3485-84-5

Usage

Uses

Used in Pharmaceutical Industry:
N-Vinylphthalimide is used as a reactant for the synthesis of trifluoromethylaryl-substituted fused piperidinecarboxamides. These compounds are significant in the development of TRPM8 cation channel inhibitors, which have potential applications in various therapeutic areas, including pain management and temperature regulation. The inhibition of TRPM8 channels can lead to the alleviation of pain and modulation of cold sensations, making them valuable targets for pharmaceutical research and development.

InChI:InChI=1/C10H7NO2/c1-2-11-9(12)7-5-3-4-6-8(7)10(11)13/h2-6H,1H2

Upstream product

• 136918-14-4 phthalimide 
• 74-86-2 acetylene 
• 3891-07-4 N-(2-Hydroxyethyl)phthalimide 
• 574-98-1 2-(2-bromoethyl)isoindoline-1,3-dione 
• 16199-06-7 potassium pyrrolide 
• 5466-90-0 2-(1,3(2H)-dioxo-1H-isoindol-2-yl)ethyl acetate 
• 22156-21-4 rac-1-(1,3-dioxoisoindolin-2-yl)ethyl acetate 
• 53701-47-6 2-(1,3-dioxoisoindolin-2-yl)propanoyl chloride 
• 5587-42-8 imidazolyl sodium 
• 95445-79-7 3-methyl 5-(1-methylethyl) 4-(3-chloro-6-fluoro-2-(trifluoromethyl)phenyl)-2-(fluoromethyl)-1,4-dihydro-6-methyl-3,5-pyridinedicarboxylate 
• 29588-89-4 (2S)-2-(1,3-dioxoisoindolin-2-yl)-3-hydroxypropanoic acid 
• 29588-96-3 N,N-diphthaloyl-L,L-cystine 
• 48165-80-6 phthaloyl cysteine 
• 185342-50-1 N-phthaloyl-S-carboxymethyl-cysteine 

Downstream Products

• 101586-53-2 N-(1-cyclohexylamino-ethyl)-phthalimide 
• 2142-04-3 2-(4-methoxyphenyl)isoindoline-1,3-dione 
• 5383-82-4 4-phthalimidobenzoic acid 
• 520-03-6 N-phenylphthalimide 
• 16260-70-1 N-vinyl-phthalamic acid 
• 39739-01-0 methyl 3-(1,3-dioxoisoindolin-2-yl)propanoate 
• 33745-25-4 methyl 2-(1,3-dioxoisoindolin-2-yl)propanoate 
• 22156-23-6 N-(1-methoxyethyl)phthalimide 
• 39895-15-3 methyl 2-(1,3-dioxoisoindolin-2-yl)propanoate 
• 75082-78-9 (S)-methyl 2-(1,3-dioxoisoindolin-2-yl)propanoate 
• 116856-62-3 4-<(tert-buthoxycarbonyl)methyl>-β-N-phthalimidostyrene 
• 51482-36-1 2-(N-phthaloylamino)propanal 
• 2436-29-5 3-(N-phthaloyl)propionaldehyde 
• 73365-03-4 (R)-(+)-2-N-phthalimidopropanal 

Relevant academic research and scientific papers

Synthesis and biological properties of novel structural analogs of isothiobarbamine

Novel structural analogs of isothiobarbamine, which differ from the prototype scaffold by the substituent at position 2 of the pyrimidine heterocycle, were for the first time synthesized and characterized. Data acquired in pharmacological experiments in vivo revealed that compounds 1b—d and 10 increase physical productivity, whereas compounds 1c and 10 exhibit a nootropic effect, compound 8a shows a psychostimulating effect, and compound 1b exhibits anxiolytic properties. The results reported herein indicate that the drug discovery based on new structural analogs of isothiobarbamine is promising since it may lead to drugs for the prevention and treatment of asthenia (chronic fatigue syndrome).

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.

Michaelis-Arbuzov-type reaction of 1-imidoalkyltriarylphosphonium salts with selected phosphorus nucleophiles

In this study, Michaelis-Arbuzov-type reaction of 1-imidoalkyltriarylphosphonium salts with phosphites, phosphonites, and phosphinites was used in the synthesis of a wide range of phosphorus analogs of α-amino acids such as 1-imidoalkylphosphonates, 1-imidoalkylphosphinates, and 1-imidoalkylphosphine oxides. Large differences were observed in the reactivity of substrates depending on their structure, especially on the type of phosphonium moiety and N-protecting group. The conditions under which the expected products can be obtained in good to excellent yields have been developed. Mechanistic aspects of the transformation have been provided.

Normal Alpha Olefin Synthesis Using Dehydroformylation or Dehydroxymethylation

The present invention discloses processes for producing normal alpha olefins, such as 1-hexene, 1-octene, 1-decene, and 1-dodecene in a multistep synthesis scheme from another normal alpha olefin. Also disclosed are reactions for converting aldehydes, primary alcohols, and terminal vicinal diols into normal alpha olefins.

Oxidative Dehydroxymethylation of Alcohols to Produce Olefins

Catalyst compositions for the conversion of aldehyde compounds and primary alcohol compounds to olefins are disclosed herein. Reactions include oxidative dehydroxymethylation processes and oxidative dehydroformylation methods, which are beneficially conducted in the presence of a sacrificial acceptor of H2 gas, such as N,N-dimethylacrylamide.

Regio- and Stereoselective Chan-Lam-Evans Enol Esterification of Carboxylic Acids with Alkenylboroxines

Efficient and scalable Cu(II)-mediated enol esterification methodology of carboxylic acids from alkenyl boroxines and boronic acids is presented. The reaction shows a wide scope in aliphatic and aromatic carboxylic acids in combination with several alkenyl boroxines. In the case of 2-substituted alkenyl boroxines the double bond configuration was fully retained in the enol ester product. Also N-hydroxyimides and imides could be transformed in the respective amidooxy vinyl enol ethers and vinyl enamides. Finally, with the exception of methionine, all other 19 canonical amino acids showed their compatibility to give the enol esters in a stereoselective fashion. (Figure presented.).

Tandem Catalysis: Transforming Alcohols to Alkenes by Oxidative Dehydroxymethylation

We report a Rh-catalyst for accessing olefins from primary alcohols by a C-C bond cleavage that results in dehomologation. This functional group interconversion proceeds by an oxidation-dehydroformylation enabled by N,N-dimethylacrylamide as a sacrificial acceptor of hydrogen gas. Alcohols with diverse functionality and structure undergo oxidative dehydroxymethylation to access the corresponding olefins. Our catalyst protocol enables a two-step semisynthesis of (+)-yohimbenone and dehomologation of feedstock olefins.

1-Imidoalkylphosphonium salts with modulated Cα–P+ bond strength: synthesis and application as new active α-imidoalkylating agents

An effective synthesis of the hitherto unknown 1-imidoalkylphosphonium salts has been developed in the reported study. The crucial step in the method included the decarboxylative α-methoxylation of N-phthaloyl- or N-succinylamino acids to the corresponding N-(1-methoxyalkyl)imides, followed by the displacement of the methoxy group by the triarylphosphonium group through melting of the imide derivative with triarylphosphonium tetrafluoroborate. The imidoalkylating properties of the obtained 1-imidoalkylphosphonium salts were tested using the Tscherniac–Einhorn-type reaction with aromatic hydrocarbons as a model reaction. It was found that the Cα–P+ bond strength can be considerably reduced and the imidoalkylation of arenes can be markedly facilitated using 1-imidoalkylphosphonium salts derived from triarylphosphines with electron-withdrawing substituents such as tris(m-chorophenyl)phosphine, tris(p-chlorophenyl)phosphine and tris[p-(trifluoromethyl)phenyl]phosphine. Microwave irradiation also considerably facilitates the cleavage of the highly polar Cα–P+ bond.

Application of Pd Nanoparticles Supported on Mesoporous Hollow Silica Nanospheres for the Efficient and Selective Semihydrogenation of Alkynes

Herein, the preparation of a heterogeneous catalyst consisting of 1-2 nm sized Pd nanoparticles supported on amino-functionalized mesoporous hollow silica nanospheres and its use for the semihydrogenation of mono- And disubstituted alkynes is reported. By utilizing this Pd nanocatalyst together with the green poisoning agent DMSO, high yields of the desired alkenes could be achieved, while suppressing the degree of over-reduction to alkanes. To our delight, the Pd nanocatalyst displayed remarkable chemoselectivity towards the alkyne moiety, allowing the transformation to be carried out in the presence of other reducible functionalities, such as halogens, carbonyl, and nitro groups.

Chiral Pool-Based Synthesis of Naphtho-Fused Isocoumarins

A variety of chiral derivatives of benzo[d]naphtho[1,2-b]pyran-6-one were prepared in a single step by Et3N-mediated condensation of homophthalic anhydride with different derivatives of (S)-amino acid chlorides at -5 °C by employing a chiral pool methodology. Chirality 27:951-957, 2015.