16748-90-6

Usage

Uses

Used in Flavor and Fragrance Industry:
2,2-DiMethylbenzofuran-3(2H)-one is used as a flavor and fragrance ingredient for its unique and pleasant aroma. It is particularly favored in the creation of perfumes, colognes, and other scented products, enhancing their appeal with its sweet and woody notes.
Used in Food and Beverage Industry:
As a synthetic flavoring agent, 2,2-DiMethylbenzofuran-3(2H)-one is incorporated into the production of various foods and beverages. It adds a distinctive and agreeable scent, improving the sensory experience of these products.
Used in Pharmaceutical and Medical Research:
2,2-DiMethylbenzofuran-3(2H)-one also holds potential in pharmaceuticals and medical research, where its aromatic properties could be leveraged for the development of new drugs or in the study of various medical conditions.

Upstream product

• 74786-53-1 1-(2-methoxyphenyl)-2-methylpropan-1-one 
• 6640-69-3 1-(2-hydroxyphenyl)-2-methylpropan-1-one 
• 18672-04-3 ethyl 2-methyl-2-phenoxypropanoate 
• 611-70-1 phenyl isopropyl ketone 
• 2058-74-4 1-methyl-1H-indole-2,3-dione 
• 7169-34-8 3-oxo-2,3-dihydrobenzo[b]furan 
• 74-88-4 methyl iodide 

Relevant academic research and scientific papers

Enantioselective Synthesis of Indanes with a Quaternary Stereocenter via Diastereoselective C(sp3)-H Functionalization

A practical synthesis of enantioenriched indane derivatives with quaternary stereocenters was developed via sequential enantioselective reduction and C-H functionalization. Good to excellent enantioselectivity could be achieved by either the CuH-catalyzed asymmetric reduction or the Corey-Bakshi-Shibata (CBS) reduction of indanone derivatives. The subsequent diastereospecific and regioselective rhodium-catalyzed silylation of the methyl C-H bond led to indane derivatives with quaternary centers. This strategy was further applied in syntheses of (nor)illudalane and botryane sesquiterpenoids.

Structure-Activity Relationships, Pharmacokinetics, and in Vivo Activity of CYP11B2 and CYP11B1 Inhibitors

CYP11B2, the aldosterone synthase, and CYP11B1, the cortisol synthase, are two highly homologous enzymes implicated in a range of cardiovascular and metabolic diseases. We have previously reported the discovery of LCI699, a dual CYP11B2 and CYP11B1 inhibi

A novel organic electron donor derived from N-methylisatin

We report the reactivity of an electron donor derived from N-methylisatin on reduction by sodium amalgam. Transfer of a clear supernatant solution to iodoarenes affords the products of two-electron reduction. Reductions of sulfones, activated arenesulfonamides, and Weinreb amides are also reported.

Pd-catalyzed sp2 C-H hydroxylation with TFA/TFAA via weak coordinations

An efficient sp2 C-H hydroxylation has been developed for the synthesis of a wide range of functionalized phenols with aryl ketones, benzoates, benzamides, acetanilides and sulfonamides through palladium(II) catalysis. A trifluoroacetic acid (TFA)/trifluoroacetic anhydride (TFAA) co-solvent system serves as the oxygen source and is the critical factor for weak coordination promoted C-H activation. Georg Thieme Verlag Stuttgart New York.

Pd-catalyzed C-H oxygenation with TFA/TFAA: Expedient access to oxygen-containing heterocycles and late-stage drug modification

Functionalized phenols are valuable industrial chemicals related to pharmaceuticals, agrochemicals, and polymers. Therefore, the direct catalytic hydroxylation of arenes to produce phenols has attracted much attention. Although tremendous progress has been made in this field, there are still difficult substrates which remain unmet challenges for direct hydroxylation in terms of regio- and chemoselectivity, as well as the practicality of current methods (Scheme 1). For example, 2-hydroxy aromatic ketones are useful synthetic intermediates for the preparation of various oxygen-containing heterocycles such as benzofuranone, chromanone, benzoxazole, and dibenzooxazepine; they also serve as key building blocks for drugs such as celiprolol, acebutolol, and propafenone. Traditional strategies for accessing 2-hydroxy aromatic ketones have mainly involved the oxidation of benzylic alcohols, the hydrolysis of aromatic halides, Fries rearrangement of esters or the demethylation of methyl phenyl ether. These methods generally suffer from one limitation or another, such as tedious reaction procedures, harsh reaction conditions, low yields, or the formation of side products. Hence, direct transformation of readily available aromatic ketones into valuable 2-hydroxylated products by transition metal-catalyzed C-H functionalization is arguably a highly efficient and atom-economic method to access these compounds. Moreover, developing a more general strategy for the regio- and chemoselective C-H oxygenation of a variety of challenging arenes would be especially desirable for phenol synthesis (Scheme 1).

Reactions of triflate esters and triflamides with an organic neutral super-electron-donor

The bis-pyridinylidene 13 converts aliphatic and aryl triflate esters to the corresponding alcohols and phenols respectively, using DMF as solvent, generally in excellent yields. While the deprotection of aryl triflates has been seen with other reagents and by more than one mechanism, the deprotection of alkyl triflates is a new reaction. Studies with 18O labelled DMF indicate that the C-O bond stays intact and hence it is the S-O bond that cleaves, underlining that the cleavage results from the extraordinary electron donor capability of 13. Trifluoromethanesulfonamides are converted to the parent amines in like manner, representing the first cleavage of such substrates by a ground-state organic reducing reagent.

One-pot reduction of aryl iodides using 4-DMAP methiodide salt

An efficient one-pot procedure is described for the reduction of aryl iodides to aryl anions using a structurally simple bis-pyridinylidene electron donor, prepared in situ by treating 4-DMAP methiodide salt with base. The results show (i) that pyridinylidene carbenes can be easily used for intermolecular C-C bond formation, (ii) that bis-pyridinylidenes demonstrate superior robustness compared to electron-donor systems based on bis-imidazolylidenes, and (iii) that electron-donor strength is enhanced in the simplified DMAP-based donor. Deuterated analogues of this donor also provide mechanistic information on the source of protons when the aryl anions are quenched in situ. Georg Thieme Verlag Stuttgart.

ORGANIC COMPOUNDS

The present invention provides a compound of formula I: said compound is inhibitor of aldosterone synthase (CYP11B2), and/or 11beta-hydroxylase (CYP11B1), and/or aromatase, and thus can be employed for the treatment of a disorder or disease mediated by al

Super-electron donors: Bis-pyridinylidene formation by base treatment of pyridinium salts

Deprotonation of bispyridinium salt 7b affords bispyridinylidene 10, a very powerful neutral organic two-electron donor [E1/2 (DMF) = -1.13 V vs Ag/AgCI/KCI (sat)], presumably via the pyridinylidene 8. Donor 10 reduces aryl iodides and bromides to aryl anions in excellent yield and also reductively cleaves selected phenylalkylsulfones very efficiently.

The generation of aryl anions by double electron transfer to aryl iodides from a neutral ground-state organic super-electron donor

(Chemical Equation Presented) It takes two to cyclize: Aryl halides are reduced to aryl anions by double electron transfer from the neutral ground-state electron donor 1 (see scheme), as shown by the formation of a cyclic ketone (2). The reduced compound (3) is also formed. Calculations show that the loss of two electrons from 1 is both thermodynamically and kinetically viable and generates a more planar resonance-stabilized structure.