15895-57-5

Upstream product

• 940-47-6 1-chloro-3-phenoxyacetone 
• 90354-26-0 1-chloro-2-methyl-3-phenoxypropan-2-ol 
• 5820-22-4 methylallyl phenyl ether 

Downstream Products

• 84866-68-2 1-phenoxy-3-(phenylselanyl)propan-2-ol 
• 90354-26-0 1-chloro-2-methyl-3-phenoxypropan-2-ol 
• 13524-74-8 2-methyl-1-phenoxy-2-propanol 
• 90354-39-5 1-Isopropylamino-2-methyl-3-phenoxy-propan-2-ol 

Relevant academic research and scientific papers

SYSTEMS AND METHODS FOR REGIOSELECTIVE CARBONYLATION OF 2,2-DISUBSTITUTED EPOXIDES

Provided are methods of carbonylating cyclic substrates to produce carbonyl ated cyclic products. The cyclic substrates may be 2, 2-di substituted epoxides and the cyclic products may be β,β-di substituted lactones. The method may be carried out by forming and pressurizing a reaction mixture of the cyclic substrate, a solvent, carbon monoxide, and a [LA+][CO(CO)4-] catalyst, where [LA+] is a Lewis acid capable of coordinating to the cyclic substrate. The method may proceed with a regioselectivity of 90:10 or greater. The resulting carbonylated cyclic products may be converted to ketone aldol products that retain the stereochemistry and enantiomeric ratio of the carbonyl ated cyclic products.

Regioselective Carbonylation of 2,2-Disubstituted Epoxides: An Alternative Route to Ketone-Based Aldol Products

We report the regioselective carbonylation of 2,2-disubstituted epoxides to β,β-disubstituted β-lactones. Mechanistic studies revealed epoxide ring-opening as the turnover limiting step, an insight that facilitated the development of improved reaction conditions using weakly donating, ethereal solvents. A wide range of epoxides can be carbonylated to β-lactones, which are subsequently ring-opened to produce ketone-based aldol adducts, providing an alternative to the Mukaiyama aldol reaction. Enantiopure epoxides were demonstrated to undergo the carbonylation/ring-opening process with retention of stereochemistry to form enantiopure β-hydroxy esters.

Iridium-Catalyzed Asymmetric Hydrogenation of 2H-Chromenes: A Highly Enantioselective Approach to Isoflavan Derivatives

A highly efficient (aS)-Ir/In-BiphPHOX-catalyzed asymmetric hydrogenation of substituted 2H-chromenes and substituted benzo[e][1,2]oxathiine 2,2-dioxides is described. A series of 2H-chromenes and benzo[e][1,2]oxathiine 2,2-dioxides were hydrogenated to give the target products in high yields (92-99%) with excellent enantioselectivities (up to 99.7% ee) using our catalytic system. This reaction provides a direct and efficient method for the construction of chiral benzo six-membered oxygen-containing compounds.

Anionic ring-opening polymerization of cyclic 1,3-dithiocarbonate and thermal depolymerization

A new anionic ring-opening polymerization (ROP) was used to synthesize polydithiocarbonates from cyclic dithiocarbonates. The polymerization was optimized in the presence of dibenzo-18-C-6 and NaH/EtOH, and carried out at 50°C to suppress any retropolymer

PROCESS FOR EPOXIDATION OF ARYL ALLYL ETHERS

A process for making an aromatic glycidyl ether epoxy compound by contacting an allyl ether made from the hydroxy moiety of a hydroxy-containing aromatic compound with an inorganic or organic hydroperoxide oxidant in the presence of a transition metal complex catalyst, wherein at least (a) the allyl ether is conformationally restricted or (b) the transition metal complex catalyst contains at least one or more stable ligands attached to the transition metal. The process of the present invention provides for epoxidizing aryl allyl ethers with high epoxidation yield (for example, greater than 70 percent to 90 percent) and high hydroperoxide selectivity (for example, greater than 70 percent to 90 percent).

Method of using calcilytic compounds

The present invention features calcilytic compounds. "Calcilytic compounds" refer to compounds able to inhibit calcium receptor activity. Also described are the use of calcilytic compounds to inhibit calcium receptor activity and/or achieve a beneficial effect in a patient; and techniques which can be used to obtain additional calcilytic compounds.

Synthesis of monofluorinated C4-building blocks based on methallyl chloride

Halofluorination of methallyl chloride using N-halosuccinimides in combination with triethylamine trishydrofluoride (Et3N*3HF) gave in each case more than 98percent of the Markovnikov products and 2percent of the regioisomers in good yield.The formal addition of methanesulfenyl fluoride with the combination of dimethyl(methylthio)sulfonium fluoroborate (DMTSF) and Et3N*3HF gave a 94:6 mixture of both regioisomers.Only small phenylsulfenyl fluorination of methallyl chloride has been observed when treated with N-phenylthiophthalimide (NPTP) and Olah's reagent.With benzenesulfenyl chloride, 1,3-dichloro-2-methyl-2-(phenylthio)propane is formed which on treatment with Olah's reagent at 0 deg C or with Et3N*3HF at 60 deg C rearranges to 1,2-dichloro-2-methyl-3-(phenylthio)propane.Treatment of 1,3-dichloro-2-methyl-2-(phenylthio)propane with silver fluoride in methylene chloride at -30 deg C gave 1-chloro-2-fluoro-2-methyl-3-(phenylthio)propane which was also obtained by reaction of 1-bromo-3-chloro-2-fluoro-2-methylpropane with thiophenolate.Chlorofluorination of methallylphenylthio ether using NCS/Et3N*3HF failed, while corresponding reactions with NBS or NIS and Et3N*3HF gave mainly the bromo- or iodo-fluorides with Markovnikov orientation in 61percent or 35percent yields.Related halofluorinations of methallylphenyl ether gave the halofluorides in good yield.All attempts to obtain chromanes or thiochromanes bearing a 3-fluorine substituent by cyclization of these halofluorinated ethers or thio ethers failed using different Lewis acids.However, the benzyl protected o-allylphenol which was bromofluorinated with NBS/Et3N*3HF in good yield gave on catalytic hydrogenation over Pd/C the 3-fluoro-2H-chromane in nearly quantitative yield. - Keywords: Electrophilic addition; Halofluorination; Sulfenylfluorination; N-Halosuccinimides; Dimethyl(methylthio)sulfonium tetrafluoroborate; Triethylamine trishydrofluoride

Synthesis and pharmacological study of aryloxypropanolamines substituted on carbon 2

In a series of aryloxypropanolamines, substitution on carbon 2 by alkyl, aryl or aralkyl groups lowers the β-blocking activity. This effect increases with the size of the substituent.