40546-94-9

Usage

Chemical Properties

White Solid

InChI:InChI=1/C16H14O2/c1-11-7-8-15-14(9-11)13(10-16(17)18-15)12-5-3-2-4-6-12/h2-9,13H,10H2,1H3

Upstream product

• 106-44-5 p-cresol 
• 140-10-3 (E)-3-phenylacrylic acid 
• 103-26-4 Methyl cinnamate 
• 621-82-9 Cinnamic acid 
• 102-92-1 cinnamoyl chloride 
• 3262-89-3 triphenylboroxine 
• 175647-90-2 (E)-ethyl 3-(2-hydroxy-5-methylphenyl)acrylate 
• 55359-68-7 2-(methoxymethoxy)-5-methylbenzaldehyde 
• 16299-22-2 6-methyl-4-phenylchromen-2-one 
• 613-84-3 2-hydroxy-5-methylbenzaldehyde 
• 345948-96-1 6-methyl-2-oxo-2H-chromen-4-yl 4-methylbenzenesulfonate 
• 92-48-8 6-methylcoumarin 
• 98-80-6 phenylboronic acid 
• 99429-99-9 4-methylphenyl cinnamate 

Downstream Products

• 109089-77-2 3-(2-methoxy-5-methyl-phenyl)-3-phenyl-propionic acid 
• 16299-22-2 6-methyl-4-phenylchromen-2-one 
• 851789-43-0 3-phenyl-3-(2'-hydroxy-5'-methyl)phenylpropanol-1 
• 124937-51-5 (R)-(+)-tolterodine 
• 209747-04-6 2-hydroxy-6-methyl-4-phenyldihydrobenzopyran 
• 854306-67-5 methyl 3-(2-benzyloxy-5-methylphenyl)-3-phenylpropionate 
• 897314-72-6 (+/-)-N,N-diisopropyl-3-(2-hydroxy-5-methylphenyl)-3-phenyl-propanamide 
• 124937-73-1 3-(2-methoxy-5-methylphenyl)-3-phenylpropan-1-ol 
• 124936-74-9 N,N-diiso-propyl-3-(2-hydroxy-5-methylphenyl)-3-phenylpropanamine 
• 882878-66-2 3-(2-methoxy-5-methylphenyl)-3-phenylpropyl-methanesulfonate 
• 1161940-88-0 N,N-diisopropyl-3-(2-methoxy-5-methylphenyl)-3-phenylpropan-1-amine hydrochloride 
• 1043911-42-7 N,N-diisopropyl-3-(2-hydroxy-5-methylphenyl)-3-phenyl-propylamine L-tartrate 
• 207679-81-0 (R)-2-[3-(diisopropylamino)-1-phenylpropyl]-4-(hydroxymethyl)-phenol 
• 389068-22-8 N,N-diisopropyl-3-(2-benzyloxy-5-methylphenyl)-3-phenylpropylamine 

Relevant academic research and scientific papers

Synthesis and Antioxidant Properties of New Substituted 8-Methyl-6-phenyl-5,6-dihydro-4H-1,3,2-benzodioxaphosphocine-2-oxide Derivatives

A new route for the synthesis of substituted 8-methyl-6-phenyl-5,6-dihydro-4H-1,3,2-benzodioxaphosphocine-2-oxide derivatives has been developed by using cinnamic acid and p-cresol via condensation, reduction, and followed by phosphorylation steps. The ti

Design, Synthesis, and Molecular Modeling of Asymmetric Tolterodine Derivatives as Anticancer Agents

An efficient and short enantioselective synthesis of (S)- and (R)-tolterodine acid isomers (7a–7i) was performed a 6-methyl-4-phenylchroman-2-one intermediate from inexpensive and commercially available starting materials. A series of tolterodine acid hyb

Palladium Catalyzed Enantioselective Hayashi-Miyaura Reaction for Pharmaceutically Important 4-Aryl-3,4-dihydrocoumarins

The first palladium-catalyzed asymmetric addition of arylboronic acids to coumarins was successfully established, providing a straightforward asymmetric approach to achieving pharmaceutically important 4-aryl-3,4-dihydrocoumarins. This methodology features easily accessible and bench-stable ligands, a wide substrate scope, mild conditions, and accommodation of electron-withdrawing arylboronic acids.

Microwave accelerated the solvent-free synthesis of 4-aryl-3,4-dihydrocoumarin via the tandem reaction of cinnamic acids with phenols catalyzed by Amberlyst 15 resin

Amberlyst 15 resin supported the tandem reaction of cinnamic acids with phenols under solvent-free reaction condition has been introduced to afford 4-aryl-3,4-dihydrocoumarin (neoflavanone) derivatives. The efficiency of solid acidic sulfonic resin (A-15) has been illustrated in two reaction activation methods such as microwave irradiation and conventional heating. The important roles of Amberlyst 15 have been emphasized strongly through the high yields of 4-aryl-3,4-dihydrocoumarin in the shorter time under the assistance of microwave irradiation than of conventional heating, and its high recovery and reusability for six catalyst runs. The original catalyst as well as the recycled catalyst were characterized by XRD and FE-SEM to study the correlation of the surface of reused catalyst and its recyclability.

Metal-free annulative hydrosulfonation of propiolate esters: synthesis of 4-sulfonates of coumarins and butenolides

An efficient metal-free and cost-effective method for the synthesis of coumarin and butenolide 4-sulfonates (46 examples) has been developed. The reaction involves addition of sulfonic acids to ethyl propiolates followed by lactonization, resulting in direct formation of coumarin and butenolide 4-sulfonates. This methodology has been elaborated to Sonogashira and Suzuki coupling including the synthesis of rac-tolterodine.

Lewis acid-catalyzed annulative partial dimerization of 3-aryloxyacrylates to 4-arylchroman-2-ones: Synthesis of analogues of tolterodine, RORγ inhibitors and a GPR40 agonist

A beguiling annulative partial dimerization of 3-aryloxyacrylates to 4-arylchroman-2-ones catalyzed by Lewis acid (BF3·OEt2) has been developed. The reaction involves two molecules of 3-aryloxyacrylate, resulting in the loss of one propiolate molecule to furnish 4-arylchroman-2-one, an important structural motif found in many natural products. This methodology has been elaborated to synthesize analogues of tolterodine, RORγ inhibitors and a GPR40 agonist.

Hydrolase-mediated resolution of the hemiacetal in 2-chromanols: The impact of remote substitution

Hydrolase-catalysed dynamic kinetic resolutions of chroman-2-ol and 3-methyl chroman-2-ol can be effected with up to 88% conversion and 92% ee through the use of organic solvents. Extension to the resolution of the tolterodine precursor 1 proved more challenging. The presence of the remote phenyl substituent had a significant impact on the resolution and it was not possible to achieve high enantioselectivity together with efficient conversion from the focussed panel of enzymes screened.

Hydroarylation of cinnamic acid with phenols catalyzed by acidic ionic liquid [H-NMP]HSO4: computational assessment on substituent effect

Hydroarylation of cinnamic acid with different substituted phenols, in the presence of acidic ionic liquid, N-methyl-2-pyrrolidonum hydrosulfate ([H-NMP]HSO4) gave the corresponding dihydrocoumarins in high yields and excellent selectivity. Amo

Single-step synthesis of 4-phenyl and 3,4-dihydro-4-phenyl coumarins using a recyclable Preyssler heteropolyacid catalyst under solvent-free reaction conditions

4-Phenyl and 3,4-dihydro-4-phenylcoumarins were prepared by direct esterification of phenols with phenylpropiolic and cinnamic acids, respectively, using a compound with Preyssler structure (H14P5NaW30O110) (PA)

Molecular iodine catalyst promoted synthesis of chromans and 4-aryl-3,4-dihydrobenzopyran-2-ones via [3+3] cyclocoupling

Molecular iodine as an inexpensive catalyst is described in the construction of 2-substituted or 2,2-disubstituted chromans and 4-aryl-3,4-dihydrobenzopyran-2-ones via [3+3] cyclocoupling. For the synthesis of chromans, phenols and allylic alcohols were refluxed in chloroform in presence of 20 mol % I2 while [3+3] cyclocoupling of phenols and cinnamic acids proceeded to give 4-aryl-3,4-dihydrobenzopyran-2-ones using 30 mol % I2. Later reaction occurs via a tandem hydroarylation- esterification process at 120-130°C under solvent free conditions. Chromans were obtained in 20-92% yields and substituted 4-aryl-3,4-dihydrobenzopyran-2- ones were obtained in 5-85% yields.