17137-11-0

Usage

Uses

Used in Pharmaceutical Industry:
1,3-dihydro-1,3-dioxo-2H-isoindole-2-propionyl chloride is used as a synthetic intermediate for the development of pharmaceuticals. Its reactivity enables the formation of new compounds with potential therapeutic properties, contributing to the advancement of medicinal chemistry.
Used in Agrochemical Industry:
In the agrochemical sector, 1,3-dihydro-1,3-dioxo-2H-isoindole-2-propionyl chloride serves as a key intermediate in the synthesis of various agrochemicals. Its ability to undergo chemical reactions allows for the creation of compounds with applications in crop protection and pest management.
Used in Chemical Reactions:
1,3-dihydro-1,3-dioxo-2H-isoindole-2-propionyl chloride is used as a reactive component in chemical reactions, particularly condensation reactions with primary amines to form amides. This property makes it a valuable building block in organic synthesis and the development of new chemical entities.
Environmental Considerations:
Given its potential as an environmental contaminant, 1,3-dihydro-1,3-dioxo-2H-isoindole-2-propionyl chloride requires proper handling and disposal to prevent adverse effects on human health and the environment. It is essential to follow safety protocols and regulations in its use and management to mitigate any negative impacts.

InChI:InChI=1/C11H8ClNO3/c12-9(14)5-6-13-10(15)7-3-1-2-4-8(7)11(13)16/h1-4H,5-6H2

Upstream product

• 3339-73-9 3-phthalimidopropanoic acid 
• 85-44-9 phthalic anhydride 
• 56-40-6 glycine 
• 107-95-9 3-amino propanoic acid 
• 88-99-3 benzene-1,2-dicarboxylic acid 
• 1219456-88-8 potassium-3-(1,3-dioxoisoindolin-2-yl)propanoate 

Downstream Products

• 87503-54-6 bis-{2-[(N,N-phthaloyl-β-alanyl)-amino]-ethyl}-disulfide 
• 112508-47-1 (+/-)-N,N-phthaloyl-β-alanine-menthyl ester 
• 112271-42-8 N,N-phthaloyl-β-alanine-(2-benzylmercapto-ethylamide) 
• 112508-47-1 N,N-phthaloyl-β-alanine-((1R)-menthyl ester) 
• 4443-34-9 3-(1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl)-N-phenylpropanamide 
• 4905-27-5 N-benzyl-3-(1,3-dioxo-1,3-dihydroisoindol-2-yl)propionamide 
• 2746-33-0 Orphidin 
• 2436-29-5 3-(N-phthaloyl)propionaldehyde 
• 53932-60-8 (E)-5-(N-phthalimido)-pent-2-enoic acid 
• 218800-38-5 (S)-4-(1-methylethyl)-3-<1-oxo-3-phthalimidopropyl>-5,5-diphenyloxazolidin-2-one 
• 7504-49-6 2-(4-diazo-3-oxobutyl)isoindoline-1,3-dione 

Relevant academic research and scientific papers

Regioselective β-Csp3-Arylation of β-Alanine: An Approach for the Exclusive Synthesis of Diverse β-Aryl-β-amino Acids

An approach for the synthesis of a variety of new β-aryl-β-amino acids has been developed via a palladium-catalyzed auxiliary-directed regioselective Csp3-H arylation of the unactivated β-methylene bond of β-alanine. The use of 8-aminoquinoline amide as an auxiliary efficiently directs the desired regioselective β-Csp3-H functionalization. The developed protocol enables the easy and straightforward access to several high-value β-aryl-β-amino acids useful for peptide engineering, starting from inexpensive and readily available β-alanine precursors in moderate to excellent yields.

Perfluorinated markers for hypoxia detection: Synthesis of sulfur-containing precursors and [18F]-labelling

Synthetic pathways of two novel sulfurated precursors for [ 18F]-labelling by oxidative fluorodesulfurization reaction are described. A three-step sequence starting from N-phthalimido-β-alanine allows the preparation of a new trithioorthoester as valuable precursor of the synthesis of [18F]-3,3,3-trifluoropropylamine, a convenient radiolabelled intermediate for [18F]-EF3. A five-step sequence for the preparation of methyl 4-phthalimido-2,2-difluoropropanedithioate from ethyl 2,2-difluoropropanoate, via the key conversion step of α,α′- difluorothioamidate to the corresponding α,α′- difluorodithioester, and the first results of its use as precursor for oxidative fluorodesulfurization in [18F]-radiochemistry are also presented.

Stereoselective sulfoxide formation from a thioproline derivative

Oxidation of the PEP inhibitor, thioprolylpyrrolidine derivative 3 affords a mixture of the two possible trans- and cis-sulfoxide isomers 4 and 5. 3-Chloroperbenzoic acid oxidation resulted almost exclusive formation of the trans-isomer (α-sulfoxide, 4, d.e. >99% in CHCl3), whereas when NaIO4 was used the cis isomer (β-sulfoxide, 5) was also obtained, the ratio of the isomers varying with the reaction conditions applied. The structures of the separated isomers 4 and 5 were assigned on the basis of the aromatic solvent-induced shifts (ASIS) in the NMR spectra.

Synthesis of N-trifluoromethyl amides from carboxylic acids

Found in biomolecules, pharmaceuticals, and agrochemicals, amide-containing molecules are ubiquitous in nature, and their derivatization represents a significant methodological goal in fluorine chemistry. Trifluoromethyl amides have emerged as important functional groups frequently found in pharmaceutical compounds. To date, there is no strategy for synthesizing N-trifluoromethyl amides from abundant organic carboxylic acid derivatives, which are ideal starting materials in amide synthesis. Here, we report the synthesis of N-trifluoromethyl amides from carboxylic acid halides and esters under mild conditions via isothiocyanates in the presence of silver fluoride at room temperature. Through this strategy, isothiocyanates are desulfurized with AgF, and then the formed derivative is acylated to afford N-trifluoromethyl amides, including previously inaccessible structures. This method shows broad scope, provides a platform for rapidly generating N-trifluoromethyl amides by virtue of the diversity and availability of both reaction partners, and should find application in the modification of advanced intermediates.

Quinazolinyl carboxylic ester derivative containing isoindolone group and application thereof

The invention discloses a quinazolinyl carboxylic ester derivative containing an isoindolone group, and the derivative has a structural general formula shown as the specification, wherein R is aryl substituted alkyl, aryl substituted cyclolky or biaryl. According to the invention, the novel isoindolone group-containing quinazolinyl carboxylic ester derivative is synthesized, can effectively inhibit the growth of antibiotic-sensitive or drug-resistant bacteria, and has a new action mechanism.

Binuclear Pd(I)-Pd(I) Catalysis Assisted by Iodide Ligands for Selective Hydroformylation of Alkenes and Alkynes

Since its discovery in 1938, hydroformylation has been thoroughly investigated and broadly applied in industry (>107 metric ton yearly). However, the ability to precisely control its regioselectivity with well-established Rh- or Co-catalysts has thus far proven elusive, thereby limiting access to many synthetically valuable aldehydes. Pd-catalysts represent an appealing alternative, yet their use remains sparse due to undesired side-processes. Here, we report a highly selective and exceptionally active catalyst system that is driven by a novel activation strategy and features a unique Pd(I)-Pd(I) mechanism, involving an iodide-assisted binuclear step to release the product. This method enables β-selective hydroformylation of a large range of alkenes and alkynes, including sensitive starting materials. Its utility is demonstrated in the synthesis of antiobesity drug Rimonabant and anti-HIV agent PNU-32945. In a broader context, the new mechanistic understanding enables the development of other carbonylation reactions of high importance to chemical industry.

A Convenient One-Pot Synthesis of 1,5-Disubstituted Tetrazoles Containing an Amino or a Carboxy Group

Abstract: A convenient method is proposed for constructing the tetrazole ring by a one-pot reaction of amides with phosphorus oxychloride and sodium azide. A series of 1,5-disubstituted tetrazoles containing an amino or a carboxy group, which present interest as buildings blocks for the synthesis of biologically active substances, were obtained.

A chemically contiguous hapten approach for a heroin-fentanyl vaccine

Background: Increased death due to the opioid epidemic in the United States has necessitated the development of new strategies to treat addiction. Monoclonal antibodies and antidrug vaccines provide a tool that both aids addiction management and reduces the potential for overdose. Dual drug vaccines formulated by successive conjugation or by mixture have certain drawbacks. The current study examines an approach for combatting the dangers of fentanyl-laced heroin, by using a hapten with one epitope that has domains for both fentanyl and heroin. Results: We evaluated a series of nine vaccines developed from chemically contiguous haptens composed of both heroin- and fentanyl-like domains. Analysis of the results obtained by SPR and ELISA revealed trends in antibody affinity and titers for heroin and fentanyl based on epitope size and linker location. In antinociception studies, the best performing vaccines offered comparable protection against heroin as our benchmark heroin vaccine, but exhibited attenuated protection against fentanyl compared to our fentanyl vaccine. Conclusion: After thorough investigation of this strategy, we have identified key considerations for the development of a chemically contiguous heroin-fentanyl vaccine. Importantly, this is the first report of such a strategy in the opioid-drug-vaccine field.

Rh(III)-Catalyzed C-H Amidation of Arenes with N-Methoxyamide as an Amidating Reagent

The Rh(III)-catalyzed amidation of C(sp2)-H bonds has been reported by employing the N-methoxyamide as a novel amino source. An excellent level of functional group tolerance can be achieved when N-methoxyamide derivatives are used as the amidating reagents. Importantly, several known bioactive compounds such as Aminalon, Pregabalin, Gabapentin, and Probenecid can be transformed to effective amidating reagents, as a way to facilitate the development of new bioactive molecules.

A Direct Approach to Decoration of Bioactive Compounds via C-H Amination Reaction

The development of new methods to achieve the direct synthesis of bioactive organic molecules is always an important topic in organic synthesis. We hereby demonstrate that N-methoxyamide is an excellent amino source in the iridium-catalyzed intermolecular C-H amination reaction. The linkage of two bioactive organic molecules can be well achieved with this new protocol. More than 20 examples of decorated bioactive compounds were reported, which can facilitate the discovery of new bioactive molecules.