73110-56-2

Usage

InChI:InChI=1/C15H12Cl2O/c16-12-4-1-10(2-5-12)14-7-3-11-9-13(17)6-8-15(11)18-14/h1-2,4-6,8-9,14H,3,7H2

Upstream product

• 2749-98-6 4-chlorophenylallene 
• 106-48-9 4-chloro-phenol 
• 93962-67-5 C₁₅H₁₄Cl₂O₂ 
• 93962-68-6 3-(5-chloro-2-hydroxyphenyl)-1-(4-chlorophenyl)propan-1-one 
• 71643-66-8 4-chloro-2-iodo phenol 
• 58824-54-7 p-chlorophenylvinylcarbinol 
• 93514-42-2 2-phenylchromene 
• 36768-48-6 (E)-1-(5-chloro-2-hydroxyphenyl)-3-(4-chlorophenyl)prop-2-en-1-one 

Relevant academic research and scientific papers

Access to Electron-Deficient 2,2-Disubstituted Chromanes: A Highly Regioselective One-Pot Synthesis via an Inverse-Electron-Demand [4 + 2] Cycloaddition of ortho-Quinone Methides

We report the one-pot synthesis of 2,2-disubstituted chromanes with electron-withdrawing substituents. This reaction provides a simple yet efficient route to a wide range of electron-deficient chromanes in high yield and excellent regioselectivity. The reaction of salicylaldehyde with 1,1-disubstituted ethylenes smoothly furnishes these electron-deficient chromanes, which can be further transformed into functionalized chromanes or chromene. For example, BW683C was effectively synthesized from 5-chlorosalicylaldehyde with 4-chlorostyrene in two steps in excellent yield. The present reaction thus provides versatile access to functionalized electron-deficient chromanes and chromenes and therefore constitutes a promising tool for the synthesis of biologically and photochemically active molecules.

Regioselective Domino Synthesis of 2-Alkylflavans via Hidden Br?nsted Acid Catalysis

A range of alkyl-substituted flavans, which are important structural elements in natural products and pharmaceutical molecules, were prepared by successive hidden Br?nsted acid catalyzed domino reaction, intermolecular hydroarylation, and intramolecular hydroalkoxylation. 1,1-Disubstituted allenes were activated under mild acidic AgOTf/t-BuCl condition to initiate the regioselective Friedel-Crafts reaction with phenol derivatives, and the consecutive reaction triggered by the 6 -endo cyclization led to the formation of a new type of 2-alkylflavan. Mechanistic study of the reaction intermediates and control experiments support the catalytic pathway and advantage of hidden Bronsted acid catalysis.

A Modular Synthesis of 2-Alkyl- and 2-Arylchromans via a Three-Step Sequence

A convergent three-step method for the synthesis of 2-substituted chromans is described. These results have been accomplished via the Heck coupling of readily accessible allylic alcohols and 2-iodophenols, followed by reduction and Mitsunobu cyclization. The utility and generality of this method is demonstrated through the synthesis of a series of 2-aryl-, 2-heteroaryl- and 2-alkylchromans, as well as an azachroman derivative. The asymmetric version of this approach via a Noyori-catalyzed ketone reduction and subsequent cyclization is likewise highlighted.

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.