13575-75-2

Usage

Uses

Used in Pharmaceutical Synthesis:
6,7-Dimethoxy-1-tetralone is used as a key intermediate for the synthesis of various pharmaceutical compounds, including 2-bromotetralones, quinolines with dopaminergic activity, naphthols with anti-inflammatory properties, and benzophenanthridine alkaloids with antitumor activity. Its diverse reactivity allows for the creation of a wide range of therapeutic agents.
Used in Chemical Research:
In the field of chemical research, 6,7-Dimethoxy-1-tetralone is utilized as a starting material for the development of new chemical entities. Its ability to react with various reagents enables researchers to explore novel chemical pathways and create innovative compounds with potential applications in various industries.
Used in the Synthesis of 5,6-Dihydro-2,3,9,10-Tetramethoxybenz[c]acridine:
6,7-Dimethoxy-1-tetralone is used as a reactant in the formation of 5,6-dihydro-2,3,9,10-tetramethoxybenz[c]acridine when combined with 2-amino-4,5-dimethoxyacetophenone. 6,7-Dimethoxy-1-tetralone may have potential applications in the pharmaceutical or chemical industries, depending on its properties and characteristics.
Overall, 6,7-Dimethoxy-1-tetralone is a valuable compound in the fields of pharmaceuticals, chemical research, and specialty chemical synthesis due to its diverse reactivity and potential applications in creating new and useful compounds.

Synthesis Reference(s)

Tetrahedron Letters, 24, p. 2939, 1983 DOI: 10.1016/S0040-4039(00)88063-6

InChI:InChI=1/C8H6BrFO/c9-5-8(11)6-3-1-2-4-7(6)10/h1-4H,5H2

Upstream product

• 13575-74-1 4-(3,4-dimethoxyphenyl)butanoic acid 
• 91-16-7 1,2-dimethoxybenzene 
• 87543-06-4 1-<4,4-(1,2-Benzenediyldithio)but-3-enyl>-4-dimethoxybenzene 
• 1178964-08-3 6',7'-dimethoxy-3',4'-dihydro-2'H-spiro[1,3]dithiane-2,1'-naphthalene 
• 1445852-57-2 dimethyl 2-((4-(3,4-dimethoxyphenyl)butanoyl)oxy)succinate 
• 137744-82-2 C₁₂H₁₄O₄ 
• 35491-95-3 6,7-dimethoxy-1-hydroxytetraline 
• 348143-75-9 4-(3,4-dimethoxyphenyl)butanoic acid chloride 
• 93-40-3 (3,4-Dimethoxyphenyl)acetic acid 
• 5703-21-9 3,4-dimethoxyphenylacetaldehyde 
• 231935-01-6 ethyl 4-(3,4-dimethoxyphenyl)butanoate 
• 2107-70-2 3,4-methoxycinnamic acid 
• 3945-85-5 1-bromo-3-(3,4-dimethoxyphenyl)propane 
• 3929-47-3 3-(3,4-dimethoxyphenyl)-1-propanol 

Downstream Products

• 78238-92-3 6,7-dimethoxy-1-phenyl-3,4-dihydronaphthalene 
• 107446-43-5 (Methoxy-3')-benzylidene-2 dimethoxy-6,7 tetralone 
• 10103-06-7 2,3-dimethoxynaphthalene 
• 52401-41-9 6,7-dimethoxy-3,4-dihydronaphthalen-1(2H)-one oxime 
• 107446-45-7 (Trimethoxy-3',4',5')-benzylidene-2 dimethoxy-6,7 tetralone 
• 25298-23-1 2-Benzyl-6,7-dimethoxy-naphthalen-1-ol 
• 107446-44-6 (Dimethoxy-3',4)-benzylidene-2 dimethoxy-6,7 tetralone 
• 65503-06-2 2-(4-benzhydryl-piperazin-1-ylmethyl)-6,7-dimethoxy-3,4-dihydro-2H-naphthalen-1-one 
• 78238-93-4 6,7-dimethoxy-1-phenyl-1,2,3,4-tetrahydronaphthalen-1-ol 
• 65332-34-5 N-(3,4-dihydro-6,7-dimethoxy-1-naphthyl)-2-methoxy-N-methylbenzamide 
• 54714-44-2 2-bromo-6,7-dimethoxy-1-tetralone 
• 15288-02-5 6-hydroxy-7-methoxy-1-tetralone 
• 15288-01-4 7-hydroxy-6-methoxy-3,4-dihydronaphthalen-1(2H)-one 
• 54549-75-6 6,7-dihydroxy-3,4-dihydro-1(2H)-naphthalenone 

Relevant academic research and scientific papers

Identification of First-in-Class Inhibitors of Kallikrein-Related Peptidase 6 That Promote Oligodendrocyte Differentiation

Multiple sclerosis (MS) is an autoimmune demyelinating disease of the central nervous system (CNS) that causes severe motor, sensory, and cognitive impairments. Kallikrein-related peptidase (KLK)6 is the most abundant serine protease secreted in the CNS, mainly by oligodendrocytes, the myelin-producing cells of the CNS, and KLK6 is assumed to be a robust biomarker of MS, since it is highly increased in the cerebrospinal fluid (CSF) of MS patients. Here, we report the design and biological evaluation of KLK6's low-molecular-weight inhibitors, para-aminobenzyl derivatives. Interestingly, selected hit compounds were selective of the KLK6 proteolytic network encompassing KLK1 and plasmin that also participate in the development of MS physiopathology. Moreover, hits were found noncytotoxic on primary cultures of murine neurons and oligodendrocyte precursor cells (OPCs). Among them, two compounds (32 and 42) were shown to promote the differentiation of OPCs into mature oligodendrocytes in vitro constituting thus emerging leads for the development of regenerative therapies.

Synthesis and evaluation of 7-substituted-5,6-dihydrobenzo[c]acridine derivatives as new c-KIT promoter G-quadruplex binding ligands

It has been shown that treatment of cancer cells with c-KIT G-quadruplex binding ligands can reduce their c-KIT expression levels thus inhibiting cell proliferation and inducing cell apoptosis. Herein, a series of new 7-substituted-5,6-dihydrobenzo[c]acri

Highly enantioselective [3+2] coupling of cyclic enamides with quinone monoimines promoted by a chiral phosphoric acid

Enantioselective [3+2] coupling of cyclic enamides with quinone monoimines was realised using a chiral phosphoric acid as a catalyst. This transformation allowed for the synthesis of highly enantioenriched polycyclic 2,3-dihydrobenzofurans (up to 99.9% ee). The absolute configuration of one product was determined by an X-ray crystal structural analysis. We also found a possible mechanism for this reaction.

Intramolecular Friedel-Crafts Acylation Reaction Promoted by 1,1,1,3,3,3-Hexafluoro-2-propanol

Simple dissolution of an arylalkyl acid chloride in 1,1,1,3,3,3-hexafluoro-2-propanol promotes an intramolecular Friedel-Crafts acylation without additional catalysts or reagents. This reaction is operationally trivial in both execution and product isolation (only requiring concentration followed by purification) and accommodates a broad range of substrates. Preliminary studies that bear upon potential reaction mechanisms are reported.

Borontribromide-mediated C-C bond formation in cyclic ketones: A transition metal free approach

Borontribromide (BBr3) is a well-known demethylating agent. The current investigation was focused on a new application of borontribromide as a C-C bond forming agent in cyclic ketones. In this study, borontribromide mediated C-C bond formation reactions of tetralones, chromenone, thiochromenone and indanones were explored. A methoxy group containing ketones showed selective C-C bond formation reaction instead of demethylation of the methoxy group. MM2 steric energy calculations for the final products showed that the reaction favored the formation of exo- or endo-cyclic double bond containing products, depending upon their low MM2 steric energy in a specific frame structure, as observed in X-ray crystallography. A comprehensive crystallographic and pi-stacking analysis of product 10a demonstrated the formation of 10a as an enantiomeric mixture, and its centre of inversion was stabilized by a set of three unique pi-pi interactions.

Sustainable flow oppenauer oxidation of secondary benzylic alcohols with a heterogeneous zirconia catalyst

A flow chemistry process for the Oppenauer oxidation of benzylic secondary alcohols using partially hydrated zirconium oxide and a simple carbonyl containing oxidant such as acetone, cyclohexanone, and neopentanal is reported. The heterogeneous oxidative system could be applied to a wide range of functionalized alcohol substrates, allowing clean and fast delivery of ketone products within a few minutes between 40 and 100 C.

Expeditious approach to pyrrolophenanthridones, phenanthridines, and benzo[ c ]phenanthridines via organocatalytic direct biaryl-coupling promoted by potassium tert -butoxide

A methodology involving a "transition metal-free" intramolecular biaryl-coupling of o-halo-N-arylbenzylamines has been developed in the presence of potassium tert-butoxide and an organic molecule as catalyst. The reaction appears to proceed through KOtBu-promoted intramolecular homolytic aromatic substitution (HAS). Interestingly, this biaryl coupling also works in the presence of potassium tert-butoxide as sole promoter. On extending our approach further, we found that N-acyl 2-bromo-N-arylbenzylamines undergo a one-pot N-deprotection/biaryl coupling followed by oxidation, thus offering an expeditious route to the phenanthridine and benzo[c]phenanthridine skeletons. The strategy has been applied to a concise synthesis of Amaryllidaceae alkaloids viz. oxoassoanine (1b), anhydrolycorinone (1d), 5,6-dihydrobicolorine (2d), trispheridine (2b), and benzo[c]phenanthridines alkaloids dihydronitidine (3b), dihydrochelerythidine (3d), dihydroavicine (3f), nornitidine (3h), and norchelerythrine (3j).

12-N-Methylated 5,6-dihydrobenzo[c]acridine derivatives: A new class of highly selective ligands for c-myc G-quadruplex DNA

12-N-Methylated and non-methylated 5,6-dihydrobenzo[c]acridine derivatives were designed and synthesized as new series of c-myc G-quadruplex binding ligands. Their interactions with c-myc G-quadruplex were evaluated using fluorescence resonance energy tra

COMPOUNDS FOR THE INHIBITION OF CELLULAR PROLIFERATION

Compositions and methods for inhibiting translation are provided. Compositions, methods and kits for treating (1) cellular proliferative disorders, (2) non-proliferative, degenerative disorders, (3) viral infections, (4) disorders associated with viral infections, and/or (5) non-proliferative metabolic disorders such as type II diabetes where inhibition of translation initiation is beneficial using the compounds disclosed herein.