935-50-2

Usage

Synthesis Reference(s)

Journal of the American Chemical Society, 100, p. 2834, 1978 DOI: 10.1021/ja00477a043

Upstream product

• 67-56-1 methanol 
• 150-76-5 4-methoxy-phenol 
• 150-78-7 1,4-dimethoxybezene 
• 17061-86-8 1-methoxy-4-(2-propynyloxy)benzene 
• 6630-18-8 4-methoxyphenyl benzyl ether 
• 13391-35-0 allyl (4-methoxyphenyl) ether 
• 84765-78-6 1-(buta-2,3-dien-1-yloxy)-4-methoxybenzene 
• 108534-64-1 tert-Butyl-diphenyl-(1,4,4-trimethoxy-cyclohexa-2,5-dienyloxy)-silane 
• 108-95-2 phenol 
• 106-41-2 4-bromo-phenol 
• 15791-03-4 1,1,4,4-tetramethoxycyclohexa-2,5-diene 
• 100-16-3 4-nitrophenylhydrazone 
• 104-94-9 4-methoxy-aniline 
• 15791-03-4 3,3,6,6-tetramethoxycyclohexa-1,4-dione 

Downstream Products

• 67045-38-9 4,4-dimethoxy-5-morpholin-4-yl-cyclohex-2-enone 
• 93969-64-3 3-(2',2'-dimethoxy-5'-oxocyclohex-3'-enyl)isobenzofuran-1(3H)-one 
• 130660-13-8 (4,4-Dimethoxy-cyclohexa-1,5-dienyloxy)-trimethyl-silane 
• 119927-91-2 5-(1,3-dithian-2-yl)-4,4-dimethoxycyclohex-2-en-1-one 
• 135639-18-8 4-(1-pentynyl)-4-hydroxycyclohexa-2,5-dienone dimethyl acetal 
• 1200-06-2 4-methoxyphenyl acetate 
• 144945-94-8 6′-chloro-3′H-spiro[cyclohexane-1,1′-isobenzofuran]-2,5-diene-3′,4-dione 
• 114251-39-7 1-(2-Isopropenyl-phenyl)-4,4-dimethoxy-cyclohexa-2,5-dienol 
• 136538-21-1 4,4-Dimethoxy-1-phenyl-2,5-cyclohexadien-1-ol 
• 119928-00-6 4,4-dimethoxy-5-phenyl-2-cyclohexenone 
• 119950-01-5 5-n-butyl-4,4-dimethoxy-2-cyclohexenone 
• 170117-32-5 [(S)R]-4-hydroxy-4-[(p-tolylsulfinyl)methyl]-2,5-cyclohexadienone dimethyl acetal 
• 14062-18-1 ethyl p-methoxyphenylacetate 
• 1516-21-8 4-methoxynitrosobenzene 

Relevant academic research and scientific papers

Concave-Convex π-π Template Approach Enables the Synthesis of [10]Cycloparaphenylene-Fullerene [2]Rotaxanes

The cycloparaphenylenes (CPPs) are a class of strained macrocycles that until 2008 were considered beyond the reach of organic synthesis. With its cyclic array of ten para-substituted phenylene rings, [10]CPP possesses a concave π-system that is perfectly preorganized for the strong supramolecular association of convex fullerenes such as C60. Although mechanically interlocked CPP architectures have been observed in the gas phase, the rational synthesis of bulk quantities has not been achieved yet, which is likely due to the fact that conventional template strategies are not amenable to CPP rings that lack heteroatoms. Here, we report the synthesis of two [2]rotaxanes in which a [10]CPP ring binds to a central fullerene bis-adduct and is prevented from dethreading by the presence of two bulky fullerene hexakis-adduct stoppers. The final step in the rotaxane synthesis is surprisingly efficient (up to ca. 40% yield) and regioselective because the fullerene acts as an efficient convex template, while [10]CPP acts as a supramolecular directing group, steering the reaction at the central fullerene exclusively toward two trans regioisomers. Comprehensive physicochemical studies confirmed the interlocked structure, shed light on the dynamic nature of the CPP-fullerene interaction, and revealed intriguing consequences of the mechanical bond on charge transfer processes. In light of recent advances in the synthesis of nanohoops and nanobelts, our concave-convex π-π templating strategy may be broadly useful and enable applications in molecular electronics or complex molecular machinery.

Oxidative Kinetic Resolution of Cyclic Benzylic Ethers

A manganese-catalyzed oxidative kinetic resolution of cyclic benzylic ethers through asymmetric C(sp3)?H oxidation is reported. The practical approach is applicable to a wide range of 1,3-dihydroisobenzofurans bearing diverse functional groups and substituent patterns at the α position with extremely efficient enantiodiscrimination. The generality of the strategy was further demonstrated by efficient oxidative kinetic resolution of another type of five-membered cyclic benzylic ether, 2,3-dihydrobenzofurans, and six-membered 6H-benzo[c]chromenes. Direct late-stage oxidative kinetic resolution of bioactive molecules that are otherwise difficult to access was further explored.

1,3-Diradicals Embedded in Curved Paraphenylene Units: Singlet versus Triplet State and In-Plane Aromaticity

Curved π-conjugated molecules and open-shell structures have attracted much attention from the perspective of fundamental chemistry, as well as materials science. In this study, the chemistry of 1,3-diradicals (DRs) embedded in curved cycloparaphenylene (

Coupling of Quinone Monoacetals with Vinyl Ethers Effected by Tetrabutylammonium Triflate: Regiocontrolled Synthesis of 2-Oxygenated Dihydrobenzofurans

The synthesis of 2-oxygenated dihydrobenzofurans involving the [3 + 2] coupling of quinone monoacetals with vinyl ethers has been realized by tetrabutylammonium triflate catalysis. The reaction involves a new activation method of the acetal moiety in quinone monoacetals under acid-free conditions affording the highly oxygenated dihydrobenzofurans. This new activation mode was achieved by using the triflate anion catalyst for stabilization of the highly reactive cationic intermediate.

METHOD FOR PRODUCING ANNULAR COMPOUND

PROBLEM TO BE SOLVED: To provide a method for producing an annular compound which can be produced in high yield. SOLUTION: There is provided a method for producing an annular compound represented by formula (M) comprising reacting particular two kinds of reactive compounds in the presence of a transition metal complex and an organic base. [In Formula (M), m' represents an integer of 5 to 15, and n' represents an integer of 1 to 10. Ara represents a group in which hydrogen atoms have been removed one by one from two sp3 carbons included in an arylene group or the like. However, at least one of Ara represents a group in which hydrogen atoms have been removed one by one from two sp3 carbons included in a cycloalkadiene, and these groups may have a substituent. Arb represents a group in which hydrogen atoms have been removed one by one from two sp3 carbons included in an arylene group or the like, and these groups may have a substituent.] SELECTED DRAWING: None COPYRIGHT: (C)2020,JPOandINPIT

Synthetic Entry to Polyfunctionalized Molecules through the [3+2]-Cycloaddition of Thiocarbonyl Ylides

Here we present a comprehensive study on the [3+2]-cycloaddition of thiocarbonyl ylides with a wide variety of alkenes and alkynes. The obtained dihydro- and tetrahydrothiophene products serve as exceptionally versatile intermediates providing access to thiophenes, dienes, dendralenes, and vic-quarternary carbon centers. The use of high-pressure conditions enables thermally unstable, sterically encumbered or moderately reactive substrates to undergo the cycloaddition under mild conditions, thereby increasing the yield by up to 58percent. In addition, we showcase its utility by the formal syntheses of the pharmaceuticals NGB 4420 and tenilapine.

Redox-Neutral α-C-H Functionalization of Pyrrolidin-3-ol

A redox-neutral α-C-H oxygenation of commercially available pyrrolidin-3-ol with a monoprotected p-quinone generated an N-aryliminium ion intermediate, which reacted in situ with boronic acid nucleophiles to produce a series of cis-2-substituted pyrrolidin-3-ols. With this strategy, 8-epi-(-)-lentiginosine was synthesized from (3R,4R)-pyrrolidine-3,4-diol in three steps.

Experimental evidence for the formation of cationic intermediates during iodine(iii)-mediated oxidative dearomatization of phenols

Iodine(iii)-based oxidants are commonly used reagents for the oxidative dearomatization of phenols. Having a better understanding of the mechanism through which these reactions proceed is important for designing new iodine(iii)-based reagents, catalysts, and reactions. We have performed a Hammett analysis of the oxidative dearomatization of substituted 4-phenylphenols. This study confirms that iodine(iii)-mediated oxidative dearomatizations likely proceed through cationic phenoxenium ions and not the direct addition of a nucleophile to an iodine-bound phenol intermediate.

Ph3P-mediated highly selective C(α)-P coupling of quinone monoacetals with R2P(O)H: Convenient and practical synthesis of: Ortho -phosphinyl phenols

A highly selective Ph3P-mediated C(α)-P coupling reaction of quinone monoacetals with secondary phosphine oxides is developed to provide an effective method for the synthesis of a wide array of ortho-phosphinylphenols in good to excellent yields. This protocol can be adopted for scale-up synthesis directly from cheap and abundant phenols, and the products can be easily obtained in high yields by simple filtration without the use of organic extraction or chromatography.

Lewis Acid-Mediated Site-Selective Synthesis of Oxygenated Biaryls from Methoxyphenols and Electron-Rich Arenes

A rapid, efficient, and metal-free Lewis acid-mediated methodology has been developed for the site-selective synthesis of unsymmetrical oxygenated biaryls. This simple and efficient methodology furnished highly oxygenated and functionalized unsymmetrical biaryls in good to excellent yields by the direct oxidative coupling of electron-rich arenes to the α-position of carbonyl functionality of in situ generated masked benzoquinones.