33993-24-7

Usage

Uses

Used in Pharmaceutical Industry:
Cyclopropanecarboxylic acid anhydride is used as a building block for the synthesis of various pharmaceuticals. Its high reactivity allows for the creation of a wide range of compounds with potential medicinal properties.
Used in Agrochemical Industry:
Cyclopropanecarboxylic acid anhydride is used as a building block for the synthesis of various agrochemicals. Its reactivity enables the production of compounds that can be used in the development of pesticides and other agricultural products.
Used in Fine Chemicals Industry:
Cyclopropanecarboxylic acid anhydride is used as a building block for the synthesis of other fine chemicals. Its versatility in organic chemistry allows for the creation of a variety of specialty chemicals used in different industries.
Note: Due to its high reactivity, precautions must be taken when handling and using cyclopropanecarboxylic acid anhydride in laboratory settings.

InChI:InChI=1/C8H10O3/c9-7(5-1-2-5)11-8(10)6-3-4-6/h5-6H,1-4H2

Upstream product

• 1759-53-1 cyclopropanecarboxylic acid 
• 4023-34-1 cyclopropanecarboxylic acid chloride 
• 117399-95-8 Cyclopropanecarboxylic acid 2-thioxo-2H-pyridin-1-yl ester 

Downstream Products

• 25256-03-5 Cyclopropanecarboxylic acid (3-isobutyrylamino-phenyl)-amide 
• 25227-92-3 C₁₄H₁₆N₂O₂ 
• 93181-95-4 Cyclopropanecarboxylic acid 1-[6-(2-chloro-phenyl)-pyridazin-3-yl]-piperidin-4-yl ester 
• 187737-37-7 propene 
• 463-49-0 1,2-propanediene 
• 50888-73-8 butadiene monoxide 
• 1759-53-1 cyclopropanecarboxylic acid 
• 156221-80-6 N-(4-amino-2-chloro-3-pyridyl)cyclopropanecarboxamide 
• 740872-83-7 cyclopropanecarboxylic acid (3-{4-[4(toluene-4-sulfonylamino)butyl]piperazin-1-yl}phenyl)amide 
• 54338-41-9 3',5'-dinitrocyclopropanecarboxanilide 
• 1422372-87-9 thiophenylmethyl-5-N-cyclopropylcarbonyl-4,7,8,9-tetra-OAc-3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopyranosylate 

Relevant academic research and scientific papers

ADAMANTYLMETHYLAMINE DERIVATIVE AND USE THEREOF AS PHARMACEUTICAL

The present invention provides a pharmaceutical composition for treating or preventing a cognitive disease or disorder, comprising a compound represented by Formula (I), an enantiomer thereof, a diastereomer thereof, or a pharmaceutically acceptable salt thereof.

Improved synthesis of buprenorphine from thebaine and/or oripavine via palladium-catalyzed N-demethylation/acylation and/or concomitant O-demethylation

An improved preparation of buprenorphine via palladium-catalyzed N-demethylation/acylation is reported. Three routes were investigated and compared in overall yield. The first involved N-demethylation/acylation of an advanced intermediate obtained from thebaine followed by hydrolysis of the N-acetamide and alkylation with cyclopropylmethyl bromide and/or reduction of the N-acetyl group with the Schwartz reagent followed by N-alkylation. The second route employed cyclopropylcarboxylic acid anhydride in the N-demethylation/acylation protocol and subsequent reduction of the cyclopropylcarboxamide by either lithium aluminum hydride or under hydrosilylation conditions. Both of these routes originated in thebaine and therefore required O-demethylation as a final step. The third route employed an N-demethylation/acylation sequence starting from oripavine rather than thebaine, thus avoiding the O-demethylation. The routes are compared for overall efficiency and experimental and spectral data are provided for all new compounds. Copyright

Zinc(0)/dimethylformamide-mediated synthesis of symmetrical carboxylic anhydrides from acid chlorides

The high yielding synthesis of symmetrical carboxylic anhydrides from acid chlorides mediated by zinc dust in the presence of dimethylformamide is presented. A mechanism involving the reductive insertion of zinc(0) into the C-Cl bond of a Vilsmeier-type iminium intermediate as the crucial step is also proposed.

In vitro optimization of non-small cell lung cancer activity with troxacitabine, L-1,3-dioxolane-cytidine, prodrugs

L-1,3-Dioxolane-cytidine, a potent anticancer agent against leukemia, has limited efficacy against solid tumors, perhaps due to its hydrophilicity. Herein, a library of prodrugs were synthesized to optimize in vitro antitumor activity against non-small cell lung cancer. N4-Substituted fatty acid amide prodrugs of 10-16 carbon chain length demonstrated significantly improved antitumor activity over L-1,3-dioxolane-cytidine. These in vitro results suggest that the in vivo therapeutic efficacy of L-1,3-dioxolane- cytidine against solid tumors may be improved with prodrug strategies.

COMPOUNDS AND COMPOSITIONS AS CATHEPSIN S INHIBITORS

The invention provides compounds, pharmaceutical compositions comprising such compounds and methods of using such compounds to treat or prevent diseases or disorders associated with the activity of Cathepsin S.

PROCESS FOR PRODUCING ACID ANHYDRIDE

According to the present invention there is provided a process for producing an acid anhydride by reacting a carboxylic acid, preferably a carboxylic acid having a polymerizable group, with a sulfonyl halide compound in the presence of a tertiary amine or in the presence of a tertiary amine and an inorganic base, wherein the tertiary amine or the tertiary amine and the inorganic base are used in an amount of 0.9 to 1.2 equivalents relative to the acid generated from the sulfonyl halide compound.

A one-step procedure for the monoacylation of symmetrical 1,2-diols

A series of lanthanide (III) salts have been shown to catalyze the monoacylation of symmetrical 1,2-diols by carboxylic acid anhydrides with surprisingly high selectivity.

Cyclopropyl-substituted Pyrylium Salts

The previously unknown 2,4,6-trisubstituted pyrylium salts 1-4, carrying cyclopropyl and methyl or phenyl substituents in the same molecule, and 5-8, substituted with isopropyl groups instead of cyclopropyl, were synthesized as perchlorates.The electronic spectra and the C-13 nmr spectra of the two groups of compounds were compared.A cyclopropyl group has a batochromic effect on the electronic spectrum roughly half that exerted by a phenyl, replacement of an alkyl by a cyclopropyl shifts the highest wavelength absorption band by about 20 nm.Presence of phenyl substituents reduces the batochromic effects of cyclopropyl substituents.The effects of both cyclopropyl and phenyl substituents on the electronic spectra are smaller for pyrylium than for tropylium.The nmr signals for all the ring carbons are shifted upfield upon replacement of isopropyl by cyclopropyl;, in particular, the effect of substituents in position 2 upon the chemical shift of C(4) indicates that the electron-releasing effect varies in the series alkyl phenyl cyclopropyl, in agreement with the findings for 2,6-disubstituted-pyrylium salts.The difference between the chemical shifts for the methine and methylene carbons of the three-membered ring is a function of the electron demand of the cationic heterocycle.

GENERATION AND FATE OF NONDECARBOXYLATING ACYLOXY RADICALS DERIVED FROM THE PHOTOLYSIS OF ACYL DERIVATIVES OF N-HYDROXY-2-THIOPYRIDONE

The acyl derivatives of 1 with the acyl group linked to aryl, vinyl etc. give on photolysis carboxy radicals.These radicals, by attack on the thiopyridone function, afford thio-peresters which are the real precursors of the anhydrides observed before.The benzoyloxy radical from 2 can be trapped by ethylvinyl ether to give adduct 14 in promising yield.