61370-75-0

Usage

Uses

Used in Chemical Synthesis:
2,2-Dimethylchromane-6-carbaldehyde is used as a key intermediate in the synthesis of various chemical compounds. Its unique structure allows for the creation of a wide range of derivatives, making it valuable in the development of new materials and pharmaceuticals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2,2-Dimethylchromane-6-carbaldehyde is used as a building block for the development of new drugs. Its structural properties enable the design of molecules with potential therapeutic applications, contributing to the advancement of medicine.
Used in Fragrance Industry:
2,2-Dimethylchromane-6-carbaldehyde is used as a fragrance ingredient in the perfumery industry. Its distinct aroma profile makes it a valuable component in the creation of various scents and perfumes.
Used in Flavor Industry:
In the flavor industry, 2,2-Dimethylchromane-6-carbaldehyde is used to impart specific taste and aroma characteristics to food and beverage products. Its unique flavor profile can enhance the sensory experience of consumers.
Used in Research and Development:
2,2-Dimethylchromane-6-carbaldehyde is used as a research compound in academic and industrial laboratories. Its properties and reactivity are studied to gain insights into chemical reactions and to develop new synthetic methods and applications.

InChI:InChI=1/C12H14O2/c1-12(2)6-5-10-7-9(8-13)3-4-11(10)14-12/h3-4,7-8H,5-6H2,1-2H3

Upstream product

• 1198-96-5 2,2-dimethylchroman 
• 68-12-2 N,N-dimethyl-formamide 
• 23446-57-3 2,2,6-trimethyl-3,4-dihydro-2H-chromene 
• 123-08-0 4-hydroxy-benzaldehyde 
• 78-79-5 isoprene 
• 28090-12-2 4-(3-methyl-but-2-enyloxy)-benzaldehyde 
• 870-63-3 prenyl bromide 
• 4167-73-1 4-(2-hydroxyphenyl)-2-methyl-2-butanol 
• 106-44-5 p-cresol 
• 54730-30-2 4-hydroxy-3-C-prenylbenzaldehyde 
• 1643-30-7 3-(4-bromophenyl)propionic acid 
• 20921-00-0 6-bromo-3,4-dihydro-2H-1-benzopyran-2-one 
• 74021-58-2 4-methoxymethoxy-3-(3-methyl-but-2-enyl)-benzaldehyde 
• 204503-25-3 1-bromo-4-((3-methylbut-2-en-1-yl)oxy)benzene 

Downstream Products

• 12772-83-7 3-[2,2-dimethyl-3,4-dihydro-(2H)-benzopyran-6-yl]-2E-propenoic acid 
• 61370-82-9 (2,2-dimethylchroman-6-yl)methanol 
• 2039-47-6 2,2-dimethylchroman-6-carboxylic acid 
• 69964-40-5 6-formyl-2,2-dimethyl-2H-chromene 
• 95604-08-3 2,2-Dimethyl-chroman-6-carbonyl bromide 
• 1253582-75-0 1-(1-(2,2-dimethylchroman-6-yl)-3-phenylprop-2-ynyl)piperidine 
• 1253582-74-9 4-(1-(2,2-dimethylchroman-6-yl)-3-phenylprop-2-ynyl)morpholine 
• 1383719-84-3 C₂₈H₃₆N₂O₄ 
• 1608121-24-9 (Z)-5-((2,2-dimethylchroman-6-yl)methylene)-4-(4-hydroxyphenyl)furan-2(5H)-one 
• 1608121-21-6 (Z)-5-(4-hydroxy-3-(3-methylbut-2-en-1-yl)benzylidene)-4-(4-hydroxyphenyl)furan-2(5H)-one 
• 71822-00-9 <1-hydroxyethyl>-2,2-dimethylchromene 

Relevant academic research and scientific papers

Synthesis and anti-inflammatory activity evaluation of novel chroman derivatives

In an effort to develop potent anti-inflammatory agents, a series of novel chroman derivatives including acyclic amidochromans, chromanyl esters and chromanyl acrylates have been designed, synthesized and fully characterized. These chroman analogues were screened for their anti-inflammatory activities through inhibition of the TNF-α-induced ICAM-1 expression on human endothelial cells. A structure-activity relationship was also established and it has been found that in the case of carboxy chromans and amidochromans, the chain length of the amide moiety, branching of the side chain and the presence of the substituents on the phenyl ring have significant effects on their inhibitory activities, while in chromanyl acrylates, the number of methoxy groups, their relative positions on the phenyl ring, and presence of functional groups in the α,β-unsaturated ester moiety played a critical role on their activities. Compound 14 (N-hexyl-7-hydroxy-2,2-dimethylchromane-6-carboxamide) was found to be the most potent compound in inhibiting the TNF-α-induced expression of ICAM-1 on endothelial cells. This journal is

Concise, stereocontrolled and modular syntheses of the anti-influenza rubrolides R and S

The fungal metabolites rubrolide R and S were synthesized in concise, entirely stereoselective fashion through the combined use of bromine-stereodirected vinylogous aldol condensation (SVAC) and Suzuki cross-coupling. A bioinspired, high-yield conversion

CHROMANE-SUBSTITUED TETRACYCLIC COMPOUNDS AND USES THEREOF FOR TREATMENT OF VIRAL DISEASES

Disclosed are novel chromane-substituted tetracyclic compounds of Formula (I), and pharmaceutically acceptable salts thereof, wherein A, A', R2 R3, R4 and R5 are as defined in the description. Also disclosed are compositions comprising a chromane-substituted tetracyclic compound, and methods of using the chromane-substituted tetracyclic compounds for treating or preventing HCV infection in a patient.

Efficient, collective synthesis and nitric oxide inhibitory activity of rubrolides E, F, R, S and their derivatives

An efficient first synthesis of biologically significant natural butenolides, rubrolides F (1f), R (1r), S (1s) & its 7″,8″-didehydro derivative (1sa), and 3″-bromo rubrolide (1fa) along with the synthesis of rubrolide E (1e) and its di-O-methyl derivative (1ea) is accomplished in a collective fashion from commercially available and inexpensive precursors in overall yields of 14–48.5%. Key features are Wittig-Horner reaction, SeO2-induced tandem allylic hydroxylation/intramolecular cyclization and Knoevenagel condensation. Next, in their inhibitory activity towards nitric oxide (NO) production in lipopolysaccharide-induced RAW 264.7 macrophages as an indicator of anti-inflammatory activity, all compounds displayed good inhibitory activity in a concentration-dependent manner. None of the compound exhibited notable cytotoxicity at the highest concentration (10?μM) and IC50values are found in the range from 8.53 to 17.85?μM.

Synthetic method for rubrolide compounds E, F, R, S and their derivatives

Rubrolide F (compound 1f), R (compound 1r), and S (compound 1s), which are biological important natural butenolides, 7andPrime;,8andPrime;-didihydro derivatives (compound 1sa) thereof, 3andPrime; -bromorubrolide (compound 1fa), rubrolide E (compound 1e) and di-O-methyl derivatives thereof (compound 1ea) can be industrially obtained and are effectively synthesized with the overall yield of 14-48.5% from low-priced precursors. The rubrolide compounds can be synthesized through a Knoevenagel condensation reaction after a Wittig-Horner reaction and SeO_2-induced tandem allylic hydroxylation/intramolecular cyclization for preparing butenolide rings and a rubrolide cores structure.COPYRIGHT KIPO 2017

Flavone acetic acid derivatives, pharmaceutical composition thereof as well as preparation methods and applications of flavone acetic acid derivatives and pharmaceutical composition

The invention belongs to the field of medication chemistry, and relates to flavone acetic acid derivatives, pharmaceutical composition thereof as well as preparation methods and applications of the flavone acetic acid derivatives and the pharmaceutical co

Discovery of Chromane Containing Hepatitis C Virus (HCV) NS5A Inhibitors with Improved Potency against Resistance-Associated Variants

The discovery of potent and pan-genotypic HCV NS5A inhibitors faces many challenges including the significant diversity among genotypes, substantial potency shift conferred on some key resistance-associated variants, inconsistent SARs between different genotypes and mutants, and the lacking of models of inhibitor/protein complexes for rational inhibitor design. As part of ongoing efforts on HCV NS5A inhibition at Merck, we now describe the discovery of a novel series of chromane containing NS5A inhibitors. SAR studies around the "Z" group of the tetracyclic indole scaffold explored fused bicyclic rings as alternates to the phenyl group of elbasvir (1, MK-8742) and identified novel chromane and 2,3-dihydrobenzofuran derivatives as "Z" group replacements offered good potency across all genotypes. This effort, incorporating the C-1 fluoro substitution at the tetracyclic indole core, led to the discovery of a new series of NS5A inhibitors, such as compounds 14 and 25-28, with significantly improved potency against resistance-associated variants, such as GT2b, GT1a Y93H, and GT1a L31V. Compound 14 also showed reasonable PK exposures in preclinical species (rat and dog).

SPIROXAZOLIDINONE COMPOUNDS

Substituted spirocyclic amines of structural formula (I) are selective antagonists of the somatostatin subtype receptor 5 (SSTR5) and are useful for the treatment, control or prevention of disorders responsive to antagonism of SSTR5, such as Type 2 diabetes, insulin resistance, lipid disorders, obesity, atherosclerosis, Metabolic Syndrome, depression, and anxiety.

Search of antimycobacterial activities in hybrid molecules with benzopyran skeleton

A series of hybrid molecules (7-9, 12, 13, and 14-18) consisting of chromans and pyrolidines or cyclic amines were prepared either by (3 + 2) cycloaddition of nitrostyrenes and azomethine ylide or by three component reactions of chromanyl aldehydes, acetylenes, and cyclic amines. All the synthesized compounds were evaluated against both avirulent (H37Ra) and virulent (H37Rv) strains of Mycobacterium tuberculosis. Out of all the compounds screened, compounds 16, 17, and 18 were found to be active against the virulent strain M. tubercolosis H37Rv displaying MIC in the range of 6.25-1.56 μg/ml against. Springer Science+Business Media, LLC 2010.

Synthesis of (±)Abyssinone I and related compounds: Their anti-oxidant and cytotoxic activities

An efficient and facile synthesis of naturally occurring prenylated flavonoids and their analogs have been described. Abyssinone I (9a) was prepared by condensing 2,2-dimethyl chrom-3-en-6-carboxaldehyde (5a) with protected resacetophenone under phase transfer conditions followed by deprotection and cyclization. The influence of prenyl group on anti-oxidant and cytotoxic activities was studied. The presence of 3′-prenyl group as in 8c enhanced radical scavenging activity but decreased reducing power activity when compared to non-prenylated analog 8f. In vitro testing in MCF-7 cell line revealed that prenylated chalcones and flavanones showed better inhibitory activity than their non-prenylated counterparts. Abyssinone I and its chalcone though exhibited negligible anti-oxidant activity their cytotoxic activities were comparable with other prenylated analogs.