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Usage

Uses

Used in Organic Synthesis:
Phenanthro[4,5-bcd]furan-3-ol is utilized as a key intermediate in organic synthesis for its ability to participate in various chemical reactions due to its furan ring and phenanthrene skeleton. Its reactivity allows for the creation of a wide range of derivative compounds, expanding the scope of chemical libraries.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, phenanthro[4,5-bcd]furan-3-ol serves as a potential lead compound for drug development. Its unique structure may offer novel binding affinities and selectivities towards biological targets, making it a candidate for the design of new pharmaceutical agents with specific therapeutic applications.
Used in Material Science:
Phenanthro[4,5-bcd]furan-3-ol is employed in material science for its potential to contribute to the development of new materials with enhanced properties. phenanthro[4,5-bcd]furan-3-ol's structural features may be leveraged to create materials with improved stability, reactivity, or other desirable characteristics for various industrial applications.
Used in Drug Development:
Phenanthro[4,5-bcd]furan-3-ol is used as a starting point in drug development due to its unique chemical properties and potential for molecular modification. Its capacity to be altered and optimized for specific biological interactions positions it as a promising candidate for the creation of new therapeutic agents.

InChI:InChI=1/C14H8O2/c15-10-7-6-9-5-4-8-2-1-3-11-12(8)13(9)14(10)16-11/h1-7,15H

Upstream product

• 6390-68-7 3,5,3',5'-Tetra-tert-butyl-6,6'-dimethyl-biphenyl-2,2'-diol 
• 94473-41-3 1,3a,5,7-t-butylphenanthro<4,5-bcd>furan-3(3aH)-one 
• 94473-39-9 1,3,6,8-tetra-t-butylphenanthrene-4,5-diol 
• 94473-33-3 1,11-dimethyl-2,4,8,10-tetra-t-butyldibenzo<1,3,2>dioxathiepine 6-oxide 
• 94473-38-8 1,3,7,9-tetra-t-butyl-phenanthro<4,5-def><1,3,2>dioxathiepine 5-oxide 
• 94473-34-4 1,3,7,9-tetra-t-butyl-10,11-dihydrophenantro<4,5-def><1,3,2>dioxathiepine 5-oxide 
• 117847-33-3 1,11-bis(bromomethyl)-2,4,8,10-tetra-t-butyldibenzo<1,3,2>dioxathiepine 6-oxide 
• 94473-42-4 1,5,7-tri-t-butylphenanthro<4,5-bcd>furan-3-ol 

Downstream Products

• 85-01-8 phenanthrene 

Relevant academic research and scientific papers

On Phenanthrene-4,5-quinones: a Synthesis of Morphenol

1,3,6,8-Tetra-t-butylphenanthrene-4,5-quinone (10) has been prepared as a short-lived species in solution, and rapidly rearranges to a dienone (12) which on debutylation yields morphenol (14): the corresponding 9,10-dihydroquinone (6) crystallises as its oxepine valence isomer (7).

Attempted characterisation of phenanthrene-4,5-quinone and electrochemical synthesis of violanthrone-16,17-quinone. How does the stability of bay quinones correlate with structural and electronic parameters?

In bay quinones, two carbonyl moieties are forced into close proximity by their spatial arrangement, resulting in an interesting axially chiral and nonplanar structure. Two representatives of this little-explored class of compounds were investigated experimentally in this work. Electrochemical oxidation of 4,5-dihydroxyphenanthrene failed to provide evidence for the reversible formation of phenanthrene-4,5-quinone. Even at temperatures as low as T = 229 K, cyclic voltammograms did not show any evidence for reversibility, indicating that phenanthrene-4,5-quinone likely is a reactive intermediate even at low temperatures. Electrochemical oxidation of the larger homologue 16,17-dihydroxyviolanthrone, on the other hand, was reversible, and the quinone could be characterised by spectroelectrochemical means. The results of quantum chemical calculations confirm the experimental findings and indicate that a bay dicarbonyl moiety, also found in a number of angucycline antibiotics, does not necessarily have to confer extreme reactivity. However, in a series of phenanthrene quinones with an equal number (zero) of Clar sextets and a varying number of bay carbonyl groups (zero to two), there was a clear correlation between the triplet energy, taken as a measure of biradical character, and the number of bay carbonyl moieties, with the lowest triplet energy predicted for phenanthrene-4,5-quinone (two bay carbonyl moieties).

Phenanthrene-4,5-quinones: a Synthesis of Morphenol

Oxidation of 1,3,6,8-tetra-t-butil-9,10-dihydrophenanthrene-4,5-diol (8), gave the corresponding 4,5-quinone (9), isolated as its oxepine valence isomer (19).Oxidation of 1,3,6,8-tetra-t-butilphenanthrene-4,5-diol (3) gave an even less stable quinone (4) which rearranged via its arene oxide valence isomer (26) to an enone (22).Acid catalysed debutylation of this produced morphenol (24).The annelated analogue (27) of the phenanthrenequinone (4) showed no tendency to rearrange.