92-47-7

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 29, p. 2971, 1964 DOI: 10.1021/jo01033a040

InChI:InChI=1/C10H10O2/c1-7-2-4-9-8(6-7)3-5-10(11)12-9/h2,4,6H,3,5H2,1H3

Upstream product

• 542-76-7 3-Chloropropionitrile 
• 106-44-5 p-cresol 
• 92-48-8 6-methylcoumarin 
• 87823-56-1 methyl-6 diethoxy-2,2 benzopyranne-1 
• 140-88-5 ethyl acrylate 
• 7664-93-9 sulfuric acid 
• 25173-37-9 3-(4-methylphenoxy)propionic acid 
• 71-43-2 benzene 
• 288310-94-1 1,1,1-trifluoro-4-(4-methylphenyl)butan-2-one 
• 85960-67-4 (±)-6-methylchroman-2-ol 
• 1119700-53-6 2-hydroxy-5-methylcinnamaldehyde 
• 3751-48-2 3-(3-methylphenyl)propanoic acid 

Downstream Products

• 103204-16-6 3-(2-hydroxy-5-methyl-phenyl)-propionitrile 
• 91843-23-1 3-(2-hydroxy-5-methyl-phenyl)-propionic acid amide 
• 76510-25-3 3-(2-hydroxy-5-methyl-phenyl)-propionic acid 
• 20921-08-8 β-(2-Hydroxy-5-methyl-phenyl)-propionsaeure-ethylester 
• 74181-03-6 2-[2-(1-Hydroxy-cyclopentyl)-ethyl]-4-methyl-phenol 
• 74181-06-9 2-[2-(1-Hydroxy-cyclohexyl)-ethyl]-4-methyl-phenol 
• 154596-79-9 2-<(4-dimethoxyphosphinyl)-3-oxobutyl>-4-methylphenol 
• 33538-75-9 3-(2-hydroxy-5-methylphenyl)propan-1-ol 
• 4359-09-5 3-(2-Methoxy-5-methyl-phenyl)-N-methyl-propionamide 
• 85960-59-4 ethyl 5-(2-hydroxy-5-methylphenyl)-2-pentenoate 
• 116990-81-9 (E)-5-(1-Acetoxy-3-methyl-6-oxo-cyclohexa-2,4-dienyl)-pent-2-enoic acid ethyl ester 
• 3722-74-5 3,4-Dihydro-6-methyl-2H-1-benzopyran 
• 33538-80-6 3-(2-methoxy-5-methyl-phenyl)-propan-1-ol 
• 33538-87-3 5-Methyl-2-methoxyhydrozimtaldehyd 

Relevant academic research and scientific papers

Facile conversion of lactols to lactones using IBX

Lactols, which are insoluble or only sparingly soluble in most of the organic solvents that are generally employed for oxidation, are converted to lactones using o-iodoxybenzoic acid (IBX) in a facile manner under modified experimental conditions [EtOAc-DMSO (9:1) mixture at reflux] in good to excellent isolated yields (66-91%).

Enantioselective Synthesis of Chromenes via a Palladium-Catalyzed Asymmetric Redox-Relay Heck Reaction

A palladium-catalyzed asymmetric redox-relay Heck reaction of 4H-chromenes and arylboronic acids has been successfully developed. The reaction proceeded in moderate to good yields with good to high enantioselectivities. The resulting product is an advanced intermediate of bio-active compound BW683C.

Hydrolase-mediated resolution of the hemiacetal in 2-chromanols: The impact of remote substitution

Hydrolase-catalysed dynamic kinetic resolutions of chroman-2-ol and 3-methyl chroman-2-ol can be effected with up to 88% conversion and 92% ee through the use of organic solvents. Extension to the resolution of the tolterodine precursor 1 proved more challenging. The presence of the remote phenyl substituent had a significant impact on the resolution and it was not possible to achieve high enantioselectivity together with efficient conversion from the focussed panel of enzymes screened.

Transition Metal Free C-N Bond Forming Dearomatizations and Aryl C-H Aminations by in Situ Release of a Hydroxylamine-Based Aminating Agent

We outline a simple protocol that accesses directly unprotected secondary amines by intramolecular C-N bond forming dearomatization or aryl C-H amination. The method is dependent on the generation of a potent electrophilic aminating agent released by in situ deprotection of O-Ts activated N-Boc hydroxylamines.

SYNTHETIC METHODS

New strategies for the synthesis of salicylaldehyde derivatives having utility production of catalytic metal complexes.

Direct oxidative cyclization of 3-arylpropionic acids using PIFA or Oxone: synthesis of 3,4-dihydrocoumarins

The direct oxidative cyclization of 3-arylpropionic acids using PIFA or Oxone is reported. In the presence of BF3·OEt2, the reaction of 3-arylpropionic acids with PIFA or Oxone proceeded smoothly at 30 °C to give 3,4-dihydrocoumarins

RENIN INHIBITORS

Compounds, pharmaceutical compositions, kits and methods are provided for use with Renin that comprise a compound selected from the group consisting of: wherein the variables are as defined herein.

Oxidative spirocyclization of phenolic sulfonamides: Scope and applications

A full account of the oxidative dearomatization of para- and ortho-phenolic sulfonamides is provided together with an overview of the chemistry of the products and their elaboration to building blocks for spirocyclic alkaloids. A concise total synthesis of putative lepadiformine complements the discussion. Making building blocks: The oxidative dearomatization of para- and ortho-phenolic sulfonamides provides building blocks for spirocyclic alkaloids (see scheme). The chemistry of the products of this reaction and a concise total synthesis of putative lepadiformine is given.

Facile syntheses of 4-hydroxy-7-methyl-1-indanone, isolated from cyanobacterium Nostoc commune

Two different high yielding synthetic routes both starting with 6-methylcoumarin 2 have been described to prepare 4-hydroxy-7-methyl-1-indanone 1, a constituent of cyanobacterium Nostoc commune having antibacterial activity. In the first route, methylative lactone ring opening of the coumarin 2 followed by catalytic hydrogenation of the cinnamyl double bond and subsequent PPA cyclization gives the methyl ether 5 of 1 which on demethylation gives 1 in excellent yield. Alternatively, catalytic hydrogenation of 2 followed by fusion with anhydrous AlCl3 gives high yield of 1 in just two steps.