92343-46-9

Basic information

• Product Name: 5-Hydroxynorbornane 2,6-Lactone
• Synonyms: Nsc311957;2-Hydroxy-4-oxo-tricyclo[4.2.1.03.7]nonan-5-one;6-Hydroxyhexahydro-2H-3,5-Methanocyclopenta[b]furan-2-one;2-Hydroxy-4-oxa-tricyclo[4.2.1.0]nonan-5-one;5-Hydroxynorbornane 2,6-Lactone;N-hydroxy-5-norbornene-2,3-second imid;N-hydroxy-5-norbornene-2,3-second imide;5-Hydroxy-2,6-norbornane carbolactone
• CAS NO: 92343-46-9
• Molecular Formula: C₈H₁₀O₃
• Molecular Weight: 154.164
• Product Categories: 1,2,4-Triazole,Triazoles ,Triazines;Norbornene Derivatives
• Mol File: 92343-46-9.mol
• Article Data: 5

Chemical Properties

• Melting Point: 156.0 to 160.0 °C
• Boiling Point: 365.2 °C at 760 mmHg
• Flash Point: 174.7 °C
• Appearance: /
• Density: 1.451 g/cm³
• Vapor Pressure: 8.15E-07mmHg at 25°C
• Refractive Index: 1.599
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: soluble in Methanol
• PKA: 14.35±0.20(Predicted)
• CAS DataBase Reference: 5-Hydroxynorbornane 2,6-Lactone(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Hydroxynorbornane 2,6-Lactone(92343-46-9)
• EPA Substance Registry System: 5-Hydroxynorbornane 2,6-Lactone(92343-46-9)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 92343-46-9(Hazardous Substances Data)

Usage

General Description

5-Hydroxynorbornane 2,6-Lactone, also known as 1,3,4,4a,5,6-hexahydro-6-hydroxy-1,4-methanonaphthalene-2(3H)-one, is a chemical compound commonly used in the synthesis of pharmaceuticals and other organic compounds. It is a cyclic ester that is derived from the structural rearrangement of norbornene and is often used as a building block in organic chemistry. 5-Hydroxynorbornane 2,6-Lactone is also known for its pleasant odor and is used as a flavor and fragrance ingredient in various products. It is important to handle this compound with care as it may be hazardous if not used properly.

InChI:InChI=1/C8H10O3/c9-6-3-1-4-5(2-3)8(10)11-7(4)6/h3-7,9H,1-2H2

Upstream product

• 120-74-1 endo-norbornenecarboxylic acid 
• 68763-55-3 dioxa-3,5 exo phenyl-4 syn carbomethoxy-9 endo tricyclo <5.2.1.0^2,6> decane 
• 117835-14-0 bicyclo[2.2.1]hept-5-ene-2-carbonyl chloride 
• 77299-91-3 Benzoic acid (1S,2S,3S,6S,7R)-5-oxo-4-oxa-tricyclo[4.2.1.0^3,7]non-2-yl ester 
• 2903-75-5 (1S,2S,4S)-Bicyclo[2.2.1]hept-5-ene-2-carboxylic acid methyl ester 

Relevant articles and documents

A new solid-phase reaction system utilizing a temperature-responsive catalyst: Oxidative cyclization with hydrogen peroxide

A switchable catalyst based on temperature change provides a novel solid-phase reaction system in water. An increase in catalyst affinity for organic substrates at higher temperature led to efficient activity driving the solid inner-phase reaction, and loss of affinity at lower temperature allowed easy separation of organic products upon completion of the reaction. Application of this catalyst intelligence to design a novel catalytic system brought about an efficient oxidative cyclization with hydrogen peroxide, a useful method of accessing oxygen heterocycles.

Application of chemical P-450 model systems to studies on drug metabolism. Part X. Novel hydroxylactonization of γ,δ- and β,γ-unsaturated carboxylic acids with an iron porphyrin-iodosylbenzene system

The oxidative hydroxylactonization of γ,δ- and β,γ-unsaturated carboxylic acids by a chemical cytochrome P-450 model and rat liver microsomal systems has been investigated. In the chemical system using meso-tetrakis(2,6-dichlorophenyl)porphyrin iron chloride [Fe(TDClPP)Cl] with iodosylbenzene (PhIO), γ,δ-unsaturated carboxylic acids have been converted into δ-hydroxy-γ-lactones in high yield and with high stereoselectivity. As an example of a β,γ-unsaturated carboxylic acid, indomethacin has been converted into the corresponding β-hydroxy γ-lactone. Several experiments directed toward mechanistic elucidation of the lactonization exclude a mechanism occurring via an epoxide intermediate. The products have been used as standards to identify the metabolites in the microsomal oxidation. In the case of indomethacin, the γ-lactone form is detected as a metabolite in the rat liver microsomal system, in a yield of 1.33%; the yield is significantly decreased in the presence of 2-diethylaminoethyl-2,2-diphenylvalerate hydrochloride (SKF-525A) and under a mixed CO-O2 (4:1) atmosphere. Thus, these metabolites are considered to be formed by a cytochrome P-450-dependent reaction.

ACTION DU N-BROMOSUCCINIMIDE SUR LES DIOXOLANNES EN SERIE BICYCLOHEPTANIQUE. LIMITATION DES TRANSPOSITIONS DE WAGNER-MEERWEIN

Vicinal benzoyloxy-trans-bicycloheptanic bromhydrins, otherwise difficult to obtain are formed from N-bromosuccinimide and norbornanes bearing a 2-aryl-1,3 dioxolane skeleton.The greater stability of the intermediate dioxolenium ion reduces the tendency towards both Wagner-Meerwein rearrangement and neighbouring group participation by chlorine, processes usually observed when a less stable intermediate is involved.Nevertheless, methoxycarbonyl neighbouring group participation and Wagner-Meerwein rearrangement occur in methoxycarbonylbicycloheptane and in a bornanic compound respectively.