79516-58-8

Usage

Uses

Used in Polymer and Resin Production:
Norbornenedimethanol is utilized as a monomer in the synthesis of a variety of polymers and resins. Its unique structure and properties contribute to the enhanced performance of these materials.
Used in Adhesives and Coatings Industry:
In the adhesives and coatings industry, norbornenedimethanol is employed as a key component due to its excellent adhesion properties and ability to improve the durability and chemical resistance of the final products.
Used in Composite Materials:
(1R,2R,3R,4S)-bicyclo[2.2.1]hept-5-ene-2,3-diyldimethanol is also used in the manufacturing of composite materials, where its rigid structure and resistance to heat and chemicals enhance the overall performance and longevity of the composites.
Used in Specialty Polymers Production:
Norbornenedimethanol serves as a vital ingredient in the production of specialty polymers, where its distinctive attributes allow for the creation of materials with specific properties tailored to various high-performance applications.
Used as a Crosslinking Agent:
In the formulation of advanced materials, norbornenedimethanol is used as a crosslinking agent. Its functional groups facilitate the formation of strong bonds between polymer chains, resulting in materials with improved mechanical strength and stability.

Upstream product

• 116404-47-8 endo,exo-bicylco[2.2.1]hept-5-ene-2,3-dicarboxylic acid dimethyl ester 
• 542-92-7 cyclopenta-1,3-diene 
• 77970-35-5 methyl (E)-2,3-dideoxy-4,5:6,7-di-O-isopropylidene-L-arabino-hept-2-enonate 
• 136520-61-1 methyl (5R,6R)-6-endo-(L-arabino-tetritol-1-yl)bicyclo<2.2.1>hept-2-eno-5-exo-carboxylate 
• 138689-91-5 (1S,2R,3R,4R)-Bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid bis-[(R)-2,2,2-trifluoro-1-(2,4,6-trimethyl-phenyl)-ethyl] ester 
• 115237-17-7 3-Hydroxymethyl-bicyclo[2.2.1]hept-5-ene-2-carbaldehyde 
• 6289-62-9 Acetic acid (1S,2R,3R,4R)-3-acetoxymethyl-bicyclo[2.2.1]hept-5-en-2-ylmethyl ester 
• 221663-97-4 (2R,3R)-3-<<(3aS,6R,7aR)-1,4,5,6,7,7a-hexahydro-8,8-dimethyl-2,2-dioxido-3H-3a,6-methano<2,1>benzisothiazol-1-yl>carbonyl>bicyclo<2.2.1>hept-5-ene-2-carboxylic acid benzyl ester 
• 125226-91-7 (1R,2R,3S,4S)-2-(Methoxycarbonyl)bicyclo<2.2.1>hept-5-ene-3-carboxylic Acid 
• 3014-58-2 dimethyl (exo,endo)-bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylate 
• 1200-88-0 norbornene-5,6-dicarboxylic acid 
• 699-96-7 (+/-)-(2-endo,3-exo)-bicyclo[2.2.1]hept-5-eno-2,3-dimethanol 
• 129-64-6 3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride 
• 96243-74-2 (1S,2R,3S,4R)-3-(methoxycarbonyl)bicyclo[2.2.1]hept-5-ene-2-carboxylic acid 

Downstream Products

• 123231-73-2 Acetic acid (1S,2R,3R,4R)-3-hydroxymethyl-bicyclo[2.2.1]hept-5-en-2-ylmethyl ester 
• 123231-73-2 Acetic acid (1R,2R,3R,4S)-3-hydroxymethyl-bicyclo[2.2.1]hept-5-en-2-ylmethyl ester 
• 6289-62-9 Acetic acid (1S,2R,3R,4R)-3-acetoxymethyl-bicyclo[2.2.1]hept-5-en-2-ylmethyl ester 
• 2434-86-8 Methanesulfonic acid (2R,3R)-3-methanesulfonyloxymethyl-bicyclo[2.2.1]hept-5-en-2-ylmethyl ester 

Relevant academic research and scientific papers

Enantioselective Construction of Modular and Asymmetric Baskets

The precise positioning of functional groups about the inner space of abiotic hosts is a challenging task and of interest for developing more effective receptors and catalysts akin to those found in nature. To address it, we herein report a synthetic methodology for preparing basket-like cavitands comprised of three different aromatics as side arms with orthogonal esters at the rim for further functionalization. First, enantioenriched A (borochloronorbornene), B (iodobromonorbornene), and C (boronorbornene) building blocks were obtained by stereoselective syntheses. Second, consecutive A-to-B and then AB-to-C Suzuki–Miyaura (SM) couplings were optimized to give enantioenriched ABC cavitand as the principal product. The robust synthetic protocol allowed us to prepare (a) an enantioenriched basket with three benzene sides and each holding either tBu, Et, or Me esters, (b) both enantiomers of a so-called “spiral staircase” basket with benzene, naphthalene, and anthracene groups surrounding the inner space, and (c) a photo-responsive basket bearing one anthracene and two benzene arms.

Synthesis and [4 + 2] cycloaddition of (2R,2′R)-N, N′fumaroylbis[fenchane-8,2-sultam] (=(2E)-1,4-bis[(3aS,6S,7aR)-1,4,5,6,7, 7a-hexahydro-7,7-dimethyl-2,2-dioxido-3H-3a,6-methano-2,1-benzothiazol-1-yl] but-2-ene-1,4-dione) to cyclopentadiene

The now corrected X-ray structure of (2R)-bornane-10,2-sultam ((-)-1a), as well as that of its already published N-crotonoyl derivative (-)-1d, were compared with those of the newly synthesized (2R)-fenchane-8,2-sultam ((+)-5a), as well as its N-crotonoyl

The first enantioselective synthesis of chiral norbornane-type 1,4-diamine ligand

The asymmetric synthesis of trans-2,3-bis(aminomethyl)norbornane was performed starting with endo-2,3-norbornene dicarboxylate anhydride. Desymmetrization of meso-anhydride 1 and following selective epimerization gave the trans-monoester (+)-3 with a high enantiomeric excess (98% e.e.). LiAlH4 reduction of the trans-monoester to the 1,4-diol, which was then treated with phthalimide under Mitsunobu conditions and, following a Gabriel type amine synthesis with hydrazine hydrate, yielded a saturated and unsaturated diamine mixture. Hydrogenation of mixture finally afforded saturated diamine (+)-8 with a yield of 37%.

Stereoselectivity in the cycloaddition of cyclopentadiene to N-fumaroyl-[2R,S(R)]-bornane-10,2-sulfinamide monomethyl ester

The cyclic [2R,S(R)]-bornane-10,2-sulfinamide (-)-2b, an analogue of Oppolzer's camphor-derived sultam (-)-2a, was synthesized by reduction of the known N-alkylidenesulfinamide (+)-1b with NaBH4. The uncatalyzed [4 + 2] cycloaddition of cyclopentadiene to the methyl ester (-)-3b of the N-fumaroylsulfinamide, obtained from (-)-2b, proceeds with lower endo and π-facial selectivity as compared to dienophiles (-)-3a, c. In contrast to these latter, the diastereoselectivity is reversed either in apolar CCl4 or in the presence of TiCl4. This inversion is explained by a competitive C(α)-si addition on the reactive anti-s-trans conformer.

Stereoselectivity in the TiCl4-catalyzed [4 + 2] cycloaddition of cyclopentadiene to (2R)-bornane-10,2-sultam derivatives of fumaric acid monoesters

The [4 + 2] cycloaddition of cyclopentadiene to the (2R)-bornane-10,2- sultam derivative (-)-1b of fumaric monomethyl ester proceeds with high endo and π-facial diastereoselectivity in the presence of 0.5 mol-equiv. of TiCl4. The major diastere

12. Complete ?-Facial Stereoselectivity in the TiCl4-Mediated Cycloaddition of Cyclopentadiene to N,N-Fumaroyldi

Under the co-operative influence of two prosthetic groups, and independent of the TiCl4 concentration, complete and constant diastereofacial ?-selection was achieved during the cycloaddition of cyclopentadiene to N,N'-fumaroyl-di((-)-1c); reactive conformations are discussed.

THERMAL AND CATALYTIC DIELS-ALDER REACTIONS BETWEEN (2E)-4,5,6-TRI-O-ACETYL-2,3-DIDEOXY-ALDEHYDO-D-ERYTHRO-HEX-2-ENOSE AND CYCLOPENTADIENE

Thermal and catalytic reactions between (2E)-4,5,6-tri-2,3-dideoxy-aldehydo-D-erythro-hex-2-enose (1) and cyclopentadiene 1ed, in each case, to the four stereoisomeric 5-formyl-6-(1,2,3-tri-O-acetyl-D-erythro-triol-1-yl)bicyclohept-2-enes (2-5).The role of the catalysts is discussed, and the face selectivity is rationalized in terms of both steric and electrostatic arguments.Upon subsequent sodium borohydride reduction, iodination, and zinc reduction, the adducts 2-5 were converted to their respective primary alcohols 6-9, that could be separated by column chromatography.Sequential basic deacetylation, oxidative cleavage of the sugar side-chain with sodium metaperiodate, and reduction with sodium borohydride, yielded the previously known (5R,6R)- or(5S,6S)-bis(hydroxymethyl)norbornene-diols 12 or 13, thus establishing the C-5 and C-6 absolute configurations of their synthetic precursors.

Enzymatic resolution of norbor(NE)nylmethanols in organic media and an application to the synthesis of (+)- and (-)-endo-norbornene lactone

The enzymatic resolution of some norbornene carboxylic acids, norbornenylmethanols and -methylamines was evaluated. The kinetic resolution of norbornyl- and norbornenylmethanols by Porcine Pancreatic Lipase (PPL)-catalyzed transesterification in methyl acetate as the solvent leads to corresponding acetates and remaining methanols both of high enantiomeric purity. A useful application is the synthesis of both enantiomers of endo-norbornene lactone 8n via transesterification of iodolactone 18. The influence of structural variations on the efficiency of the PPL-catalyzed resolution of lactone methanols 21, 23, 25 and 28, at the optimal reaction conditions established for iodolactone 18, was investigated.

1-Mesityl-2,2,2-trifluoroethanol, an outstanding new chiral controller for catalyzed diels-alder reactions

The R2AlCl-catalyzed Diels-Alder reactions of cyclopentadiene with the (R)-1-mesityl-2,2,2-trifluoroethyl esters of acrylic and fumaric acid proceed with ? 97:3 diastereoselectivity.

Asymmetric Diels-Alder Reaction with use of (S)-5-(Trityloxymethyl)pyrrolidin-2-one as a Chiral Auxiliary

(S)-5-(Trityloxymethyl)pyrrolidin-2-one (1) is an efficient and recyclable chiral auxiliary in the asymmetric Diels-Alder reaction of the imide (2) with dienes, affording cycloadducts (3) with excellent diastereofacial selectivity.