4737-26-2

Usage

InChI:InChI=1/C15H14O/c1-2-6-12(7-3-1)14-10-13-8-4-5-9-15(13)16-11-14/h1-9,14H,10-11H2

Upstream product

• 6054-00-8 3-phenyl-2H-benzopyran 
• 78950-74-0 2-morpholinoisoflav-3-ene 
• 109790-37-6 6-chloro-3-(4-chlorophenyl)-2H-benzopyran 
• 100976-02-1 2-phenyl-3-(2-hydroxyphenyl)-1-propanol 
• 5533-05-1 (2-methoxymethoxyphenyl)methanol 
• 90-02-8 salicylaldehyde 
• 5330-38-1 4-chloro-2-hydroxymethylphenol 
• 90-01-7 salicylic alcohol 
• 109790-47-8 2-(o-hydroxymethylphenoxy)-1-phenylethanone 
• 109790-44-5 {5-Chloro-2-[2-(4-chloro-phenyl)-2-oxo-ethoxy]-benzyl}-triphenyl-phosphonium; bromide 
• 536-38-9 4-chlorobenzoylmethyl bromide 
• 1029608-17-0 C₁₆H₁₆O₂ 
• 33255-30-0 3-phenyl-2,3,4,5-tetrahydro-benzo[f][1,4]oxazepine 
• 37434-59-6 dimethyl 2-phenylmalonate 

Relevant academic research and scientific papers

Skeletal editing through direct nitrogen deletion of secondary amines

Synthetic chemistry aims to build up molecular complexity from simple feedstocks1. However, the ability to exert precise changes that manipulate the connectivity of the molecular skeleton itself remains limited, despite possessing substantial potential to expand the accessible chemical space2,3. Here we report a reaction that ‘deletes’ nitrogen from organic molecules. We show that N-pivaloyloxy-N-alkoxyamides, a subclass of anomeric amides, promote the intermolecular activation of secondary aliphatic amines to yield intramolecular carbon–carbon coupling products. Mechanistic experiments indicate that the reactions proceed via isodiazene intermediates that extrude the nitrogen atom as dinitrogen, producing short-lived diradicals that rapidly couple to form the new carbon–carbon bond. The reaction shows broad functional-group tolerance, which enables the translation of routine amine synthesis protocols into a strategy for carbon–carbon bond constructions and ring syntheses. This is highlighted by the use of this reaction in the syntheses and skeletal editing of bioactive compounds.

A concise route towards isoflavans

Isoflavans have gained considerable interest owing to their potential health benefits. Herein, we have presented a straightforward strategy for isoflavans synthesis. The strategy features an intermolecular [Cu]-catalyzed arylation of malonates and an intr

2-Morpholinoisoflav-3-enes as flexible intermediates in the synthesis of phenoxodiol, isophenoxodiol, equol and analogues: Vasorelaxant properties, estrogen receptor binding and Rho/RhoA kinase pathway inhibition

Isoflavone consumption correlates with reduced rates of cardiovascular disease. Epidemiological studies and clinical data provide evidence that isoflavone metabolites, such as the isoflavan equol, contribute to these beneficial effects. In this study we developed a new route to isoflavans and isoflavenes via 2-morpholinoisoflavenes derived from a condensation reaction of phenylacetaldehydes, salicylaldehydes and morpholine. We report the synthesis of the isoflavans equol and deoxygenated analogues, and the isoflavenes 7,4′-dihydroxyisoflav-3-ene (phenoxodiol, haganin E) and 7,4′-dihydroxyisoflav-2-ene (isophenoxodiol). Vascular pharmacology studies reveal that all oxygenated isoflavans and isoflavenes can attenuate phenylephrine-induced vasoconstriction, which was unaffected by the estrogen receptor antagonist ICI 182,780. Furthermore, the compounds inhibited U46619 (a thromboxane A2 analogue) induced vasoconstriction in endothelium-denuded rat aortae, and reduced the formation of GTP RhoA, with the effects being greatest for equol and phenoxodiol. Ligand displacement studies of rat uterine cytosol estrogen receptor revealed the compounds to be generally weak binders. These data are consistent with the vasorelaxation activity of equol and phenoxodiol deriving at least in part by inhibition of the RhoA/Rho-kinase pathway, and along with the limited estrogen receptor affinity supports a role for equol and phenoxodiol as useful agents for maintaining cardiovascular function with limited estrogenic effects.

o-Quinone methide based approach to isoflavans: application to the total syntheses of equol, 3′-hydroxyequol and vestitol

A concise strategy is developed for the synthesis of isoflavans employing a Diels-Alder reaction between o-quinone methides and aryl-substituted enol ethers followed by reductive cleavage of the acetal group. The method is extended towards the total syntheses of equol, 3′-hydroxyequol and vestitol.

The direct synthesis of isoflavans VIA α-alkylation of phenylacetates

Deprotonation of oxygenated phenylacetates and quenching of the enolates with oxygenated benzylic electrophiles, afforded 2,3-diarylpropanoates which served as precursors to the isoflavans following consecutive reduction and cyclization steps.

A new route to 3,4-dihydro-2H-1-benzopyrans substituted at 3-position via palladium-catalysed reactions

3,4-Dihydro-2H-1-benzopyrans substituted at 3-position were prepared via palladium-catalysed reactions between a triflate and several coupling reagnets (alkyl or aryl tin reagents and borane derivatives) according to Stille or Suzuki methodologies.

THE FIRST DIRECT SYNTHESIS OF ISOFLAVANS VIA α-ALKYLATION OF PHENYLACETATES

Deprotonation of phenylacetates and quenching of the enolates with benzylic electrophiles, afford 2,3-diarylpropanoates which serve as precursors to isoflavans following consecutive reduction and cyclization steps.

Preparation of Some Chromans Substituted at the 3- or 4-Position by an Aryl or Benzyl Group, by the Rhodium-catalysed Intramolecular Nucleophilic Substitution of the Corresponding 3-(2-Fluorophenyl)propanols

The bis(hexafluorophosphate) salt of the (η5-ethyltetramethylcyclopentadienyl)(η6-benzene)rhodium(III) cation has been used as a catalyst to prepare 3-phenyl-, 3-(4-methoxyphenyl)-, 3-(4-nitrophenyl)-, and 4-benzylchroman by cyclisation of the corresponding substituted 3-(2-fluorophenyl)-propanols in nitromethane-acetone solution. 3-Phenyl-4-hydroxymethylchroman and 3-hydroxymethyl-4-phenylchroman were prepared similarly.An attempt to prepare a bis(chroman) by a double cyclisation with 2-propane-1,3-diol afforded only the monochroman, 4-(2-fluorophenyl)-3-hydroxymethylchroman.Under the conditions of the cyclisation, the erythro and threo forms of 1,4-di(2-fluorophenyl)-butane-2,3-diol afforded only the corresponding 1,3-dioxolanes as the result of the diols reacting with the acetone used as cosolvent.The 1H n.m.r. spectra of the 3-substituted and 3,4-disubstituted chromans which have been prepared are consistent with the heterocyclic ring being in the half-chair conformation (6).

Chemotherapeutic agents

A method of treating or preventing viral infections, in particular rhinovirus infections comprising the administration of an effective amount of a 2-phenyltetralin derivative or a heterocyclic analogue thereof. Pharmaceutical compositions containing these compounds, and some novel compounds are also disclosed.

SYNTHESIS AND ANTI-RHINOVIRUS ACTIVITY OF HALOGEN-SUBSTITUTED ISOFLAVENES AND ISOFLAVANS

Halogenated 3(2H)-isoflavenes and (+/-)isoflavans were synthesized in order to study their in vitro activity against rhinovirus 1B by comparison with the known anti-viral compound, 4',6-dichloroflavan.The Wittig intramolecular cyclization of halogen subst