201801-48-1

Usage

Physical state

Colorless liquid

Odor

Strong, aromatic

Usage

Fragrance in perfumes, soaps, and personal care products; flavoring agent in food products; solvent in industrial processes

Safety precautions

Can be harmful if ingested or inhaled, should be handled with care and in accordance with safety guidelines.

Upstream product

• 4009-98-7 (methoxymethyl)triphenylphosphonium chloride 
• 529-34-0 3,4-dihydronaphthalene-1(2H)-one 

Downstream Products

• 93340-32-0 3,4-dihydro-1-naphthalenecarboxaldehyde 
• 25634-94-0 (1-methyl-1,2,3,4-tetrahydronaphthalen-1-yl)methanol 
• 66377-63-7 (1,2,3,4-tetrahydronaphthalen-4-yl)methanol 
• 107424-67-9 1,2,3,4-tetrahydro-1-naphthalenecarboxylic acid phenyl ester 
• 1914-65-4 tetralin-1-carboxylic acid 
• 155566-54-4 1,2,3,4-tetrahydro-1-naphthalenecarbaldehyde 

Relevant academic research and scientific papers

Rhodium-Catalyzed Desymmetric Arylation of γ,γ-Disubsituted Cyclohexadienones: Asymmetric Synthesis of Chiral All-Carbon Quaternary Centers

The desymmetric arylation of prochiral cyclohexadienones with ArZnCl in the presence of an (R)-segphos-rhodium catalyst gave high yields of the corresponding cyclohexenones, which contain a chiral arylated carbon center at the β-position and a chiral all-carbon quaternary center at the γ-position, with high diastereo- and enantioselectivities. This catalytic system was also applied to the arylation of spirocarbocyclic cyclohexadienones and afforded the corresponding cyclohexenones bearing a chiral spiro quaternary carbon with high dr and ee.

Palladium-Catalyzed Allenamide Carbopalladation/Allylation with Active Methine Compounds

A palladium-catalyzed allenamide carbopalladation/allylation with active methine compounds has been developed. Various indoles and isoquinolinones bearing a quaternary carbon center were achieved with good efficiency, a broad substrate scope and good functional group tolerance. This reaction underwent cascade oxidative addition, carbopalladation, and allylic alkylation, and two new C-C bonds were formed in one pot.

Nickel-Catalyzed Desymmetric Hydrogenation of Cyclohexadienones: An Efficient Approach to All-Carbon Quaternary Stereocenters

Nickel-catalyzed desymmetric hydrogenation has been achieved. With the Ni(OTf)2/(S,S)-Ph-BPE system, a series of ?,?-disubstituted cyclohexadienones were transformed to the corresponding cyclohexenones with a chiral all-carbon quaternary center at the γposition in high yields (92-98%) and excellent enantioselectivities (92%-99% ee). This catalytic system can also tolerate the desymmetric reaction of spirocarbocyclic cyclohexadienones to produce the corresponding cyclohexenones bearing a chiral spiro quaternary carbon with high yields (94%-98%) and ee values (96%-99% ee). Furthermore, this methodology provides an efficient and concise synthetic route to the intermediate of natural products cannabispirenones A and B.

Oxidative cleavage of α-aryl aldehydes using iodosylbenzene

We found that α-aryl aldehydes can be cleaved to chain-shortened carbonyl compounds and formaldehyde by various iodosylbenzene complexes. A mechanistic scheme is presented that accounts for the loss of one carbon atom. Formaldehyde is further oxidized to CO and CO2 under the reaction conditions.

Synthesis and biological activity of both enantiomers of kujigamberol isolated from 85-million-years-old Kuji amber

The full-structure of a norlabdane terpenoid, kujigamberol (1) was determined by total synthesis. Key features of the total synthesis are (1) installation of isopentyl group through an o-lithiation of benzamide, (2) construction of tetralone by the RCM reaction, and (3) optical resolution of (±)-1 using chromatographical separation of the corresponding camphanates. X-ray crystallographical analysis of p-bromobenzoate obtained from the more polar camphanate that was identical with a natural derivative, revealed natural kujigamberol to have an S-configuration. Both the natural enantiomer and its (R)-antipode showed the same inhibitory activity toward the mutant yeast and HL-60 cells, while simple analogs without alkyl groups at the C-8 and 9 positions of (±)-1 had no such activity.

Enantioselective synthesis of allenecarboxylates from phenyl acetates through C-C bond forming reactions

A variety of optically active 4,4-disubstituted allenecarboxylic acid methyl esters were prepared from simple α,α-disubstituted phenyl acetate through base treatment of the esters to generate ketenes, followed by successive Horner-Wadsworth-Emmons reaction. The transformation was further developed as a one-pot procedure with satisfactory yields and high enantioselectivity.