6622-73-7

Usage

Uses

Used in Pharmaceutical Industry:
4-ALLYLOXYACETANILIDE is used as a pharmaceutical intermediate for its potential role in the development of new drugs. Its unique structure allows it to be a key component in the synthesis of various medicinal compounds.
Used in Organic Chemistry:
In the field of organic chemistry, 4-ALLYLOXYACETANILIDE serves as a useful building block, facilitating the creation of a range of organic molecules. Its reactivity and functional groups make it a valuable asset in the synthesis of complex organic compounds.

InChI:InChI=1/C11H13NO2/c1-3-8-14-11-6-4-10(5-7-11)12-9(2)13/h3-7H,1,8H2,2H3,(H,12,13)

Upstream product

• 2089-30-7 C₁₁H₁₃NO₂ 
• 95-55-6 2-amino-phenol 
• 106-95-6 allyl bromide 
• 614-80-2 2-(acetylamino)phenol 
• 2079-53-0 1-(4-(allyloxy)phenyl)ethanone 
• 123-30-8 4-amino-phenol 
• 42061-89-2 5-cyano-2-furancarboxaldehyde 
• 617-90-3 2-furancarbonitrile 
• 623-17-6 furfurylacetate 
• 60838-00-8 5-cyano-furan-2-carboxylic acid methyl ester 
• 68-12-2 N,N-dimethyl-formamide 
• 57-48-7 fructose 
• 57-48-7 D-Fructose 
• 1688-69-3 p-allyloxyaniline 

Downstream Products

• 100610-04-6 1-(4-acetylamino-phenoxy)-3-acetylsulfanyl-propane 
• 84176-62-5 N-(3-allyl-4-hydroxyphenyl)acetamide 
• 36895-26-8 N-[4-(3-phenyl-4,5-dihydro-isoxazol-5-ylmethoxy)-phenyl]-acetamide 
• 114544-51-3 cis-N-<<5-(4-acetamidophenoxy)methyl-2-methyl-3-phenylisoxazolidin-3-yl>methyl>-1H-1,2,4-triazole 
• 114544-56-8 cis-N-<<5-(4-acetamidophenyloxy)methyl-3-(4-chlorophenyl)-2-methylisoxazolidin-3-yl>methyl>-1H-1,2,4-triazole 
• 88271-75-4 4-(allyloxy)aniline hydrochloride 
• 103-90-2 4-acetaminophenol 
• 41432-48-8 (2R)-1-(4-acetamidophenoxy)-2,3-propanediol 
• 56715-20-9 (2S)-1-(4-acetamidophenoxy)-2,3-propanediol 
• 114544-51-3 3-Phenyl-3-(1H-1,2,4-triazol-1-yl)methyl-2-methyl-5-[(4-acetamidophenoxy) methyl]isoxazolidine 
• 114544-56-8 3-(4-Chlorophenyl)-3-(1H-1,2,4-triazol-1-yl)methyl-2-methyl-5-[(4-acetamidophenoxy)methyl]isoxazolidine 
• 1337990-72-3 C₁₁H₁₃NO₂ 
• 1394965-64-0 C₂₆H₃₇NO₂ 
• 27096-64-6 2-(allyloxy)aniline 

Relevant academic research and scientific papers

Nickel-catalyzed deallylation of aryl allyl ethers with hydrosilanes

An efficient and mild catalytic deallylation method of aryl allyl ethers is developed, with commercially available Ni(COD)2 as catalyst precursor, simple substituted bipyridine as ligand and air-stable hydrosilanes. The process is compatible with a variety of functional groups and the desired phenol products can be obtained with excellent yields and selectivity. Besides, by detection or isolation of key intermediates, mechanism studies confirm that the deallylation undergoes η3-allylnickel intermediate pathway.

Exploring the Electronic Properties of Extended Benzofuran-Cyanovinyl Derivatives Obtained from Lignocellulosic and Carbohydrate Platforms Raw Materials

Two series of linear extended benzofuran derivatives associating cyanovinyl unit and phenyl or furan moieties obtained from benzaldehyde-lignocellulosic (Be series) or furaldehyde –saccharide (Fu series) platforms were prepared in order to investigate their emission and electrochemical properties. For the fluorescence in solution and solid states, contrasting results between the two series were demonstrated. For Be series a net aggregation induced emission effect was observed with high fluorescence quantum yield for the solid state. A [2+2] cycloaddition under irradiation at 350 nm was also revealed for one derivative of Be series. In contrast, for Fu series the fluorescence in solution is higher than in the solid state. The X-ray crystallography studies for the compounds reveal the formation of strong π-π stacking for the derivatives without emissive property in the solid state and the presence of essentially lateral contacts for emissive compounds. Taking advantage of the propensity to develop 2D π-stacking mode for the more extended derivative with a central furan cycle, organic field effect transistors presenting hole mobility have been made.

Highly Efficient Oxidative Cyanation of Aldehydes to Nitriles over Se,S,N-tri-Doped Hierarchically Porous Carbon Nanosheets

Oxidative cyanation of aldehydes provides a promising strategy for the cyanide-free synthesis of organic nitriles. Design of robust and cost-effective catalysts is the key for this route. Herein, we designed a series of Se,S,N-tri-doped carbon nanosheets with a hierarchical porous structure (denoted as Se,S,N-CNs-x, x represents the pyrolysis temperature). It was found that the obtained Se,S,N-CNs-1000 was very selective and efficient for oxidative cyanation of various aldehydes including those containing other oxidizable groups into the corresponding nitriles using ammonia as the nitrogen resource below 100 °C. Detailed investigations revealed that the excellent performance of Se,S,N-CNs-1000 originated mainly from the graphitic-N species with lower electron density and synergistic effect between the Se, S, N, and C in the catalyst. Besides, the hierarchically porous structure could also promote the reaction. Notably, the unique feature of this metal-free catalyst is that it tolerated other oxidizable groups, and showed no activity on further reaction of the products, thereby resulting in high selectivity. As far as we know, this is the first work for the synthesis of nitriles via oxidative cyanation of aldehydes over heterogeneous metal-free catalysts.

Metabolically stable 5-HMF derivatives for the treatment of hypoxia

5-HMF derivative compounds that bind covalently with hemoglobin are provided. Methods of treating sickle cell disease and other hypoxia-related disorders by administering such compounds are also provided.

Direct synthesis of secondary amides from ketones through Beckmann rearrangement using O-(mesitylsulfonyl)hydroxylamine

The Beckmann rearrangement is a versatile method for the preparation of secondary amides from ketones via oxime intermediates and has been widely used in the synthesis of bioactive natural products and pharmaceuticals. Herein, we have developed a highly efficient direct method for the preparation of secondary amides and lactams from ketones using O-(mesitylsulfonyl)hydroxylamine (MSH). The reactions proceed rapidly at room temperature under mild condition without requiring any additive, and tolerate multiple functional groups. A simple aqueous work-up often furnished the products in excellent yield with high purity.

Zinc(II)-Catalyzed Synthesis of Secondary Amides from Ketones via Beckmann Rearrangement Using Hydroxylamine-O-sulfonic Acid in Aqueous Media

A zinc(II)-catalyzed single-step protocol for the Beckmann rearrangement using hydroxylamine-O-sulfonic acid (HOSA) as the nitrogen source in water was developed. This direct method efficiently produces secondary amides under open atmosphere in a pure form after basic aqueous workup. It isenvironmentally benign and operationally simple.

CHEMICAL COMPOUNDS

The invention is directed to substituted salicylamide derivatives. Specifically, the invention is directed to compounds according to FormμLa (I): wherein R, R1,P, X, Y, and Z are as defined herein; or a pharmaceutically acceptable salt thereof. The compounds of the invention are inhibitors of CD73 and can be usefμL in the treatment of cancer, pre-cancerous syndromes and diseases associated with CD73 inhibition, such as AIDS, the treatment of HIV, autoimmune diseases, infections, atherosclerosis, and ischemia–reperfusion injury. Accordingly, the invention is further directed to pharmaceutical compositions comprising a compound of the invention. The invention is still further directed to methods of inhibiting CD73 activity and treatment of disorders associated therewith using a compound of the invention or a pharmaceutical composition comprising a compound of the invention.

Copper-Catalyzed 1,2-Bistrifluoromethylation of Terminal Alkenes

Many efficient catalytic methods for the introduction of trifluoromethyl group (CF3) have been reported. Among them, the addition of CF3 and other components to alkenes is well known, and many components such as azides, cyanides, amines, and halides have been inserted into alkenes with CF3. However, to date the double catalytic insertion of CF3 into an alkene is unknown. Herein, we report the catalytic 1,2-bistrifluoromethylations of alkenes catalyzed by Copper (Cu). We used two CF3 sources, namely Umemoto's reagent and (trifluoromethyl)trimethylsilane (TMSCF3). Each reagent plays a unique role during this transformation; Umemoto's reagent generates CF3 radicals, while TMSCF3 is used to form CF3 anions. Copper (I) bromide (CuBr) exhibited the best catalytic activity for this reaction. We believe that CuBr oxidizes the alkyl radical, which is produced by the addition of the CF3 radical to the alkene, to the corresponding alkyl cation, which then reacts with the CF3 anion from TMSCF3 to produce the desired product. This reaction tolerates a diverse set of substrates bearing functional groups such as amides, esters, ethers, ketones, protected amines, tertiary amines, and phthalimides; hence this transformation is widely applicable to a wide variety of substrates. (Figure presented.).

Cu(OTf) 2 -Catalyzed Beckmann Rearrangement of Ketones Using Hydroxylamine- O -sulfonic Acid (HOSA)

The Beckmann rearrangement (BKR) of ketones to secondary amides often requires harsh reaction conditions that limit its practicality and scope. Herein, the Cu(OTf) 2 -catalyzed BKR of ketones under mild reaction conditions using hydroxylamine- O -sulfonic acid (HOSA), a commercial water soluble aminating agent, is described. This method is compatible with most functional groups and directly provides the desired amides in good to excellent yields.

Method for preparing 5-hydroxymethyl-2-furannitrile through catalytic ammoxidation

The invention belongs to the organic synthesis field and particularly relates to a method for preparing 5-hydroxymethyl-2-furannitrile through catalytic ammoxidation. The method comprises the steps ofcarrying out ammoxidation reaction under the effect of a catalyst by taking 5-hydroxymethyl furfural as the raw material, one or two of oxygen or air as an oxidant and one or at least two of liquid ammonia, ammonia water or ammonia salt as a nitrogen source, carrying out centrifugation so as to remove the catalyst, carrying out rotary evaporation so as to remove a solvent, and carrying out purification by virtue of a column chromatography, so as to obtain a 5-hydroxymethyl-2-furannitrile product. The product of the method is high in yield and easy to separate and has very good application prospects.