24402-95-7

Usage

Structure

Cyclic compound with a tetracyclic core

Reactivity

Capable of undergoing reduction, oxidation, and Diels-Alder reactions

Applications

Building block in organic synthesis, used in the production of pharmaceuticals, agrochemicals, and other fine chemicals

Biological activity

Exhibits biological activity, of interest in medicinal chemistry research

Upstream product

• 542-92-7 cyclopenta-1,3-diene 
• 130-15-4 [1,4]naphthoquinone 

Downstream Products

• 24402-98-0 1.2.3.4.4a.9a-Hexahydro-1.4-endomethylen-anthrachinon 
• 32745-55-4 methanoanthraquinone 
• 542-92-7 cyclopenta-1,3-diene 
• 130-15-4 [1,4]naphthoquinone 
• 32745-55-4 1,4-Methano-1,4-dihydro-9,10-anthraquinone 
• 75171-64-1 C₁₅H₁₂O₃ 
• 75171-66-3 C₁₅H₁₂O₃ 
• 52457-25-7 1,4-dihydro-9,10-dimethoxy-1,4-methanoanthracene 
• 52457-25-7 1,4-Dihydro-1,4-methano-9,10-dimethoxyanthracene 

Relevant academic research and scientific papers

Diels-Alder Reaction in Water. Effects of Hydrophobicity and Hydrogen Bonding

In order to check whether the activated complex for the Diels-Alder reactions of 5-substituted 1,4-naphthoquinones 1a-e with cyclopentadiene (2) is more polar in water than in other solvents, we have determined the substituent effects in seven different solvents.The substituent effects gradually decrease with increasing rate of the reaction in a specific solvent, indicating that the charge separation in the activated complex in water is not much different from that in the other solvents.We also compared solvent effects on the Diels-Alder reaction of methyl vinyl ketone (3) with cyclopentadiene with effects on the corresponding reaction of methyl vinyl sulfone (4).The medium effects were separated into effects on initial state and activated complex.The destabilization of the initial state by water and the stabilization of the activated complex by 2,2,2-trifluoroethanol were less pronounced for the sulfone than for the ketone.These results further underline the importance of enforced hydrophobic interactions and changes in hydrogen bonding during the activation process in explaining the acceleration of Diels-Alder reactions in water.

Surfactant-assisted specific-acid catalysis of Diels-Alder reactions in aqueous media

Surfactant-assisted specific-acid catalysis (SASAC) for Diels-Alder reactions of dienophiles 1 and 4 with cyclopentadiene 2 in aqueous media at 32°C was studied. This study showed that acidified aniohic surfactants (pH 2) such as sodium dodecyl sulfate (S

Specific acid catalysis and Lewis acid catalysis of Diels-Alder reactions in aqueous media

A comparative study of specific acid catalysis and Lewis acid catalysis of Diels-Alder reactions between dienophiles (1, 4 and 6) and cyclopentadiene (2) in water and mixed aqueous media is reported. The reactions were performed in water with copper(II) nitrate as the Lewis acid catalyst whereas hydrochloric acid was employed for specific acid catalysis. At equimolar amounts of copper(II) nitrate and hydrochloric acid (0.01 M, for example) and under the same reaction conditions, the reaction rate for 1a with 2 is about 40 times faster with copper catalysis than with specific acid catalysis. Moreover, at 32°C and 0.01 M HCl, the reaction of 1b with 2 is about 21 times faster than the same uncatalyzed reaction in pure water under the same reaction conditions. The inverse solvent kinetic isotope effect shows that these Diels-Alder reactions undergo specific acid catalysis. Copyright

Kinetics study of a Diels-Alder reaction in mixtures of an ionic liquid with molecular solvents

The second-order rate constants for cycloaddition reaction of cyclopentadiene with naphthoquinone were determined spectrophotometrically in various compositions of 1-(1-butyl)-3-methylimidazolium terafluoroborate ([bmim]BF4) with water and methanol at 25°C. Rate constants of the reaction in pure solvents are in the order of water > [bmim]BF 4 > methanol. Rate constants of the reaction decrease sharply with mole fraction of the ionic liquid in aqueous solutions and increase slightly to a maximum in alcoholic mixtures. Multi-parameter correlation of logk 2 versus solute-solvent interaction parameters demonstrated that solvophobicity parameter (Sp), hydrogen-bond donor acidity (α) and hydrogen-bond acceptor basicity (β) of media are the main factors influencing the reaction rate constant. The proposed three-parameter model shows that the reaction rate constant increases with Sp, α and β parameters. Copyright

Lewis acid catalyst system for Diels–Alder reaction

Abstract: Ca(OTf)2/Bu4NPF6 catalytic system has been illustrated for the synthesis of Diels–Alder adduct for the first time. This procedure tolerates substrate diversity and delivers high yield. Use of environmentally benign catalyst, high yields and substrate diversity are the highlight of the existing method. Graphic Abstract: Ca(OTf)2, along with n-Bu4NPF6 as the co-catalyst, is shown to be an effective Lewis acidic catalyst system for the Diels–Alder reaction. Apart from being sustainable and efficient, this procedure is robust and products are obtained in near-quantitative yields.[Figure not available: see fulltext.].

10-substituted -1, 4-dihydro -1, 4-methano spiroanthracene-9-(meth) acrylate compound MS41-and its manufacturing method

PROBLEM TO BE SOLVED: To provide an acrylate compound having a high refractive index and causing no problem of ultraviolet absorption or fluorescence observed in an anthracene ring and a fluorene ring. SOLUTION: The acrylate compound having a high refractive index is a 10-substituted-1,4-dihydro-1,4-methanoanthracene-9-yl-(meth)acrylate compound.One example of methods of producing the compound is shown by chemical reaction formula (A). In the reaction formula: R1, R2, R3, R4, R5and R6may be the same or different mutually, and each are a hydrogen atom or a methyl group; X is a hydrogen atom, an alkyl group or a halogen atom; and L is a halogen atom. COPYRIGHT: (C)2013,JPO&INPIT

Design, synthesis and evaluation of small molecule reactive oxygen species generators as selective Mycobacterium tuberculosis inhibitors

Here, we report 5-hydroxy-1,2,3,4,4a,9a-hexahydro-1,4-ethano-9,10- anthraquinone (13), a small molecule generating reactive oxygen species (ROS) in pH 7.4 buffer under ambient aerobic conditions that has selective and potent Mycobacterium tuberculosis gro

Aqueous solutions that model the cytosol: Studies on polarity, chemical reactivity and enzyme kinetics

Concentrated solutions of a series of organic compounds have been prepared and the effects of these solutes on the properties of the solvent system assessed as a function of their concentration and nature. Polarity, as measured by Reichardt's ET/sub

Diversification of shotgun process

Three protocols for shotgun process are put forth in which simultaneous multi-fold reactions occur exclusively to each other. The first one involves simple combination of selective and non-selective reactions. Even if the simple protocol fails to give rise to the high selectivity, satisfactory outcome can be achieved by kinetic control or adjustment of functional groups.

Dilithium 2,2'-methylenebis(4,6-di-tert-butylphenoxide) as a bidentate Lewis acid in organic synthesis

Dilithium 2,2'-methylenebis(4,6-di-tert-butylphenoxide) can be successfully utilized as a bidentate Lewis acid for simultaneous coordination to carbonyl groups, thereby accelerating the Diels-Alder reactions. The double activation ability of the bidentate lithium reagent toward carbonyls is emphasized in comparison with the corresponding monodentate lithium reagent.