6372-63-0

Basic information

• Product Name: 9,10-dihydro-9,10-ethanoanthracen-11-one
• Synonyms: 9,10-DIHYDRO-9,10-ETHANOANTRACEN-11-ONE;9,10-Ethanoanthracen-11-one, 9,10-dihydro-
• CAS NO: 6372-63-0
• Molecular Formula: C₁₆H₁₂O
• Molecular Weight: 220.2659
• Mol File: 6372-63-0.mol

Chemical Properties

• Boiling Point: 382.6°C at 760 mmHg
• Flash Point: 169.3°C
• Density: 1.23g/cm³
• Vapor Pressure: 4.66E-06mmHg at 25°C
• Refractive Index: 1.656
• CAS DataBase Reference: 9,10-dihydro-9,10-ethanoanthracen-11-one(CAS DataBase Reference)
• NIST Chemistry Reference: 9,10-dihydro-9,10-ethanoanthracen-11-one(6372-63-0)
• EPA Substance Registry System: 9,10-dihydro-9,10-ethanoanthracen-11-one(6372-63-0)

Safety Data

• Hazardous Substances Data: 6372-63-0(Hazardous Substances Data)

Upstream product

• 1521-59-1 9,10-dihydro-9,10-ethano-anthracen-11-ol 
• 108-94-1 cyclohexanone 
• 556-91-2 aluminum tri-tert-butoxide 
• 106-51-4 p-benzoquinone 
• 33988-20-4 C₁₉H₁₅NO₂ 
• 1871-17-6 11-acetoxy-9,10-dihydro-9,10-ethanoanthracene 
• 33988-20-4 11-Acetoxy-9,10-dihydro-9,10-ethanoanthracen-11-carbonitril 
• 120-12-7 anthracene 
• 92855-58-8 11-Nitro-9,10-aethanoanthracen 
• 73301-18-5 C₂₂H₁₈O₂S 
• 29179-06-4 C₃₀H₂₂O 
• 3008-09-1 Dibenzobicyclo<2.2.2>octa-5,7-diene-2-carbonitrile 
• 91759-14-7 9,10-dihydro-9,10-ethenoanthracen-11-yl triflate 
• 210405-50-8 C₁₆H₁₂OS 

Downstream Products

• 22612-93-7 dibenzobicyclo<2.2.2>octane-2,3-dione 
• 104635-90-7 1,4<1',2'>-benzeno-1,2,3,4-tetrahydro-2-ethenylnaphthalen-2-ol 
• 1521-59-1 9,10-dihydro-9,10-ethano-anthracen-11-ol 
• 158465-35-1 3-Nitro-9,10-dihydro-11-keto-9,10-ethanoanthracene 
• 158465-34-0 2-Nitro-9,10-dihydro-11-keto-9,10-ethanoanthracene 
• 79965-52-9 15-ethyl-16-phenyltetracyclo[6.6.2.0^2,7.0^9,14]hexadeca-2⁽⁷⁾,3,5,9⁽¹⁴⁾,10,12,15-heptaene 
• 79979-60-5 11-methyl-12-phenyl-9,10-dihydro-9,10-etheno-anthracene 
• 79965-56-3 C₂₄H₂₀ 
• 79965-57-4 C₂₅H₂₂ 
• 79965-53-0 C₂₉H₂₂ 
• 79965-59-6 C₃₂H₃₈N₂O₂S 
• 79965-60-9 C₃₃H₄₀N₂O₂S 
• 79965-61-0 C₃₈H₄₂N₂O₂S 
• 91759-14-7 9,10-dihydro-9,10-ethenoanthracen-11-yl triflate 

Relevant articles and documents

Stereoselective Diels-Alder Reactions of gem-Diborylalkenes: Toward the Synthesis of gem-Diboron-Based Polymers

Although gem-diborylalkenes are known to be among the most valuable reagents in modern organic synthesis, providing a rapid access to a wide array of transformations, including the construction of C-C and C-heteroatom bonds, their use as dienophile-reactive groups has been rare. Herein we report the Diels-Alder (DA) reaction of (unsymmetrical) gem-diborylalkenes. These reactions provide a general and efficient method for the stereoselective conversion of gem-diborylalkenes to rapidly access 1,1-bisborylcyclohexenes. Using the same DA reaction manifold with borylated-dienes and gem-diborylalkenes, we also developed a concise, highly regioselective synthesis of 1,1,2-tris- A nd 1,1,3,4-tetrakis(boronates)cyclohexenes, a family of compounds that currently lack efficient synthetic access. Furthermore, DFT calculations provided insight into the underlying factors that control the chemo-, regio-, and stereoselectivity of these DA reactions. This method also provides stereodivergent syntheses of gem-diborylnorbornenes. The utility of the gem-diborylnorbornene building blocks was demonstrated by ring-opening metathesis polymerization (ROMP), providing a highly modular approach to the first synthesis of the gem-diboron-based polymers. Additionally, these polymers have been successfully submitted to postpolymerization modification reactions. Given its simplicity and versatility, we believe that this novel DA and ROMP approach holds great promise for organoboron synthesis as well as organoboron-based polymers and that it will result in more novel transformations in both academic and industrial research.

In search for thioketene S-oxide. A vinyl sulfoxide to sulfine rearrangement

Two approaches to thioketene S-oxide have been tested. This reactive heterocumulene was tentatively characterized by low temperature IR spectroscopy. In the course of this study, an unexpected vinyl sulfoxide to sulfine rearrangement was observed.

Distortion of Olefin and Carbonyl ?-Orbitals in Dibenzobicyclooctatrienes and Dibenzobicyclooctadienones. Unsymmetrization of ? Lobes Arising from ?-? Orbital Interactions

We have detected the unsymmetrical ? faces of the olefin group in 2-substituted dibenzobicyclooctatrienes (2-substituted 9,10-dihydro-9,10-ethenoanthracenes) and the carbonyl groups of 2-substituted and 3-substituted dibenzobicyclooctadienones (2-substituted and 3-substituted 9,10-dihydro-9,10-(11-ketoethano)anthracenes), wherein ?-type overlaps of the ? orbitals are involved, in a similar manner to longicyclic conjugation.An intrinsically nonequivalent substituent at distal positions modulates the epoxidation and dihydroxylation of the olefin group and the reduction of the carbonyl group.Both systems exhibit similar substituent effects: an "electron-withdrawing" substituent such as a nitro or fluoro group gave a large to moderate bias (preferred syn attack with respect to the substituent) whereas an "electron-donating" methoxy substituent exhibited a negligible bias.Herein we interpret these biases or nonbiases in terms of unsymmetrization of ? lobes of the olefin and carbonyl ? orbitals, arising from nonequivalent ?-? interactions rather than from an electron-donating or -withdrawing effect.

Reactions retrodieniques XX. Synthese et thermolyse eclair de bis-adduits de Diels-Alder : creation d'une triple liaison fonctionnalisee par double cycloreversion

La thermolyse eclair de bis-adduits de Diels-Alder appropries peut conduire a des alcynes fonctionnels.Cette reaction a ete testee sur les bis-adduits 1-3 du propiolate de methyle avec le cyclopentadiene, le furanne et l'anthracene respectivement et une double cycloreversion specifique en les composes de depart a ete obtenue a partir de 3.Une application a la mise en evidence de l'ethynol et de l'ethynamine a ete tentee avec la synthese et la thermolyse eclair des bis-adduits 9 et 10.Alors que seuls les tautomeres stables, cetene ou acetonitrile, ont ete detectes par RMN ou spectrometrie de masse, l'analyse par IR a basse temperature montre de plus des bandes faibles disparaissant a - 150 deg C et qui pourraient etre respectivement attribuees a l'ethynol (2230 cm-1) et a l'ethynamine (2160 cm-1).

Solvolysis of Ethenoanthracenyl Triflates. Novel Stabilized Cyclic Vinyl Cations

The solvolytic behaviot of ethenoanthracenyl (3a) and etheno-9,10-dimethylanthracenyl (3b) triflates was examined.Despite the strain inherent in these systems, 3a reacts 105 times faster than cyclohexenyl triflate and 11 times faster than the unstrained cis-2-butenyl triflate.These results are explained by an unusual aryl stabilization of the incipient vinyl cations.

1-Aza- and 1,9-Diazatriptycenes

The polycyclic 1,5-diketone 4 is synthesized via the enamine 2 from ketone 1 and phenyl vinyl ketone (3).On reacting the 1,5-diketone 4 with hydroxylamine the expected ring closure to the 1-azatriptycene 6 competes with a ring cleavage by an anomalous Beckmann rearrangement of the oxime yielding the intermediate nitrile 10 which cyclizes to afford the β-anthracenyl-α-amino-pyridine 7. Cycloaddition of dehydrobenzene, generated by diazotation of anthranilic acid, with the pyridoquinolines 13a, b produces the diazatriptycenes 15a,b.

Oxidative Decyanation of Secondary Nitriles to Ketones

Procedures for the oxidative decyanation of secondary nitriles to ketones involve (1) iodination of N-(trialkylsilyl)ketenimines derived from secondary nitriles and subsequent hydrolysis of the α-iodo nitriles with silver oxide, (2) addition of nitrosobenzene to N-(trialkylsilyl)ketenimines, (3) conversion of secondary nitriles to α-(phenylthio) nitriles and subsequent hydrolysis with N-bromosuccinimide in aqueous acetonitrile, and (4) preparation of α-hydroperoxy nitriles by direct oxygenation of anions of secondary nitriles and subsequent reductive hydrolysis with stannous chloride followed by sodium hydroxide.The latter general procedure was applied to various secondary nitriles bearing dialkyl, aryl and alkyl, and diaryl substituents to provide ketones in good yield and was extended to the oxidative decyanation of α,β-unsaturated nitriles to furnish α,β-unsaturated ketones.

OXIDATIVE DESULFONYLATION. PHENYL VINYL SULFONE AS A KETENE SYNTHETIC EQUIVALENT

α-Sulfonyl carbanions undergo oxidative desulfonylation to form ketones upon treatment with molybdenum peroxide MoO5*Py*HMPA (MoOPH) in THF at -78 deg C.