41888-64-6

Usage

Uses

Used in Organic Synthesis:
5(4H)-Oxazolone, 4-[(3-methoxyphenyl)methylene]-2-methylis used as a building block in organic synthesis for the creation of various complex organic molecules. Its unique structural features, including the oxazolone ring and the attached functional groups, make it a versatile component in the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, 5(4H)-Oxazolone, 4-[(3-methoxyphenyl)methylene]-2-methylis used as a starting material or intermediate in the development of new drugs. Its structural features may contribute to the design of novel therapeutic agents with improved pharmacological properties, such as enhanced potency, selectivity, and reduced side effects.
Used in Research and Development:
5(4H)-Oxazolone, 4-[(3-methoxyphenyl)methylene]-2-methylis a subject of interest in research and development for the discovery of new drugs and materials. Its unique properties and reactivity make it a valuable tool for exploring new chemical reactions and synthetic pathways, as well as for investigating its potential pharmacological applications.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 5(4H)-Oxazolone, 4-[(3-methoxyphenyl)methylene]-2-methylis used as a key intermediate in the synthesis of various drug candidates. Its structural features and potential pharmacological properties make it a promising candidate for the development of new therapeutic agents with novel mechanisms of action and improved therapeutic profiles.
Used in Material Science:
5(4H)-Oxazolone, 4-[(3-methoxyphenyl)methylene]-2-methylmay also find applications in material science, where its unique structural features and properties can be exploited to develop new materials with specific properties, such as improved stability, reactivity, or selectivity. This can lead to the creation of innovative materials for various applications, including sensors, catalysts, and advanced materials for energy storage and conversion.

Upstream product

• 591-31-1 3-methoxy-benzaldehyde 
• 543-24-8 N-acetylglycine 
• 1906-82-7 ethyl acetamidoacetate 

Downstream Products

• 139596-77-3 N-{4-[1-(3-Methoxy-phenyl)-meth-(Z)-ylidene]-2-methyl-5-oxo-4,5-dihydro-imidazol-1-yl}-isonicotinamide 
• 138973-28-1 1,4-Bis(5'-(3-methoxybenzylidene)-2'-methyl-4'-imidazolinone-3'-ylamino)phthalazine 
• 68262-20-4 3-(3-methoxy-phenyl)-2-oxopropionic acid 
• 564441-55-0 (Z)-2-acetylamino-N-methyl-3-(3-methoxyphenyl)-2-propenamide 
• 114926-78-2 (+/-)-1-(3-methoxybenzyl)-1,2,3,4-tetrahydro-β-carboline 
• 4792-58-9 ethyl 5-methoxy-1H-indole-2-carboxylate 
• 171095-27-5 C₁₂H₁₃NO₄ 
• 158214-14-3 C₁₂H₁₅NO₄ 
• 171095-11-7 methyl (S)-2-acetylamino-3-(3-methoxyphenyl)propanoate 

Relevant academic research and scientific papers

The meta-green fluorescent protein chromophore

m-Hydroxy isomer of the green fluorescent protein synthetic analogue (m-HBDI) was synthesized. By analogy to hydroxystilbenes, longer singlet lifetimes and lower isomerization quantum yields were observed for the meta versus para isomer of the chromophore

Topology-Based Functionalization of Robust Chiral Zr-Based Metal-Organic Frameworks for Catalytic Enantioselective Hydrogenation

The design and development of robust and porous supported catalysts with high activity and selectivity is extremely significant but very challenging for eco-friendly synthesis of fine chemicals and pharmaceuticals. We report here the design and synthesis of highly stable chiral Zr(IV)-based MOFs with different topologies to support Ir complexes and demonstrate their network structures-dependent asymmetric catalytic performance. Guided by the modulated synthesis and isoreticular expansion strategy, five chiral Zr-MOFs with a flu or ith topology are constructed from enantiopure 1,1′-biphenol-derived tetracarboxylate linkers and Zr6, Zr9, or Zr12 clusters. The obtained MOFs all show high chemical stability in boiling water, strongly acidic, and weakly basic aqueous solutions. The two flu MOFs featuring the dihydroxyl groups of biphenol in open and large cages, after sequential postsynthetic modification with P(NMe2)3 and [Ir(COD)Cl]2, can be highly efficient and recyclable heterogeneous catalysts for hydrogenation of α-dehydroamino acid esters with up to 98% ee, whereas the three ith MOFs featuring the dihydroxyl groups in small cages cannot be installed with P(NMe2)3 to support the Ir complex. Incorporation of Ir-phosphorus catalysts into Zr-MOFs leads to great enhancement of their chemical stability, durability, and even stereoselectivity. This work therefore not only advances Zr-MOFs as stable supports for labile metal catalysts for heterogeneous asymmetric catalysis but also provides a new insight into how highly active chiral centers can result due to the framework topology.

Silver-Promoted Direct Phosphorylation of Bulky C(sp2)-H Bond to Build Fully Substituted β-Phosphonodehydroamino Acids

A general and practical cross-dehydrogenative coupling protocol between readily available trisubstituted α,β-dehydro α-amino carboxylic esters and H-phosphites is described. This C(sp2)-H phosphorylation reaction proceeds with absolute Z-selectivity promoted by silver salt in a radical relay manner. The bulky tetrasubstituted β-phosphonodehydroamino acids were obtained in grams and added new modules to the toolkit for peptide modifications.

Chiral bisphosphine ligands based on quinoline oligoamide foldamers: application in asymmetric hydrogenation

A series of chiral bisphosphine ligands were designed and synthesized based on single-handed quinoline oligoamide foldamers. The bisphosphine ligands can coordinate with Rh(cod)2BF4 in a 1 : 1 stoichiometry and the resulted chiral Rh(i) catalysts were applied in the asymmetric hydrogenation of α-dehydroamino acid esters, in which excellent conversions and promising levels of enantioselectivity were achieved.

An Atropos Chiral Biphenyl Bisphosphine Ligand Bearing Only 2,2′-Substituents and Its Application in Rh-Catalyzed Asymmetric Hydrogenation

An atropos chiral biphenyl bisphosphine ligand bearing only 2,2′-substituents was rationally designed and easily synthesized utilizing a bulky chiral t-butylmethylphosphino block. Computational results showed a large difference in the free energies betwee

An Atropos Biphenyl Bisphosphine Ligand with 2,2′-tert-Butylmethylphosphino Groups for the Rhodium-Catalyzed Asymmetric Hydrogenation of Enol Esters

This is an update of our previous work concerning the development of Atropos biphenyl bisphosphine ligands. An unexpected Atropos structural property was confirmed by single crystal X-ray diffraction and this result is consistent with the computational calculations described in our previous work. This P-stereogenic bisphosphine ligand possessing a biphenyl backbone and 2,2′-tert-butylmethylphosphino groups has been applied to the Rh-catalyzed asymmetric hydrogenation of enol esters, which has not been widely studied and can be used for the synthesis of several important bioactive compounds. Although there is room for further improvement in enantioselectivity, the results reported herein provide a further understanding of such types of ligands. (Figure presented.).

Synthesis of Indole-2-carboxylate Derivatives via Palladium-Catalyzed Aerobic Amination of Aryl C-H Bonds

A direct oxidative C-H amination affording 1-acetyl indolecarboxylates starting from 2-acetamido-3-arylacrylates has been achieved. Indole-2-carboxylates can be targeted with a straightforward deacetylation of the initial reaction products. The C-H amination reaction is carried out using a catalytic Pd(II) source with oxygen as the terminal oxidant. The scope and application of this chemistry is demonstrated with good to high yields for numerous electron-rich and electron-poor substrates. Further reaction of selected products via Suzuki arylation and deacetylation provides access to highly functionalized indole structures.

Cation-triggered switchable asymmetric catalysis with chiral aza-crownphos

An aza-crown ether, modified phosphoramidite ligand, has been designed and synthesized. The ON/OFF reversible switch of catalytic activity for its rhodium catalyst was thoroughly investigated in the asymmetric hydrogenation of dehydroamino acid esters modulated by host-guest interactions. In the OFF state, the catalyst is almost inactive (less than 1% conversion) because of the formation of an intermolecular sandwich complex by two aza-crown ether moities and the cationic rhodium metal center. In using alkali-metal-cations as the trigger, the catalytic activity was turned ON and consequently resulted in full conversions and excellent enantioselectivities (up to 98% ee).

Synthesis of new simplified hemiasterlin derivatives with α,β-unsaturated carbonyl moiety

In this Letter, we report a convenient and efficient method for the synthesis of new simplified derivatives of hemiasterlin in which the α,α-dimethylbenzylic moiety A is replaced by α,β- unsaturated aryl groups as Michael acceptor. Most of these derivatives have a strong cytotoxic activity on three human tumor cell lines (KB, Hep-G2 and MCF7). Analogs 17b and 17f showed a high cytotoxicity against KB and Hep-G2 cancer cell lines comparable to paclitaxel and ellipticine.

Asymmetric synthesis of unnatural amino acids and tamsulosin chiral intermediate

An efficient and enantioselective hydrogenation of N-acetylamino phenyl acrylic acids was successfully developed by using ruthenium catalyst. This methodology is important in the field of pharmaceuticals and provides a new process for the preparation of unnatural amino acids and tamsulosin chiral intermediate.