18491-21-9

Usage

InChI:InChI=1/C12H16O/c1-10(2)4-5-11-6-8-12(13-3)9-7-11/h6-9H,1,4-5H2,2-3H3

Upstream product

• 104-20-1 4-(4-methoxyphenyl)-2-butanone 
• 1779-49-3 Methyltriphenylphosphonium bromide 
• 18272-88-3 1-methoxy-4-(2-methylbut-3-en-2-yl)benzene 
• 90433-31-1 1-(p-methoxyphenyl)-2,2-dimethylcyclopropane 
• 18292-38-1 2-methallyltrimethylsilane 
• 17988-20-4 (4-methoxy-benzyl)-trimethyl-silane 
• 1822-00-0 trimethylsilylmethyllithium 
• 122948-45-2 4-(p-Methoxyphenyl)-2-butanone dimethyl acetal 
• 290309-44-3 4-(p-Methoxyphenyl)-2-butanone ethylene acetal 
• 104-21-2 p-methoxybenzyl acetate 
• 943-88-4 4-(p-methoxyphenyl)-3-butene-2-one 
• 123-11-5 4-methoxy-benzaldehyde 
• 14425-64-0 4-methoxyphenethyl bromide 
• 131161-70-1 1-(2-cyclopropylethyl)-4-methoxybenzene 

Downstream Products

• 4957-18-0 1-methoxy-4-(3-methyl-but-2-enyl)benzene 
• 14305-29-4 3-hydroxy-1-(4-methoxyphenyl)-3-methylbutane 
• 184779-69-9 1-Methoxy-4-[3-methyl-3-(2,2,2-trifluoro-ethoxy)-butyl]-benzene 
• 1615227-20-7 2-(4-(4-methoxyphenyl)-2-methylbutan-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 

Relevant academic research and scientific papers

Mechanistic imperatives for the reaction catalyzed by isopentenyl pyrophosphate isomerase: Free energy profile for stepwise isomerization in water through a tertiary carbocation intermediate

Rate and equilibrium constants are reported for the stepwise allylic 1,3-isomerization of 4-(4-methoxyphenyl)-2-methyl-1-butene (2) to give 4-(4-methoxyphenyl)-2-methyl-2-butene (3) in water through a simple tertiary carbocation intermediate 1+

Dehalogenative Deuteration of Unactivated Alkyl Halides Using D2O as the Deuterium Source

The general dehalogenation of alkyl halides with zinc using D2O or H2O as a deuterium or hydrogen donor has been developed. The method provides an efficient and economic protocol for deuterium-labeled derivatives with a wide substrate scope under mild reaction conditions. Mechanistic studies indicated that a radical process is involved for the formation of organozinc intermediates. The facile hydrolysis of the organozinc intermediates provides the driving force for this transformation.

Synthesis of α-Tertiary Amine Derivatives by Intermolecular Hydroamination of Unfunctionalized Alkenes with Sulfamates under Trifluoromethanesulfonic Acid Catalysis

An efficient and mild trifluoromethanesulfonic acid-catalyzed hydroamination of unfunctionalized alkenes to afford α-tertiary amine derivatives at temperatures as low as room temperature is reported. 2,2,2-Trifluoroethyl sulfamate was found to be the optimal nitrogen source because its good solubility in both organic solvents and water facilitated both conversion and purification. The reaction conditions were compatible with a variety of substrate functional groups and afforded moderate to good yields. The desired amine compounds could be obtained easily by means of a mild, one-pot, redox-neutral deprotection procedure. Caryolane amine was synthesized with excellent chemo- and regioselectivities by means of a cascade hydroamination reaction of β-caryophyllene.

Directing group enhanced carbonylative ring expansions of amino-substituted cyclopropanes: Rhodium-catalyzed multicomponent synthesis of N-heterobicyclic enones

Aminocyclopropanes equipped with suitable N-directing groups undergo efficient and regioselective Rh-catalyzed carbonylative C-C bond activation. Trapping of the resultant metallacycles with tethered alkynes provides an atom-economic entry to diverse N-heterobicyclic enones. These studies provide a blueprint for myriad N-heterocyclic methodologies.

Rhodium-catalyzed allylation of benzyl acetates with allylsilanes

Benzyl acetate reacted with allyltrimethylsilane to give an allylation product in the presence of a catalytic amount of the (cyclooctadiene)rhodium(I) chloride dimer {[Rh(cod)Cl]2}, sodium tetrakis[3,5- bis(trifluoromethyl)phenyl]borate (NaBARF), and triphenyl phosphite [P(OPh) 3] in refluxing 1,2-dichloroethane. Primary, secondary and tertiary benzyl acetates could be used for the reaction. Moreover, allylation of gem-benzyl acetate was possible with [Rh(cod)Cl]2, NaBARF, and P(OPh)3. Monoallylation and diallylation of gem-benzyl acetate could be controlled by altering the reaction conditions. Cationic rhodium species generated in situ act as a Lewis acid catalyst to give a benzyl carbocation by elimination of the acetoxy group from the benzylic carbon. Copyright

Versatile friedel-crafts-type alkylation of benzene derivatives using a molybdenum complex/ortho-chloranil catalytic system

A variety of molybdenum complexes catalyze Friedel-Crafts-type alkylation reactions of benzene derivatives with alkenes and alcohols in the presence of an organic oxidant, o-chloranil. The utilization of [Mo(CO)6] and two equivalents of o-chloranil catalytically furnished the hydroarylation product of norbornene with p-xylene at 80°C, whereas [Cr(CO)6] and [W(CO)6] failed to catalyze the same reaction, thus indicating the importance of the molybdenum source. The best results were obtained when a molybdenum(II) complex [CpMoCl(CO)3] (Cp = cyclopentadienyl) was used as a precatalyst. The hydroarylation reactions also took place with styrenes, cyclohexenes, and 1 -hexene as olefin substrates. The electrophilic-substitution mechanism was proposed on the basis of the ortho/para selectivities and the Markovnikov selectivities observed for the hydroarylation products. Our hypothesis was further corroborated by the fact that in the presence of the [CpMoCl(CO)3]/o-chloranil catalytic system, secondary, benzylic, or allylic alcohols participated in the alkylation of benzenes with similar selectivities.

A new ruthenium-catalyzed cleavage of a carbon-carbon triple bond: Efficient transformation of ethynyl alcohol into alkene and carbon monoxide

We report a new and efficient ruthenium-catalyzed reaction that transforms ethynyl alcohol into alkene and carbon monoxide. The most efficient catalysts are TpRu(PPh3)(CH3CN)2PF6 (10 mol %) and lithium triflate

Magnesium cyclopropylidenes generated from 1-chlorocyclopropyl phenyl sulfoxides with Grignard reagents: Their properties, and a sulfoxide version of the Doering-Moore-Skattebol reaction

Magnesium cyclopropylidenes were generated from 1-chlorocyclopropyl phenyl sulfoxides with Grignard reagents (EtMgCl or i-PrMgCl) in THF at -78°C in high yields by a sulfoxide-magnesium exchange reaction. The generated magnesium cyclopropylidenes were found to be stable at below -60°C for at least 3 h. It was also found that the pyramidal inversion of the magnesium carbenoid was quite slow at below -60°C. When the sulfoxide-magnesium exchange reaction was conducted with phenylmagnesium chloride at 0°C, the 1-chlorocyclopropyl phenyl sulfoxides gave allenes in good to high yields.

New olefination of acetals with TMSCH2Cu(PBu3)·LiI under the influence of BF3·OEt2

Peterson-type olefination of acetals can be conveniently performed by reaction with TMSCH2Cu(PBu3)LiI, which is prepared in-situ from TMSCH2Li, CuI and PBu3, under the influence of BF3·OEt2 via Lewis acid-promoted β- elimination of β-alkoxysilanes.

Mechanism for nucleophilic substitution and elimination reactions at tertiary carbon in largely aqueous solutions: Lifetime of a simple tertiary carbocation

The rate constants and the yields of the products of the nucleophilic substitution and elimination reactions of 1-(4-methoxyphenyl)-3-methyl-3-butyl derivatives (1-X) have been determined in mostly aqueous solvents, and the absolute rate constant for reac