26231-23-2

Usage

Uses

Used in Fragrance and Flavor Industry:
4-Dihydro-6-Methoxynaphthalen-1(2H)-one is used as a key ingredient in the production of fragrances and flavors due to its appealing scent. Its aromatic properties contribute to the creation of various perfumes, colognes, and food flavorings, enhancing the sensory experience of consumers.
Used in Pharmaceutical Industry:
In the pharmaceutical sector, 4-Dihydro-6-Methoxynaphthalen-1(2H)-one serves as an important intermediate in the synthesis of various medicinal compounds. Its unique chemical structure allows for the development of new drugs with potential therapeutic applications.
Used in Organic Synthesis:
4-Dihydro-6-Methoxynaphthalen-1(2H)-one is utilized as a versatile building block in organic synthesis. Its reactivity and functional groups make it suitable for the preparation of a wide range of organic compounds, including dyes, agrochemicals, and other specialty chemicals.
Used in Research:
4-Dihydro-6-Methoxynaphthalen-1(2H)-one is of particular interest to scientists studying organic chemistry and fragrance compounds. Its unique structure and properties provide valuable insights into the behavior of naphthalenones and contribute to the advancement of chemical knowledge in these fields.

Upstream product

• 1078-19-9 6-methoxy-3,4-dihydro-1(2H)-naphthalenone 
• 584-08-7 potassium carbonate 
• 107318-16-1 5-bromo-6-hydroxy-3,4-dihydro-1(2H)-naphthalenone 
• 74-88-4 methyl iodide 

Downstream Products

• 144619-97-6 5-benzyloxy-6-methoxy-1-tetralone 

Relevant academic research and scientific papers

Synthesis of a macrocycle bearing a carbon framework of [16]Cyclophenacene as a Carbon Nanobelt

A synthetic pathway to a functionalized tetrahydro[5]phenacene was developed, which served as a precursor, leading to a dehydrobenzo[32]annulene macrocycle containing four carbon-carbon triple bonds. The high efficiency of the macrocyclization step can be

Synthesis of dihydronaphthalene analogues inspired by combretastatin A-4 and their biological evaluation as anticancer agents

The natural products colchicine and combretastatin A-4 (CA4) have provided inspiration for the discovery and development of a wide array of derivatives and analogues that inhibit tubulin polymerization through a binding interaction at the colchicine site on β-tubulin. A water-soluble phosphate prodrug salt of CA4 (referred to as CA4P) has demonstrated the ability to selectively damage tumor-associated vasculature and ushered in a new class of developmental anticancer agents known as vascular disrupting agents (VDAs). Through a long-term program of structure activity relationship (SAR) driven inquiry, we discovered that the dihydronaphthalene molecular scaffold provided access to small-molecule inhibitors of tubulin polymerization. In particular, a dihydronaphthalene analogue bearing a pendant trimethoxy aryl ring (referred to as KGP03) and a similar aroyl ring (referred to as KGP413) were potent inhibitors of tubulin polymerization (IC50 = 1.0 and 1.2 μM, respectively) and displayed low nM cytotoxicity against human cancer cell lines. In order to enhance water-solubility for in vivo evaluation, the corresponding phosphate prodrug salts (KGP04 and KGP152, respectively) were synthesized. In a preliminary in vivo study in a SCID-BALB/c mouse model bearing the human breast tumor MDA-MB-231-luc, a 99% reduction in signal was observed with bioluminescence imaging (BLI) 4 h after IP administration of KGP152 (200 mg kg?1) indicating reduced tumor blood flow. In a separate study, disruption of tumor-associated blood flow in a Fischer rat bearing an A549-luc human lung tumor was observed by color Doppler ultrasound following administration of KGP04 (15 mg kg?1).

Construction of Axially Chiral Arylborons via Atroposelective Miyaura Borylation

Compared with the well-developed centrally chiral boron chemistry, C-B axially chiral chemistry remains elusive and challenging. Herein we report the first atroposelective Miyaura borylation of bromoarenes with unsymmetrical diboron reagents for the direct catalytic synthesis of optically active atropisomeric arylborons. This reaction features broad substrate scope and produces axially chiral arylborons with high yields and good enantioselectivities.

Formal total synthesis of atropurpuran

Atropurpuran, isolated from the roots of Aconitum hemsleyanum, is a non-alkaloidal diterpene which possesses a unique pentacyclic skeleton that contains an unprecedented tetracyclo[5.3.3.04,9.04,12]tridecane unit. We report herein the formal total synthes

4H-THIENO[3,2-C]CHROMENE-BASED INHIBITORS OF NOTUM PECTINACETYLESTERASE AND METHODS OF THEIR USE

Compounds that may be used to inhibit Notum Pectinacetylesterase are described, as well as compositions comprising them, and methods of their use to treat diseases and disorders affecting bone.

Environmentally benign electrophilic and radical bromination 'on water': H2O2-HBr system versus N-bromosuccinimide

A H2O2-HBr system and N-bromosuccinimide in an aqueous medium were used as a 'green' approach to electrophilic and radical bromination. Several activated and less activated aromatic molecules, phenylsubstituted ketones and styrene were efficiently brominated 'on water' using both systems at ambient temperature and without an added metal or acid catalyst, whereas various non-activated toluenes were functionalized at the benzyl position in the presence of visible light as a radical activator. A comparison of reactivity and selectivity of both brominating systems reveals the H2O2-HBr system to be more reactive than NBS for benzyl bromination and for the bromination of ketones, while for electrophilic aromatic substitution of methoxy-substituted tetralone it was higher for NBS. Also, higher yields of brominated aromatics were observed when using H2O2-HBr 'on water'. Bromination of styrene reveals that not just the structure of the brominating reagent but the reaction conditions: amount of water, organic solvent, stirring rate and interface structure, play a key role in defining the outcome of bromination (dibromination vs bromohydroxylation). In addition, mild reaction conditions, a straightforward isolation procedure, inexpensive reagents and a lower environment impact make aqueous brominating methods a possible alternative to other reported brominating protocols.

Directed regioselectivity of bromination of ketones with NBS: solvent-free conditions versus water

The reaction conditions employed directed the site of functionalisation of ketones with NBS: under solvent-free conditions α-bromination was the exclusive process, while in water, ring functionalisation occurred in the case of methoxy substituted aromatic ketones.

TETRAHYDRO-6,7-DIMETHOXY-1H-BENZ[E]ISOINODOLINES USEFUL IN THE TREATMENT OF HYPERTENSION AND AS SEDATIVES

Disclosed herein are tetrahydro-benzo e!isoindolines represented by the formula STR1 wherein R, R 1 and R 2 are independently selected from hydrogen, loweralkyl of 1 to 4 carbon atoms, hydroxy, loweralkoxy of 1 to 3 carbon atoms, allyloxy, benzyloxy, benzoyloxy, thiomethyl, halo, STR2 wherein t is 0 or 1, n is 0 to 5 and R 11 and R 14 are independently selected from hydrogen, halo, hydroxy, loweralkyl of 1 to 4 carbon atoms, loweralkoxy of 1 to 3 carbon atoms or amino; orR and R. sub.1, or R 1 and R 2 can be taken together to form a methylenedioxy or ethylenedioxy bridge; with the proviso that at least one of R, R 1 or R 2 must be other than hydrogen and the proviso that two of R, R 1, or R 2 must be other than methoxy in the 7 and 8 positions when the remaining one of R, R 1 or R 2 is hydrogen; andR 3 is hydrogen, loweralkyl of 1 to 4 carbon atoms, halo-substituted loweralkyl of 1 to 4 carbon atoms, amino-substituted loweralkyl of 1 to 4 carbon atoms, amino-substituted arylalkyl, allyl, thioloweralkyl, loweralkanol, or STR3 wherein R 12 and R 13 are independently selected from hydrogen, hydroxy, amino, loweralkoxy of 1 to 3 carbon atoms and s is 1 to 3; or STR4 wherein m is 0, 1 or 2, p is 0 or 1, R 7 is hydrogen or loweralkyl of 1 to 4 carbon atoms and R 8 and R 9 are independently selected from hydrogen, hydroxy, methoxy, loweralkyl of 1 to 4 carbon atoms, or halo, or R 8 and R 9 can be taken together to form a methylenedioxy or ethylenedioxy bridge; or 1,4-benzodioxan of the formula STR5 wherein q is 1, 2 or 3, and R 10 is hydrogen, methoxy, amino, or halo; and the pharmaceutically acceptable salts thereof.