17720-64-8

Usage

General Description

2-(acetyloxy)-1H-isoindole-1,3(2H)-dione, also known as acetylsalicylic acid, is a common pain reliever and anti-inflammatory medication. It is a white, crystalline powder that is widely used to alleviate minor aches and pains, reduce fever, and help relieve inflammation. Acetylsalicylic acid works by blocking the production of certain natural substances that cause pain, fever, and inflammation in the body. It is a nonsteroidal anti-inflammatory drug (NSAID) and is also used for the prevention of heart attacks, strokes, and blood clot formation. However, it is important to use this medication as directed by a doctor, as it can have potential side effects and interactions with other drugs.

Upstream product

• 524-38-9 N-hydroxyphthalimide 
• 64-19-7 acetic acid 
• 75-36-5 acetyl chloride 
• 506-96-7 Acetyl bromide 
• 108-24-7 acetic anhydride 
• 637-92-3 Ethyl tert-butyl ether 
• 136918-14-4 phthalimide 
• 3249-68-1 ethyl butyroyl acetate 
• 15263-19-1 N-chlorocarbonyloxy-phthalimide 
• 78816-91-8 bis(1,3-dioxoisoindolin-2-yl)carbonate 
• 17698-09-8 2-[(hydroxyamino)carbonyl]benzoic acid 

Downstream Products

• 33861-55-1 N³-Ac-N⁶-Z-L-β-lys-OtBu 
• 33861-54-0 N⁶-Ac-N³-(di-Ac-L-β-lys)-L-β-lys-OMe 
• 33861-49-3 N³-Acetyl-N⁶-(diacetyl-L-β-lys)-L-β-lys-OMe 
• 17698-09-8 2-[(hydroxyamino)carbonyl]benzoic acid 
• 118-92-3 anthranilic acid 
• 195062-57-8 p-tolylboronic pinacol ester 
• 53380-21-5 γ-ethyl-γ-phenyl-butyrolactone 
• 180295-28-7 triethyl(1-methyl-3-phenyl-propoxy)silane 
• 13350-45-3 methyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside 
• 524-38-9 N-hydroxyphthalimide 
• 160809-34-7 4-acetyl-piperidine-1-carboxylic acid benzyl ester 
• 2445-82-1 3-methylcoumarine 
• 1198-37-4 2,4-dimethylquinoline 
• 82863-69-2 (R)-(+)-2-Phenylbutyronitrile 

Relevant academic research and scientific papers

From Esters to Ketones via a Photoredox-Assisted Reductive Acyl Cross-Coupling Strategy

A method was developed for ketone synthesis via a photoredox-assisted reductive acyl cross-coupling (PARAC) using a nickel/photoredox dual-catalyzed cross-electrophile coupling of two different carboxylic acid esters. A variety of aryl, 1°, 2°, 3°-alkyl 2-pyridyl esters can act as acyl electrophiles while N-(acyloxy)phthalimides (NHPI esters) act as 1°, 2°, 3°-radical precursors. Our PARAC strategy provides an alternative and reliable way to synthesize various sterically congested 3°-3°, 3°-2°, and aryl-3° ketones under mild and highly unified conditions, which have been otherwise difficult to access. The combined experimental and computational studies identified a Ni0/NiI/NiIII pathway for ketone formation.

PCET-Based Ligand Limits Charge Recombination with an Ir(III) Photoredox Catalyst

Upon photoinitiated electron transfer, charge recombination limits the quantum yield of photoredox reactions for which the rates for the forward reaction and back electron transfer are competitive. Taking inspiration from a proton-coupled electron transfe

Organophotoredox-Catalyzed Formation of Alkyl-Aryl and -Alkyl C-S/Se Bonds from Coupling of Redox-Active Esters with Thio/Selenosulfonates

A mild organophotoredox synthetic protocol for forming a Csp3-S/Se bond by reacting widespread redox-active esters with thio/selenosulfonates has been developed. The power of the synthetic manifold is fueled by an unprecedented broad substrate scope and wide functional group tolerance.

KMnO4-catalyzed chemoselective deprotection of acetate and controllable deacetylation-oxidation in one pot

A novel and efficient protocol for chemoselective deacetylation under ambient conditions was developed using catalytic KMnO4. The stoichiometric use of KMnO4 highlighted the dual role of a heterogeneous oxidant enabling direct access to aromatic aldehydes in one-pot sequential deacetylation-oxidation. The reaction employed an alternative solvent system and allowed the clean transformation of benzyl acetate to sensitive aldehyde in a single step while preventing over-oxidation to acids. Use of inexpensive and readily accessible KMnO4 as an environmentally benign reagent and the ease of the reaction operation were particularly attractive, and enabled the controlled oxidation and facile cleavage of acetate in a preceding step. This journal is

Visible-light-induced regioselective alkylation of coumarins via decarboxylative coupling with N-hydroxyphthalimide esters

An efficient photocatalytic decarboxylative 3-position alkylation of coumarins by using alkyl N-hydroxyphthalimide esters as alkylation reagents has been developed. A variety of NHP esters derived from aliphatic carboxylic acids (primary, secondary, and tertiary) has been proved to be tolerated for this decarboxylation process, affording a broad scope of 3-alkylated coumarin derivatives in moderate to excellent yields. This protocol was highlighted by its mild conditions, readily available starting materials, operational simplicity, and wide functional group tolerance.

Ketones from Nickel-Catalyzed Decarboxylative, Non-Symmetric Cross-Electrophile Coupling of Carboxylic Acid Esters

Synthesis of the C?C bonds of ketones relies upon one high-availability reagent (carboxylic acids) and one low-availability reagent (organometallic reagents or alkyl iodides). We demonstrate here a ketone synthesis that couples two different carboxylic acid esters, N-hydroxyphthalimide esters and S-2-pyridyl thioesters, to form aryl alkyl and dialkyl ketones in high yields. The keys to this approach are the use of a nickel catalyst with an electron-poor bipyridine or terpyridine ligand, a THF/DMA mixed solvent system, and ZnCl2 to enhance the reactivity of the NHP ester. The resulting reaction can be used to form ketones that have previously been difficult to access, such as hindered tertiary/tertiary ketones with strained rings and ketones with α-heteroatoms. The conditions can be employed in the coupling of complex fragments, including a 20-mer peptide fragment analog of Exendin(9–39) on solid support.

Organocatalyzed, Visible-Light Photoredox-Mediated, One-Pot Minisci Reaction Using Carboxylic Acids via N-(Acyloxy)phthalimides

An improved, one-pot Minisci reaction has been developed using visible light, an organic photocatalyst, and carboxylic acids as radical precursors via the intermediacy of in situ-generated N-(acyloxy)phthalimides. The conditions employed are mild, demonstrate a high degree of functional group tolerance, and do not require a large excess of the carboxylic acid reactant. As a result, this reaction can be applied to drug-like scaffolds and molecules with sensitive functional groups, enabling late-stage functionalization, which is of high interest to medicinal chemistry.

Photoredox-Catalysed Decarboxylative Alkylation of N-Heteroarenes with N-(Acyloxy)phthalimides

An iridium photoredox catalyst in combination with either a stoichiometric amount of Br?nsted acid or a catalytic amount of Lewis acid is capable of catalyzing regioselective alkylation of N-heteroarenes with N-(acyloxy)phthalimides at room temperature un

Copper nitrate-catalyzed oxidative coupling of unactivated C(sp3)-H bonds of ethers and alkanes with: N -hydroxyphthalimide: Synthesis of N -hydroxyimide esters

A copper nitrate-catalyzed cross-dehydrogenative coupling reaction between N-hydroxyphthalimide (NHPI) and ethers/alkanes has been described. The reaction is accomplished smoothly by using simple and green molecular oxygen as the oxidant, providing an alternative for the efficient synthesis of N-alkoxyphthalimides. In addition, it was found that when tert-butyl ethers were used as substrates, unexpected N-hydroxyimide ester derivatives were obtained in moderate to excellent yields. To further understand this unusual transformation, control experiments were performed and a plausible mechanism was proposed.