including the precursors to Ebalzotan, Robalzotan, Alnespirone and 5-OH-DPAT. We also present a convergent chemo-enzymatic total synthesis of the Parkinson's disease therapy Rotigotine in 63 % overall yield and 92 % ee.

Carbonyl 1,2-transposition through triflate-mediated a-amination

To date, it remains challenging to selectively migrate a carbonyl oxygen within a given molecular scaffold, especially to an adjacent carbon. In this work, we describe a simple one- or two-pot protocol that transposes a ketone to the vicinal carbon. This approach first converts the ketone to the corresponding alkenyl triflate, which can then undergo the palladium- and norbornene-catalyzed regioselective a-amination and ipso-hydrogenation enabled by a bifunctional hydrogen and nitrogen donor. The resulting "transposed enamine" intermediate can subsequently be hydrolyzed to produce the 1,2-carbonyl-migrated product. This method allows rapid access to unusual bioactive analogs through late-stage functionalization.

Bifunctional Br?nsted Base Catalyst Enables Regio-, Diastereo-, and Enantioselective Cα-Alkylation of β-Tetralones and Related Aromatic-Ring-Fused Cycloalkanones

The catalytic asymmetric synthesis of both α-substituted and α,α-disubstituted (quaternary) β-tetralones through direct α-functionalization of the corresponding β-tetralone precursor remains elusive. A designed Br?nsted base-squaramide bifunctional catalyst promotes the conjugate addition of either unsubstituted or α-monosubstituted β-tetralones to nitroalkenes. Under these reaction conditions, not only enolization, and thus functionalization, occurs at the α-carbon atom of the β-tetralone exclusively, but adducts including all-carbon quaternary centers are also formed in highly diastereo- and enantioselective manner.

POTENT SMALL MOLECULE INHIBITORS OF AUTOPHAGY, AND METHODS OF USE THEREOF

Certain aspects of the invention relate to small molecule autophagy inhibitors, and their use for treatment and prevention of cancers and acute pancreatitis. Medicinal chemistry studies led to small molecular autophagy inhibitors with improved potency and selectivity.

Rh-catalyzed intramolecular aromatic C-H insertion of α-diazo β-ketoesters: Synthesis of 4-carbonyl chroman derivatives

A Rh-catalyzed intramolecular aromatic C-H insertion of α-diazo β-ketoesters was developed. This protocol offers a practical strategy for the synthesis of 4-carbonyl chroman derivatives with high yield and is compatible with a wide variety of substituents

Rapid access to chroman-3-ones through gold-catalyzed oxidation of propargyl aryl ethers

The two-step: Chroman-3-ones are important intermediates for organic synthesis and medicinal chemistry. However, their syntheses require multiple steps and are not efficient. By using gold-catalyzed alkyne oxidation, this versatile heterocycle can be prepared in only two steps from readily available phenols and with mostly high efficiencies (see scheme).

ANTAGONISTS OF THE TRPV1 RECEPTOR AND USES THEREOF

The present application is directed to compounds that are TRPV1 antagonists and have formula (I) wherein variables Ar1, L1, R1, R2, R3, R4, R5, Y1, Y2, and Y3, are as defined in the description, which are useful for treating disorders caused by or exacerbated by vanilloid receptor activity.

Efficient syntheses of new heteroarotinoids through functional pyridylzinc reagents and palladium-catalyzed cross-coupling reactions

A convergent synthesis of heteroarotinoids 4, 5a, and 5b, bearing chromene rings in association with pyridyl or ethynylpyridyl moieties, from 6-bromo-2-pyridylzinc chloride (11) is described. This new functional heteroarylzinc reagent, readily accessible

STUDIES ON OXYGEN HETEROCYCLES PART-1 : ACID CATALYSED AND PHOTOCHEMICAL REACTIONS OF SOME ARYLDIAZOKETONES

Trifluoroacetic acid catalysed reaction of 2-methoxyphenyldiazomethylketone (4a), 2-acetoxyphenyldiazomethylketone (4b) and 3-(2-anisyl)-α-diazo-2-propanone (11) leads to the formation of coumaranone (6) and 3-chromanone (12), while 4-(2-anisyl)-α-diazo-2-butanone (16) affords benzo-1-oxepan-3-one (17) and 5-methoxy-2-tetralone (18) in moderate yield.The photochemical decomposition of the said diazoketones (4a, 11 and 16) gave products depending on the length of the side chain present in the substrates.