32820-10-3

Usage

Uses

Used in Pharmaceutical Industry:
1-Hydroxy-7-Methoxy-1,2,3,4-tetrahydronaphthalene is used as an intermediate for the synthesis of dimeric 1,2,3,4-Tetrahydro-naphthalenylamine and Indan-1-ylamine derivatives. These derivatives exhibit mast cell-stabilizing and anti-allergic activity, making them valuable in the development of medications for treating allergic reactions and related conditions.
Used in Chemical Industry:
1-Hydroxy-7-Methoxy-1,2,3,4-tetrahydronaphthalene can also be utilized as a building block in the synthesis of other complex organic molecules, contributing to the development of novel compounds with diverse applications in various industries, such as materials science, agrochemicals, and specialty chemicals.

Upstream product

• 75-91-2 tert.-butylhydroperoxide 
• 1730-48-9 6-methoxy-1,2,3,4-tetrahydronaphthalene 
• 6836-19-7 7-Methoxy-1-tetralone 
• 3536-96-7 vinylmagnesium chloride 
• 1190118-13-8 C₁₆H₂₂O₃ 
• 6836-18-6 4-(4-methoxyphenyl) butanoyl chloride 
• 1068-55-9 isopropylmagnesium chloride 

Downstream Products

• 6836-19-7 7-Methoxy-1-tetralone 
• 182965-69-1 (+)-(S)-7-Methoxy-1-tetralol 
• 1313511-67-9 C₂₉H₂₈O₂Si 
• 1251857-71-2 7-methoxy-1-tosyl-1,2,3,4-tetrahydronaphthalene 
• 214401-42-0 [7-(4-Cyano-benzyloxy)-1,2,3,4-tetrahydro-naphthalen-2-yl]-acetic acid ethyl ester 
• 214401-46-4 ethyl {7-[2-(4-cyanophenyl)ethyl]-1,2,3,4-tetrahydro-2-naphthalenyl}acetate 
• 214401-43-1 [7-(4-Cyano-benzyloxy)-naphthalen-2-yl]-acetic acid ethyl ester 
• 63320-02-5 6-methoxy-1a,2,3,7b-tetrahydronaphtho[1,2-b]oxirene 
• 4133-34-0 7-methoxyl-2-tetralone 
• 1730-48-9 6-methoxy-1,2,3,4-tetrahydronaphthalene 
• 854234-34-7 7,7'-Dimethoxy-1,2,3,4,1',2',3',4'-octahydro-[1,1']binaphthyl 

Relevant academic research and scientific papers

New 5-carba-pterocarpans: Synthesis and preliminary antiproliferative activity on a panel of human cancer cells

Natural pterocarpans and synthetic 5-carba-pterocarpans are isosteres in which the oxygen atom at position 5 in the pyran-ring of pterocarpans is replaced by a methylene group. These 5-carba-analogues were obtained in good yields through the palladium-catalyzed oxyarylation of alcoxy-1,2-dihydronaphthalens with o-iodophenols in PEG-400. They were evaluated on human cancer cell lineages derived respectively from prostate tumor (PC3, IC50 = 11.84 μmol L?1, SI > 12)) and acute myeloid leukemia (HL-60, IC50 = 8.81 μmol L?1, SI > 16), highly incident cancer types presenting resistance against traditional chemotherapeutics. Compound 6c (LQB-492) was the most potent (IC50 = 3.85 μmol L?1, SI > 37) in SF-295 cell lineage (glioblastoma). Such findings suggest that 5-carba-pterocarpan can potentially be new hit compounds for further development of novel antiproliferative agents.

An oxidative dearomatization cyclization model for cortistatin A

The feasibility of a hypervalent iodine-mediated oxidative dearomatization/cyclization to produce the oxabicyclo[3.2.1]octene of cortistatin A has been demonstrated through a model study. An interesting tandem cyclization via a Ritter intermediate has been observed when a slightly different substrate was used.

Development of Novel Phosphino-Oxazoline Ligands and Their Application in Asymmetric Alkynlylation of Benzylic Halides

A new set of stereochemically diverse phosphino-oxazoline ligands derived from simple L-amino acids and 2-(diphenylphosphaneyl)benzoic acid were developed. Those mono anionic tridentated N,N,P-ligands promote the Cu-catalyzed enantioselective radical coupling of terminal alkynes with a broad range of benzylic halides including benzo-fused cyclic α-halides and α-silyl benzyl halides in high yield and excellent enantioselectivity under mild reaction conditions. With multi distinct sites for structural modification, a diverse pool of chiral N,N,P-ligands is readily accessed, allowing for rapid optimization of the ligand structure for a specific substrate. Notably, the enantioselective alkynlylation of benzylic halides bonds in benzo-cyclic molecules has also been realized for the first time.

Green Organic Solvent-Free Oxidation of Alkylarenes with tert-Butyl Hydroperoxide Catalyzed by Water-Soluble Copper Complex

Different benzylic compounds were efficiently oxidized to the corresponding ketones with aqueous 70% tert-butyl hydroperoxide (TBHP) and the catalytic system composed of CuCl2.2H2O and 2,2'-biquinoline-4,4'-dicarboxylic acid dipotassium salt (BQC). The catalytic system CuCl2/BQC/TBHP allows obtaining high yields at room temperature under organic solvent-free conditions. The interest of this system lies in its cost effectiveness and its benign nature towards the environment. Benzylic tertbutylperoxy ethers and benzylic alcohols were observed and suggested as the reaction intermediates. Analysis of organic products by atomic absorption did not show any contamination with copper metal. In terms of efficiency, CuCl2/BQC system is comparable or superior to the most of the catalytic systems described in the literature and which are based on toxic organic solvent.

Oxidative β-Halogenation of Alcohols: A Concise and Diastereoselective Approach to Halohydrins

β-Halohydrins bearing transformable halo- and hydroxyl groups, are easily converted into various valuable blocks in organic and pharmaceutical synthesis. A diastereoselective β-halogenation of benzylic alcohols was achieved under simple and low-cost conditions, which provided a direct synthesis of β-halohydrins. The simple reaction conditions, easily available reagents, high diastereoselectivities, and additional oxidant-free make this reaction very attractive and practical.

Synthesis method of C5a receptor antagonist W-54011

The invention discloses a synthesis method of a C5a receptor antagonist W-54011. The synthesis method comprises the following steps: performing Wittig reaction, demethylation, enol interconversion, oxidation and the like to obtain 7-methoxy-1,2,3,4-tetrah

11a-N-tosyl-5-carbapterocarpans: Synthesis, antineoplastic evaluation and in silico prediction of ADMETox properties

11a-N-tosyl-5-carbapterocarpans (5a–c and 6a–c), 9-N-tosyl-4,4a,9,9a-tetrahydro-3H-carbazole (7), 11a-N-tosyl-5-carbapterocarpen (8) analogues of LQB-223 (4a), were synthesized through palladium catalyzed azaarylation of substituted dihydronaphtalenes (14a–c) and cyclohexadiene (15), respectively, with N-tosyl-o-iodoaniline (11). In order to understand the role of the N-tosyl moiety for the pharmacological activity, the azacarbapterocarpen (9) was also synthesized by Fischer indol reaction. The structural requirements at the A and D-rings for the antineoplastic activity toward human leukemias and breast cancer cells were evaluated as well. Substitutions on the A-ring of 4a and analogues alter the effect on different breast cancer subtypes. On the other hand, A-ring is not essential for antileukemic activity since compound 7, which does not contain the A-ring, showed efficacy with high selectivity indices for drug-resistant leukemias. On the other hand, substitutions on the D-ring of 4a for fluorine or iodine did not improve the antileukemic activity. In silico studies concerning Lipinskís rule of five, ADMET properties and drug scores of those compounds were performed, indicating good physicochemical properties for all compounds, in special for compound 7.

Iodine(III)-mediated ring contraction reactions: Synthesis of oxygen-And nitrogen-substituted indanes

The synthesis of oxygen-And nitrogen-substituted indanes was successfully performed by iodine(III)-mediated ring contraction of 1,2-dihydronaphthalenes. Acetoxy and benzoyloxy alkenes afforded indanes in 60-71percent yield, irrespective of their position on aromatic ring. Similarly, the nitrogen containing substrates protected with 9-fluorenylmethyloxycarbonyl (Fmoc) and benzoyl (Bz) groups smoothly undergoes ring contraction giving indanes in 64-77percent yield. The tosyl-protected substrate resulted only in addition products.

Ansa-Ruthenium(II) Complexes of R2NSO2DPEN-(CH2)n(η6-Aryl) Conjugate Ligands for Asymmetric Transfer Hydrogenation of Aryl Ketones

New 3rd generation designer ansa-ruthenium(II) complexes featuring N,C-alkylene-tethered N,N-dialkylsulfamoyl-DPEN/η6-arene ligands, exhibited good catalytic performance in the asymmetric transfer hydrogenation (ATH) of various classes of (het)aryl ketones in formic acid/triethylamine mixture. In particular, benzo-fused cyclic ketones furnished 98 to >99.9% ee using a low catalyst loading.

Synthesis of 11a- N -Arylsulfonyl-5-carbapterocarpans (Tetrahydro-5 H -benzo[ a ]carbazoles) by Azaarylation of Dihydronaphthalenes with o -Iodo- N -(Arylsulfonyl)anilines in Poly(ethylene glycol)

11a-N-Arylsulfonyl-5-carbapterocarpans (tetrahydro-5H-benzo[a]carbazoles) were synthesized by palladium-catalyzed azaarylation of dihydronaphthalenes with o-iodo-N-(arylsulfonyl)anilines in poly(ethylene glycol) (PEG-400). Better chemical yields (moderate