66377-63-7

Usage

Uses

Used in Fragrance Industry:
(1,2,3,4-tetrahydronaphthalen-4-yl)methanol is used as a fragrance ingredient for its pleasant, floral odor. It is incorporated into perfumes and cosmetics to provide a desirable scent, enhancing the sensory experience for consumers.
Used in Organic Synthesis:
(1,2,3,4-tetrahydronaphthalen-4-yl)methanol serves as a starting material in the synthesis of various organic compounds. Its unique structure allows for further chemical reactions and modifications, making it a valuable precursor in the development of new chemical entities for a range of applications, including pharmaceuticals, agrochemicals, and specialty chemicals.

Upstream product

• 21919-44-8 1-allyl-2-vinylbenzene 
• 1914-65-4 tetralin-1-carboxylic acid 
• 17502-86-2 Methyl 1,2,3,4-tetrahydronaphthalene-1-carboxylate 
• 113967-23-0 methyl 1-methyl-1,2,3,4-tetrahydronaphthalene-1-carboxylate 
• 155566-54-4 1,2,3,4-tetrahydro-1-naphthalenecarbaldehyde 
• 93340-32-0 3,4-dihydro-1-naphthalenecarboxaldehyde 
• 4009-98-7 (methoxymethyl)triphenylphosphonium chloride 
• 201801-48-1 1,2,3,4-tetrahydro-1-(methoxymethylene)naphthalene 
• 25108-63-8 1-methylene-1,2,3,4-tetrahydronaphthalene 
• 529-34-0 3,4-dihydronaphthalene-1(2H)-one 
• 2510-03-4 1,2,3,4-tetrahydro-1-naphthylidene malononitrile 
• 70755-03-2 (1,2,3,4-tetrahydronaphthalen-1-yl)methyl acetate 
• 7125-62-4 1,2-benzo-1,3-cycloheptadiene 
• 447-53-0 1,2-Dihydronaphthalene 

Downstream Products

• 91-20-3 naphthalene 
• 90-12-0 1-Methylnaphthalene 
• 19063-23-1 (1,2,3,4-tetrahydronaphthalen-1-yl)methyl 4-methylbenzenesulfonate 
• 117941-64-7 2-<(hydroxyimino)methyl>-3-methyl-1-<<(1',2',3',4'-tetrahydronaphth-1'-yl)methoxy>methyl>imidazolium chloride 
• 117408-87-4 1-Iodomethyl-1,2,3,4-tetrahydro-naphthalene 
• 529-34-0 3,4-dihydronaphthalene-1(2H)-one 

Relevant academic research and scientific papers

Stereoselective Synthesis of Carbobicyclics via Organoyttrium-Catalyzed Sequential Cyclization/Silylation Reactions

The sequential cyclization/silylation of 1,5-dienes and 1,6-dienes was effected under mild reaction conditions using catalytic quantities of Cp2*YMe-THF. The process provides carbobicyclics in high yields and with excellent selectivities. The active catalyst is postulated to be Cp2*YH-THF, which is generated in situ. A variety of alkenyl-substituted cyclopentane and cyclohexane substrates were examined. The high diastereoselectivities apparently originate from a preference for a chairlike transition structure that minimizes unfavorable steric interactions between the bulky Cp* ligands of the catalyst and the preexisting ring of the substrate. Acyclic triene precursors, 4-ethenyl-substituted 1,5-heptadienes and 5-ethenyl-substituted 1,8-nonadienes were also examined. These triene substrates, when exposed to the cyclization/silylation protocol, provide the strained trans-bicyclo[3.3.0]octanes and trans-decalin systems in high yield with excellent diastereoselectivity. The high selectivity is again attributed to the preference for a chairlike transition structure. The cyclized organosilane products isolated from these reactions were easily converted to the more versatile alcohols utilizing known oxidation methods.

Exploiting sequential lipase-catalyzed reactions to achieve enantiomerically pure chiral primary alcohols

The lipase-catalyzed enantioselective acetylation of benzofused cycloalkane-containing primary alcohols with vinyl acetate was performed and allowed the isolation of enantiopure alcohols. Lipases from P. cepacia, C. rugosa, C. antarctica, P. fluorescens, C. cylindracea and M. miehei exhibited remarkable activity towards acetylation of these alcohols, affording the corresponding acetates with high conversion. Due to the high lipase activity toward primary alcohols, the enantioselectivity was low. To circumvent this problem, sequential kinetic resolution was employed with enantiocomplementary lipases leading to enantiomerically pure primary alcohols. This method represents a new approach to obtain chiral building blocks bearing ring systems, such as indanes, chromanes and tetralins.

Palladium/TY-Phos-Catalyzed Asymmetric Intermolecular α-Arylation of Aldehydes with Aryl Bromides

Despite much progress has been made in the asymmetric α-arylation reactions of cyclic ketones, lactones and lactams, the enantioselective α-arylation of acyclic carbonyl compounds lagged much behind due to the in situ generated Z/E-enolate intermediates l

Functional Group Interconversion of Alkylidenemalononitriles to Primary Alcohols by a Cooperative Redox Operation

Functional group interconversions are essential chemical processes enabling synthesis. In this report, we describe a strategy to convert alkylidenemalononitriles into primary alcohols in one step. The reaction relies on a choreographed redox process invol

Visible-Light-Mediated Anti-Markovnikov Hydration of Olefins

Considering that stoichiometric borane and oxidant are required in the classical alkene anti-Markovnikov hydration process, it remains appealing to achieve the transformation in a catalytic protocol. Herein, a visible-light-mediated anti-Markovnikov addition of water to alkenes by using an organic photoredox catalyst in conjunction with a redox-active hydrogen atom donor was developed, which avoided the need for a transition-metal catalyst, stoichiometric borane, as well as oxidant. Both terminal and internal olefins are readily accommodated in this transformation to obtain corresponding primary and secondary alcohols in good yields with single regioselectivity. This procedure can be scaled up to gram scale with a 230 turnover number based on photocatalyst.

Tryptamine-Based Derivatives as Transient Receptor Potential Melastatin Type 8 (TRPM8) Channel Modulators

Pharmacological modulation of the transient receptor potential melastatin type 8 (TRPM8) is currently under investigation as a new approach for the treatment of pain and other diseases. In this study, a series of N-substituted tryptamines was prepared to explore the structural requirements determining TRPM8 modulation. Using a fluorescence-based screening assay, we identified two compounds acting as an activator (2-(1H-indol-3-yl)-N-(4-phenoxybenzyl)ethanamine, 21) or an inhibitor (N,N-dibenzyl-2-(1H-indol-3-yl)ethanamine, 12) of calcium influx in HEK293 cells. In patch-clamp recordings, compound 21 displayed a significantly higher potency (EC50 = 40 ± 4 μM) and a similar efficacy when compared to menthol; by contrast, compound 12 produced a concentration-dependent inhibition of menthol-induced TRPM8 currents (IC50 = 367 ± 24 nM). Molecular modeling studies using a homology model of a single rat TRPM8 subunit identified a putative binding site located between the VSD and the TRP box, disclosing differences in the binding modes for the agonist and the antagonist.

Oxidative rearrangement of alkenes using in situ generated hypervalent iodine(III)

A novel protocol for the oxidative rearrangement of alkenes using in situ generated hypervalent iodine(III) was developed. This approach uses inexpensive, readily available, and stable chemicals (PhI, mCPBA, and TsOH) giving rearrangement products in yields comparable to those obtained using the more expensive commercially available [hydroxy(tosyloxy)iodo]benzene [HTIB or Koser's reagent]. Additionally, an alternative protocol for the synthesis of 1-methyl-2-tetralone through the one-step epoxidation/rearrangement of 4-methyl-1,2-dihydronaphthalene using mCPBA and TsOH was developed.

COLCHICINE DERIVATIVES OR PHARMACEUTICALLY ACCEPTABLE SALTS THEREOF, METHOD FOR PREPARING SAID DERIVATIVES, AND PHARMACEUTICAL COMPOSITION COMPRISING SAID DERIVATIVES

The present invention relates to colchicine derivatives expressed in chemical formula 1, or to pharmaceutically acceptable salts thereof, to a method for preparing said derivatives, and to a pharmaceutical composition comprising said derivatives. The colchicine derivatives according to the present invention exhibit superior immunomodulatory effects as compared with conventional immunomodulators or colchicines, and therefore can be valuably used as an immunomodulator for modulating an acute or chronic immune response in organ transplantation.

COLCHICINE DERIVATIVES OR PHARMACEUTICALLY ACCEPTABLE SALTS THEREOF, METHOD FOR PREPARING SAID DERIVATIVES, AND PHARMACEUTICAL COMPOSITION COMPRISING SAID DERIVATIVES

The present invention relates to colchicine derivatives expressed in chemical formula 1, or to pharmaceutically acceptable salts thereof, to a method for preparing said derivatives, and to a pharmaceutical composition comprising said derivatives. The colchicine derivatives according to the present invention exhibit superior immunomodulatory effects as compared with conventional immunomodulators or colchicines, and therefore can be valuably used as an immunomodulator for modulating an acute or chronic immune response in organ transplantation.

Synthesis of alcohols via a rhodium-catalyzed hydroformylation-reduction sequence using tertiary bidentate amine ligands

The synthesis of alcohols from aromatic olefins is described using a rhodium-catalyzed hydroformylation-reduction sequence with the assistance of a tertiary diamine ligand. The alcohols are produced in excellent branched to linear ratios and in good to excellent isolated yields. In all cases no aldehyde product, from hydroformylation, or alkyl product, from olefin reduction, was detected. Copyright