1712-69-2

Usage

Synthesis Reference(s)

Journal of the American Chemical Society, 70, p. 1177, 1948 DOI: 10.1021/ja01183a087The Journal of Organic Chemistry, 52, p. 3683, 1987 DOI: 10.1021/jo00392a035

InChI:InChI=1/C10H12O/c1-8(2)9-4-6-10(11-3)7-5-9/h4-7H,1H2,2-3H3

Upstream product

• 67-64-1 acetone 
• 917-64-6 methyl magnesium iodide 
• 128155-61-3 2-(4-Methoxyphenyl)-2-thiomethoxy-1,3-dithiane 
• 7144-49-2 2-methanesulfonylbenzothiazole 
• 100-06-1 1-(4-methoxyphenyl)ethanone 
• 21399-34-8 1,2-bis(1-(4-methoxyphenyl)ethylidene)hydrazine 
• 87931-47-3 3-(p-methoxyphenyl)-3-butenoic acid 
• 917-54-4 methyllithium 
• 2065-66-9 methyl-triphenylphosphonium iodide 
• 24406-16-4 lithium di-n-butylcuprate 
• 109125-10-2 <2-(4-methoxyphenyl)prop-1-en-3-yl>trimethylammonium iodide 
• 1779-49-3 Methyltriphenylphosphonium bromide 
• 2955-46-6 2-(4-methoxyphenyl)-2-methylpropanoic acid 
• 121-98-2 methyl 4-methoxybenzoate 

Downstream Products

• 62748-39-4 2,5-Dimethoxy-2,5-bis-(4-methoxyphenyl)hexan 
• 37548-27-9 S-(α,α'-Dimethyl-4-methoxybenzyl)-N-acetyl-L-cystein-methylamid 
• 65761-04-8 1-tert-Butylamino-2-(4-methoxy-phenyl)-propan-2-ol 
• 93397-63-8 2-(4-methoxyphenyl)propan-1-ol 
• 14090-96-1 S-<2-(4-Methoxy-phenyl)-propylmercapto>-essigsaeure-methylester 
• 93731-73-8 N'-Phenyl-N-<4-methoxy-α.α-dimethyl-benzyl>-harnstoff 
• 120-12-7 anthracene 
• 4132-48-3 1-methoxy-4-(1-methylethyl)benzene 
• 25108-68-3 p-(2,2-dichloro-1-methylcyclopropyl)-anisole 
• 22666-71-3 4-methoxycumyl cation 
• 98-83-9 isopropenylbenzene 
• 4286-23-1 4-isopropenylphenol 
• 150-76-5 4-methoxy-phenol 
• 56077-92-0 peroxymethylene radical 

Relevant academic research and scientific papers

Arylation and vinylation of alkenes based on unusual sequential semipinacol rearrangement/Grob fragmentation of allylic alcohols

(Chemical Equation Presented) Alkenes can be stereoselectively arylated and vinylated without transition-metal catalyst under mild conditions through an interesting NBS-promoted semipinacol rearrangement and a subsequent unusual NaOH-mediated Grob fragmentation.

Catalytic nucleophilic addition of olefinic C-H bond to α,β-unsaturated-γ-lactams

A novel catalytic nucleophilic addition of olefins to α,β-unsaturated-γ-lactams has been developed with a cyclic N-acyliminium ion as a key intermediate. It provides an efficient approach to 5-alkenyl-2-pyrrolidinones from simple and readily available starting materials and the desired products could be obtained in moderate to good yields (23-85%).

Absolute reactivity of the 4-methoxycumyl cation in non-acid zeolites

The reactivity of the 4-methoxycumyl cation in a series of alkali metal cation-exchanged zeolites (LiY, NaY, KY, RbY CsY, NaX, NaMor, and Naβ) in the absence and presence of coadsorbed alcohols and water is examined using nanosecond laser flash photolysis. In dry zeolites, the absolute reactivity of the carbocation is found to be strongly dependent on the nature of the alkali counterion, the Si/Al ratio, and the framework morphology, with the lifetime of the carbocation in Naβ being almost 10000-fold longer than in CsY. The results suggest a mechanism for carbocation decay involving direct participation of the zeolite framework as a nucleophile, leading to the generation of a framework-bound alkoxy species. Intrazeolite addition reactions of alcohols and water to the 4-methoxycumyl cation can be described in terms of both dynamic and static quenching involving molecular diffusion through the heterogeneous topology and rapid coupling between the alcohol and the carbocation encapsulated within the same cavity. The dynamics of the quenching reactions are different from similar reactions in homogeneous solution due to both the passive and active influences of the zeolite environment. In a passive sense, the zeolite decreases the reactivity of the nucleophilic quencher by hindering molecular diffusion. However, the zeolite actively promotes the efficiency of intracavity coupling by enhancing the deprotonation of the oxonium ion intermediate, allowing the reaction to go to completion.

METHOD FOR OXIDATIVE CLEAVAGE OF COMPOUNDS WITH UNSATURATED DOUBLE BOND

A method for oxidative cleavage of a compound with an unsaturated double bond is provided. The method includes the steps of: (A) providing a compound (I) with an unsaturated double bond, a trifluoromethyl-containing reagent, and a catalyst; wherein, the catalyst is represented by Formula (II): M(O)mL1yL2z??(II);wherein, M, L1, L2, m, y, z, R1, R2 and R3 are defined in the specification; and(B) mixing the compound with an unsaturated double bond and the trifluoromethyl-containing reagent to perform an oxidative cleavage of the compound with the unsaturated double bond by using the catalyst in air or under oxygen atmosphere condition to obtain a compound represented by Formula (III):

Method for oxidative cracking of compound containing unsaturated double bonds

The invention relates to a method for oxidative cracking of a compound containing unsaturated double bonds. The method comprises the following steps: (A) providing a compound (I) containing unsaturated double bonds, a trifluoromethyl-containing reagent and a catalyst, wherein the catalyst is shown as a formula (II): M(O)mL1yL2z (II), M, L1, L2, m, y, z, R1, R2 and R3 being defined in the specification; and (B) mixing the compound containing the unsaturated double bonds and the trifluoromethyl-containing reagent, and performing an oxidative cracking reaction on the compound containing the unsaturated double bonds in the presence of air or oxygen by using the catalyst to obtain a compound represented by formula (III),.

METHOD FOR OXIDATIVE CLEAVAGE OF COMPOUNDS WITH UNSATURATED DOUBLE BOND

A method for oxidative cleavage of a compound with an unsaturated double bond is provided. The method comprises the following step: (A) providing a compound (I) with an unsaturated double bond, a reagent with trifluoromethyl, and a catalyst; wherein the catalyst is represented by the following formula (II): M(O)mL1yL2z (II); wherein, M, L1, L2, m, y, z, R1, R2 and R3 are defined in the specification; and (B) mixing the compound with an unsaturated double bond and the reagent with a trifluoromethyl to perform an oxidation of the compound with the unsaturated double bond by using the catalyst at air or an oxygen condition to get a compound presented as formula (III):

Metal-Free Deoxygenation of Chiral Nitroalkanes: An Easy Entry to α-Substituted Enantiomerically Enriched Nitriles

A metal-free, mild and chemodivergent transformation involving nitroalkanes has been developed. Under optimized reaction conditions, in the presence of trichlorosilane and a tertiary amine, aliphatic nitroalkanes were selectively converted into amines or nitriles. Furthermore, when chiral β-substituted nitro compounds were reacted, the stereochemical integrity of the stereocenter was maintained and α-functionalized nitriles were obtained with no loss of enantiomeric excess. The methodology was successfully applied to the synthesis of chiral β-cyano esters, α-aryl alkylnitriles, and TBS-protected cyanohydrins, including direct precursors of four active pharmaceutical ingredients (ibuprofen, tembamide, aegeline and denopamine).

1,3-Difunctionalization of β-alkyl nitroalkenes via combination of Lewis base catalysis and radical oxidation

Upon treatment with a Lewis base catalyst, β-alkyl-substituted nitroalkenes could be readily converted into allylic nitro compounds. Examples of either C-1 or C-3 functionalization methods have been reported through nitro-elimination, giving alkene products. In this work, successful 1,3-difunctionalization was achieved through a synergetic Lewis base catalysis and TBHP radical oxidation, giving vinylic alkoxyamines in good to excellent yields. This work further extended the general synthetic application of β-alkyl nitroalkenes.

Formal Allylation and Enantioselective Cyclopropanation of Donor/Acceptor Rhodium(II) Azavinyl Carbenes

A highly efficient formal allylation of dihydronaphthotriazoles with alkenes under rhodium(II) catalysis is reported. Various allyl dihydronaphthalene derivatives were furnished via rhodium(II) azavinyl carbenes with moderate to good yields and excellent chemoselectivity. When monosubstituted alkenes are used, cyclopropanation occurs and good to excellent enantioselectivities have been achieved. Particularly noteworthy is the allylic C(sp2)-H activation instead of traditional C(sp3)-H activation in the formal allylation process.

Palladium-Catalyzed Markovnikov Hydroaminocarbonylation of 1,1-Disubstituted and 1,1,2-Trisubstituted Alkenes for Formation of Amides with Quaternary Carbon

Hydroaminocarbonylation of alkenes is one of the most promising yet challenging methods for the synthesis of amides. Herein, we reported the development of a novel and effective Pd-catalyzed Markovnikov hydroaminocarbonylation of 1,1-disubstituted or 1,1,2-trisubstituted alkenes with aniline hydrochloride salts to afford amides bearing an α quaternary carbon. The reaction makes use of readily available starting materials, tolerates a wide range of functional groups, and provides a facile and straightforward approach to a diverse array of amides bearing an α quaternary carbon. Mechanistic investigations suggested that the reaction proceeded through a palladium hydride pathway. The hydropalladation and CO insertion are reversible, and the aminolysis is probably the rate-limiting step.