494-12-2

Usage

Uses

Used in Pharmaceutical Research:
3,4-Dihydro-2-phenyl-2H-1-benzopyran is used as a research compound for studying the pharmacological effects of selective agonists on estrogen receptors, specifically ERβ. Its unique structure and high affinity for ERβ make it instrumental in elucidating the receptor's functions and signaling pathways.
Used in Disease Prevention and Treatment:
In the field of medicine, 3,4-Dihydro-2-phenyl-2H-1-benzopyran is being investigated for its potential therapeutic applications. It has shown promise in the prevention and treatment of various diseases, such as osteoporosis, cardiovascular disease, and cancer. 3,4-Dihydro-2-phenyl-2H-1-benzopyran's ability to selectively target ERβ may contribute to the development of novel treatments with fewer side effects compared to traditional hormone therapies.
Used in Drug Development:
3,4-Dihydro-2-phenyl-2H-1-benzopyran's unique pharmacological properties and its interaction with estrogen receptor beta make it a valuable asset in drug development. Researchers are exploring its potential as a lead compound for the creation of new medications targeting ERβ-related conditions, aiming to improve patient outcomes and provide more targeted treatment options.

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

Upstream product

• 100-42-5 styrene 
• 90-01-7 salicylic alcohol 
• 24114-57-6 3-(2-hydroxyphenyl)-1-phenyl-1-propene 
• 55539-49-6 3-(2-hydroxyphenyl)-1-phenyl-1-propanol 
• 56052-53-0 3-(2-hydroxy-phenyl)-1-phenyl-propan-1-one 
• 5435-44-9 (E)-3-Ureido-but-2-enoic acid ethyl ester 
• 4526-41-4 o-(methylthiomethyl)-phenol 
• 122588-16-3 3-methyl-4H-1,2-benzoxazine 
• 127383-38-4 3-phenyl-4H-1,2-benzoxazine 
• 487-26-3 Flavanone 
• 23925-16-8 (E)-3-(2-hydroxyphenyl)-1-phenylpropene 
• 6272-41-9 2-phenylchromenylium perchlorate 
• 88214-92-0 2-methoxyflavan 
• 10035-10-6 hydrogen bromide 

Downstream Products

• 1481-90-9 2-(3-phenylpropyl)phenol 
• 260-94-6 acridine 
• 779-84-0 N-phenylsalicylaldimine 
• 3526-45-2 2-((phenylamino)methyl)phenol 
• 38997-00-1 2-(2-aminobenzyl)phenol 
• 525-82-6 FLAVONE 
• 73303-04-5 Acetic acid 2-(2-acetylamino-benzyl)-phenyl ester 

Relevant academic research and scientific papers

Montmorillonite-mediated hetero-Diels-Alder reaction of alkenes and o-quinomethanes generated in situ by dehydration of o-hydroxybenzyl alcohols

The intermolecular hetero-Diels-Alder reaction of in situ-generated o-quinomethanes and unactivated alkenes has been accomplished through a wet montmorillonite catalyst in a LiClO4-MeNO2 solution to give good yields of varied chromane skeletons.

Boron insertion into alkyl ether bonds via zinc/nickel tandem catalysis

Mild methods to cleave the carbon-oxygen (C?O) bond in alkyl ethers could simplify chemical syntheses through the elaboration of these robust, readily available precursors. Here we report that dibromoboranes react with alkyl ethers in the presence of a nickel catalyst and zinc reductant to insert boron into the C?O bond. Subsequent reactivity can effect oxygen-to-nitrogen substitution or one-carbon homologation of cyclic ethers and more broadly streamline preparation of bioactive compounds. Mechanistic studies reveal a cleavage-then-rebound pathway via zinc/nickel tandem catalysis.

One pot tandem dual CC and CO bond reductions in the β-alkylation of secondary alcohols with primary alcohols by ruthenium complexes of amido and picolyl functionalized N-heterocyclic carbenes

Two different classes of ruthenium complexes, namely, [1-mesityl-3-(2,6-Me2-phenylacetamido)-imidazol-2-ylidene]Ru(p-cymene)Cl (1c) and {[1-(pyridin-2-ylmethyl)-3-(2,6-Me2-phenyl)-imidazol-2-ylidene]Ru(p-cymene)Cl}Cl (2c), successfully catalyzed the one-pot tandem alcohol-alcohol coupling reactions of a variety of secondary and primary alcohols, in moderate to good yields of ca. 63-89%. The mechanistic investigation performed on two representative catalytic substrates, 1-phenylethanol and benzyl alcohol using the neutral ruthenium (1c) complex showed that the catalysis proceeded via a partially reduced CC hydrogenated carbonyl species, [PhCOCH2CH2Ph] (3′), to the fully reduced CO and CC hydrogenated secondary alcohol, [PhCH(OH)CH2CH2Ph] (3). Furthermore, the time dependent study showed that the major product of the catalysis modulated between (3′) and (3) during the catalysis run performed over an extended period of 120 hours. Finally, the practical utility of the alcohol-alcohol coupling reaction was demonstrated by preparing five different flavan derivatives (13-17) related to various bioactive flavonoid natural products, in a one-pot tandem fashion.

Axially Chiral 1,1'-Binaphthyl-2-Carboxylic Acid (BINA-Cox) as Ligands for Titanium-Catalyzed Asymmetric Hydroalkoxylation

Axially chiral, enantiopure 1,1'-binaphthyl-2-carboxylic acids (BINA-Cox) have recently been introduced as chiral ligands for transition metal catalysis. Together with equimolar, co-catalytic amounts of Ti(OiPr)4 and water they form an in situ catalyst that performs the asymmetric catalytic hydroalkoxylation of 2-allylphenols to 2-methylcoumarans at high temperature (240 °C, microwave heating). The synthesis of reference ligand 2'-MeO-BINA-Cox (L1) has been optimized and performed at molar scale. Synthetic routes have been developed to access a variety of substituted BINA-Cox ligands (>30 examples), which have been tested for ligand effects on the reference asymmetric cyclization of 2-allylphenol. The substrate range of asymmetric catalytic hydroalkoxylation has been explored through systematic substrate structure variations to define scope and limitations of the titanium-catalyzed process. The new substrates 2-(1-vinylcycloalkyl)phenols (1j, 1k), 2-(2-vinylphenyl)propan-2-ol (1t), and 2'-vinyl-[1,1'-biphenyl]-2-ol (1u) are shown to undergo asymmetric catalytic cyclization to benzodihydrofurans and benzo[c]chromene, respectively.

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.

Manganese-Catalyzed β-Alkylation of Secondary Alcohols with Primary Alcohols under Phosphine-Free Conditions

Manganese(I) complexes bearing a pyridyl-supported pyrazolyl-imidazolyl ligand efficiently catalyzed the direct β-alkylation of secondary alcohols with primary alcohols under phosphine-free conditions. The β-alkylated secondary alcohols were obtained in moderate to good yields with water formed as the byproduct through a borrowing hydrogen pathway. β-Alkylation of cholesterols was also effectively achieved. The present protocol provides a concise atom-economical method for C-C bond formation from primary and secondary alcohols.

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.

Tandem Cross Coupling Reaction of Alcohols for Sustainable Synthesis of β-Alkylated Secondary Alcohols and Flavan Derivatives

A Ru(II) NHC complex (loading down to 0.001 mol%) catalyzed cross coupling of a broad range of aromatic, aliphatic and heterocyclic alcohols is reported. This protocol also functioned efficiently under solvent-free conditions. Remarkably, this catalytic system disclosed so far the highest TON of 288000 for the cross coupling of alcohols. Notably, this methodology was successfully applied for the one-pot synthesis of a range of flavan derivatives. A detailed DFT studies and kinetic experiments were performed to understand the reaction mechanism as well as the high reactivity of this catalytic system. (Figure presented.).

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.

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.