29602-11-7

Usage

InChI:InChI=1/C13H23NO5Si/c1-4-17-20(18-5-2,19-6-3)11-7-10-14-12(15)8-9-13(14)16/h8-9H,4-7,10-11H2,1-3H3

Upstream product

• 108-31-6 maleic anhydride 
• 919-30-2 3-aminopropyltriethoxysilane 
• 33525-68-7 maleic anhydride 
• 75-77-4 chloro-trimethyl-silane 
• 50488-14-7 Si(OC₂H₅)3C₃H₈NC₂H₂OC₂O₂ 

Relevant academic research and scientific papers

Studies on the attachment of DNA to silica-coated nanoparticles through a Diels-Alder reaction

A new method has been investigated for the functionalization of gold nanoparticles with DNA. Silica-coated nanoparticles functionalized with a maleimide have been prepared. These particles are designed to react with modified DNA containing a diene functionality at one end of the molecule. The result would be the formation of a more stable attachment of the DNA to the particle through a Diels-Alder reaction. This covalent attachment would not be susceptible to ligand exchanges, which are known to occur in the conventional DNA functionalization of gold nanoparticles. Copyright Taylor & Francis, Inc.

Novel method for the covalent immobilization of oligonucleotides via Diels-Alder bioconjugation

The synthesis of cyclohexadiene and maleimide derivatives and their use for the functionalization of oligonucleotides and the coating of glass surfaces is reported. A method for the covalent attachment of diene or maleimide modified oligonucleotides to the coated glass surfaces via aqueous Diels-Alder reactions is presented.

A molecular nanocap activated by superparamagnetic heating for externally stimulated cargo release

A novel thermoresponsive snaptop for stimulated cargo release from superparamagnetic iron oxide core - mesoporous silica shell nanoparticles based on a [2 + 4] cycloreversion reaction (retro-Diels Alder reaction) is presented. The non-invasive external actuation through alternating magnetic fields makes this material a promising candidate for future applications in externally triggered drug delivery.

METHOD FOR MANUFACTURING IMIDE COMPOUND

PROBLEM TO BE SOLVED: To provide a method capable of manufacturing an imide compound that can remove a by-product more easily than conventional methods at inexpensive manufacturing costs. SOLUTION: There is provided a method for manufacturing an imide compound from an amine compound including a first process of reacting a ketone compound with an amine compound represented by the formula (1): R-NH2 (1), where R represents a monovalent organic group, and a second process of reacting carboxylic acid anhydride with the compound obtained in the first process. COPYRIGHT: (C)2015,JPOandINPIT

DENTAL MATERIALS BASED ON MONOMERS HAVING DEBONDING-ON-DEMAND PROPERTIES

The invention relates to a dental restorative material which comprises a thermolabile or photolabile polymerizable compound of Formula I: [(Z1)m-Q1-X)]k-T-[Y-Q2-(Z2)n]1??Formula I, in which T represents a thermolabile or photolabile group, Z1 and Z2 in each case independently represent a polymerizable group selected from vinyl groups, CH2═CR1—CO—O— and CH2═CR1—CO—NR2— or an adhesive group selected from —Si(OR)3, —COOH, —O—PO(OH)2, —PO(OH)2, —SO2OH and —SH, wherein at least one Z1 or Z2 is a polymerizable group, Q1 in each case independently is missing or represents an (m+1)-valent linear or branched aliphatic C1-C20 radical which can be interrupted by —O—, —S—, —CO—O—, —O—CO—, —CO—NR3—, —NR3—CO—, —O—CO—NR3—, —NR3—CO—O— or —NR3—CO—NR3—, Q2 in each case independently is missing or represents an (n+1)-valent linear or branched aliphatic C1-C20 radical which can be interrupted by —O—, —S—, —CO—O—, —O—CO—, —CO—NR3—, —NR3—CO—, —O—CO—NR3—, —NR3—CO—O— or —NR3—CO—NR3—, X and Y in each case independently are missing or represent —O—, —S—, CO—O—, —O—CO—, —CO—NR3—, —NR3—CO—, —O—CO—NR3—, —NR3—CO—O— or —NR3—CO—NR3—, R, R1, R2 and R3 in each case independently represent H or a C1-C7 alkyl radical and k, l, m and n in each case independently are 1, 2 or 3.

Thermoreversible reactions on inorganic nanoparticle surfaces: Diels-alder reactions on sterically crowded surfaces

Organically surface-functionalized nanoparticles are important cross-linkers for nanocomposites. In the past, many cross-linking reactions were based on simple radical additions. However, novel smart materials require reversible reactions. These reactions, such as the Diels-Alder reaction, often have a specific sterical demand, e.g., a six-centered transition state. In this study, 5 nm silica particles were functionalized with maleimide groups, and their reactivity with regard to Diels-Alder reactions were investigated, applying various techniques. A new method for the surface modification of silica nanoparticles is presented, minimizing agglomeration in organic solvents and thus increasing the accessibility of the functional groups on the particle surface. Kinetic studies of substituted model compounds were carried out to evaluate the reactivity of the maleimide functionality. The Diels-Alder reaction between 2,5-dimethylfuran and N-propylmaleimide, N-ethyl(N-propylcarbamato) maleimide, and N-phenylmaleimide was followed by UV/Vis spectroscopy. The reaction rate increases in this order, showing the effect of maleimide substitution. Afterwards N-((3-triethoxysilyl)propyl)maleimide was used to graft maleimidopropyl functional groups onto the nanoparticle surface. 3-Aminopropyltriethoxysilane, which could then be reacted with 1,1′-(methylenedi-4,1-phenylene)bismaleimide, was used to attach phenyl-substituted maleimide functionality to the surface. 3- Isocyanatopropyltriethoxysilane introduced the electron-drawing carbamato functionality into the system. The surface coverage of the samples was characterized applying CHN analysis, TGA-FTIR coupling, and FTIR spectroscopy. All analytical methods revealed that the functional groups are covalently bonded to the silica surface and the maleimide rings remain intact. Diels-Alder reactions of the surface groups show that the reactivity of the molecules attached to the particles depends on sterical crowding, but the reaction rate is not significantly changed by surface effects.

Process for preparing unsaturated imidoalkoxysilanes

A process is provided for preparing unsaturated imidoalkoxysilane which comprises imidating substantially water-free Diels-Alder protected unsaturated N-substituted cyclic imide with aminosilane to provide Diels-Alder protected unsaturated imidoalkoxysilane without the use of chemical desiccants. The Diels-Alder protected unsaturated imidoalkoxysilane produced is then deprotected to provide unsaturated imidoalkoxysilane and the Diels-Alder protecting diene is regenerated to the process. A Diels-Alder intermediate is also provided.