66053-97-2

Usage

Synthesis Reference(s)

Synthesis, p. 1216, 1991 DOI: 10.1055/s-1991-28422

Upstream product

• 91-16-7 1,2-dimethoxybenzene 
• 2082-59-9 pentanoic anhydride 
• 26429-16-3 trimethylsilyl pentanoate 
• 109-52-4 valeric acid 
• 107-08-4 1-iodo-propane 
• 1131-62-0 1-(3,4-dimethoxyphenyl)ethanone 
• 693-03-8 n-butyl magnesium bromide 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 109-72-8 n-butyllithium 
• 3943-77-9 ethyl veratrate 
• 93-07-2 Veratric acid 
• 538-75-0 dicyclohexyl-carbodiimide 
• 638-29-9 n-valeryl chloride 
• 109057-50-3 Pentaneselenoic acid Se-phenyl ester 

Downstream Products

• 128349-87-1 1,2-dimethoxy-4-pentylbenzene 
• 100619-32-7 3',4'-dimethoxyvalerophenone oxime 
• 2525-11-3 4-pentyl-pyrocatechol 
• 850442-84-1 1-(3,4-dimethoxyphenyl)-2-pyrrolidin-1-yl-pentan-1-one 

Relevant academic research and scientific papers

Simple one pot synthesis of ketone from carboxylic acid using DCC as an activator

Simple one pot procedure for the conversion of carboxylic acid to ketone is described. Various carboxylic acids were converted to the corresponding ketones in excellent manner in presence of N,N′-dicyclohexylcarbodiimide (DCC) and organometallic reagents. Aromatic, heteroaromatic and aliphatic acids were converted to the corresponding ketones smoothly under the optimum conditions using organolithium reagents. In this process, desired products have been isolated from the crude reaction mixtures in moderate yields during the purification process.

P -Selective (sp2)-C-H functionalization for an acylation/alkylation reaction using organic photoredox catalysis

p-Selective (sp2)-C-H functionalization of electron rich arenes has been achieved for acylation and alkylation reactions, respectively, with acyl/alkylselenides by organic photoredox catalysis involving an interesting mechanistic pathway.

SUBSTITUTED 6, 7-DIALKOXY-3-ISOQUINOLINE DERIVATIVES AS INHIBITORS OF PHOSPHODIESTERASE 10 (PDE 10A)

The invention relates to compounds of the formula or a pharmaceutically acceptable salt thereof, wherein R′, R1 through R7 and Ar are as defined herein. These compounds are useful as inhibitors of phosphodiesterase 10 (PDE10A) which are useful in treating central nervous system diseases such as psychosis and also in treating, for example, obesity, type II diabetes, metabolic syndrome, glucose intolerance, pain and ophthalmic diseases.

Hypervalent iodine mediated direct one pot transformation of aldehydes to ketones

An environmentally benign, step economical synthesis of ketones directly from aldehydes has been developed using hypervalent iodine as an oxidant. The key features of this protocol are its mild conditions without the use of any heavy and toxic metals for the synthesis of a wide range of ketones. the Partner Organisations 2014.

SUBSTITUTED 6,7-DIALKOXY-3-ISOQUINOLINE DERIVATIVES AS INHIBITORS OF PHOSPHODIESTERASE 10 (PDE10A)

The invention relates to compounds of formula (I) or a pharmaceutically acceptable salt thereof, wherein R', R1 through R7 and Ar are as defined herein. These compounds are useful as inhibitors of phosphodiesterase 10 (PDE10A) which are useful in treating central nervous system diseases such as psychosis and also in treating, for example, obesity, type II diabetes, metabolic syndrome, glucose intolerance, pain and ophthalmic diseases.

Mild and direct conversion of esters to morpholine amides using diisobutyl(morpholino)aluminum: Application to efficient one-pot synthesis of ketones and aldehydes from esters

Morpholine amide intermediates, which are easily prepared by aminolysis of various esters with diisobutyl(morpholino)aluminum, react with organolithium and reducing agents (DIBALH or LDBMA) without isolation of the aminolysis intermediates to give ketones in 83-95% yields and aldehydes quantitatively.

PYROVALERONE ANALOGS AND THERAPEUTIC USES THEREOF

New compounds that bind to monoamine transporters are described. The compounds of the present invention can be racemic or pure R-or S-enantiomers. Certain preferred compounds of the present invention have a high selectively dopamine transporter versus the serotonin transporter. Preferred monoamine transporters for the practice of the present invention include the dopamine transporter, the serotonin transporter and the norepinephrine transporter.

Conception, characterization and correlation of new marine odorants

Via a synthetic sequence consisting of PPA-mediated Friedel-Crafts acylation of veratrol (8), Clemmensen reduction, demethylation with TMSI, Williamson ether synthesis employing 3-chloro-2-(chloromethyl)prop-1-ene and in-situ ruthenium tetroxide oxidation, numerous substituted benzo[b][1,4]dioxepinones 15-27 and 2,3-dihydro-1H-5,9-di-oxacyclohepta[f]indenones 7, 13 and 14 were prepared to study their odor-structure correlation. In the course of these studies, we discovered the extremely powerful new marine odorant 7-(3′ -methylbutyl)benzo[b][1,4]dioxepin-3-one (16). On the basis of the measured odor threshold data, an olfactophore model was constructed that rationalizes the observed odor intensities, and indicates an aliphatic hydrophobe at a distance of 6.3 A from the centre of the aromatic-ring binding site. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.

Substituted imides

Novel imides are inhibitors of tumor necrosis factor α and can be used to combat cachexia, endotoxic shock, and retrovirus replication. A typical embodiment is 2-Phthalimido-3-(3′,4′-dimethoxyphenyl)propane.

The catalytic Friedel-Crafts acylation reaction starting from aromatic compounds and free carboxylic acids (or their trimethylsilyl esters) by promotion of silicon (IV) cationic species via mixed anhydrides

In the presence of active cationic species generated from silicon(IV) chloride and silver perchlorate, carboxylic acids or their trimethylsilyl esters react with p-trifluoromethylbenzoic anhydride to form corresponding mixed anhydrides in situ. Then the catalytic Friedel-Crafts acylation reaction between initially formed mixed anhydrides and coexisted aromatic compounds smoothly proceeds at room temperature to afford the corresponding aromatic ketones in high yields. The above two sequential reactions are effectively promoted by the active silicon(IV) catalyst under mild conditions.