56563-37-2

Usage

Chemical Properties

Brown crystalline powder

InChI:InChI=1/C11H12O3S/c1-3-4-9-14-15(12,13)11-7-5-10(2)6-8-11/h5-8H,9H2,1-2H3

Upstream product

• 764-01-2 methyl propargyl alcohol 
• 104-15-4 toluene-4-sulfonic acid 
• 98-59-9 p-toluenesulfonyl chloride 
• 4124-41-8 p-toluenesulfonylanhydride 

Downstream Products

• 79802-28-1 (methyl-1 propadienyl)-1 t-butyldimethylsilyloxymethyl-6 methyl-3 cyclohexene trans 
• 18476-67-0 2-(4-methoxyphenyl)-5-methylbenzofuran 
• 13610-03-2 but-2-yn-1-yl(phenyl)sulfide 
• 64070-51-5 Mn(CO)4(P(C₆H₅)3)CH₂CCCH₃ 
• 375387-31-8 Rh(SbPh3)2(CO)Cl(OTs)(η1-CH2CCMe) 
• 375387-32-9 Rh(SbPh3)3Cl(η2-C(O)C(Me)=C(OTs)CH2) 
• 375387-33-0 Rh(SbPh3)3(OTs)(η2-C(O)C(Me)=C(Cl)CH2) 
• 375387-35-2 Rh(SbPh3)3Br(η2-C(O)C(Me)=C(OTs)CH2) 
• 408535-18-2 ((CO)6Co₂(CH₃CCCH₂))2O 
• 408535-31-9 [Co2(μ-η3-CH3CCCH2)(CO)6][OTs] 
• 173539-27-0 [(PPh3)2Pt(η(3)-CH2CCMe)]OSO2C6H4CH3 
• 173539-37-2 [(PPh3)2Pd(η(3)-CH2CCMe)]OSO2C6H4CH3 
• 482649-59-2 methyl 2-(but-2-yn-1-yl)-2-phenylhex-4-ynoate 
• 60011-63-4 N-(but-2-yn-1-yl)-N-methylaniline 

Relevant academic research and scientific papers

Copper-catalyzed regiodivergent silacarboxylation of allenes with carbon dioxide and a silylborane

A regiodivergent silacarboxylation of allenes under a CO2 atmosphere with PhMe2Si-B(pin) as a silicon source in the presence of a copper catalyst at 70 °C has been developed. The regioselectivity of the reaction is successfully rever

Rapid Access to Nitrogenous Heterobicycles via RhIII-Catalyzed Isomerization from Alkynes to Allenes

We show that N-alkynylnitrones are efficiently converted to nitrogenous heterobicyclic compounds with a nitrogen atom at the bridgehead position by using a RhIII-catalyst. Our mechanistic studies suggest that the reaction proceeds via an allene

Directed Cobalt-Catalyzed anti-Markovnikov Hydroalkylation of Unactivated Alkenes Enabled by "co-H" Catalysis

The earth-abundant cobalt-catalyzed anti-Markovnikov hydroalkylation of unactivated alkenes with oxime esters was achieved by introducing an 8-aminoquinoline directing group on the alkenes. The catalytic system, consisting of commercially available Co(acac)3 and PhMeSiH2, enables the construction of unfunctionalized C(sp3)-C(sp3) bonds and features exclusive anti-Markovnikov selectivity, good functional group tolerance, and the avoidance of an extra ligand, oxidant, or base. Mechanistic insight into this new catalytic system indicates the involvement of both alkyl radical and cobalt hydride intermediates.

Bioinspired Divergent Oxidative Cyclizations of Geissoschizine: Total Synthesis of (–)-17-nor-Excelsinidine, (+)-16-epi-Pleiocarpamine, (+)-16-Hydroxymethyl-Pleiocarpamine and (+)-Taberdivarine H

We report a full account of our efforts towards bioinspired oxidative cyclizations of geissochizine and analogs to mimic the biosynthesis of the mavacuran, akuammilan, and excelsinidine groups of monoterpene indole alkaloids. The construction of the A,B,C,D ring system of geissoschizine was first achieved by merging two known syntheses of this alkaloid. Modified Ma's oxidative conditions (KHMDS/I2) applied directly to geissoschizine induced formation of the N4–C16 bond encountered in the excelsinidines core. Identical conditions applied to C16-dimethylmalonate-containing N4-quaternized substrates ended in the formation of the mavacurans core (N1–C16 bond). With this unified oxidative cyclization strategy: (–)-17-nor-excelsinidine, (+)-16-epi-pleiocarpamine, (+)-16-hydroxymethyl-pleiocarpamine, 16-formyl-pleiocarpamine and (+)-taberdivarine H were synthetized. We also report a shortened total synthesis of 16-epi-pleiocarpamine compared to our preliminary communication from a C16-monoester analog. Alternatively, 17-nor-excelsinidine was synthesized via an intramolecular nucleophilic substitution of a 7-membered ring α-chlorolactam prepared from 16-desformyl-geissoschizine.

Construction of All-Carbon Chiral Quaternary Centers through CuI-Catalyzed Enantioselective Reductive Hydroxymethylation of 1,1-Disubstituted Allenes with CO2

A catalytic enantioselective construction of all-carbon chiral quaternary centers through reductive hydroxymethylation of 1,1-disubstituted allenes with CO2 has been developed. In the presence of a copper/Mandyphos catalyst, CO2 is t

Pd(ii)-SDP-catalyzed enantioselective 5-exo-dig cyclization of γ-alkynoic acids: Application to the synthesis of functionalized dihydofuran-2(3H)-ones containing a chiral quaternary carbon center

The Pd(ii)-SDP-catalyzed first enantioselective intramolecular cyclization of α,α-disubstituted γ-alkynoic acids is described. This 5-exo-dig cyclization afforded dihydrofuran-2(3H)-ones bearing a chiral quaternary carbon center in excellent yields with e

Fused ring aziridines as a facile entry into triazole fused tricyclic and bicyclic heterocycles

The intramolecular dipolar cycloaddition of an azide with an alkyne has provided a useful entry into triazole fused tricyclic heterocycles containing both the triazole ring and the oxazolidin-2-one ring system. The requisite azido-alkynes have been prepared via a two-step sequence from fused ring aziridines. A series of 6-12 membered rings containing both the oxazolidinone and triazole rings have been prepared. These ring systems have been designed as conformationally restrained analogs of RNA-binding oxazolidinones. The Royal Society of Chemistry 2012.

2-(3-AMINOPIPERIDIN-1-YL)-[1,2,4]TRIAZOLO[1,5-C]PYRIMIDINE-5,7(3H,6H)-DIONE DERIVATES AS DIPEPTIDYL PEPTIDASE IV(DPP-IV) INHIBITORS

Provided are 2-(3-aminopiperidin-1-yl)-[1,2,4]triazolo[1,5-c]pyrimidine-5,7(3H,6H)-dione derivates as dipeptidyl peptidase IV (DPP-IV) inhibitors, pharmaceutical compositions thereof, and methods of use thereof

CERTAIN DIPEPTIDYL PEPTIDASE INHIBITORS

Provided are certain dipeptidyl peptidase inhibitors, pharmaceutical compositions thereof, and methods of use therefor.

Synthetic applications of the nickel-catalyzed cyclization of alkynes combined with addition reactions in a domino process

Carbonickelations of alkynes and functionalization of the resulting vinylnickel moiety have been performed efficiently in a nickel-catalyzed domino cyclization-condensation process. This reaction, which does not require the preparation of any other organometallic reagent, proceeds only by exo-dig cyclization. This convenient and mild method constitutes a one-pot synthesis of substituted dihydrobenzofurans, chromans, isochromans, indoles, or indanes. Theses valuable products are generally obtained in good yields and high stereoselectivity. They are shown to be useful synthons for rapid access to functionalized polycyclic skeletons. Yes nickel can! Carbonickelation of alkynes and functionalization of the resulting vinylnickel moiety occurs efficiently. Overall, a domino cyclization-condensation process propagated by substoichiometric nickel catalysis takes place (see scheme). This one-pot synthesis provides substituted polyheterocyclic compounds in good yields and high stereoselectivity.