5594-98-9

Upstream product

• 34811-90-0 2-(4'-methoxyphenyl)-4H-chromene 
• 88214-95-3 2,4'-dimethoxyflavan 
• 84391-91-3 2-[(2E)-3-(4-methoxyphenyl)-2-propen-1-yl]phenol 
• 4143-74-2 4'-methoxyflavone 
• 88187-04-6 3-bromo-2,4'-dimethoxyflavan-4-one 
• 15402-17-2 4'-Methoxy-flavyliumchlorid 
• 6607-92-7 trans-2-hydroxy-4'-methoxychalcone 
• 3034-08-0 2-(4-methoxyphenyl)-2,3-dihydro-4H-chromen-4-one 
• 58721-41-8 2-hydroxy-4'-methoxychalcone 
• 20337-98-8 3-(2-hydroxy-phenyl)-1-(4-methoxy-phenyl)-propan-1-ol 
• 90-02-8 salicylaldehyde 
• 100-06-1 1-(4-methoxyphenyl)ethanone 
• 88214-90-8 2-hydroxy-4'-methoxy-α,β-dihydrochalcone 
• 637-69-4 4-Methoxystyrene 

Downstream Products

• 22928-33-2 1-(2-benzoyloxy-phenyl)-3-(4-methoxy-phenyl)-propane 
• 101431-35-0 2-[3-(4-methoxyphenyl)propyl]phenol 
• 102956-88-7 3-(2-methoxy-phenyl)-1,1-bis-(4-methoxy-phenyl)-propane 

Relevant academic research and scientific papers

Photocyclization of 2-cinnamylphenols via excited state proton transfer (ESPT) involving the lowest-lying styrenic singlet

The attachment of substituents to the styrenic ring of trans-2-cinnamylphenol produces a decrease in the singlet energy of the styrenic moiety. As a consequence, the resulting chromophore becomes responsible for the photophysical and photochemical properties of this type of bichromophoric compounds. Both fluorescence emission and photocyclization occur predominantly from the lowest-lying styrenic singlet. The result is a marked regioselectivity towards 6-membered ring products, via an excited state proton transfer.

One-Pot Synthesis of O-Heterocycles or Aryl Ketones Using an InCl3/Et3SiH System by Switching the Solvent

An efficient one-pot synthesis of O-heterocycles or aryl ketones has been achieved using Et3SiH in the presence of InCl3 via a sequential ionic hydrogenation reaction by switching the solvent. This methodology can be used to construct C-O bonds and to prepare conjugate reduction products, including chromans, tetrahydrofurans, tetrahydropyrans, dihydroisobenzofurans, dihydrochalcones, and 1,4-diones in a facile manner. In addition, a novel plausible mechanism involving a conjugate reduction and a tandem reductive cyclization was verified by experimental investigations.

One step synthesis of 2-alkenylchromanes via inverse electron-demand Hetero-Diels–Alder reaction of o-quinone methide with unactivated dienes

The synthetically important 2-alkenylchromane derivatives were constructed in good yields under metal-free condition via inverse electron demand Hetero-Diels–Alder reaction of o-quinone methides with unactivated dienes. This strategy features mild conditi

Tosylhydrazine mediated conjugate reduction and sequential reductive coupling cyclization: Synthesis of 2-arylchromans

Tosylhydrazine mediated conjugate reduction of 2-hydroxyl chalcones and sequential reductive coupling cyclization is described. This is an unprecedented protocol and an extremely efficient method for a one-pot domino synthesis of 2-arylchromans in good to excellent yields from commercially available, cheap starting materials. More importantly, the two-step reactions can be easily controlled to afford dihydrochalcones or 2-arylchromans by the mole amounts of tosylhydrazine. Furthermore, the operational simplicity of the process and the high functional group tolerance are remarkable.

An efficient synthesis of flavans from salicylaldehyde and acetophenone derivatives

An efficient total synthesis of flavans from the reactions of salicylaldehyde and acetophenone derivatives is reported. The synthesis involves preparation of chalcones through an aldol reaction followed by reduction of both the double bond and the ketone using NaBH4 and an acetic acid mediated cyclization. Methoxy groups on the aromatic rings did not affect significantly the yields of the procedure.

Reduction of some flavanones and E-3-benzylideneflavanones under modified Clemmensen reduction condition

A mild and efficient method for reduction of flavanones and E-3-benzylideneflavanones has been developed by using modified Clemmensen reduction condition [Zn(Hg), CH3COOH, EtOH, reflux, 1.5 h]. Flavanones gave flavans and E-3-benzylideneflavanones gave 3-benzylflavans and 3-benzylflav-3-enes.

Amino-substituted flavans useful as anti-viral agents

Novel compounds of formula (IID) STR1 wherein either both X and Y represent groups independently selected from amino and lower alkylamino, or one of X and Y represents a group selected from amino and lower alkylamino and the other of X and Y represents a hydrogen atom have been found to be active against rhinoviruses and other viruses. Processes for producing these compounds include reduction of flavanone derivatives or of flavenes. Alternatively, reductive cyclization of chalcones affords the compounds. These may also be prepared by condensation of o-(substituted methyl)phenols with styrene derivatives. Pharmaceutical formulations and methods for the administration of the compounds are described.

Reactions of Flav-2-enes and Flav-2-en-4-ones (Flavones)

Flav-2-enes, flavones, and 3-alkyl ethers of flavonols add alcohols and carboxylic acids in the presence of N-bromosuccinimide to give 2-alkoxy- and 2-acyloxy-3-bromoflavans which provide routes to cis-3-bromoflavans by reduction and to 3,4-diols by elimination and reaction with osmium tetraoxide.The 2-acyloxyflavans react with alcohols yielding 2-alkoxyflavans.Flavonols react with N-bromosuccinimide and alcohols to give bromine-free hemiacetals, the known 2,3-dialkoxy-3-hydroxyflavanones.