5826-73-3

Usage

Uses

Used in Chemical Production:
DIMETHYL 5-NORBORNENE-2,3-DICARBOXYLATE is used as a key intermediate for the synthesis of various chemicals and materials. Its role in this application is due to its ability to undergo polymerization and other chemical reactions, contributing to the creation of a wide range of products.
Used in Polymer Industry:
DIMETHYL 5-NORBORNENE-2,3-DICARBOXYLATE is used as a monomer for the production of polymers. It is valued for its contribution to polymers with high thermal stability, which is crucial for applications requiring materials that can withstand high temperatures without degradation.
Used in Adhesive Formulation:
DIMETHYL 5-NORBORNENE-2,3-DICARBOXYLATE is used as a component in the formulation of adhesives. Its inclusion enhances the adhesion properties of these products, making them more effective in bonding various surfaces.
Used in Pharmaceutical Industry:
DIMETHYL 5-NORBORNENE-2,3-DICARBOXYLATE is used as a starting material in the synthesis of pharmaceuticals. Its unique chemical structure allows it to be a building block for the development of new drugs, potentially leading to advancements in medicine.
Used in Resin Production:
DIMETHYL 5-NORBORNENE-2,3-DICARBOXYLATE is used in the production of resins. Its chemical properties lend themselves to the creation of resins with specific characteristics, such as resistance to heat and chemicals, which are important in various industrial applications.

InChI:InChI=1/C11H14O4/c1-14-9(12)8-6-11(10(13)15-2)4-3-7(8)5-11/h3-4,7-8H,5-6H2,1-2H3

Upstream product

• 39589-98-5 endo-bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic dimethyl ester 
• 124-41-4 sodium methylate 
• 542-92-7 cyclopenta-1,3-diene 
• 624-48-6 dimethyl cis-but-2-ene-1,4-dioate 
• 624-49-7 dimethylfumarate 
• 67-56-1 methanol 
• 2746-19-2 (1R,2R,6S,7S)-4-oxa-tricyclo[5.2.1.0^2,6]dec-8-ene-3,5-dione 
• 77-78-1 dimethyl sulfate 
• 14166-28-0 exo-bicyclo[2.2.1]heptane-2,3-dicarboxylic anhydride 
• 83303-35-9 cyclopentadienyldimethylsilane 
• 77-73-6 bi(cyclopentadiene) 
• 186581-53-3 diazomethane 
• 3813-52-3 (1S,2S,3S,4R)-3-carboxy-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid ester 
• 84565-17-3 C₁₁H₁₂O₄^(2-)*2Li⁽¹⁺⁾ 

Downstream Products

• 20727-93-9 2-cyclohexyl-3ξ-propyl-(3at,7at)-octahydro-4r,7c-methano-benzo[d]isoxazol-5ξ,6ξ-dicarboxylic acid dimethyl ester 
• 20521-06-6 (8at,12at,12bc)-5,8a,9,10,11,12,12a,12b-octahydro-6H-9r,12c-methano-benzo[4,5]thiazolo[3,2-a]isoquinoline-10ξ,11ξ-dicarboxylic acid dimethyl ester 
• 56613-23-1 6,7-Divinyl-1,4-methano-cis-decalin-2,3-dicarbonsaeure-dimethylester 
• 56613-24-2 6,7-Divinyl-1,4-methano-cis-Δ²⁽³⁾-octalin-2,3-dicarbonsaeure-dimethylester 
• 64853-29-8 2-(1-Carboxy-ethyl)-1-oxo-octahydro-4,7-methano-indene-5,6-dicarboxylic acid dimethyl ester 
• 74976-75-3 dimethyl 4-methylenetricyclo<5.2.1.0^2,6>dec-8-ene-2,6-dicarboxylate 
• 130799-61-0 (1R,2S,4R,5S,6R,7S)-3-{1-[(Z)-Toluene-4-sulfonylimino]-ethyl}-tricyclo[3.2.1.0^2,4]octane-6,7-dicarboxylic acid dimethyl ester 
• 85-39-2 5,6-bis(hydroxymethyl)bicyclo<2.2.1>hept-2-ene 
• 4098-47-9 (2R,3R)-dimethyl bicyclo[2.2.1]heptane-2,3-dicarboxylate 
• 107798-27-6 exo-2,3-dicarbomethoxy-exo-5-(dimethylchlorosilyl)bicyclo<2.2.1>heptane 
• 4098-47-9 Dimethyl norbornane-trans-2,3-dicarboxylate 

Relevant academic research and scientific papers

Oxathiaborolium-Catalyzed Enantioselective [4 + 2] Cycloaddition and Its Application in Lewis Acid Coordinated and Chiral Lewis Acid Catalyzed [4 + 2] Cycloaddition

The nascency of second-generation sulfur-stabilized borenium cations by halophilic Lewis acid SnCl4 leads to highly active chiral Lewis acids that are very effective catalysts for [4 + 2] cycloaddition. Oxathiaborolium pentachlorostannate (5-10 mol %) successfully catalyzed cycloaddition of various dienes and dienophiles to afford cycloadducts with excellent enantioselectivity (20 examples, up to 99% ee). This super Lewis acid also exhibited good enantioselectivity for the first Lewis acid coordinated and chiral Lewis acid catalyzed [4 + 2] cycloaddition to α,β-unsaturated mixed ester amide.

TETRACARBOXYLIC DIANHYDRIDE, CARBONYL COMPOUND, POLYIMIDE PRECURSOR RESIN, AND POLYIMIDE

A tetracarboxylic dianhydride which is a compound represented by the following general formula (1): [in the formula (1), A represents one selected from the group consisting of optionally substituted divalent aromatic groups in each of which the number of carbon atoms forming an aromatic ring is 6 to 30, and Ras each independently represent a hydrogen atom or the like], wherein 60% by mass or more of a stereoisomer contained in the compound is an exo/exo type stereoisomer represented by a specific general formula.

Norbornane-based cationic antimicrobial peptidomimetics targeting the bacterial membrane

The design, synthesis and evaluation of a small series of potent amphiphilic norbornane antibacterial agents has been performed (compound 10 MIC = 0.25 μg/mL against MRSA). Molecular modelling indicates rapid aggregation of this class of antibacterial agent prior to membrane association and insertion. Two fluorescent analogues (compound 29 with 4-amino-naphthalimide and 34 with 4-nitrobenz-2-oxa-1,3-diazole fluorophores) with good activity (MIC = 0.5 μg/mL against MRSA) were also constructed and confocal microscopy studies indicate that the primary site of interaction for this family of compounds is the bacterial membrane.

Design, Synthesis, and Self-Assembly of Polymers with Tailored Graft Distributions

Grafting density and graft distribution impact the chain dimensions and physical properties of polymers. However, achieving precise control over these structural parameters presents long-standing synthetic challenges. In this report, we introduce a versatile strategy to synthesize polymers with tailored architectures via grafting-through ring-opening metathesis polymerization (ROMP). One-pot copolymerization of an ω-norbornenyl macromonomer and a discrete norbornenyl comonomer (diluent) provides opportunities to control the backbone sequence and therefore the side chain distribution. Toward sequence control, the homopolymerization kinetics of 23 diluents were studied, representing diverse variations in the stereochemistry, anchor groups, and substituents. These modifications tuned the homopolymerization rate constants over 2 orders of magnitude (0.36 M-1 s-1 homo -1 s-1). Rate trends were identified and elucidated by complementary mechanistic and density functional theory (DFT) studies. Building on this foundation, complex architectures were achieved through copolymerizations of selected diluents with a poly(d,l-lactide) (PLA), polydimethylsiloxane (PDMS), or polystyrene (PS) macromonomer. The cross-propagation rate constants were obtained by nonlinear least-squares fitting of the instantaneous comonomer concentrations according to the Mayo-Lewis terminal model. In-depth kinetic analyses indicate a wide range of accessible macromonomer/diluent reactivity ratios (0.08 1/r2 20), corresponding to blocky, gradient, or random backbone sequences. We further demonstrated the versatility of this copolymerization approach by synthesizing AB graft diblock polymers with tapered, uniform, and inverse-tapered molecular "shapes." Small-angle X-ray scattering analysis of the self-assembled structures illustrates effects of the graft distribution on the domain spacing and backbone conformation. Collectively, the insights provided herein into the ROMP mechanism, monomer design, and homo- and copolymerization rate trends offer a general strategy for the design and synthesis of graft polymers with arbitrary architectures. Controlled copolymerization therefore expands the parameter space for molecular and materials design.

Dye functionalized-ROMP based terpolymers for the use as a light up-converting material: Via triplet-triplet annihilation

In this paper we introduce and compare different terpolymers comprising covalently attached sensitizer and emitter chromophores for the use as a light up-converting material via triplet-triplet annihilation (TTA). Using the advantages of ring opening metathesis polymerisation it was possible to prepare five different polymer architectures in order to investigate the influence of polymer architecture and chromophore arrangement on the photon up-conversion behaviour. First, two new monomers containing the chromophores have been synthesized and characterized in regard to their photophysical characteristics suitable for triplet-triplet annihilation dye pair. For this purpose, a derivative of Pt(ii) meso-tetraphenyltetra(tert-butyl)benzoporphyrin as sensitizer and a perylenediester as emitter were attached to norbornene moieties via ester linkages. Polymerisations of these monomeric chromophores were performed in combination with dimethyl 5-norbornene-2,3-dicarboxylate as matrix monomer. Depending on the location of the dye molecules on the polymer chain, large differences in the TTA efficiency were observed. The best quantum yields have been achieved with a completely statistically distributed terpolymer showing an up-conversion quantum yield of up to 3% in solution.

Tetracarboxylic dianhydride, polyamic acid, polyimide, methods for producing same, and polyamic acid solution

A compound represented by general formula (1): (in formula (1), A shows a C6-30 divalent aromatic group for forming an aromatic ring, or the like, and the plurality of R1 each independently show a hydrogen atom or the like), tetracarboxylic dianhydride, polyamic acid obtained by reacting this tetracarboxylic dianhydride and an aromatic diamine, and polyimide obtained by imidizing this polyamic acid.

Synthesis and evaluation of cationic norbornanes as peptidomimetic antibacterial agents

A series of structurally amphiphilic biscationic norbornanes have been synthesised as rigidified, low molecular weight peptidomimetics of cationic antimicrobial peptides. A variety of charged hydrophilic functionalities were attached to the norbornane scaffold including aminium, guanidinium, imidazolium and pyridinium moieties. Additionally, a range of hydrophobic groups of differing sizes were incorporated through an acetal linkage. The compounds were evaluated for antibacterial activity against both Gram-negative and Gram-positive bacteria. Activity was observed across the series; the most potent of which exhibited an MIC's ≤ 1 μg mL-1 against Streptococcus pneumoniae, Enterococcus faecalis and several strains of Staphylococcus aureus, including multi-resistant methicillin resistant (mMRSA), glycopeptide-intermediate (GISA) and vancomycin-intermediate (VISA) S. aureus.

Ionic liquids are compatible with on-water catalysis

A major limitation of on-water catalysis has been the need for liquid reactants to enable emulsification. We demonstrate that ionic liquids are compatible with on-water catalysis, enabling on-water catalysed reactions for otherwise unreactive solid-solid systems. The unique solvation properties of ionic liquids dramatically expands the scope of on-water catalysis.

Stabilization and controlled release of reactive molecules by solid-state van der waals capsules

Control by encapsulation: A dimeric capsule assembled from a tripodal host by van der Waals forces can stabilize a series of reactive molecules, such as cyclopentadiene and trichlorosilane, in the crystalline state even under relatively harsh conditions. Moreover, these reactive molecules can be controllably released into liquid media for further chemical reaction by thermal programming, leaving the insoluble host molecules behind for easy separation and reuse (see scheme). Copyright

NOVEL HEPATITIS C VIRUS INHIBITORS

The invention provides compounds of formula (I): wherein Rings A and A' are independently 5-membered optionally substituted aromatic heterocycles; Q is C(=O)NR1R1' or formula U is C(R4)2, O, S, S(=O)2, C(R4)2C(R4)2, CH2O, OCH2, CH2S, SCH2, CH2S(=O)2, S(=O)CH2 or C=C(Ru )2; X is CH2, CHR12, CR12R12, O, S, S(=O)2 or NRx; m is 0, 1, 2 or 3; n is 0, 1, 2 or 3; the other variables are as defined in the claims, which are of use in the treatment or prophylaxis of hepatitis C virus infection, and related aspects.