80234-04-4

Upstream product

• 64-17-5 ethanol 
• 112919-42-3 1-ethoxy-2-phenylcyclopropene 
• 122-51-0 orthoformic acid triethyl ester 
• 2415-80-7 1,1-dichloro-2-phenylcyclopropane 
• 100-42-5 styrene 
• 3054-95-3 acrylaldehyde diethyl acetal 
• 10160-86-8 2,3-dibromo-1,1-diethoxypropane 
• 17592-40-4 2-bromo-3,3-diethoxypropene 
• 5123-13-7 5,5-dimethyl-2-phenyl-1,3,2-dioxaborinane 
• 24388-23-6 2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole 
• 98-80-6 phenylboronic acid 
• 6175-45-7 2,2-diethoxyacetophenone 
• 1779-49-3 Methyltriphenylphosphonium bromide 

Downstream Products

• 112919-41-2 (3,3-dimethoxyprop-1-en-2-yl)benzene 
• 87698-10-0 (E)-2-(3-Ethoxy-2-phenyl-2-propenyl)-2-methyl-1,3-cyclopentanedione 
• 87698-11-1 (Z)-2-(3-Ethoxy-2-phenyl-2-propenyl)-2-methyl-1,3-cyclopentanedione 
• 156020-80-3 2,2-dichloro-1-phenylcyclopropanecarbaldehyde diethyl acetal 
• 87698-58-6 Ethyl 1-(3-ethoxy-2-phenyl-2-propenyl)-2-oxocyclopentanecarboxylate 
• 166189-48-6 (2S,4S,5R)-4-methyl-5-phenyl-2-(1-phenyl-vinyl)-3-(toluene-4'-sulfonyl)-oxazolidine 
• 4432-63-7 2-phenylacrolein 
• 96248-16-7 3,3-Diaethoxy-2-phenyl-propanol-⁽¹⁾ 
• 351026-98-7 (4R)-(+)-cis-2-benzoyl-4-methyl-1,3-dioxane 
• 209803-50-9 (4-hydroxy-[1,1′-biphenyl]-3-yl)(phenyl)methanone 
• 50781-46-9 2-phenyl-9H-xanthen-9-one 
• 17504-13-1 methyl 4-hydroxy-[1,1’-biphenyl]-3-carboxylate 
• 1666-96-2 3-phenylquinoline 

Relevant academic research and scientific papers

Acid-catalyzed cleavage of C-C bonds enables atropaldehyde acetals as masked C2 electrophiles for organic synthesis

Acid-catalyzed tandem reactions of atropaldehyde acetals were established for the synthesis of three important molecules, 2,2-disubstituted indolin-3-ones, naphthofurans and stilbenes. The synthesis was realized using novel reaction cascades, which involved the same two initial steps: (i) SN2′ substitution, in which the atropaldehyde acted as an electrophile; and (ii) oxidative cleavage of the carbon-carbon bond of the generated phenylacetaldehyde-type products. Compared with literature methods, the present protocol not only avoided the use of expensive noble metal catalysts, but also enabled a simple operation.

Modular Synthesis of α-Substituted Alkenyl Acetals by a Palladium-Catalyzed Suzuki Reaction of α-Haloalkenyl Acetals with Organoboranes

A modular and straightforward synthetic strategy for the preparation of α-substituted alkenyl acetals has been developed. α-Haloalkenyl acetals react smoothly with (het)aryl boronic acids, aryl boronates, or B-Alkyl-9-borabicyclo[3.3.1]nonanes through Pd-catalyzed Suzuki cross-coupling under mild conditions with good to high yields. This protocol features a broad substrate scope and good functional-group compatibility, and is easily scaled up.

Catalytic Asymmetric Cycloadditions of Silyl Nitronates Bearing α-Aryl Group

1,3-Dipolar cycloadditions of 2-alkylacroleins or atropaldehyde with triisopropylsilyl nitronates bearing an α-aryl group produced 3-aryl-2-isoxazolines having a chiral quaternary center in up to 94% ee and up to 88% yield with the aid of Corey’s oxazaborolidine catalyst. Specifically, the TIPS nitronate with an α-(p-methoxyphenyl) group gave mainly the 2-isoxazolines having an all-carbon quaternary center.

PEG400-enhanced synthesis of gem-dichloroaziridines and gem-dichlorocyclopropanes via in situ generated dichlorocarbene

PEG400 is employed as an efficient phase transfer catalyst for the cycloaddition reaction of imines with dichlorocarbene, which is generated in situ from chloroform and sodium hydroxide, to give gem-dichloroaziridines in moderate to excellent yields at ambient temperature. This protocol is also extended to the synthesis of cyclopropanes from a variety of alkenes. In this study, PEG400 behaves as a phase transfer reagent thanks to its ability to coordinate with alkali metal cations. Notably, the one-pot synthesis of gem-dichloroaziridines from benzaldehyde and aromatic amines has also been successfully performed. The in situ generated acid, derived from CO2 and H2O, can also be effectively applied to promote the amide synthesis via the gem-dichloroaziridine pathway. The application of the gem-dichlorocyclopropane as a platform chemical is also briefly demonstrated, to afford the 2-phenylacrylaldehyde derivative via a ring-opening reaction. The Royal Society of Chemistry 2013.

AMINE-BASED AND AMIDE-BASED INHIBITORS OF SEMICARBAZIDE-SENSITIVE AMINE OXIDASE (SSAO) ENZYME ACTIVITY AND VAP-1 MEDIATED ADHESION USEFUL FOR TREATMENT OF DISEASES

Compositions and methods are disclosed for inhibiting semicarbazide-sensitive amine oxidase (SSAO), also known as vascular adhesion protein-1 (VAP-1). The compounds disclosed are amine-containing and amide-containing compounds. The compounds and compositions are useful for treatment of diseases, including inflammation, inflammatory diseases and autoimmune disorders.

Grignard reactions of 4-substituted-2-keto-1,3-dioxanes: Highly diastereoselective additions controlled by a remote alkyl group

(matrix presented) The reactions of Grignard reagents with a representative series of simple cis-2-keto-4-substituted-1,3-dioxanes have been investigated. The stereochemical outcome of these highly diastereoselective additions (dr > 90:10) is consonant wi

Synthesis and in vitro reactivity of 3-carbamoyl-2- phenylpropionaldehyde and 2-phenylpropenal: Putative reactive metabolites of felbamate

We propose that 3-carbamoyl-2-phenylpropionaldehyde is an intermediate in the metabolism of felbamate, an anti-epileptic drug with a unique profile of therapeutic activity, and undergoes a cascade of chemical reactions responsible for the toxic properties of the parent drug. To test this hypothesis, we have synthesized 3-carbamoyl-2-phenylpropionaldehyde and evaluated its in vitro reactivity. This molecule was found to be highly unstable at physiological pH (t(1/2) ≤ 30 s) and to undergo facile elimination to 2-phenylpropenal, an α, β-unsaturated aldehyde commonly termed atropaldehyde. However, the predominant reaction pathway for 3- carbamoyl-2-phenylpropionaldehyde was reversible cyclization to generate 4- hydroxy-5-phenyltetrahydro-1,3-oxazin-2-one, a urethane that has a considerably longer half-life at physiological pH (t(1/2) ≤ 5 h) and may serve as a stable reservoir of the reactive aldehyde both in vitro and in vivo. Atropaldehyde is a potent electrophile and was found to exhibit cytotoxicity to cultured fibroblasts (50% growth inhibition (GI50) = 4.1 ± 1.1 μM) comparable to the known unsaturated aldehyde toxins, 4-hydroxy-2- nonenal and acrolein. 3-Carbamoyl-2-phenylpropionaldehyde also exhibited significant cytotoxicity (GI50 = 53 ± 8 μM), whereas 2-phenyl-1, 3- propanediol monocarbamate (GI50 > 500 μM) and 3-carbamoyl-2- phenylpropionic acid (GI50 > 500 μM) were nontoxic. We have additionally demonstrated the formation of a glutathione-atropaldehyde conjugate from the in vitro incubation of 3-carbamoyl-2-phenylpropionaldehyde with glutathione. Thus, the potent cytotoxicity and potential allergenicity of atropaldehyde implicate this unsaturated aldehyde as a possible causative agent in the toxicities observed with felbamate treatment.