74592-36-2

Usage

Uses

Used in Chemical Synthesis:
Ethyl 2-[(1E)-cyclopropylidene]acetate is used as a reactant in the regioand stereoselective palladiumand platinum-catalyzed silaboration of methylenecyclopropanes with dioxaborolane. This reaction allows for the formation of new chemical bonds and the synthesis of complex organic molecules with specific spatial arrangements, which is crucial for the development of pharmaceuticals and other specialty chemicals.

Upstream product

• 682-19-9 Triethyl Phosphonoacetate 
• 74592-24-8 Cyclopropanone Ethyl Hemiketal Magnesium Iodide 
• 13837-45-1 1-ethoxy-1-cyclopropanol 
• 1099-45-2 ethyl (triphenylphosphoranylidene)acetate 
• 27374-25-0 [(1-Ethoxycyclopropyl)oxy]trimethylsilane 
• 5009-27-8 cyclopropanone 
• 867-13-0 diethoxyphosphoryl-acetic acid ethyl ester 

Downstream Products

• 298181-33-6 C₂₃H₃₈O₄Si 
• 298181-34-7 C₂₃H₃₈O₄Si 
• 64566-39-8 (1E,2Z)-1,2-bis(ethoxycarbonylmethylidene)cyclohexane 
• 64566-40-1 diethyl (1E,2E)-cyclohexane-1,2-diylidenediacetate 
• 61934-55-2 3-bromomethyl-2-butenolide 
• 540133-68-4 2-[1-(4-methoxybenzyloxy)cyclopropyl]acetic acid 

Relevant academic research and scientific papers

BICYCLIC HETEROARYL COMPOUNDS AND USES THEREOF

The present disclosure is directed to modulators of SOS1 and their use in the treatment of disease. Also disclosed are pharmaceutical compositions comprising the same.

PROCESS OF MAKING CFTR MODULATORS

The disclosure provides processes for synthesizing Compound I, and pharmaceutically acceptable salts thereof.

OXADIAZOLE COMPOUNDS

Provided herein are compounds and pharmaceutical compositions comprising said compounds that are useful for treating cancers. Specific cancers include those that are mediated by YAP/TAZ or those that are modulated by the interaction between YAP/TAZ and TEAD.

Cycloaddition of Fluorenone N-Aryl Nitrones with Methylenecyclopropanes and Sequential 1,3-Rearrangement: An Entry to Synthesis of Spirofluorenylpiperidin-4-ones

A facile synthesis of various spirofluorenylpiperidin-4-ones has been achieved in good yields from fluorenone N-aryl nitrones and methylenecyclopropanes. This method involved an initial cycloaddition to form a 5-spirocyclopropane-isoxazoline, which underwent a highly selective 1,3-rearrangement to give the desired product. The stereochemistry of the spirofluorenylpiperidin-4-one could be controlled by the cycloaddition and sequential rearrangement strategy. Furthermore, the spirofluorenylpiperidin-4-ones could be not only prepared in one-pot procedure but also converted to useful scaffolds by reduction or oxidation conditions.

Olefin-Migrative Cleavage of Cyclopropane Rings through the Nickel-Catalyzed Hydrocyanation of Allenes and Alkenes

A nickel-catalyzed hydrocyanation triggered by hydronickelation of the carbon-carbon double bonds of allenes followed by cyclopropane cleavage is described. The observed regio- and stereochemistries in the products are strongly influenced by the initial hydronickelation step, and allenyl- and methylenecyclopropanes reacted smoothly to promote the cleavage of cyclopropane. In contrast, this cleavage was not observed with vinylidenecyclopropanes, because the initial hydronickelation does not give a suitable intermediate for cleavage of the cyclopropanes. (Figure presented.).

NOVEL PROCESS FOR PREPARATION OF SPIRO[2.5]OCTANE-5,7-DIONE AND SPIRO[3.5]NONANE-6,8-DIONE

This invention relates to methods for the synthesis of spiro[2.5]octane-5, 7-dione and spiro[3.5]nonane-6, 8-dione which are useful as intermediates in the manufacture of pharmaceutically active ingredients.

The synthesis of α,α-disubstituted α-amino acids via ichikawa rearrangement

An approach to α,α-disubstituted α-amino acids is reported. The key step is allyl cyanate-to-isocyanate rearrangement. As demonstrated, the resultant allyl isocyanates can be directly trapped with various nucleophiles, for instance, alcohols, amines, and organometallic reagents, to provide a broad range of N-functionalized allylamines. The developed method has been successfully applied in the synthesis of two bioactive peptides: 2-aminoadamantane-2-carboxylic acid derived P2X7-evoked glutamate release inhibitor and 4-amino-tetrahydropyranyl-4-carboxylic acid derived dipeptide GSK-2793660, which is currently in clinical trials as cathepsin C inhibitor for the treatment of cystic fibrosis, noncystic fibrosis bronchiectasis, ANCA-associated vasculitis and bronchiectasis.

Short and tandem syntheses of spiro[2.5]octane-5,7-dione and spiro[3.5]nonane-6,8-dione via diethyl acetonedicarboxylate

A general synthetic route to spiro[2.5]octane-5,7-dione and spiro[3.5]nonane-6,8-dione that involves cyclization of the related acrylates and diethyl acetonedicarboxylate, followed by decarboxylation, has been developed. Compared with previous synthetic methods, the developed protocol avoids the use of column chromatography in each of the synthetic steps. Therefore, it can be readily scaled-up. The use of diethyl acetonedicarboxylate under mild conditions to build the skeleton of 1,3-cyclohexanedione has proved to be very efficient.

Bicyclic-Fused Heteroaryl or Aryl Compounds

Compounds, tautomers and pharmaceutically acceptable salts of the compounds are disclosed, wherein the compounds have the structure of Formula Ia, as defined in the specification. Corresponding pharmaceutical compositions, methods of treatment, methods of synthesis, and intermediates are also disclosed.

INHIBITORS OF THE RENAL OUTER MEDULLARY POTASSIUM CHANNEL

Novel spirocyclic compounds of formula I: and pharmaceutically acceptable salts thereof are disclosed as inhibitors of the ROMK (Kir1.1) channel. The compounds may be used as diuretic and/or natriuretic agents and for the therapy and prophylaxis of medical conditions including cardiovascular diseases such as hypertension, heart failure and chronic kidney disease and conditions associated with excessive salt and water retention. Pharmaceutical compositions and methods of treatment are also included.