1459-16-1

Basic information

• Product Name: (3aR,9aS)-3a,4,9,9a-tetrahydronaphtho[2,3-c]furan-1,3-dione
• Synonyms: 3a,4,9,9a-tetrahydronaphtho[2,3-c]furan-1,3-dione
• CAS NO: 1459-16-1
• Molecular Formula: C₁₂H₁₀O₃
• Molecular Weight: 202.206
• Mol File: 1459-16-1.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 401.3°C at 760 mmHg
• Flash Point: 200.8°C
• Density: 1.308g/cm³
• Vapor Pressure: 1.19E-06mmHg at 25°C
• Refractive Index: 1.59
• CAS DataBase Reference: (3aR,9aS)-3a,4,9,9a-tetrahydronaphtho[2,3-c]furan-1,3-dione(CAS DataBase Reference)
• NIST Chemistry Reference: (3aR,9aS)-3a,4,9,9a-tetrahydronaphtho[2,3-c]furan-1,3-dione(1459-16-1)
• EPA Substance Registry System: (3aR,9aS)-3a,4,9,9a-tetrahydronaphtho[2,3-c]furan-1,3-dione(1459-16-1)

Safety Data

• Hazardous Substances Data: 1459-16-1(Hazardous Substances Data)

Usage

General Description

The chemical (3aR,9aS)-3a,4,9,9a-tetrahydronaphtho[2,3-c]furan-1,3-dione, also known as ambradiol, is a synthetic compound with a molecular formula C12H10O3. It is a naphthofuran derivative with potential pharmacological and biological activities. It has been studied for its anti-inflammatory and anticancer properties, as well as its potential as an analgesic and antipyretic agent. Research has shown that ambradiol can inhibit the production of pro-inflammatory cytokines and possess cytotoxic effects on cancer cells. (3aR,9aS)-3a,4,9,9a-tetrahydronaphtho[2,3-c]furan-1,3-dione has potential therapeutic applications for various medical conditions, and further studies are ongoing to explore its pharmacological properties and potential clinical uses.

Upstream product

• 108-31-6 maleic anhydride 
• 91-13-4 α,α'-dibromo-o-xylene 
• 87061-73-2 1,2,3,4,5,6,7,8-octahydro-1ξ,4ξ-etheno-naphthalene-6r,7c-dicarboxylic acid-anhydride 
• 5926-51-2 bromomaleic anhydride 
• 78808-36-3 1,2-bis[(phenylseleno)methyl]benzene 
• 105961-94-2 1,2-bis(phenylthiomethyl)benzene 

Downstream Products

• 101789-59-7 (+/-)-cis-3-benzyl-1,2,3,4-tetrahydro-[2]naphthoic acid 
• 7463-95-8 (3ar,9ac)-3a,4,9,9a-tetrahydro-3H-naphtho[2,3-c]furan-1-one 
• 101723-54-0 (+/-)-cis-3-benzoyl-1,2,3,4-tetrahydro-[2]naphthoic acid 
• 133326-05-3 (+/-)-3c-phenylcarbamoyl-1,2,3,4-tetrahydro-[2r]naphthoic acid 

Relevant articles and documents

KrF excimer laser photolysis of 1,2-bis(substituted-methyl)benzenes in the presence of alkenes and acetylene; two-photon formation of o-quinodimethane and its cycloaddition with dienophiles

o-Quinodimethane 3 is generated effectively by KrF excimer laser (248 nm) photolysis of 1,2-bis(phenoxymethyl)-, 1,2-bis(phenylthiomethyl)- and 1,2-bis(phenylselenomethyl)-benzene via a two-photon process; cycloaddition of 3 with several dienophiles gives corresponding adducts in a maximum yield of 48%.

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Electrochemical generation and reaction of o-quinodimethanes from {[[2-(2,2-dibutyl-2-stannahexyl)phenyl]-methyl]thio} benzenes

(equation presented) The anodic oxidation of {[[2-(2,2-dibutyl-2-stannahexyl)phenyl]methyl]thio}benzenes gave o-quinodimethanes which were trapped in situ by dienophiles to give the corresponding cycloadducts in excellent yields. The electron transfer and succeeding 1,4-elimination reaction was efficiently completed in a solution of lithium perchlorate/nitromethane in the presence of acetic acid. The reaction progress was quantitatively controlled by the passage of charge. By using this new method, an aryltetralin lignan skeleton was also synthesized.

Metallic Nickel Assisted Room-Temperature Generation and Diels-Alder Chemistry of o-Xylylene Intermediates

Highly reactive metallic nickel, prepared by the lithium metal reduction of nickel iodide using naphthalene as an electron carrier, was found to induce 1,4-dehalogenation of α,α'-dihalo-o-xylene derivatives at room temperature.The reaction proceeds in the presence of a variety of electron-deficient olefins, giving Diels-Alder cycloadducts in moderate to good yields presumably via the highly reactive intermediate o-xylylene 2. 1,3-Dibromoindan and 1,4-dibromo-1,2,3,4-tetrahydronaphthalene also react in the presence of electron-deficient olefins to give bridged cycloadducts in moderate yields.Methoxy as well as electron-deficient substituents such as bromide and nitrile groups on the aromatic ring of the starting dibromide were shown to be compatible with the reaction conditions yielding substituted cycloadducts in good yields.