2181-22-8

Usage

Uses

Used in the Production of Polyurethane Foams:
2,2'-Methylenebis(5,5-dimethylcyclohexane-1,3-dione) is used as a chemical intermediate in the production of polyurethane foams for its ability to contribute to the formation of the foam's structure and properties. The reactive nature of MDH allows it to participate in the polymerization reactions that create the foam's rigid or flexible characteristics, depending on the application requirements.
Used in the Production of Coatings:
In the coatings industry, 2,2'-Methylenebis(5,5-dimethylcyclohexane-1,3-dione) is utilized as a component in the formulation of various types of coatings. Its reactivity plays a crucial role in the curing process, enhancing the durability, adhesion, and other performance attributes of the final coating product.

Upstream product

• 562-13-0 2,2-dimethyl-1,3-cyclohexanedione 
• 100-97-0 hexamethylenetetramine 
• 126-81-8 dimedone 
• 50-00-0 formaldehyd 
• 142-96-1 dibutyl ether 
• 17450-22-5 bis(4-methylphenylamino)methane 
• 53654-69-6 N,N'-bis-(4-chloro-phenyl)-methanediyldiamine 
• 78666-54-3 N,N'-bis-(4-methoxy-phenyl)-methanediamine 
• 44826-45-1 3-sulfopropanoic acid 
• 100-34-5 benzene diazonium chloride 
• 73633-55-3 3,3',4,4',5,5'-hexamethyl-2,2'-dipyrrylmethane 
• 67-68-5 dimethyl sulfoxide 
• 1192-37-6 methylenecyclohexane 
• 7732-18-5 water 

Downstream Products

• 83231-61-2 3,3,6,6-Tetramethyl-10-p-tolyl-3,4,6,7,9,10-hexahydro-2H,5H-acridine-1,8-dione 
• 83231-60-1 3,3,6,6-tetramethyl-9-phenyl-1,2,3,4,5,6,7,8,9,10-decahydroacridine-1,8-dione 
• 83231-63-4 10-(2-Hydroxy-phenyl)-3,3,6,6-tetramethyl-3,4,6,7,9,10-hexahydro-2H,5H-acridine-1,8-dione 
• 701-58-6 5,5-dimethyl-3-methylamino-2-cyclohexenone 
• 309972-04-1 10-benzyl-3,3,6,6-tetramethyl-1,2,3,4,5,6,7,8,9,10-decahydroacridine-1,8-dione 
• 27361-25-7 3,3,6,6-tetramethyl-1,2,3,4,5,6,7,8,9,10-decahydroacridine-1,8-dione 

Relevant academic research and scientific papers

Unusual course of the reaction of N-(tosylmethyl)thiourea and n-(azidomethyl)thiourea with sodium enolate of dimedone

The end product of the reaction of N-(tosylmethyl)thiourea or N-(azidomethyl)thiourea with sodium enolate of dimedone is bis(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-enyl)methane (methylenebisdimedone) instead of the expected 8a-hydroxy-7,7-dimethyl-2-thiox

Thermal and microwave assisted synthesis of N-aroylamino acridinediones

A series of N-aroylamino acridinediones (3a-3d and 6a-6e) have been synthesized from tetraketones (1 and 4) and benzoic hydrazides (2a-2d and 5a-5e) under thermal and microwave irradiation conditions with solid supports.

Conversion of 10-bromo-10,11-dihydrocinchonidine into 8-oxa-1-azabicyclo[4. 3.0]nonane derivatives and related compounds: A structural study

The structure of dehydrobromination products of 10-bromo-10,11- dihydrocinchonidine 2c has been investigated in order to explore the scope of the conversions so far observed for quinine and cinchonine. The 2c rearranges into a mixture of 4(S)-(E-propenyl)-6(S),7(R)-(quinol-4-yl)-8-oxa-1(R)- azabicyclo[4.3.0]nonane 6 and its Z-propenyl diastereomer 8 in the ratio 3: 1 and also provides Z-3,10-didehydro-10,11-dihydrocinchonidine 18. The mixture of 6 and 8 undergoes catalytic hydrogenation giving 4(S)-propylo-6(S),7(R)-(quinol- 4-yl)-8-oxa-1(R)-azabicyclo[4.3.0]nonane 10. On treatment with an acid the alkaloid 6 yields [4(S)-E-propenyl-2(S)-piperidinyl]-4-quinoline α(R)-methanol 14. Its side chain undergoes hydrogenation affording 4(S)-propylo-derivative 12 which also forms on treatment of 10 by acid. The alkaloids 6, 8, 10, 12 and 14 appear as dominating conformers in their equilibrium mixtures.

Selective Conversion of Carbon Dioxide to Formaldehyde via a Bis(silyl)acetal: Incorporation of Isotopically Labeled C1 Moieties Derived from Carbon Dioxide into Organic Molecules

The conversion of carbon dioxide to formaldehyde is a transformation that is of considerable significance in view of the fact that formaldehyde is a widely used chemical, but this conversion is challenging because CO2 is resistant to chemical transformations. Therefore, we report here that formaldehyde can be readily obtained from CO2 at room temperature via the bis(silyl)acetal, H2C(OSiPh3)2. Specifically, formaldehyde is released from H2C(OSiPh3)2 upon treatment with CsF at room temperature. H2C(OSiPh3)2 thus serves as a formaldehyde surrogate and provides a means to incorporate CHx (x = 1 or 2) moieties into organic molecules. Isotopologues of H2C(OSiPh3)2 may also be synthesized, thereby providing a convenient means to use CO2 as a source of isotopic labels in organic molecules.

Merging supramolecular catalysis and aminocatalysis: Amino-appended β-cyclodextrins (ACDs) as efficient and recyclable supramolecular catalysts for the synthesis of tetraketones

Well-designed amino-appended β-cyclodextrins (ACDs) with an amino side chain of different lengths at the primary face of β-CD were synthesized and employed in the catalytic synthesis of a series of tetraketones as supramolecular catalysts in water for the first time. Yields of 58-97% were obtained with up to 30 examples of substrate. The catalyst could be recycled easily, while a 92% yield and 84% rate of catalyst recovery could be achieved after 8 cycles of catalyst recycling. Moreover, a catalytic mechanism merging supramolecular catalysis and aminocatalysis could be proposed through detailed 1D and 2D NMR, ESI-MS and Job plot analyses. This protocol retained the promising characteristics of ambient temperature, green medium, simple operation, broad substrate scope, excellent yields, superb catalyst recycling performance and unique catalytic mechanism.

The crystal structure and conformational studies of acridinedione derivatives

Two crystal structures of acridinediones namely, TMHAD and MPHAD were studied by X-ray crystallographic method in view of their occurrence in numerous commercial products including pharmaceuticals, fragrances and dyes. Crystal data of TMHAD are: C17H23NO2, orthorhombic, Fdd2, with cell parameters a = 40.417(6) A, b = 5.744(1) A, c = 12.979(2) A, V = 3013.1(7) A3, Z = 8, Dcal = 1.205 Mg/m3, μ = 0.078 mm-1. Crystal data of MPHAD are: C20H18NO3; monoclinic, P21/c with cell parameters a = 10.182(9) A, b = 17.105(14) A, c = 10.895(9) A, β = 117.857(1)°, V = 1678(2) A3, Z = 4, Dcal = 1.268 Mg/m3, μ = 0.085 mm-1. Both data were collected using λ (MoKα) = 0.71073 A. The central ring in the acridinedione moieties tends to be planar while the outer two rings adopt sofa conformations. Intermolecular interactions of C-H...O type of hydrogen bond help the molecules to stabilize into the crystal packing. Interestingly, a week forces of C-H...π interactions also helps the molecules for stabilization. Graphical Abstract: Two crystal structures of acridinediones namely, TMHAD and MPHAD have been synthesized and its structural chemistry has been proved by crystallographic study.

A novel three-component reaction of anilines, formaldehyde and dimedone: simple synthesis of spirosubstituted piperidines

A three-component condensation of anilines with dimedone and formaldehyde leads to the formation of 3,5-dispirosubstituted piperidines. This simple reaction can serve as a convenient source of 3,5-disubstituted piperidines as well as polyfunctional 3-spir

APOPTOSIS INHIBITORS

Apoptosis inhibitors containing as the active ingredient compounds represented by general formula (I) or salts thereof, wherein W1 represents -O-, -CH2-, etc.; W2 represents -CH2-, etc.; W3 represents -O-, -CH2-, etc.; X represent CH, C-, etc.; and A represents formula (α) wherein W4 represents -O-, -CH2-, etc.; W5 represents -CH2 -, etc.; and W6 represents -O-, CH2 -, etc. These apoptosis inhibitors inhibit apoptosis of WC8 cells induced by Fas ligand. In animal models, they potently inhibit the progress of fulminant hepatitis and relieve alopecia caused by anticancer agents. Because of being highly safe, these apoptosis inhibitors are usable as beneficial drugs.

Synthesis, characterization, and electrochemistry of some acridine-1,8-dione dyes

The synthesis, characterization, and electrochemical behavior of some acridinedione derivatives are reported. Cyclic voltammetric studies show that all the dyes undergo irreversible oxidation irrespective of the substitution on the nitrogen. The product formed on oxidation is the aromatic derivative in the case of N-H compounds and the acridinium salt in the case of the N-substituted compounds, which have been isolated and characterized. Formation of an intermediate carbon-centered radical is observed as evidenced by ESR spin-trapping experiments. A mechanistic scheme for the electrochemical oxidation is proposed. On carrying out reduction after oxidation, different products are formed depending on the substitution on the nitrogen. There is no reduction of the oxidized product in the case of N-H compounds, and compounds with substitution on nitrogen undergo reduction consistent with the observation in N-alkylpyridinium salts.

3,3,6,6-tetramethyl-10-(4-methylphenyl)-3,4,6,7,9,10-hexahydro-1,8(2H,5H)- acridinedione

The title molecule, C24H29NO2, consists of a partially hydrogenated acridine ring system with one phenyl substituent on the dihydropyridine ring. The compound crystallizes with a half molecule per asymmetric unit, which ha