16299-22-2

Usage

Uses

Used in Pharmaceutical Industry:
6-Methyl-4-phenylcoumarin is used as a chemical intermediate for the synthesis of Tolterodine, a medication used in the treatment of overactive bladder and urinary incontinence. Its role in the production process is crucial for creating effective pharmaceutical compounds.
Additionally, it is used in the synthesis of other coumarin derivatives, which have potential applications in various fields, including medicine, agriculture, and materials science. The versatility of 6-Methyl-4-phenylcoumarin as an intermediate makes it a valuable component in the development of new and innovative products.

Upstream product

• 106-44-5 p-cresol 
• 94-02-0 ethyl 3-oxo-3-phenylpropionate 
• 93696-59-4 3-bromo-6-methyl-4-phenyl-3,4-dihydrocoumarin 
• 345948-96-1 6-methyl-2-oxo-2H-chromen-4-yl 4-methylbenzenesulfonate 
• 98-80-6 phenylboronic acid 
• 6627-55-0 2-bromo-p-cresol 
• 103-26-4 Methyl cinnamate 
• 99429-99-9 4-methylphenyl (2E)-3-phenylprop-2-enoate 
• 7299-58-3 phenylpropiolyl chloride 
• 1470-57-1 2-hydroxy-5-methylbenzophenone 
• 911217-72-6 C₁₇H₁₁F₁₃O₃ 
• 13252-83-0 4-hydroxy-6-methylcoumarin 
• 1099-45-2 ethyl (triphenylphosphoranylidene)acetate 
• 108-24-7 acetic anhydride 

Downstream Products

• 827007-19-2 (R)-6-methyl-4-phenyl-3,4-dihydrochromen-2-one 
• 349547-18-8 (S)-6-methyl-4-phenylchroman-2-one 
• 828933-86-4 (4R)-6-methyl-4-phenylchroman-2-ol 
• 851789-43-0 3-phenyl-3-(2'-hydroxy-5'-methyl)phenylpropanol-1 
• 851789-51-0 (R)-2-(3-hydroxy-1-phenylpropyl)-4-methylphenol 
• 851789-53-2 (S)-2-(3-hydroxy-1-phenylpropyl)-4-methylphenol 
• 40546-94-9 6-methyl-4-phenyl-3,4-dihydrocoumarin 
• 73779-10-9 3-(2-hydroxy-5-methyl-phenyl)-3-phenyl-propionic acid 
• 124937-51-5 (R)-(+)-tolterodine 
• 124937-53-7 (S)-tolterodine 

Relevant academic research and scientific papers

Magnetothermia-Induced Catalytic Hollow Nanoreactor for Bioorthogonal Organic Synthesis in Living Cells

Nanoreactors, in which the reactions are remotely controlled by magnetic fields, are potentially valuable in bioorthogonal chemistry for future applications. Here, we develop a silica-confined magnetothermia-induced nanoreactor (MAG-NER) by selectively gr

Cyclization of aryl 3-aryl propynoates into 4-arylcoumarins catalyzed by cyclometalated Platinum(II) complexes

Cyclometalated (ppy)PtII complexes (ppy = 2-phenylpyridinato-C2,N) catalyze the intramolecular cyclization of aryl propynoates to form coumarins and benzocoumarins. The complex [(ppy)PtCl(MeCN)] (5 mol %) was the most active and effi

Cascade Synthesis of 4-Arylcoumarins: Pd-Catalyzed Arylations and Cyclizations with (E)-Ethyl 3-(2-Hydroxyaryl)acrylates and Triarylantimony Difluorides

Herein, we describe a simple general method for the synthesis of 4-arylcoumarins using pentavalent organoantimony compounds. The reactions of 3-(2-hydroxyaryl)acrylates with triarylantimony difluorides in the presence of Pd(OAc)2 (10 mol-%) and 2,2'-bipyridyl (10 mol-%) at 80 °C under aerobic conditions afforded 4-arylcoumarins in good-to-excellent yields. This protocol involves a cascade oxidative Heck-type arylation followed by cyclization, with all the aryl groups in the triarylantimony difluoride transferred to the coupling products. Triarylantimony difluorides resulted in better outcomes than those obtained with other pentavalent organoantimony or bismuth compounds.

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.

Zeolite-promoted Synthesis of Coumarins and Thiocoumarins

Acidic zeolites, especially faujasites, efficiently promote the intramolecular cyclization of aryl propynoates and propynethioates, which produces coumarins and thiocoumarins, usually in high yields. Comparison with homogeneous Lewis or Br?nsted acids and

Photoinduced cyclization of alkynoates to coumarins with N-Iodosuccinimide as a free-radical initiator under ambient and metal-free conditions

An efficient photoinduced strategy for the preparation of coumarins was developed. In the presence of N-iodosuccinimide (NIS) as a free-radical initiator and under LED (380–385 nm) irradiation and metal-free conditions, the reaction of alkynoates underwen

Heck and oxidative boron Heck reactions employing Pd(II) supported amphiphilized polyethyleneimine-functionalized MCM-41 (MCM-41@aPEI-Pd) as an efficient and recyclable nanocatalyst

A novel nanocatalyst was developed based on covalent surface functionalization of MCM-41 with polyethyleneimine (PEI) using [3-(2,3-Epoxypropoxy)propyl] trimethoxysilane (EPO) as a cross-linker. Amine functional groups on the surface of MCM-41 were then conjugated with iodododecane to render an amphiphilic property to the catalyst. Palladium (II) was finally immobilized onto the MCM-41@PEI-dodecane and the resulted MCM-41@aPEI-Pd nanocatalyst was characterized by FT-IR, TEM, ICP-AES and XPS. Our designed nanocatalyst with a distinguished core-shell structure and Pd2+ ions as catalytic centers was explored as an efficient and recyclable catalyst for Heck and oxidative boron Heck coupling reactions. In Heck coupling reaction, the catalytic activity of MCM-41@aPEI-Pd in the presence of triethylamine as base led to very high yields and selectivity. Meanwhile, the MCM-41@aPEI-Pd as the first semi-heterogeneous palladium catalyst was examined in the C-4 regioselective arylation of coumarin via the direct C-H activation and the moderate to excellent yields were obtained toward different functional groups. Leaching test indicated the high stability of palladium on the surface of MCM-41@aPEI-Pd as it could be recycled for several runs without significant loss of its catalytic activity.

Transition-Metal-Free Lactonization of sp2 C-H Bonds with CO2

The transition-metal-free lactonization of heteroaryl and alkenyl C-H bonds with carbon dioxide is reported to synthesize important coumarin derivatives in moderate to excellent yields. These redox-neutral reactions feature a broad substrate scope, good functional group tolerance, facile scalability, and easy product derivatization.

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)

Pd-catalyzed chemo-selective mono-arylations and bis-arylations of functionalized 4-chlorocoumarins with triarylbismuths as threefold arylating reagents

Cross-coupling reactions of differently substituted 4-chlorocoumarins were studied under palladium catalysis using triarylbismuths as threefold arylating reagents. The high reactivity of 4-chlorocoumarins was demonstrated delivering mono- and bis-arylation products in a chemo-selective manner. The reaction conditions employed are simple, robust and the threefold coupling reactivity of triarylbismuth reagents was witnessed with good to high yields in 2-4 h conditions. The utility of the methodology was explored in the synthesis of a few natural occurring neoflavones (3.27-3.30). In addition, the 4-arylcoumarin 3.1 product is a useful precursor for the preparation of (R)-tolterodine.