10024-90-5

Usage

Preparation

Preparation by reaction of acetic anhydride with 2-methylanisole in the presence of lithium perchlorate at 60° for 1.5 h (99%).

InChI:InChI=1/C10H12O2/c1-7-6-9(8(2)11)4-5-10(7)12-3/h4-6H,1-3H3

Upstream product

• 578-58-5 2-methylmethoxybenzene 
• 75-36-5 acetyl chloride 
• 31040-84-3 4-tert-butyl-2-methylanisole 
• 64-19-7 acetic acid 
• 7646-78-8 tin(IV) chloride 
• 71-43-2 benzene 
• 876-02-8 4-hydroxy-3-methylphenyl methyl ketone 
• 74-88-4 methyl iodide 
• 584-08-7 potassium carbonate 
• 24766-96-9 3-acetoxy-2,5-dioxo-tetrahydrofuran 
• 2364-65-0 diethyl 2,3-diacetoxysuccinate 
• 92381-33-4 Dimethyl (R,S)-2-O-Acetylmalate 
• 7554-25-8 diethyl 2-acetoxysuccinate 
• 1445852-64-1 1-allyl-2,5-dioxopyrrolidine-3,4-diyl diacetate 

Downstream Products

• 6880-04-2 4-methoxy-3-methylbenzoic acid 
• 64597-54-2 (E)-2-Cyano-3-(4-methoxy-3-methyl-phenyl)-but-2-enoic acid ethyl ester 
• 876-02-8 4-hydroxy-3-methylphenyl methyl ketone 
• 90843-06-4 4‐ethynyl‐1‐methoxy‐2‐methylbenzene 
• 188716-73-6 3-[2-(4-Methoxy-3-methyl-phenyl)-2-oxo-ethyl]-3H-isobenzofuran-1-one 
• 858213-43-1 2,3-bis-(4-methoxy-3-methyl-phenyl)-butane-2,3-diol 
• 65081-26-7 1-(3'-methyl-4'-methoxyphenyl)-3-phenylprop-2-ene-1-one 
• 855174-77-5 1-(3'-methyl-4'-methoxyphenyl)-3-(4''-methoxyphenyl)prop-2-ene-1-one 
• 433732-65-1 (E)-3-(4-Methoxy-3-methyl-phenyl)-but-2-enoic acid ethyl ester 
• 853655-44-4 1-(3-bromomethyl-4-methoxy-phenyl)-ethanone 
• 304647-94-7 4-[3-difluoromethyl-5-(4-methoxy-3-methyl-phenyl)-pyrazol-1-yl]-2-hydroxymethyl-benzenesulfonamide 
• 304647-49-2 2-hydroxymethyl-4-[5-(4-methoxy-3-methyl-phenyl)-3-trifluoromethyl-pyrazol-1-yl]-benzenesulfonamide 

Relevant academic research and scientific papers

Synthetic Studies on Nogarol Anthracyclines. Enantioselective Total Synthesis of an Aminohydroxy Epoxybenzoxocin

A chiral synthesis of the aminohydroxy expoxybenzoxocin 6 is described. Enantioselective Friedel-Crafts coupling using a chiral titanium catalyst was employed to produce the optically active atrolactic ester 16a from the phenol 11 and l-menthyl pyruvate (12). The phenolic group in 16a was protected as the benzyl ether and the t-alcohol functionality as the MEM ether to give 20, which after sequential reduction/oxidation provided the aldehyde 22. Addition of the acetylide anion of propargyl aldehyde diethyl acetal (23) to aldehyde 22, followed by oxidation of the resultant diastereoisomeric carbinols, gave the acetylenic ketone 24. Lindlar reduction of 24 afforded the trans-enone 26. Reaction of 26 with thiophenylate anion furnished 27, which was then cyclized to the α-methyl pyranoside 29. Oxidation of 29 to the sulfoxide and subsequent thermolysis afforded the hexenulose 30. Sequential epoxidation of 30, reduction of the keto epoxide 31, and reaction of the resultant epoxycarbinol 32 with dimethylamine produced the aminohydroxy pyranose 33a. Debenzylation of 33a to the phenol 33b, followed by intramolecular cyclization, completed the fabrication of the optically active aminohydroxy epoxybenzoxocin 6. The 17-step sequence from the phenol 11 to 6 was achieved in 22% overall yield.

Photoinduced Acetylation of Anilines under Aqueous and Catalyst-Free Conditions

A green and efficient visible-light induced functionalization of anilines under mild conditions has been reported. Utilizing nontoxic, cost-effective, and water-soluble diacetyl as photosensitizer and acetylating reagent, and water as the solvent, a variety of anilines were converted into the corresponding aryl ketones, iodides, and bromides. With advantages of environmentally friendly conditions, simple operation, broad substrate scope, and functional group tolerance, this reaction represents a valuable method in organic synthesis.

THIADIAZINE DERIVATIVES

The invention relates to thiadiazine derivatives, or pharmaceutically acceptable salts, biologically active metabolites, pro-drugs, racemates, enantiomers, diastereomers, solvates and hydrates thereof, as well as to pharmaceutical compositions containing

Vanadium-Catalyzed Oxidative Intramolecular Coupling of Tethered Phenols: Formation of Phenol-Dienone Products

A mild and efficient method for the vanadium-catalyzed intramolecular coupling of tethered free phenols is described. The corresponding phenol-dienone products are prepared directly in good yields with low catalyst loadings. Electronically diverse tethered phenol precursors are well tolerated, and the catalytic method was effectively applied as the key step in syntheses of three natural products and a synthetically useful morphinan alkaloid precursor.

Facile preparation of 5-alkyl-1-aryltetrazoles with arenes, acyl chlorides, hydroxylamine, and diphenylphosphoryl azide

Successive treatment of arenes with acyl chlorides and AlCl3, the addition of water and removal of solvent, the reaction with NH2OH?HCl and K2CO3, and the reaction with diphenylphosphoryl azide and DBU under warming conditions gave the corresponding 5-alkyl-1-aryltetrazoles efficiently in good to moderate yields. The present method is one-pot transformation of arenes into 5-alkyl-1-aryltetrazoles using the Friedel-Crafts acylation and the Beckmann rearrangement under transition-metal-free conditions.

A methylation platform of unconventional inert aryl electrophiles: Trimethylboroxine as a universal methylating reagent

Methylation is one of the most fundamental conversions in medicinal and material chemistry. Extension of substrate types from aromatic halides to other unconventional aromatic electrophiles is a highly important yet challenging task in catalytic methylation. Disclosed herein is a series of transition metal-catalyzed methylations of unconventional inert aryl electrophiles using trimethylboroxine (TMB) as the methylating reagent. This transformation features a broad substrate type, including nitroarenes, benzoic amides, benzoic esters, aryl cyanides, phenol ethers, aryl pivalates and aryl fluorides. Another important merit of this work is that these widespread "inert"functionalities are capable of serving as directing or activating groups for selective functionalization of aromatic rings before methylation, which greatly expands the connotation of methylation chemistry.

Metal-Free Photoinduced Transformation of Aryl Halides and Diketones into Aryl Ketones

The acylation of aryl halides to prepare aryl ketones without metal catalyst represents an important yet challenging topic towards more sustainable ketone synthesis. Herein, we describe a simple and efficient metal-free protocol for the acylation of aryl halides with diketone under the irradiation of light utilizing N-methylpiperidine as base under an air atmosphere. This reaction can tolerate a wide range of functional groups and the corresponding ketones can be obtained in modest to good yields.

Synthesis of Highly Enantio-Enriched Heliespirones A and C by a Diastereoselective Aromatic Claisen Rearrangement

Computational methods were used to investigate the stereochemical course of the extra-annular Claisen rearrangement. The stereochemical fidelity of the synthetic strategy and comparison of the optical properties support the hypothesis that the heliespirones are scalemic natural products.

Synthesis and catalytic reactivity in Friedel–Crafts acylations of monobridged bis(cyclopentadienyl)molybdenum(I) carbonyl complexes

When the monobridged biscyclopentadienes (C5H5)R(C5H5) [R = C(CH3)2 (1), Si(CH3)2 (2), C(CH2)5 (3)] reacted with Mo(CO)6 in refluxing xylene, the corresponding complexes [(η5-C5H4)2R][Mo(CO)3]2 [R = C(CH3)2 (4), Si(CH3)2 (5), C(CH2)5 (6)] were obtained. These complexes were separated by chromatography and characterized by elemental analysis, IR, and 1H NMR spectroscopy. The molecular structures of 4 and 5 were determined by X-ray diffraction analysis. Friedel–Crafts acylation reactions of anisole derivatives with aromatic or aliphatic acyl chlorides catalyzed by complexes 4–6 showed that all of these monobridged bis(cyclopentadienyl)molybdenum carbonyl complexes have catalytic activity.

Air-stable μ2-hydroxyl bridged cationic binuclear complexes of zirconocene perfluorooctanesulfonates: their structures, characterization and application

Three air-stable zirconocene perfluoro-octanesulfonates were successfully synthesized by treatment of C8F17SO3Ag with (RCp)2ZrCl2 [R = H, n-Bu, t-Bu]. According to X-ray analysis, they have μ2-hydroxyl bridged cationic binuclear structures: (i) [CpZr(OH2)3]2(μ2-OH)2(OSO2C8F17)4·2THF·4H2O (1a·2THF·4H2O), (ii) [n-BuCpZr(OH2)3]2(μ2-OH)2(OSO2C8F17)4·6H2O (2a·6H2O), and (iii) [t-BuCpZr(OH2)3]2(μ2-OH)2(OSO2C8F17)4·2C3H6O·8H2O (3a·2C3H6O·8H2O). The ligands of water and organic molecules in the complexes originated from the moist air and solvent during their recrystallization. These complexes were characterized with different techniques, and found to show water tolerance, air/thermal stability as well as strong Lewis acidity. Moreover, the complexes showed highly catalytic activity in various reactions of C–C bond formation. With good recyclability, they should find wide applications in organic chemistry.