605-55-0

Usage

Chemical Properties

Off-White Solid

Uses

A labelled metabolite of Phenanthrene.

InChI:InChI=1/C14H10O/c15-12-7-8-14-11(9-12)6-5-10-3-1-2-4-13(10)14/h1-9,15H

Upstream product

• 41105-40-2 phenanthrene-2-sulfonic acid 
• 85-01-8 phenanthrene 
• 38499-81-9 1-methylsulfinyl-4-(naphthalen-1'-yl)butan-2-one 
• 82381-07-5 (+/-)-7-hydroxy-(4arH.10acH)-1.2.3.4.4a.9.10.10a-octahydro-phenanthrene 
• 92729-50-5 Phenanthrone 
• 13837-48-4 2-methoxyphenanthrene 
• 54125-02-9 danishefsky's diene 
• 86-57-7 1-Nitronaphthalene 
• 15254-66-7 acetic acid-[2]phenanthryl ester 
• 16191-32-5 2-(2-furanyl)-benzaldehyde 
• 106-96-7 propargyl bromide 
• 1392144-13-6 C₂₈H₂₆N₄O₅S₂ 
• 98-80-6 phenylboronic acid 
• 1030863-10-5 4-hydroxy-[1,1'-biphenyl]-2-carbaldehyde 

Downstream Products

• 4120-77-8 N-[2]phenanthryl-acetamide 
• 23070-75-9 1-Amino-phenanthrol-(2) 
• 117978-17-3 2-hydroxy-phenanthrene-3-carboxylic acid 
• 573-12-6 phenanthrene 1,2-quinone 
• 94688-53-6 Phenyl-phenanthryl-⁽²⁾-aether 
• 3366-65-2 2-aminophenanthrene 
• 60917-41-1 trans-1,2-dihydroxy-1,2-dihydrophenanthrene 
• 19551-05-4 1,2-Diacetoxy-phenanthren 
• 13837-48-4 2-methoxyphenanthrene 

Relevant academic research and scientific papers

In-Fjord Substitution in Expanded Helicenes: Effects of the Insert on the Inversion Barrier and Helical Pitch

A series of expanded helicenes of different sizes and shapes incorporating phenyl- and biphenyl-substituents at the deepest part of their fjord have been synthesized via sequential Au-catalyzed hydroarylation of appropriately designed diynes, and their racemization barriers have been calculated employing electronic structure methods. These show that the overall profile of the inversions (energies, number of transition states and intermediates, and their relative position) is intensively affected by the interplay of steric and attractive London dispersion interactions. Hence, in-fjord substitution constitutes an additional tool to handle the mechanical properties in helicenes of uncommonly large diameter. The photochemical characterization of the newly prepared helical structures is also reported.

Nitronaphthalenes as Diels-Alder dienophiles

1-Nitronaphthalene, 2-nitronaphthalene and 1,3-dinitronaphthalene react with Danishefsky diene as normal electron demand Diels-Alder dienophiles to give hydroxyphenanthrene derivatives as principal products in reasonable yields. The aromatization is an ex

Experimental and theoretical studies on polar Diels-Alder reactions of 1-nitronaphathalene developed in ionic liquids

The reactions between 1-nitronaphthalene 1 and two nucleophilic dienes, Danishefskys diene 2 and 1-trimethylsilyloxy-1,3-butadiene 3, to yield phenanthrenols 7 and 8 developed in protic and aprotic ionic liquids (ILs) with an imidazolium cation base permit to conclude that the reactions occur in better experimental conditions than in molecular solvents. The yields obtained with protic ILs are better than those observed with aprotic ILs. In this sense, the higher yields obtained with aprotic ILs, (working at 60°C, 48 h) are comparable with the lower yields observed in protic ILs (60°C, 24 h). DFT calculations for the reaction of 1-nitronaphthalene 1 with diene 3, in the absence and in the presence of tetrafluoroborate of 1-metilimidazolium [HMIM][BF4] as protic ILs, indicate that this reaction is a domino process that comprises two consecutive processes: i) a polar Diels-Alder (P-DA) reaction between 1 and 3, and ii) an elimination of nitroso acid 5 to yield dihydrophenanthrene 11. Thermodynamic calculations indicate that while the first reaction is the rate-determining step of this domino process, the nitroso acid elimination is the driving force responsible for the formation of dihydrophenanthrene 11. Implicit and explicit solvent effects indicate that while the hydrogen bond formation between HMIM and one oxygen atom of the nitro groups favour the two reactions, implicit solvent effects modelled by PCM decelerate the P-DA reaction by a large solvation of reagents. Finally, DFT analysis of reagents offers an explanation of the catalytic role of protic ILs in these P-DA reactions.

Rhodium(II)-catalyzed cyclization of bis(N-tosylhydrazone)s: An efficient approach towards polycyclic aromatic compounds

Ahead of the PAC: Polycyclic aromatic compounds (PACs) can be easily accessed by the combination of Suzuki-Miyaura cross-coupling and a [Rh 2(OAc)4]-catalyzed carbene reaction using easily available bis(N-tosylhydrazone)s as intermediates (see scheme; Ts=4-toluenesulfonyl). Copyright

Intramolecular gold(III) catalysed Diels-Alder reaction of 1-(2-furyl)-hex-1-en-5-yn-3-ol derivatives: A short and generalised route for the synthesis of hydroxyphenanthrene derivatives

Gold(III) catalysed intramolecular Diels-Alder reaction of various 1-(2-furyl)-hex-1-en-5-yn-3-ol derivatives has been studied to synthesise hydroxyphenanthrenes and other polynuclear aromatic hydroxyl compounds. The required precursors were synthesised by indium mediated propargylation of suitable β-furyl-α,β-unsaturated aldehydes.

Regiospecific oxidation of polycyclic aromatic phenols to quinones by hypervalent iodine reagents

The hypervalent iodine reagents o-iodoxybenzoic acid (IBX) and bis(trifluoro-acetoxy)iodobenzene (BTI) are shown to be general reagents for regio-controlled oxidation of polycyclic aromatic phenols (PAPs) to specific isomers (ortho, para, or remote) of polycyclic aromatic quinones (PAQs). The oxidations of a series of PAPs with IBX take place under mild conditions to furnish the corresponding ortho-PAQs. In contrast, oxidations of the same series of PAPs with BTI exhibit variable regiospecificity, affording para-PAQs where structurally feasible and ortho-PAQs or remote PAQ isomers in other cases. The structures of the specific PAQ isomers formed are predictable on the basis of the inherent regioselectivities of the hypervalent iodine reagents in combination with the structural requirements of the phenol precursors. IBX and BTI are recommended as the preferred reagents for regio-controlled oxidation of PAPs to PAQs.

Is the Hoveyda-Grubbs complex a vinylogous fischer-type carbene? Aromaticity-controlled activity of ruthenium metathesis catalysts

Three naphthalene-based analogues (4a-c) of the Hoveyda-Grubbs metathesis catalyst exhibited immense differences in reactivity. Systematic structural and spectroscopic studies revealed that the ruthenafurane ring present in all 2-isopropoxyarylidene chelates possesses some aromatic character, which inhibits catalyst activity. This aromatic stabilization within the chelate ring may be controlled by variation of the polycyclic core topology as was demonstrated for tetraline and phenanthrene derivatives (4d,e). General conclusions about a new mode of ligand-structure tuning in catalytic systems are presented.

A novel application of the Diels-Alder reaction: nitronaphthalenes as normal electron demand dienophiles

Thermal reactions between nitronaphthalenes and butadienes were studied. It was demonstrated that these reactions are capable of undergoing the normal electron demand Diels-Alder reaction, with a variety of dienes affording the phenanthrene derivatives. The influence of the extension and type of substitution was also discussed. When the electron-withdrawing activation of the naphthalenic nucleus or the donor properties of the dienes were not enough, N-naphthylpyrroles were detected as main product, suggesting that a competitive reaction would probably take place. The results clearly confirmed the dienophilic nature of nitronaphthalenic double bonds and provided an alternative procedure for phenanthrene derivatives and N-naphthylpyrroles' synthesis. The relative reactivity of the reactants and the viability of the reactions were discussed from a theoretical point of view.

Synthesis of cyclopentadiene or substituted cyclopentadiene compounds

Substituted or unsubstituted cyclopentadienyl are prepared by reducing 4-ketocyclopentene to an alcohol, replacing the hydroxyl functionality with a leaving group and deprotonating the resulting product under base induced elimination conditions.

Glucocorticoid receptor modulators

The present invention provides non-steroidal compounds of formula I which are selective modulators (i.e., agonists and antagonists) of a steroid receptor, specifically, the glucocorticoid receptor. The present invention also provides pharmaceutical compositions containing these compounds and methods for using these compounds to treat animals requiring glucocorticoid receptor agonist or antagonist therapy. Glucocorticoid receptor modulators are useful to treat diseases, such as obesity, diabetes, inflammation and others as described below. The present invention also provides intermediates and processes for preparing these compounds. STR1