5597-27-3

Usage

Uses

Used in Organic Synthesis:
3-Methylene-2-norbornanone is used as a reactant in the preparation of various organic compounds. Its reactivity and unique structure make it a valuable intermediate in the synthesis of complex organic molecules.
Used in Pharmaceutical Industry:
3-Methylene-2-norbornanone is used as a reactant to prepare 3-(2-(4-methoxyphenyl)-2-oxoethyl)bicyclo[2.2.1]heptan-2-one by reacting with 4-anisaldehyde in the presence of tetrabutylammonium decatungstate (TBADT) photocatalyst. 3-METHYLENE-2-NORBORNANONE may have potential applications in the development of pharmaceutical agents.
Used in Chemical Research:
3-Methylene-2-norbornanone is also used in the preparation of 2-aryl-3-methylene-endo-norbornanols by treating with corresponding aryl lithium reagents. This reaction provides insights into the reactivity of the norbornane ring system and contributes to the understanding of organic chemistry.

InChI:InChI=1/C8H10O/c1-5-6-2-3-7(4-6)8(5)9/h6-7H,1-4H2/t6-,7+/m1/s1

Upstream product

• 497-35-8 2-methylenebicyclo[2.2.1]heptane 
• 694-92-8 2-methylnorborn-2-ene 
• 50-00-0 formaldehyd 
• 497-38-1 Norbornan-2-on 
• 497-38-1 2-norbornanone 
• 74713-07-8 3-(diethylaminomethyl)bicyclo[2.2.1]heptan-2-one 
• 5597-29-5 3-methylenenbicyclo<2.2.1>heptan-endo-2-ol 
• 99173-09-8 (+/-)-3endo-acetoxymethyl-norbornan-2-one 

Downstream Products

• 82741-93-3 3-benzylbicyclo<2.2.1>heptan-2-one 
• 122901-86-4 3-<<(4-tert-Butylphenyl)hydroxyamino>methyl>bicyclo<2.2.1>heptan-2-on 
• 126811-98-1 2-(1-Benzyl-4,5-dihydro-1H-imidazol-2-yl)-3-(3-oxo-bicyclo[2.2.1]hept-2-yl)-propionic acid ethyl ester 
• 74726-32-2 3-[(Dibenzylamino)-methyl]-bicyclo[2.2.1]heptan-2-one 

Relevant academic research and scientific papers

PROCESS FOR THE PREPARATION OF BETA-SANTALOL AND DERIVATIVES THEREOF

The present invention concerns a process for the preparation of a compound of formula (I) wherein R represents a Me or Et group, as well as said compound in the form of any one of its stereoisomers or mixture thereof. The invention concerns also the use of compound (I) for the synthesis of β-santalol or of derivatives thereof.

Dibromomethane as one-carbon source in organic synthesis: Microwave-accelerated α-methylenation of ketones with dibromomethane and diethylamine

The reactivity of aryl alkyl ketone with a preheated mixture of dibromomethane and diethylamine is poor and gives an α-methylenation product in very low yield even under refluxing condition. It can be accelerated dramatically by microwave irradiation. Under microwave condition, the cyclic 1,3-dicarbonyls, aryl alkyl ketones, heteroaryl alkyl ketones and acyclic benzyl ketone give α-methylenation products in modest to good yields.

Process for the preparation of bicyclic diketone salts

The present invention relates to a process for the preparation of bicyclic 1,3-diketone salts of formula I wherein R1, R2, R3 and R4 are each independently of the others hydrogen or C1-C4alkyl; A and E are each independently of the other C1-C2alkylene, which may be substituted once or up to four times by a C1-C4alkyl group, and M+ is an alkali metal ion, alkaline earth metal ion or ammonium ion, by oxidation of a compound of formula II to a compound of formula III and subsequent conversion to a compound of formula I either in the presence of a base and a catalytic amount of a cyanide or in the presence of an alkali metal alcoholate or alkaline earth metal alcoholate, and to novel bicyclic enol lactone intermediates of formula III for use in that process.

Radical Reactions of Bicycloheptan-3-spiro-2'-oxiranes

Tributyltin hydride reduction of 2-bromo- and 2-keto-bicycloheptan-3-spiro-2'-oxiranes gives ring opening of the oxirane-ringes via intermediate 3-(spiro-2'-oxiranyl)bicycloheptan-2-yl radicals, whereas reduction of the analogous 2-(thiocarbonyl)imidazolides) unusually yields the 2-methoxy derivatives and does not proceed by the expected normal fragmentation to yield 3-(spiro-2'-oxiranyl)bicycloheptan-2-yl radicals and subsequent ring-opening of the oxirane rings.