3759-31-7

Upstream product

• 64-19-7 acetic acid 
• 98-86-2 acetophenone 
• 79-11-8 chloroacetic acid 
• 14368-31-1 3-hydroxy-3-phenylbutanenitrile 
• 64-69-7 Iodoacetic acid 
• 91970-87-5 (rac)-methyl 3-hydroxy-3-phenylbutanoate 
• 898562-69-1 benzyl 3-hydroxy-3-phenylbutanoate 
• 2293-60-9 ethyl 3-hydroxy-3-phenylbutyrate 
• 4743-74-2 2-phenylpent-4-en-2-ol 

Downstream Products

• 704-80-3 (E)-3-phenyl-2-butenoic acid 
• 98-83-9 isopropenylbenzene 
• 880-65-9 (-)S β-hydroxy β-phenyl n-butanoate de methyle 
• 7210-37-9 (R)-3-hydroxy-3-phenylbutyric acid methyl ester 
• 81467-21-2 3-Hydroxy-3-phenylbutyrohydroxamsaeure 
• 81467-25-6 3-(2-Hydroxy-2-phenylpropyl)-1,4,2-dioxazol-5-on 
• 7133-68-8 3-phenylbutane-1,3-diol 
• 898562-69-1 benzyl 3-hydroxy-3-phenylbutanoate 

Relevant academic research and scientific papers

Isothiourea-Catalyzed Acylative Kinetic Resolution of Tertiary α-Hydroxy Esters

A highly enantioselective isothiourea-catalyzed acylative kinetic resolution (KR) of acyclic tertiary alcohols has been developed. Selectivity factors of up to 200 were achieved for the KR of tertiary alcohols bearing an adjacent ester substituent, with both reaction conversion and enantioselectivity found to be sensitive to the steric and electronic environment at the stereogenic tertiary carbinol centre. For more sterically congested alcohols, the use of a recently-developed isoselenourea catalyst was optimal, with equivalent enantioselectivity but higher conversion achieved in comparison to the isothiourea HyperBTM. Diastereomeric acylation transition state models are proposed to rationalize the origins of enantiodiscrimination in this process. This KR procedure was also translated to a continuous-flow process using a polymer-supported variant of the catalyst.

Synthesis and antitumour activity of β-hydroxyisovalerylshikonin analogues

A series of novel β-hydroxyisovalerylshikonin analogues bearing oxygen-containing substituents at the side-chain hydroxyl of shikonin were designed and synthesized. The cytotoxicities of these compounds were evaluated in vitro against multi-drug resistant (MDR) cell lines DU-145 and HeLa. Most compounds exhibited significant inhibitory activity on both cell lines. The structure-activity relationship showed the analogues with ether substituents displayed the most potent antitumour activity and selective cytotoxicity towards DU-145. Among the compounds with ether substituents, increasing the steric hindrance in the carbon bearing β-hydroxyl or replace the β-hydroxyl with acetoxy or methoxy would lead to the decline of cytotoxicity.

Base-catalyzed dehydrogenative Si-o coupling of dihydrosilanes: Silylene protection of diols

The direct dehydrogenative coupling of 1,3- and 1,4-diols and dihydrosilanes is efficiently catalyzed by CsO(10 mol%), cleanly affording six- and seven-membered 1,3-dioxo-2-silacycles with dihydrogen as the sole by-product. Conversely, 1,2-diols do not yield the expected 1,3-dioxo-2- silacyclopentanes, essentially forming cyclic disiloxanes instead. Aside from the synthetic convenience, the procedure itself is also useful for straight-forward diol derivatization prior to GLC analysis. Georg Thieme Verlag Stuttgart · New York.

Aldol-type reactions of unmasked iodoacetic acid with carbonyl compounds promoted by samarium diiodide: Efficient synthesis of carboxylic 3-hydroxyacids and their derivatives

An easy, direct, general, and efficient samarium diiodide-mediated preparation of 3-hydroxyacids 1 in high yield by reaction of different aldehydes or ketones with commercially available iodoacetic acid is described. The application of different esterific

A convenient generation of acetic acid dianion

The lithium enediolate of acetic acid can be generated efficiently, as a 0.5 M solution in THF, using lithium amides prepared from n-butyllithium in THF and either diethylamine or 1,3,3-trimethyl-6-azabicyclo-(3.2.1)-octane (AZA). Its reaction with carbon

Direct catalytic aldol-type reactions using RCH2CN

(Matrix presented) A copper fluoride-catalyzed cyanomethylation that can be applied to a wide range of ketones and aldehydes was developed using TMSCH2CN as a nucleophile. The reaction was extended to a conceptually more advanced copper alkoxid

Lithium- α-lithioacetate and β-lithiopropionate: Useful intermediates in organic synthesis

The reaction of chloroacetic acid and 3-chloropropionic acid with a base (LDA or Bu(n)Li, respectively) and then with an excess of lithium and a catalytic amount of 4,4'-di-tert-butylbiphenyl (DTBB, 5%) in the presence of different electrophiles [Bu'CHO, PhCHO, Et2CO, (CH2)5CO, PhCOMe] in THF at -78°C leads, after hydrolysis with water, to the expected hydroxy acids, which in the second case are directly cyclised under acidic conditions to give the expected γ-lactones. (C) 2000 Elsevier Science Ltd.

Synthesis of perhydrooxazinones from 2-aza-3-trimethylsilyloxy-1,3- butadiene. A general route to 3,3-disubstituted-β-hydroxy acids

1-Phenyl-2-aza-3-trimethylsilyloxy-1,3-butadiene reacts with aliphatic, aromatic and cyclic ketones to give in good to excellent yields 6,6- disubstituted-1,3-perhydro-oxazin-4-ones which, in turn, have been readily converted into β-hydroxy carboxylic acids.

Samarium(II) iodide mediated intermolecular coupling reactions of N,N-dibenzyl-α-haloamides with carbonyl compounds

Samarium(II) iodide mediated coupling reactions of α-haloamides with carbonyl compounds are found to give N,N-dibenzyl-β-hydroxyamides (4a-i, 5a-i, and 6a) in good yields under mild reaction conditions. The transformation of 4a and 5a to N,N-dibenzyl-3-phenylpropanamide (7) and β-hydroxycarboxylic acid (8), respectively, are described.

Synthesis and Structure-Activity Relationships of 1-Acyl-4-(2-methyl-3-pyridyl)cyanomethyl)piperazines as PAF Antagonists

A second generation of (cyanomethyl)piperazines, 1-acyl-4-((2-methyl-3-pyridyl)cyanomethyl)piperazines, with increased oral activity was prepared and evaluated in vitro in PAF-induced platelet aggregation assay (PAG) and in vivo in a PAF-induced hypotension test in normotensive rats (HYP).Oral activity was ascertained through a PAF-induced mortality test in mice (MOR).Attachment of a methyl group at position 2 of our earlier pyridine derivatives resulted in an improvement of 1 order of magnitude or greater in the ID50 of the oral test.Three different types of acylsubstituents of similar potency emerge from this work: N-(diphenylmethylamino)acetyl, 3-substituted 3-hydroxy-3-phenylpropionyl, and N-substituted 3-amino-3-phenylpropionyl groups.The most interesting compounds, 26 (UR-12460, PAG IC50 = 0.040 μM, HYP, ID50 = 0.021 mg/kg iv, MOR, ID50 = 0.30 mg/kg po) and 58 (UR-12519, PAG IC50 = 0.041 μM, HYP, ID50 = 0.015 mg/kg iv, MOR, ID50 = 0.044 mg/kg po), compare favorably with WEB-2086.Compounds 26 and 58 were also tested in active anaphylactic shock (AAS) and endotoxin-induced mortality (EIM) tests.On the basis of these data, compounds 26 and 58 have been selected for further pharmacological development.