36832-63-0

Upstream product

• 689-97-4 3-buten-1-yne 
• 106-45-6 para-thiocresol 
• 38771-21-0 4-bromobut-1-yne 
• 36832-51-6 1-(but-3-yn-1-ylsulfonyl)-4-methylbenzene 
• 72486-09-0 methanesulfonic acid but-3-ynyl ester 
• 23418-85-1 3-butyn-1-yl p-toluenesulfonate 
• 10486-08-5 sodium p-thiocresolate 

Downstream Products

• 1772-10-7 2-(m-tolyl)butane 
• 16491-20-6 (R)-1-methyl-4-(phenylsulfinyl)benzene 
• 36832-51-6 1-(but-3-yn-1-ylsulfonyl)-4-methylbenzene 

Relevant academic research and scientific papers

Discovery of a novel family of FKBP12 “reshapers” and their use as calcium modulators in skeletal muscle under nitro-oxidative stress

The hypothesis of rescuing FKBP12/RyR1 interaction and intracellular calcium homeostasis through molecular “reshaping” of FKBP12 was investigated. To this end, novel 4-arylthioalkyl-1-carboxyalkyl-1,2,3-triazoles were designed and synthesized, and their e

Repurposing π Electrophilic Cyclization/Dealkylation for Group Transfer

A metal-free regio- and stereocontrolled group-transfer route toward the synthesis of trisubstituted alkenes is described. In this route, an electrophilic heterocyclization is followed by ring-opening group transfer. Specifically, a thioboration reaction

Investigation of functionalized α-chloroalkyllithiums for a stereospecific reagent-controlled homologation approach to the analgesic alkaloid (-)-epibatidine

Four putative functionalized α-chloroakyllithiums RCH 2CHLiCl, where R=CHCH2 (18 a), CCH (18 b), CH 2OBn (18 c), and CH[O(CH2)2O] (18 d), were generated in situ by sulfoxide-lithium exchange from α-chlorosulfoxides, and investigated for the stereospecific reagent-controlled homologation (StReCH) of phenethyl and 2-chloropyrid-5-yl (17) pinacol boronic esters. Deuterium labeling experiments revealed that α-chloroalkyllithiums are quenched by proton transfer from their α-chlorosulfoxide precursors and it was established that this effect compromises the yield of StReCH reactions. Use of α-deuterated α-chlorosulfoxides was discovered to ameliorate the problem by retarding the rate of acid-base chemistry between the carbenoid and its precursor. Carbenoids 18 a and 18 b showed poor StReCH efficacy, particularly the propargyl group bearing carbenoid 18 b, the instability of which was attributed to a facile 1,2-hydride shift. By contrast, 18 d, a carbenoid that benefits from a stabilizing interaction between O and Li atoms gave good StReCH yields. Boronate 17 was chain extended by carbenoids 18 a, 18 b, and 18 d in 16, 0, and 68 % yield, respectively; α-deuterated isotopomers D-18 a and D-18 d gave yields of 33 and 79 % for the same reaction. Double StReCH of 17 was pursued to target contiguous stereodiads appropriate for the total synthesis of (-)-epibatidine (15). One-pot double StReCH of boronate 17 by two exposures to (S)-D-18 a (≤66 % ee), followed by work-up with KOOH, gave the expected stereodiad product in 16 % yield (d.r.～67:33). The comparable reaction using two exposures to (S)-D-18 d (≤90 % ee) delivered the expected bisacetal containing stereodiad (R,R)-DD-48 in 40 % yield (≥98 % ee, d.r.=85:15). Double StReCH of 17 using (S)-D-18 d (≤90 % ee) followed by (R)-D-18 d (≤90 % ee) likewise gave (R,S)-DD-48 in 49 % yield (≥97 % ee, d.r.=79:21). (R,S)-DD-48 was converted to a dideuterated isotopomer of a synthetic intermediate in Corey's synthesis of 15. Copyright

Tin Radical Addition to Alkynyl Sulfides: Reactivity of the Intermediate Thioalkyl-Substituted β-(Tributylstannyl)vinyl Radicals

Phenyl and benzyl alkynyl sulfides 1a-g and 3a, phenylalkynylamines 19a,b, ethers 22a,b, and selenide 31 reacted with tributyltin radicals to give intermediate β-stannylvinyl radicals, whose fate depended on the nature of the side chain. 4-Phenylthio-substituted but-1-en-2-yl radicals underwent stereospecific 5-exo cyclization on the adjacent phenyl ring.The resulting spirocyclohexadienyl radicals gave thiophenes and thiopyrans by carbon-sulfur bond scission or ring expansion on the exocyclic double bond, respectively.Similar behavior was exhibited by the corresponding selenium-containing radical, which afforded a selenophene almost exclusively. (Benzylthio)alkyl-substituted radicals gave products deriving from intramolecular SH2 substitution at the sulfur atom, whereas propargyl sulfides yielded a stannylallene via a β-scission reaction.No 6(or more)-membered ring closure was observed with pentynyl and hexynyl phenyl sulfides 1b,c, which gave only the (E)-addition products of tin hydride; oxygen- and nitrogen-containing vinyl radicals also gave the (E)-adducts exclusively.An interaction between the unpaired electron orbital and the empty low-energy orbitals of the heteroatom might explain why sulfur and selenium can undergo 5-exo cyclization.