37765-76-7

Upstream product

• 18880-00-7 1-(bromomethyl)-4-(1,1-dimethylethyl)benzene 
• 105-53-3 diethyl malonate 
• 253185-03-4 tert-butylbenzene 
• 159838-29-6 diethyl 2,2-bis(4-tert-butylbenzyl)malonate 
• 877-65-6 p-tert-butylbenzyl alcohol 
• 19692-45-6 4-tert-butylbenzyl chloride 

Downstream Products

• 172477-52-0 2-(4-tert-butylbenzyl)-1,3-propanediol 
• 1208-64-6 3-(4-tert-butylphenyl)propionic acid 
• 130872-28-5 ethyl 3-(4-(tert-butyl)phenyl)propanoate 
• 78574-08-0 3-(4-tert-butylphenyl)propan-1-ol 
• 141499-24-3 4-(3-bromopropyl)-1-(1,1-dimethylethyl)benzene 
• 79253-37-5 (S)-3-(4-(tert-butyl)phenyl)-2-methylpropan-1-ol 
• 173379-60-7 (S)-(+)-<2-(4-tert-butylbenzyl)-2-(tolylsulfonyloxymethyl)>ethyl acetate 
• 172477-58-6 5-(4-tert-butylbenzyl)-1,3,2-dioxathiane-2,2-dioxide 
• 173379-58-3 (S)-(+)-<2-(4-tert-butylbenzyl)-2-chloromethyl>ethyl acetate 
• 173379-57-2 (R)-(+)-<2-(4-tert-butylbenzyl)-2-hydroxymethyl>ethyl acetate 
• 173379-59-4 (S)-(-)-2-(chloromethyl)-2-(4-tert-butylbenzyl)ethanol 
• 138320-32-8 (S)-(+)-2-(4-tert-butylbenzyl)-1-chloropropane 
• 76492-90-5 fenpropimorph 
• 58249-45-9 (4-tert-butylbenzyl)cyclopropane 

Relevant academic research and scientific papers

Amphipathic Barbiturates as Mimics of Antimicrobial Peptides and the Marine Natural Products Eusynstyelamides with Activity against Multi-resistant Clinical Isolates

We report a series of synthetic cationic amphipathic barbiturates inspired by the pharmacophore model of small antimicrobial peptides (AMPs) and the marine antimicrobials eusynstyelamides. These N,N′-dialkylated-5,5-disubstituted barbiturates consist of an achiral barbiturate scaffold with two cationic groups and two lipophilic side chains. Minimum inhibitory concentrations of 2-8 μg/mL were achieved against 30 multi-resistant clinical isolates of Gram-positive and Gram-negative bacteria, including isolates with extended spectrum β-lactamase-carbapenemase production. The guanidine barbiturate 7e (3,5-di-Br) demonstrated promising in vivo antibiotic efficacy in mice infected with clinical isolates of Escherichia coli and Klebsiella pneumoniae using a neutropenic peritonitis model. Mode of action studies showed a strong membrane disrupting effect and was supported by nuclear magnetic resonance and molecular dynamics simulations. The results express how the pharmacophore model of small AMPs and the structure of the marine eusynstyelamides can be used to design highly potent lead peptidomimetics against multi-resistant bacteria.

Aryltrifluoromethylative cyclization of unactivated alkenes by the use of PhICF3Cl under catalyst-free conditions

A concise and catalyst-free aryltrifluoromethylative cyclization of unactivated alkenes has been developed herein. The use of PhICF3Cl as a powerful trifluoromethylating agent allows easy transformations. A set of trifluoroethylated carbocycles and aza-hereocycles were efficiently synthesized in good yield and selectivity. A broad substrate scope, mild reaction conditions, and easy operation would make this method well-suited for applications.

A General Catalytic Method for Highly Cost- and Atom-Efficient Nucleophilic Substitutions

A general formamide-catalyzed protocol for the efficient transformation of alcohols into alkyl chlorides, which is promoted by substoichiometric amounts (down to 34 mol %) of inexpensive trichlorotriazine (TCT), is introduced. This is the first example of a TCT-mediated dihydroxychlorination of an OH-containing substrate (e.g., alcohols and carboxylic acids) in which all three chlorine atoms of TCT are transferred to the starting material. The consequently enhanced atom economy facilitates a significantly improved waste balance (E-factors down to 4), cost efficiency, and scalability (>50 g). Furthermore, the current procedure is distinguished by high levels of functional-group compatibility and stereoselectivity, as only weakly acidic cyanuric acid is released as exclusive byproduct. Finally, a one-pot protocol for the preparation of amines, azides, ethers, and sulfides enabled the synthesis of the drug rivastigmine with twofold SN2 inversion, which demonstrates the high practical value of the presented method.

Anodic benzylic C(sp3)-H amination: Unified access to pyrrolidines and piperidines

An electrochemical aliphatic C-H amination strategy was developed to access the important heterocyclic motifs of pyrrolidines and piperidines within a uniform reaction protocol. The mechanism of this unprecedented C-H amination strategy involves anodic C-H activation to generate a benzylic cation, which is efficiently trapped by a nitrogen nucleophile. The applicability of the process is demonstrated for 40 examples comprising both 5- and 6-membered ring formations.

Highly efficient synthesis of functionalized dihydronaphthalenes, tetrahydronaphthalenes, and tetrahydroisoquinolines by iron-catalyzed intramolecular Friedel-Crafts reaction of aryl-containing propargylic alcohols

An efficient, convenient, and one-pot procedure for the synthesis of a series of new dihydro- and tetrahydronaphthalenes as well as tetrahydroisoquinolines has been established through Lewis acid-catalyzed intramolecular Friedel-Crafts reaction of aryl-substituted propargylic alcohols.

Controllable one-step synthesis of spirocycles, polycycles, and di- and tetrahydronaphthalenes from aryl-substituted propargylic alcohols

(Chemical Equation Presented) A novel, convenient, and efficient method has been developed for selective synthesis of spirocycle, polycycle, and di-and tetrahydronaphthalene systems from aryl-substituted propargylic alcohols by FeCl3- or TsOH-catalyzed multiple activations of unsaturated C-C bonds and C-H bonds.

Vanilloid analogues containing resinferatoxin pharmacophores as potent vanilloid receptor agonists and analgesics, compositions and uses thereof

The present invention is related to new vanilloid analogues containing resiniferatoxin pharmacophores, pharmaceutical compositions comprising such analogues, and their uses as vanilloid receptor agonists and potent analgesics. The present invention provides a pharmaceutical composition for treating acute, chronic, inflammatory or neuropathic pains or for treating bladder hypersensitivity.

N-(3-acyloxy-2-benzylpropyl)-N′-(4-hydroxy-3-methoxybenzyl)thiourea derivatives as potent vanilloid receptor agonists and analgesics

A series of N-(3-acyloxy-2-benzylpropyl)-N′-(4-hydroxy-3-methoxybenzyl)thiourea derivatives were investigated as vanilloid receptor ligands in an effort to discover a novel class of analgesics. The proposed pharmacophore model of resiniferatoxin, which includes the C20-homovanillic moiety, the C3-carbonyl and the orthoester phenyl ring as key pharmacophoric groups, was utilized as a guide for drug design. The compounds were synthesized after several steps from diethylmalonate and evaluated in vitro in a receptor binding assay and in a capsaicin-activated channel assay. Additional evaluation of analgesic activity, anti-inflammatory activity and pungency was conducted in animal models by the writhing test, the ear edema assay, and the eye-wiping test, respectively. Among the new compounds, 23 and 28 were found to be the most potent receptor agonists of the series with Ki values of 19 nM and 11 nM, respectively. Their strong in vitro potencies were also reflected by an excellent analgesic profile in animal tests with ED50 values of 0.5 μg/kg for 23 and 1.0 μg/kg for 28. Relative to capsaicin these compounds appear to be ca. 600 and 300 times more potent. Both 23 and 28 were found to be less pungent than capsaicin based on the eye-wiping test. However, the compounds did not show significant anti-inflammatory activity. A molecular modeling study comparing the energy-minimized structures of resiniferatoxin and 35 demonstrated a good correlation in the spatial disposition of the corresponding key pharmacophores. The thioureas described in this investigation, which were designed as simplified resiniferatoxin surrogates, represent a novel class of potent vanilloid receptor agonists endowed with potent analgesic activity and reduced pungency.

Anodic oxidation of 3-phenylpropionic acid

The electrochemical oxidation of 3-phenylpropionic acid has been performed on platinum, graphite and PtO2/Ti anodes. Two types of products have been obtained, either formed by one-electron oxidation, or by two-electron oxidation. The influence of the anode material, current density and solvent nature on the products distribution has been studied. The electrochemical oxidations of 3-(p-t-butylphenyl)propionic, 3,3-d-3-phenylpropionic and 2,2-d-3-phenylpropionic acids have been studied in order to get information concerning the carbonium-type intermediate in the two-electron oxidation. Unlike the chemical generation, the 2-phenylethyl carbocation formed by two-electron oxidation stabilises, leading mainly to rearranged products. The obtained results are in agreement with the assumption that either phenyl or σC-H bond assists the carbocation formation.

Synthesis of substituted cyclopropanes from 1,3-diols through the corresponding cyclic sulfates

The reaction of different cyclic sulfates 2 (easily prepared from the corresponding 1,3-diols 1 following the Sharpless methodology) with an excess of lithium powder and a catalytic amount of DTBB (5 mol %) leads to the corresponding substituted cyclopropanes 3 through a γ-elimination process, the sulfate ion acting as leaving group.