89844-08-6

Upstream product

• 106-95-6 allyl bromide 
• 69-72-7 salicylic acid 
• 201230-82-2 carbon monoxide 
• 107-18-6 allyl alcohol 
• 151414-76-5 o-(prop-2-enyloxy)phenylboronic acid 

Downstream Products

• 59086-52-1 2-allyloxybenzoic acid 
• 16982-86-8 3-methyl-chroman-4-one 
• 1454663-48-9 diethyl (2-(allyloxy)benzoyl)phosphonate 
• 1613331-67-1 2-oxopropyl 2-(2-oxopropoxy)benzoate 
• 167864-75-7 methyl 2-diazo-3-(2-allyloxyphenyl)-3-oxopropionate 
• 167864-65-5 2-(2-Allyloxy-benzoyl)-acrylic acid methyl ester 
• 52542-42-4 2-allyloxybenzoyl chloride 
• 69-72-7 salicylic acid 
• 10484-09-0 allyl salicylate 

Relevant academic research and scientific papers

Cobalt-catalyzed cyclization with the introduction of cyano, acyl and aminoalkyl groups

An efficient synthesis of carbo-and heterocycles using CC, CO and CN bonds under cobalt catalysis is described. The substituents on olefins are key for controlling the regio-and chemoselectivity in the initial hydrogen atom transfer step and quaternary carbons are efficiently constructed under mild conditions. Cyclopropane cleavage and tandem cyclization give highly functionalized bicyclic skeletons in a single operation.

Repurposing a Library of Human Cathepsin L Ligands: Identification of Macrocyclic Lactams as Potent Rhodesain and Trypanosoma brucei Inhibitors

Rhodesain (RD) is a parasitic, human cathepsin L (hCatL) like cysteine protease produced by Trypanosoma brucei (T. b.) species and a potential drug target for the treatment of human African trypanosomiasis (HAT). A library of hCatL inhibitors was screened, and macrocyclic lactams were identified as potent RD inhibitors (Ki 50 400 nM). SARs addressing the S2 and S3 pockets of RD were established. Three cocrystal structures with RD revealed a noncovalent binding mode of this ligand class due to oxidation of the catalytic Cys25 to a sulfenic acid (Cys-SOH) during crystallization. The P-glycoprotein efflux ratio was measured and the in vivo brain penetration in rats determined. When tested in vivo in acute HAT model, the compounds permitted up to 16.25 (vs 13.0 for untreated controls) mean days of survival.

Observations concerning the synthesis of heteroatom-containing 9-membered benzo-fused rings by ring-closing metathesis

A set of benzo-fused dienes with a 1,9-relationship and containing a variety of nitrogen and oxygen heteroatoms was readily synthesized. These dienes were then treated with the Grubbs second generation catalyst with the aim of synthesizing the 9-membered benzannelated heterocycles containing two heteroatoms (either O,O, NR,NR or O,NR where R = Ts or Boc). As previously observed in the literature, many of the dienes did not give the expected ring-closed product. However, a number of the desired products did form, namely with the 1,2-dihydrobenzo[c][1,5]oxazonin-7(5H)-one, 5,7-dihydrobenzo[b][1,5]oxazonine-6(2H)-carboxylate and 2,5,6,7-tetrahydrobenzo[b][1,5]oxazonine cores, albeit in poor yields. Rather surprisingly, the N-allyl-N-(2-(N-allyl-4-methylphenylsulfonamido)benzyl)-4-methylbenzenesulfonamide scaffold gave the desired ring-closed 1,6-ditosyl-2,5,6,7-tetrahydro-1H-benzo[b][1,5]diazonine in a high yield. Furthermore, when treated with the catalyst [RuClH(CO)(PPh3)3] the alkene isomerized into conjugation only with the benzylic NTs group and not with the phenyl NTs group to afford the 1,6-ditosyl-2,3,6,7-tetrahydro-1H-benzo[b][1,5]diazonine structure.

Thiol-Ene Elastomers Derived from Biobased Phenolic Acids with Varying Functionality

The synthesis and physical properties of thiol-ene elastomers derived from plant-based phenolic acids were explored. Phenolic acids of varying functionality (ranging from 2 to 4 hydroxyl and carboxyl groups per molecule) and relative placement of function

Synthesis and Physical Properties of Thiol-Ene Networks Utilizing Plant-Derived Phenolic Acids

Elastomeric polymer films synthesized through thiol-ene chemistry, suitable in applications as coatings and adhesives due to their ease of preparation and superior physical properties, are traditionally derived from petroleum sources. Of recent interest i

The first general and selective palladium(II)-catalyzed alkoxycarbonylation of arylboronates: Interplay among benzoquinone-ligated palladium(0) complex, organoboron, and alcohol solvent

Methoxycarbonylation of aryl- and alken-ylboron compounds was performed using the palladium (II) acetate/triphenylphosphine [PdACHTUNGTRENNUNG(OAc) 2/PPh3] catalyst with p-benzoquinone as a stoichiometric oxidant in methanol at ambient temperature to obtain the corresponding methyl esters in good yields. A wide variety of functional groups including various carbonyl functionalities, nitrile, nitro, sulfone, and unprotected pyrrole rings were tolerated in the methoxycarbonlation, while the use of higher alcohols except for tert-butanol afforded various pchlorobenzoates in moderate to high yields. The catalytic alkoxycarbonylation proceeded without any acid or base additive, and an oxidative transmetalation step is proposed to explain the exceptional efficacy of this protocol. DFT and MP2 calculations support the proposed mechanism.

Synthesis of novel aromatic macrolactones via ring closing metathesis of substituted phenylalkanoic acid allylic esters

(Chemical Equation Presented) Stable aromatic macrolactones have been synthesized and characterized from 2- and 3-substituted phenylalkanoic acid systems in modest yields.

Chemoselectivity and stereoselectivity of cyclisation of α-diazocarbonyls leading to oxygen and sulfur heterocycles catalysed by chiral rhodium copper catalysts

Good levels of enantioselectivity have been achieved in intramiolecular C-H insertion reactions of α-diazocarbonyl compounds leading to six-membered oxygen heterocycles (chromanones) through the use of chiral rhodium(II) carboxylates as catalysts.Competition between C-H insertion and sigmatropic rearrangement, the latter leading to five-membered oxygen heterocycles (furanones), was observed with precursors containing a proximal O-allyl side chain.Whereas rhodium carboxylates produced C-H insertion products predominantly, a copper catalyst produced sigmatropic rearrangement products exclusively.A precursor with S-allyl side chain exhibited cyclisation via sigmatropic rearrangement with both copper and rhodium catalyst.