4586-90-7

Usage

Uses

Used in Flavoring and Fragrance Industry:
5-(4-methoxyphenyl)-2-methylpentan-2-ol is used as a flavoring and fragrance ingredient for its distinctive sweet, floral scent. It is incorporated into various consumer products such as perfumes, soaps, and other personal care items to enhance their aroma and appeal to consumers.
Used in Pharmaceutical Industry:
Due to its biological activity, 5-(4-methoxyphenyl)-2-methylpentan-2-ol has potential applications in the pharmaceutical industry. Its specific uses in this field, however, are not detailed in the provided materials and would require further research to explore its full potential in medicinal applications.

Upstream product

• 917-64-6 methyl magnesium iodide 
• 4586-89-4 ethyl 4-(4-methoxyphenyl)butanoate 
• 140-67-0 Estragole 
• 67-64-1 acetone 
• 20637-08-5 4-(4-methoxyphenyl)butyric acid methyl ester 
• 75-16-1 methylmagnesium bromide 
• 870-63-3 prenyl bromide 
• 824-94-2 p-methoxybenzyl chloride 
• 4586-91-8 1-methoxy-4-(4-methylpent-3-en-1-yl)benzene 
• 74-88-4 methyl iodide 
• 3153-44-4 4-(4-methoxy-phenyl)-4-oxo-butyric acid 
• 100-66-3 methoxybenzene 
• 4521-28-2 4-(4-Methoxyphenyl)butyric acid 
• 36237-14-6 C₁₀H₁₃BrMgO 

Downstream Products

• 1332285-42-3 5-(4-methoxyphenyl)-2-methylpentan-2-yl 2,3,4,5-tetrafluorobenzoate 
• 66265-54-1 4-(4-methoxyphenyl)-1,1-dimethylbutylamine 
• 802021-53-0 6-Methoxy-4,4-dimethyl-1,2,3,4-tetrahydro-naphthalen-2-ylamine 
• 23203-51-2 6-methoxy-4,4-dimethyl-3,4-dihydronaphthalen-1(2H)-one 

Relevant academic research and scientific papers

Cathodic Regioselective Coupling of Unactivated Aliphatic Ketones with Alkenes

A regioselective coupling of aliphatic ketones with alkenes has been realized by cathodic reduction. This reaction enables the formation of ketyl radicals and the activation of challenging alkenes under mild electrolysis conditions, providing an effective protocol for accessing diverse tertiary alcohols with substrate-dependent regioselectivity. The practicability of this reaction is demonstrated by scale-up experiments. The hydrogen source for the products, the migration isomerization of allylarenes, and the applicability of internal alkenes are demonstrated by control experiments.

An Iron-Mesoionic Carbene Complex for Catalytic Intramolecular C-H Amination Utilizing Organic Azides

The synthesis of N-heterocycles is of paramount importance for the pharmaceutical industry. They are often synthesized through atom economic and environmentally unfriendly methods, generating significant waste. A less explored, but greener, alternative is

Efficient C-H Amination Catalysis Using Nickel-Dipyrrin Complexes

A dipyrrin-supported nickel catalyst (AdFL)Ni(py) (AdFL: 1,9-di(1-adamantyl)-5-perfluorophenyldipyrrin; py: pyridine) displays productive intramolecular C-H bond amination to afford N-heterocyclic products using aliphatic azide substrates. The catalytic amination conditions are mild, requiring 0.1-2 mol% catalyst loading and operational at room temperature. The scope of C-H bond substrates was explored and benzylic, tertiary, secondary, and primary C-H bonds are successfully aminated. The amination chemoselectivity was examined using substrates featuring multiple activatable C-H bonds. Uniformly, the catalyst showcases high chemoselectivity favoring C-H bonds with lower bond dissociation energy as well as a wide range of functional group tolerance (e.g., ethers, halides, thioetheres, esters, etc.). Sequential cyclization of substrates with ester groups could be achieved, providing facile preparation of an indolizidine framework commonly found in a variety of alkaloids. The amination cyclization reaction mechanism was examined employing nuclear magnetic resonance (NMR) spectroscopy to determine the reaction kinetic profile. A large, primary intermolecular kinetic isotope effect (KIE = 31.9 ± 1.0) suggests H-atom abstraction (HAA) is the rate-determining step, indicative of H-atom tunneling being operative. The reaction rate has first order dependence in the catalyst and zeroth order in substrate, consistent with the resting state of the catalyst as the corresponding nickel iminyl radical. The presence of the nickel iminyl was determined by multinuclear NMR spectroscopy observed during catalysis. The activation parameters (ΔH? = 13.4 ± 0.5 kcal/mol; ΔS?= -24.3 ± 1.7 cal/mol·K) were measured using Eyring analysis, implying a highly ordered transition state during the HAA step. The proposed mechanism of rapid iminyl formation, rate-determining HAA, and subsequent radical recombination was corroborated by intramolecular isotope labeling experiments and theoretical calculations.

Catalytic C-H Amination Mediated by Dipyrrin Cobalt Imidos

Reduction of (ArL)CoIIBr (ArL = 5-mesityl-1,9-(2,4,6-Ph3C6H2)dipyrrin) with potassium graphite afforded the novel CoI synthon (ArL)CoI. Treatment of (ArL)CoI with a stoichiometric amount of various alkyl azides (N3R) furnished three-coordinate CoIII alkyl imidos (ArL)Co(NR), as confirmed by single-crystal X-ray diffraction (R: CMe2Bu, CMe2(CH2)2CHMe2). The exclusive formation of four-coordinate cobalt tetrazido complexes (ArL)Co(κ2-N4R2) was observed upon addition of excess azide, inhibiting any subsequent C-H amination. However, when a weak C-H bond is appended to the imido moiety, as in the case of (4-azido-4-methylpentyl)benzene, intramolecular C-H amination kinetically outcompetes formation of the corresponding tetrazene species to generate 2,2-dimethyl-5-phenylpyrrolidine in a catalytic fashion without requiring product sequestration. The imido (ArL)Co(NAd) exists in equilibrium in the presence of pyridine with a four-coordinate cobalt imido (ArL)Co(NAd)(py) (Ka = 8.04 M-1), as determined by 1H NMR titration experiments. Kinetic studies revealed that pyridine binding slows down the formation of the tetrazido complex by blocking azide coordination to the CoIII imido. Further, (ArL)Co(NR)(py) displays enhanced C-H amination reactivity compared to that of the pyridine-free complex, enabling higher catalytic turnover numbers under milder conditions. The mechanism of C-H amination was probed via kinetic isotope effect experiments [kH/kD = 10.2(9)] and initial rate analysis with para-substituted azides, suggesting a two-step radical pathway. Lastly, the enhanced reactivity of (ArL)Co(NR)(py) can be correlated to a higher spin-state population, resulting in a decreased crystal field due to a geometry change upon pyridine coordination.

Enantiospecific bromonium ion generation and intramolecular capture: A model system for asymmetric bromonium ion-induced polyene cyclisations

Scalemic bromonium ions generated enantiospecifically by the action of catalytic triflic acid on scalemic regioisomeric bromohydrin derivatives are trapped intramolecularly, enantiospecifically and regioselectively to give bicyclic brominated carbocycles in excellent yield and high enantiomeric excess. This enantiospecific pathway is not significantly perturbed by the addition of a trisubstituted alkene.

Synthesis of an intermediate, 7,8-dimethyl-2-tetralone, for occidol isomer-I and occidol isomer-II

Anisole is succinoylated with succinic anhydride to yield 3-(p-methoxybenzoyl) propionic acid 3.The acid on Clemmensen reduction gives 4-(p-methoxy phenyl) butyric acid 4 which on esterification affords methyl 4-(p-methoxy-phenyl)butyrate 5.The ester 5 on reaction with methyl-magnesium iodide gives 5-(p-methoxyphenyl)-2-methyl-pentan-2-ol 6 which is cyclised with PPA to furnish 7-methoxy-1,1-dimethyltetralin 7.The tetralin 7 undergoes aromatization with p-chloranil or DDQ to afford 7-methoxy-1,2-dimethyl naphthalene 8, tike reduction of which with sodium in liquid ammonia as welt as with sodium in ethanol yields 7,8-dimethyl-2-tetralone 10.