80866-48-4

Upstream product

• 623-53-0 ethyl methyl carbonate 
• 6746-94-7 Cyclopropylacetylene 
• 79-22-1 methyl chloroformate 
• 122244-78-4 1,1-dibromo-2-cyclopropylehylene 

Downstream Products

• 7358-93-2 3‐cyclopropyl‐2‐propynoic acid 
• 1616135-74-0 (E)-methyl 3-cyclopropyl-3-(dimethyl(phenyl)silyl)acrylate 
• 1245704-14-6 methyl 6-cyclopropyl-2-tosyl-2,3,3a,4-tetrahydro-1H-isoindole-5-carboxylate 
• 854928-24-8 3-cyano-4-cyclopropyl-6-oxo-1,6-dihydro-pyridine-2-thiol morpholine salt 
• 268542-56-9 cyclopropyl-propynoyl chloride 
• 375384-93-3 6-((Z)-3-cyclopropyl-3-iodoprop-2-en-1-yl)-3-isobutoxycyclohex-2-en-1-one 
• 375385-01-6 4-((Z)-3-cyclopropyl-3-iodoprop-2-en-1-yl)cyclohex-2-en-1-one 
• 263874-45-9 1-(3-cyclopropylbuten-2(Z)-enyl-1-oxy)-3-phenylprop-2-yne 
• 104462-89-7 4-Cyclopropyl-3-furancarbonsaeure-methylester 

Relevant academic research and scientific papers

Synthesis of 1-Substituted Cyclopropylamines via Formal Tertiary Csp3-H Amination of Cyclopropanes

A novel and facile approach to synthesis of 1-substituted cyclopropylamines via phosphine-catalyzed formal tertiary Csp3-H amination of cyclopropanes was described. The indoles, pyrroles, imidazoles, uracils, 2-pyridone, pyrimidin-4(3H)-one, and phthalimide had been proven as good aminating partners. The present protocol features transition-metal-free, excellent regioselectivity, high-atom-economy, and mild reaction conditions and a broad range of substrates. The practicability of this protocol can also be demonstrated with late-stage modification of bioactive molecules, scaled up reaction, and divergent derivatization. Notably, the method has been used in the formal synthesis of the hormone-sensitive lipase (HSL) inhibitor. The mechanistic aspects were elucidated by both experimental and computational studies.

Organocatalytic trans Phosphinoboration of Internal Alkynes

We report the first trans phosphinoboration of internal alkynes. With an organophosphine catalyst, alkynoate esters and the phosphinoboronate Ph2P-Bpin are efficiently converted into the corresponding trans-α-phosphino-β-boryl acrylate products in moderate to good yield with high regio- and Z-selectivity. This reaction operates under mild conditions and demonstrates good atom economy, requiring only a modest excess of the phosphinoboronate. X-ray crystallography experiments allowed structural assignment of the unprecedented and densely functionalized (Z)-α-phosphino-β-boryl acrylate products.

N-triflyl-propiolamides: Preparation and transamidation reactions

N-Trifluoromethylsulfonyl-propiolamides have been prepared by two methods: a) N-triflation of secondary acetylenic carboxanilides, prepared in two steps from terminal alkynes, with triflic anhydride (Tf2O) and b) from terminal alkynes and an aryl or alkyl isocyanate followed by Tf2O in a consecutive one-pot reaction. The title compounds are bench-stable and insensitive to water and alcohols but amenable to transamidation reactions with a wide range of amine nucleophiles. Conversely, they are excellent reagents for the propynoylation of ammonia, primary and secondary amines, anilines, and hydrazines.

Trans-Hydroboration of Propiolamides: Access to Primary and Secondary (E)-β-Borylacrylamides

A base-mediated trans-hydroboration of propiolamides that provides access to previously elusive primary and secondary (E)-β-borylacrylamide products has been developed. In the presence of n-butyllithium and pinacolborane, complete regioselectivity and ste

Transition Metal-Free Trans Hydroboration of Alkynoic Acid Derivatives: Experimental and Theoretical Studies

We report a phosphine-catalyzed trans hydroboration of alkynoate esters and amides. The reaction proceeds under mild conditions with exclusive (E)-selectivity to afford (E)-β-boryl acrylates and (E)-β-boryl acrylamides in good to excellent yields. The reaction is tolerant of a variety of functional groups and allows efficient access to novel oxaboroles as well as a pargyline derivative (MAO inhibitor). Theoretical calculations suggest an internal hydride generates a phosphonium allenoxyborane followed by the formation of a key phosphonocyclobutene intermediate that collapses in a stereoselective, rate-limiting step.

SULFONAMIDE DERIVATIVE AND MEDICINAL USE THEREOF

Provided are sulfonamide derivatives of a specific chemical structure in which a sulfonamide group having, as a substituent, a phenyl group or a heterocyclic group having a hetero atom(s) as a constituent element(s) is present at its terminal, and pharmaceutically acceptable salts thereof. These compounds are novel compounds having excellent α4 integrin-inhibitory action.

COMPOUNDS AND METHODS FOR MODULATING FXR

Compounds of formula (I) wherein variables are as defined herein and their pharmaceutical compositions and methods of use are disclosed as useful for treating dyslipidemia and related diseases.

Syntheses of seven-membered rings: Ruthenium-catalyzed intramolecular [5+2] cycloadditions

The Ru-catalyzed intramolecular [5+2] cycloaddition of cyclopropylenynes is investigated with respect to the regio- and diastereoselectivity as well as the functional group compatibility of the reaction. Evidence for the mechanism as occurring through a ruthenacyclopentene intermediate is elucidated from 1) the study of the diastereoselectivity of the cycloaddition; 2) the effect of variation of substituents on the regioselectivity of cyclopropyl bond cleavage in 1,2-trans- and 1,2-cis-disubstituted cyclopropanes and 3) examples that clearly do not involve ruthenacyclohexene as intermediates as products still incorporate the cyclo propyl moiety. The scope and limitations of the Ru-catalyzed cycloaddition are discussed and compared with the Rh-catalyzed reaction. The potential power of this methodology towards natural product total synthesis is demonstrated by the formation of several polycyclic systems with the chosen reaction conditions and readily available cyclopropylenyne substrates.

SUBSTITUTED 3-AMINO-THIENO[2,3-B] PYRIDINE-2-CARBOXYLIC ACID AMIDE COMPOUNDS AS IKK INHIBITORS

Disclosed are compounds of formula (I): wherein the variables R1, R2, R3 and Z are described herein, which are useful as inhibitors of the kinase activity of the IκB kinase (IKK) complex. The compounds are therefore useful in the treatment of IKK mediated diseases including autoimmune diseases inflammatory diseases and cancer. Also disclosed are pharmaceutical compositions comprising these compounds and processes for preparing these compounds.

Ethynylogization of a coarctate fragmentation

Coarctate reactions form a separate class of elementary closed-shell processes in addition to polar and pericyclic reactions. Hence, they also follow a different homology principle. Whereas vinylogous polar and pericyclic reactions differ in the length of the reacting system by a double bond, coarctate reactions can be homologized (ethynylogized) by extending a known system by a triple bond. The prediction, which is based on theoretical considerations, is confirmed experimentally by the fragmentation of cyclopropylethynyl nitrene to cyano acetylene and ethylene, a reaction that is "ethynyloguous" to the known fragmentation of cyclopropyl nitrene to ethylene and HCN.