6950-92-1

Usage

Chemical Properties

white mass or fluffy needles

InChI:InChI=1/C11H16O/c1-8-6-9(2)11(4-5-12)10(3)7-8/h6-7,12H,4-5H2,1-3H3

Upstream product

• 75-21-8 oxirane 
• 2633-66-1 2-mesitylmagnesium bromide 
• 4170-90-5 2,4,6-trimethylbenzyl alcohol 
• 4408-60-0 2-mesitylacetic acid 
• 769-25-5 2,4,6-trimethylstyrene 
• 576-83-0 2,4,6-trimethylphenyl bromide 
• 769-26-6 2-ethynyl-1,3,5-trimethylbenzene 
• 41841-19-4 methyl 2-mesitylacetate 
• 938-18-1 mesitylene-2-carboxylic acid chloride 
• 480-63-7 mesitylenecarboxylic acid 

Downstream Products

• 91345-52-7 2-(2-bromoethyl)-1,3,5-trimethylbenzene 
• 94712-76-2 1-Mesityl-2-(mesitylmercapto)-aethanol 
• 58047-52-2 2-(2,4,6-trimethylphenyl)acetaldehyde 
• 910470-67-6 acetic acid 2-(2,4,6-trimethyl-phenyl)-ethyl ester 
• 480-63-7 mesitylenecarboxylic acid 
• 4408-60-0 2-mesitylacetic acid 
• 1208109-83-4 1'-(2-mesitylethyl)-6-methoxy-3,4-dihydro-1H-spiro[naphthalene-2,2'-piperidin]-1-one hydrochloride 
• 94265-41-5 2-(2,4,6-Trimethyl-phenyl)-ethyl-p-toluolsulfonat 
• 3982-67-0 ethylmesitylene 
• 1333343-66-0 [1-(4-chlorobenzoyl)-5-methoxy-2methyl-1H-indol-3-yl]acetic acid 2-(2,4,6-trimethylphenyl)ethyl ester 
• 868372-54-7 2-amino-5-mesityl-3,7-dimethyl-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one 
• 868372-53-6 2-amino-5-mesityl-7-methyl-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one 

Relevant academic research and scientific papers

Synthesis and Biological Evaluation of Fentanyl Analogues Modified at Phenyl Groups with Alkyls

A series of fentanyl analogues modified at the phenyl group of the phenethyl with alkyl and/or hydroxyl and alkoxy, and the phenyl group in the anilido moiety replaced with benzyl or substituted benzyl, were synthesized. The in vitro opioid receptor functional activity of these compounds was evaluated by assessment of their ability to modulate forskolin-stimulated cAMP accumulation and by their ability to induce β-arrestin2 recruitment. Compound 12 is a potent μ-opioid (MOP) receptor agonist, a potent κ-opioid (KOP) receptor antagonist with weak β-arrestin2 recruitment activity. Compounds 10 and 11 are potent MOP receptor agonists with weak δ-opioid (DOP) receptor antagonist activity and moderate KOP receptor antagonist activity as well as weak β-arrestin2 recruitment activity at the MOP receptor. These compounds are promising leads for discovery of potent opioid analgesics with reduced side effects relative to clinically available strong opioid analgesics.

Fentanyl analogue and application thereof

The invention discloses a fentanyl analogue and application thereof. A general structural formula of a compound is as follows (described in the following description), wherein R1 is a hydrogen group,a methyl group, a hydroxyl group, a methoxyl group, a halogen and a cyano group, and R2 is a phenyl group, a benzyl group and 3,5-benzyldimethyl. The compound provided by the invention embodies the activating effect of a mu-opioid receptor and the recruitment function of weak beta-arrestin 2, and therefore, the compound can be used as an analgesic drug and can overcome the respiration inhibition effect caused by activating a beta-arrestin 2 signal pathway.

Discovery, synthesis, and structure-activity relations of 3,4-dihydro-1H-spiro(naphthalene-2,2′-piperidin)-1-ones as potassium-competitive acid blockers

With the aim to discover a gastric antisecretory agent more potent than the existing proton pump inhibitors, novel 3,4-dihydro-1H-spiro(naphthalene-2,2′-piperidin)-1-one derivatives, which could occupy two important lipophilic pockets (described as LP-1 and LP-2) of H+,K+-ATPase and can strongly bind to the K+-binding site, were designed based on a docking model. Among the compounds synthesized, compound 4d showed a strong H+,K+-ATPase-inhibitory activity and a high stomach concentration in rats, resulting in potent inhibitory action on histamine-stimulated gastric acid secretion in rats. Furthermore, 4d exerted significant inhibitory action on histamine-stimulated gastric-acid secretion in rats with a rapid onset and moderate duration of action after the administration. These findings may lead to a new insight into the drug design of potassium-competitive acid blockers.

A highly active and air-stable ruthenium complex for the ambient temperature anti-markovnikov reductive hydration of terminal alkynes

The conversion of terminal alkynes to functionalized products by the direct addition of heteroatom-based nucleophiles is an important aim in catalysis. We report the design, synthesis, and mechanistic studies of the half-sandwich ruthenium complex 12, which is a highly active catalyst for the anti-Markovnikov reductive hydration of alkynes. The key design element of 12 involves a tridentate nitrogen-based ligand that contains a hemilabile 3-(dimethylamino) propyl substituent. Under neutral conditions, the dimethylamino substituent coordinates to the ruthenium center to generate an air-stable, 18-electron, κ3-complex. Mechanistic studies show that the dimethylamino substituent is partially dissociated from the ruthenium center (by protonation) in the reaction media, thereby generating a vacant coordination site for catalysis. These studies also show that this substituent increases hydrogenation activity by promoting activation of the reductant. At least three catalytic cycles, involving the decarboxylation of formic acid, hydration of the alkyne, and hydrogenation of the intermediate aldehyde, operate concurrently in reactions mediated by 12. A wide array of terminal alkynes are efficiently processed to linear alcohols using as little as 2 mol % of 12 at ambient temperature, and the complex 12 is stable for at least two weeks under air. The studies outlined herein establish 12 as the most active and practical catalyst for anti-Markovnikov reductive hydration discovered to date, define the structural parameters of 12 underlying its activity and stability, and delineate design strategies for synthesis of other multifunctional catalysts.

Temporal separation of catalytic activities allows anti-Markovnikov reductive functionalization of terminal alkynes

There is currently great interest in the development of multistep catalytic processes in which one or several catalysts act sequentially to rapidly build complex molecular structures. Many enzymes - often the inspiration for new synthetic transformations - are capable of processing a single substrate through a chain of discrete, mechanistically distinct catalytic steps. Here, we describe an approach to emulate the efficiency of these natural reaction cascades within a synthetic catalyst by the temporal separation of catalytic activities. In this approach, a single catalyst exhibits multiple catalytic activities sequentially, allowing for the efficient processing of a substrate through a cascade pathway. Application of this design strategy has led to the development of a method to effect the anti-Markovnikov (linear-selective) reductive functionalization of terminal alkynes. The strategy of temporal separation may facilitate the development of other efficient synthetic reaction cascades.

Total synthesis of pterosines B and C via a photochemical key step

A total synthesis of pterosines B and C is reported. Starting with a fourfold substituted benzene derivative, the introduction of the remaining substituents is mainly based on Sonogashira couplings followed by different transformations of the ethyne moiety. The key step is a photochemical ring-closure of an α-mesyloxy ketone forming the 1-indanone skeleton. Georg Thieme Verlag Stuttgart.

The scope of catalytic asymmetric hydroboration/oxidation with rhodium complexes of 1,1'-(2-diarylphosphino-1-naphthyl)isoquinolines

Preformed cationic Rh complexes of the title ligands are effective for the asymmetric hydroboration/oxidation of vinylarenes at ambient temperature. These vinylarenes may carry E- or Z-β substituents but not a substituents. Enantiomer excesses of up to 97% can be obtained in the most favourable cases. The enantioselectivity is moderately sensitive to the structure of the ligand: the difurylphosphino ligand gave superior results for electron-poor styrenes and the diphenylphosphino ligand the best results for electron-rich reactants. Mechanistic aspects are discussed.

Asymmetric hydroboration of styrenes catalyzed by cationic chiral phosphine-rhodium(I) complexes

Reaction of styrene with catecholborane in the presence of 1 mol % of a cationic phosphine-rhodium catalyst prepared in situ from [Rh(COD)2]BF4 and 1,4-bis(diphenylphosphino)butane proceeded regioselectively to give, after oxidation, 1-phenylethanol in a quantitative yield. The regioselectivity forming benzylic alcohols was also observed in the reaction of substituted styrenes. Use of (R)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (BINAP) as a chiral ligand for the rhodium-catalyzed hydroboration of substituted styrenes (ArCH=CH2) gave optically active (R)-1-arylethanols (ArCH(OH)Me) in high yields. The enantiomeric purities of the alcohols are 96% ee, 94% ee, 91% ee, 85% ee, 89% ee, and 82% ee for Ar=Ph, 4-MeC6H4, 4-ClC6H4, 3-ClC6H4, 4-MeOC6H4, and 2-MeOC6H4, respectively.