19967-24-9

Upstream product

• 96-47-9 2-methyltetrahydrofuran 
• 71-43-2 benzene 
• 16433-43-5 4-phenyl-1-pentanoic acid 
• 101971-56-6 3-chloro-2-methyl-2-phenyltetrahydrofuran 
• 174090-36-9 4,4,5,5-tetramethyl-2-(1-phenyl-ethyl)-[1,3,2]dioxaborolane 
• 74-95-3 1,1-dibromomethane 
• 2406-17-9 2-methyl-2-phenyltetrahydrofuran 
• 591-50-4 iodobenzene 
• 821-09-0 n-Pent-4-enyl alcohol 
• 115476-97-6 (E)-ethyl 4-phenylpent-2-enoate 
• 7446-70-0 aluminium trichloride 
• 51259-14-4 ethyl 4-phenylpentanoate 
• 20796-33-2 4-phenyl-pent-3-en-1-ol 
• 724774-93-0 2-(iodomethyl)-2-phenyltetrahydrofuran 

Downstream Products

• 50334-08-2 4-phenylpentyl bromide 
• 1281027-53-9 C₁₅H₁₉NO₂ 
• 102753-70-8 8-phenyl-nonanoic acid 
• 101277-49-0 4-Oxo-8-phenyl-nonansaeure-methylester 
• 94383-08-1 4-phenyl-pentane-1-sulfonic acid 
• 15197-68-9 4-phenylpentanal 

Relevant academic research and scientific papers

Palladium-catalyzed double-bond migration of unsaturated hydrocarbons accelerated by tantalum chloride

The operationally simple palladium-catalyzed double-bond migration without heteroatom-containing coordinating functional groups is described. Addition of TaCl5 as a second catalyst greatly enhanced the migration efficiency to provide β-alkylsty

Agent for reduction of sensory irritation

Provision of a TRPA1 activity inhibitor capable of reducing sensory irritation to skin or mucous membrane and an agent for reduction of sensory irritation for skin or mucous membrane. A TRPA1 inhibitor and an agent for reduction of sensory irritation for skin or mucous membrane comprising as an active ingredient a compound represented by the following formula (1) wherein R1 and R3 each independently represent a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, R2 represents an alkyl group having 1 to 6 carbon atoms, R4 represents a hydrogen atom, a methyl group or an ethyl group, and a double line composed of a dotted line and a solid line represents a single bond or a double bond.

Practical Intermolecular Hydroarylation of Diverse Alkenes via Reductive Heck Coupling

The hydroarylation of alkenes is an attractive approach to construct carbon-carbon (C-C) bonds from abundant and structurally diverse starting materials. Herein we report a palladium-catalyzed reductive Heck hydroarylation of aliphatic and heteroatom-substituted terminal alkenes and select internal alkenes with an array of (hetero)aryl iodides. The reaction is anti-Markovnikov selective with terminal alkenes and tolerates a wide variety of functional groups on both the alkene and (hetero)aryl coupling partners. Additionally, applications of this method to complex molecule diversifications are demonstrated. Mechanistic experiments are consistent with a mechanism in which the key alkylpalladium(II) intermediate is intercepted with formate and undergoes a decarboxylation/C-H reductive elimination cascade to afford the saturated product and turn over the cycle.

Reagents for diverse iodosilane-mediated transformations

It was observed that a PhSiH2I-mediated protocol using PhSiH3 and cat. I2 caused the deiodination of 2-(iodomethyl)-2-phenyltetrahydrofuran. Stemming from the investigation of the mechanism, we found that the PhSiH3/

AGENT FOR REDUCTION OF SENSORY IRRITATION

Provision of a TRPA1 activity inhibitor capable of reducing sensory irritation to skin or mucous membrane and an agent for reduction of sensory irritation for skin or mucous membrane. A TRPA1 inhibitor and an agent for reduction of sensory irritation for skin or mucous membrane comprising as an active ingredient a compound represented by the following formula (1) wherein R1 and R3 each independently represent a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, R2 represents an alkyl group having 1 to 6 carbon atoms, R4 represents a hydrogen atom, a methyl group or an ethyl group, and a double line composed of a dotted line and a solid line represents a single bond or a double bond.

Etheric C-O bond hydrogenolysis using a tandem lanthanide triflate/supported palladium nanoparticle catalyst system

Selective hydrogenolysis of cyclic and linear ether C-O bonds is accomplished by a tandem catalytic system consisting of lanthanide triflates and sinter-resistant supported palladium nanoparticles in an ionic liquid. The lanthanide triflates catalyze endothermic dehydroalkoxylation, while the palladium nanoparticles hydrogenate the resulting intermediate alkenols to afford saturated alkanols with high overall selectivity. The catalytic C-O hydrogenolysis is shown to have significant scope, and the C-O bond cleavage is turnover-limiting.

Homologations of boronate esters: the first observation of sequential insertions

By employing dibromo or diiodomethane as halomethyllithium precursors, the in situ double and triple homologation of boronate esters has been obtained for the first time.

β-Halogeno Ether Synthesis of Olefinic Alcohols: Stereochemistry of the Ring-scission of 2-Substituted 3-Halogenotetrahydro-pyrans and -furans

The stereochemical outcome of the sodium ring-scission of 2-substituted 3-halogenotetrahydro-pyrans and -furans, with 2-substitution represented by alkyl, alkenyl or aryl, is presented.Although the cis- and the trans-tetrahydropyran scissions are hyghly stereoselective for (E)-5-substituted pent-4-enol, this stereoselectivity breaks down when the 2-substituent is conformationally undiscriminating (deuterium) or has substantial anomeric effects (methoxy).Consideration of this, along with conformational data from the preceding paper, provides an explanation of the stereoselectivity of the tetrahydropyran scission.Evidence against a radical, and for a carbanion intermediate is presented and a common, very rapidly inverting, 3-carbanion is considered to be formed from either cis- or trans-stereoisomers.Ring scission is also rapid (the carbanion cannot be trapped), but less rapid than carbanion inversion, and takes place before the slower conformational inversion can occur so that the (E)/(Z)-nature of the unsaturated alcohol produced is controlled by the initial tetrahydropyran conformation.The unstereospecific nature of the ring scission of both cis- and trans-2-alkyl-3-chlorotetrahydrofurans is explained as a consequence of their existence in conformational equilibria. The high stereoselectivity of the ring scission of cis- and trans-3-chloro-2,3-dimethyltetrahydropyrans, and the poor stereoselectivity of the scission of 2-alkyl-3-chloro-2-methyltetrahydrpyrans, is explained; the reaction of sodium with 2-butyl-3,3-dichlorotetrahydropyran is considered.Using the ring-scission of 3-chlor-2-ethyltetrahydropyran, short syntheses of (+/-)-endo-brevicomin are described to illustrate the utility of β-halogen ether synthesis.