6143-29-9

Usage

Uses

Used in Chemical Research and Development:
5-NORBORNEN-2-YL ACETATE is used as a research compound for studying the ring-opening metathesis polymerization (ROMP) of norbornene. This process is catalyzed by dinuclear complex Cp2Os2Br4 (Cp = pentamethylcyclopentadienyl) and related compounds. The study of ROMP is essential for understanding the behavior of norbornene derivatives and their potential applications in various fields.
Used in Polymer Industry:
5-NORBORNEN-2-YL ACETATE is used as a monomer in the polymer industry for the synthesis of various polymers through the ring-opening metathesis polymerization process. These polymers have potential applications in coatings, adhesives, and other materials due to their unique properties.
Used in Pharmaceutical Industry:
Although not explicitly mentioned in the provided materials, 5-NORBORNEN-2-YL ACETATE could potentially be used in the pharmaceutical industry as an intermediate in the synthesis of various drugs or drug candidates. Its unique chemical structure may offer new opportunities for drug development.
Used in Material Science:
5-NORBORNEN-2-YL ACETATE may also be used in material science for the development of new materials with specific properties. The ring-opening metathesis polymerization process allows for the creation of polymers with tailored characteristics, which could be useful in various applications such as automotive, aerospace, or electronics industries.

Biochem/physiol Actions

5-Norbornen-2-yl acetate undergoes copolymerisation with ethylene by nickel catalyst system to form high molecular weight functionalized polyethylene bearing ester functionalities. -Norbornen-2-yl acetate is the starting reagent for synthesis of urea condensation products from a-dicarbonyl compounds using Bi (OTf)3 catalyst.

InChI:InChI=1/C23H23NO4/c25-22(23-12-15-9-16(13-23)11-17(10-15)14-23)8-6-18-5-7-21(28-18)19-3-1-2-4-20(19)24(26)27/h1-8,15-17H,9-14H2/b8-6+

Upstream product

• 279-19-6 nortricyclane 
• 64-19-7 acetic acid 
• 108-05-4 vinyl acetate 
• 542-92-7 cyclopenta-1,3-diene 
• 694-98-4 norborn-5-en-2-one 
• 72150-05-1 Essigsaeure-<6exo-tosyloxy-2endo-norbornyl>ester 
• 72150-05-1 Essigsaeure<6endo-tosyloxy-2endo-norbornyl>ester 

Downstream Products

• 29583-33-3 (+/-)-endo-norborneol acetate 
• 694-97-3 (1S,2S,4S)-bicyclo[2.2.1]hept-5-en-2-ol 
• 106928-44-3 (1R,2R,4R)-endo-bicyclo[2.2.1]hept-5-en-2-ol 
• 154278-40-7 (1S,2S,4S)-bicyclo[2.2.1]hept-5-en-2-yl acetate 
• 75305-52-1 Essigsaeure-<6exo-hydroxy-2endo-norbornyl>ester 
• 615249-15-5 Essigsaeure-<5exo-hydroxy-2endo-norbornyl>ester 
• 75305-52-1 Essigsaeur-<6endo-hydroxy-2endo-norbornyl>ester 
• 112836-09-6 (1R,2R,4R)-bicyclo[2.2.1]hept-5-en-2-yl acetate 
• 497-38-1 (1S,4R)-bicyclo[2.2.1]heptan-2-one 
• 497-38-1 Norbornan-2-on 
• 694-98-4 norborn-5-en-2-one 
• 497-36-9 (+/-)-endo-2-norborneol 
• 61242-45-3 (+/-)-phthalic acid mono-[2endo]norbornyl ester 
• 100871-13-4 (+/-)-3,5-dinitro-benzoic acid-[2endo]norbornyl ester 

Relevant academic research and scientific papers

(Meth) acrylate derivative, polymer and photoresist composition having lactone structure, and method for forming pattern by using it

There are here disclosed a photoresist material for lithography using a light of 220 nm or less which comprises at least a polymer represented by the following formula (2) and a photo-acid generator for generating an acid by exposure: wherein R1, R2, R3 and R5 are each a hydrogen atom or a methyl group; R4 is an acid-labile group, an alicyclic hydrocarbon group having 7 to 13 carbon atoms, which has an acid labile group, an alicyclic hydrocarbon group having 7 to 13 carbon atoms, which has a carboxyl group, or a hydrocarbon group having 3 to 13 carbon atoms, which has an epoxy group; R6 is a hydrogen atom, a hydrocarbon group having 1 to 12 carbon atoms, or an alicyclic hydrocarbon group having 7 to 13 carbon atoms, which has a carboxyl group; x, y and z are optional values which meet x+y+z=1, 0a weight-average molecular weight of the polymer is in the range of 2000 to 200000, and a resin having a (meth)acrylate unit of an alicyclic lactone structure represented by the formula (3): wherein R8 is a hydrogen atom or a methyl group, and R9 is a hydrocarbon group of 7 to 16 carbon atoms having an alicyclic lactone structure.

Gas-phase Diels-Alder cycloaddition reaction in the presence of methanol and water vapor

Hydrogen bonding effects of protic solvents, apart from bulk properties, on the reaction rate of the cycloaddition of cylopentadiene and vinyl acetate in the presence of water and methanol in the gas phase were investigated. The results showed that methan

Ring-opening metathesis - Cross-metathesis reactions (ROM-CM) of substituted norbornadienes and norbornenes

Ring-opening metathesis - cross-metathesis reactions (ROM-CM) of substituted norbornadienes and norbornenes were investigated. The reactions with symmetrical 2,3-disubstituted norbornadienes were found to be highly chemoselective, with the ROM reactions occurring only on the less substituted or less sterically hindered double bonds regardless of the electronic nature of the substituents, giving highly substituted cyclopentenes in moderate to good yields. This study provides an efficient method for the stereoselective synthesis of highly substituted cyclopentenoids. Long-range electronic effect of a remote substituent on unsymmetrical norbornenes in the ROM-CM reactions was also investigated. Low levels of regioselectivities were observed (50:50 to 69:31) with various remote substituents on the norbornenes.

Remote substituent effects on the oxymercuration of 2-substituted norbornenes: An experimental and theoretical study

The effect of a remote substituent on regioselectivity in the oxymercuration of 2-substituted norbornenes has been investigated experimentally and theoretically using density functional theory (DFT). Regioselectivities of 1:1 to 14:1 were observed with various 2-substituted norbornenes. Exo-2-substituted norbornenes always gave greater regioselectivities compared to the corresponding endo-2-substituted norbornenes. The effects of solvents on the regioselectivity have also been examined, and ethereal solvents were found to be the best choice giving the optimal yield and regioselectivity. The relative rate of oxymercuration was estimated by competition experiments. The least reactive substrate (X = OAc) gave the highest regioselectivity. According to DFT predictions, the increased difference between the reaction barriers that results in the greater regioselectivity is correlated directly with the larger polarity of the C=C double bond, which is attacked by the mercury and oxygen. A number of stable exo and endo conformers were predicted. All exo conformers show the same polarity of the double bond, while some endo conformers have a reversal of this polarity. All the conformers except those with the OAc substituent are very close in energy and thus should react. The existence of a mixture of endo conformers with the C=C double bond of opposite polarity clearly explains a decrease in regioselectivity for the endo species. The origin of the greatest regioselectivity for the OAc-2-norbornenes lies in the fact that the conformer with the largest polarity is notably lower in energy than others due to an internal C-H-O hydrogen bond.

Enantiomers of cis- and trans-3-(4-propyl-cyclopent-2-enyl) propyl acetate. A study on the bioactive conformation and chiral recognition of a moth sex pheromone component

The enantiomers of cis- and trans-3-(4-propyl-cyclopent-2-enyl) propyl acetate, which are conformationally constrained analogues of (Z)-5-decenyl acetate (1), a sex pheromone component of the turnip moth, Agrotis segetum, have been synthesized and tested using the elcctrophysiological single-sensillum technique. The analogues mimic a cisoid and transoid conformation of 1, respectively. In addition, the enantiomers of each of the cis- and trans-isomers are conformationally constrained analogues of enantiomeric cisoid and transoid conformations of 1. Thus, the compounds prepared and tested are well suited to investigate the nature of the bioactive conformation of the natural pheromone component 1 and the chiral sense of its interaction with the receptor. Electrophysiological single-sensillum recordings show that the activity of the most active cis-isomer, which has a (1S,4R)-configuration, is more than two orders of magnitude higher than that of the most active trans-isomer. Furthermore, the (1S,4R)-isomer is at least 100 times more active than its enantiomer. These results strongly support a previously proposed cisoid bioactive conformation of 1. Furthermore, the (1S,4R)-configuration of most active stereoisomer identifies the chiral sense of the interaction between the natural pheromone component 1 and its receptor.

Polar versus Steric Effects in the Solvolysis of 6endo-substituted 2endo-Norbornyl p-Toluenesulfonates

The solvolysis rates and products of the 6endo-R-substituted 2endo-norbornyl toluenesulfonates 6a-6i have been determined.The rates of 6a-6g correlate with the inductive constants ?qI of the 6endo-substituents and are not related to the size of the latter.It is therefore concluded that polar rather than steric effects control the exo/endo-rate ratios of norbornyl sulfonates.Products are derived mainly from rearranged 6exo-R-norbornyl cations when the substituent is an electron donor and from unrearranged 6endo-R-substituted cations when the substituent is an electron acceptor.

Synthese und Hydrolyse von 6endo-substituierten p-Toluolsulfonsaeure-estern.

The Synthesis and Hydrolysis of 6endo-Substituted 2endo-Norbornyl p-Toluenesulfonates; The hydrolysis products of the p-toluenesulfonates of several hitherto unknown 6endo-substituted 2endo-norbornanols have been determined.

Carbon Participation in the Solvolysis of 6-endo-substituted 2-exo-Norbornyl Toluenesulfonates. Norbornanes Part 6

The solvolysis rate constants k for the 6-endo-substituted 2-exo-norbornyl toluenesulfonates 7 have been determined.Values of logk correlate well with the respective inductive constants of the substituents except when the latter are nucleophilic and therefore lead to endo-cyclization, or when they are n-electron donors and cause concerted fragmentation.In general 6-endo-substituted tosylates 7 react somewhat more slowly than their 6-exo-epimers. Identical or different mixtures were obtained from the C(6)-epimers 7 and 1 depending on whether the substituent was an electron donor or acceptor.It is concluded that donor substituents at C(6) enhance 1,3-bridging in the intermediate epimeric cations and lead to their rapid and complete equilibration, and that electron acceptors reduce bridging and hence their equilibration rates.

POLAR AND ANCHIMERIC EFFECTS IN THE SOLVOLYSIS OF 6-endo-SUBSTITUTED 2-NORBORNYL-p-TOLUENE-SULFONATES

A study of the influence of 6-endo substituents on the reactivity of 2-exo- and 2-endo-norbornyl p-toluenesulfonates 3 and 4, respectively, confirms that polar rather than steric effects control relative rates.