33348-51-5

Upstream product

• 762-04-9 Diethyl phosphonate 
• 1074-12-0 phenylglyoxal hydrate 
• 67353-83-7 tetrabutylammonim salt of diethylphosphoric acid 
• 70-11-1 α-bromoacetophenone 
• 814-49-3 diethyl chlorophosphate 
• 582-24-1 1-phenyl-2-hydroxyethanone 
• 762-04-9 phosphonic acid diethyl ester 
• 98-86-2 acetophenone 
• 64-18-6 formic acid 
• 122-52-1 triethyl phosphite 
• 36126-89-3 (1-hydroxy-2-oxo-2-phenylethyl)phosphonic acid diethyl ester 
• 132170-16-2 2-<(diethoxyphosphinyl)oxy>-2-phenyloxirane 

Downstream Products

• 103-82-2 phenylacetic acid 
• 98-86-2 acetophenone 
• 495-71-6 phenacylacetophenone 
• 598-02-7 Diethyl phosphate 

Relevant academic research and scientific papers

Fast-Synthesis of α-Phosphonyloxy Ketones as Drug Scaffolds in a Capillary Microreactor

A simple, room temperature approach for the fast single-step synthesis of α-phosphonyloxy ketone, a drug scaffold, has been developed which involves highly reactive species i.e., 1,2-dicarbonyls that readily react with trialkyl phosphites and formic acids in batch as well as in continuous-flow with the flow rate of 3 ml/min (tR = ～4 s). The present approach reduced the synthesis time from hours to minutes in batch, which was further lowered to a few seconds precisely controlled by single capillary microfluidics. A wide range of 1,2-dicarbonyl derivatives were smoothly transformed to their corresponding α-phosphonyloxy ketones in moderate to good yields (50–82 %) under optimized flow-reaction conditions. Further, the α-phosphonyloxy ketones produced can be utilized in batch process to form benzoin, oxazole core, and α,α′-diarylated carbonyl compounds in 82 %, 50 %, and 54 % yields, respectively, which are alternative key precursors/scaffolds of natural products and active pharmaceutical ingredients (APIs).

A Multiheteroatom [3,3]-Sigmatropic Rearrangement: Disproportionative Entries into 2-(N-Heteroaryl)methyl Phosphates and α-Keto Phosphates

A novel multiheteroatom (N, O and P) [3,3]-sigmatropic rearrangement is disclosed, based on two important types of organophosphates, 2-(N-heteroaryl) methyl phosphates and α-keto phosphates, being accessed smoothly and efficiently.

Aroyl group driven [1,2] phosphonate-phosphate/phosphine oxide-phosphinate rearrangement

Aroyl group driven phosphonate-phosphate rearrangement in dialkyl/aryl(α-hydroxy-β-oxo-β-arylethyl)phosphonates having α-proton under basic conditions is presented and extended to a novel one-pot direct coupling method between 2-oxoaldehydes (2OA) and H-p

TBAI/TBHP mediated oxidative cross coupling of aryl alkyl ketones with H-phosphonates and H-phosphine oxides in water: Facile access to ketol phosphates and phosphinates

A metal free cross coupling of aryl alkyl ketones with alkyl/aryl H-phosphonates and H-phosphine oxides using tetrabutylammonium iodide (TBAI) catalyst in the presence of tert-butyl hydroperoxide (TBHP) as terminal oxidant in aqueous media is developed. T

I2O5/DBU mediated direct α-phosphoryloxylation of ketones with H-phosphonates leading to α-hydroxyketone phosphates

A simple and convenient procedure has been developed for the construction of α-hydroxyketone phosphates via I2O5/DBU mediated direct α-phosphoryloxylation of ketones with H-phosphonates. This new reaction proceeds through three steps involving α-iodination of ketones, oxidation of H-phosphonates, and nucleophilic substitution of α-iodo ketones to access a series of α-hydroxyketone phosphates of biological importance.

A time-resolved spectroscopic study of the bichromophoric phototrigger 3',5'-dimethoxybenzoin diethyl phosphate: Interaction between the two chromophores determines the reaction pathway

3',5'-Dimethoxybenzoin (DMB) is a bichromophoric system that has widespread application as a highly efficient photoremovable protecting group (PRPG) for the release of diverse functional groups. The photodeprotection of DMB phototriggers is remarkably cle

Photoreleasable protecting groups on alcohols, phosphates and diacids and the use thereof

Alcohol, phosphate, and diacid derivatives that may be deprotected by irradiation are disclosed. The protecting group is an arylacyl or heteroarylacyl group.

Photoreleasable protecting groups based on electron transfer chemistry. Donor sensitized release of phenacyl groups from alcohols, phosphates and diacids

The electron transfer mediated photochemical release of alcohols, phosphates and diacids is examined. The alcohols can be protected as mixed phenacyl carbonate esters. Irradiation of mixtures containing electron donating sensitizers and phenacyl alkyl carbonate ester initiates a series of bond scission reactions that result in clean release of the corresponding alcohols. This was demonstrated for a variety of primary, secondary and tertiary hydroxyl groups, including the 5'-hydroxy group of thymidine. Sensitizers that were effective in promoting photolytic release include 9,10- dimethylanthracene and 9-methylcarbazole. GC/MS and NMR analysis of the by- products formed in these release reactions implicates the intermediacy of radical ion intermediates in these reactions. It is further demonstrated that the electron transfer sensitized release method can be extended to phosphate esters and di-functional acids.

New photoactivated protecting groups. 6. p-Hydroxyphenacyl: A phototrigger for chemical and biochemical probes

p-Hydroxyphenacyl, a new photoactive, aqueous soluble protecting group is proposed as a second generation α-keto 'cage' reagent, a phototrigger for the efficient, rapid release of bioactive phosphates, e.g., inorganic phosphate (P(i)) and ATP (Givens, R.S.; Park, C.-H. Tetrahedron Lett. 1996, 37, 6259-6262). p-Hydroxyphenacyl esters 6c and 7 trigger the release of P(i) and ATP when irradiated at wavelengths between 300-350 nm also yielding p-hydroxyphenylacetic acid (8) from the rearrangement of the intermediate α-keto carbocation or its equivalent. In contrast, unsubstituted and m-substituted phenacyl esters yield only photoreduction and radical coupling products and none of the rearrangement product. Quantum efficiencies of 0.38 ± 0.04 were measured for the disappearance of the p-hydroxyphenacyl phosphate esters 6c and 7; the appearance efficiencies for 8 and ATP were 0.30 ± 0.03. Rates of release of ~107 s-1 or better are observed for these esters with only minor variations in efficiencies and rate constants between these two examples of the p-hydroxyphenacyl phototrigger. Just as was found for the desyl 'cage' series reported earlier (Givens, R.S.; Athey, P.S.; Kueper, L.W., III; Matuszewski, B.; Xue, J.-y.; Fister, T.J. Am. Chem. Soc. 1993, 115, 6001-6010), the p-hydroxyphenacyl derivatives react via their triplet states. Amino substituents, i.e., p-amino-, p-acetamido-, and p-(carbomethoxyamino)phenacyl phosphates 6f-h, were also investigated, but these analogues proved to be inferior as phototriggers when compared with p-hydroxyphenacyl.

Epoxidation of Enol Silyl Ethers, Phosphates, Esters, and Lactones by Dimethyldioxirane

The epoxides 2a-u (Table 1) of the enol silyl ethers 1a, b, enol phosphates 1c-k, and enol esters and lactones 1l-u were prepared in excellent yields by epoxidation with isolated dimethyldioxirane (4) (as acetone solution).These labile epoxides (stable be