511-59-1

Usage

Uses

Used in Pharmaceutical Industry:
(1S-exo)-2-methyl-3-methylene-2-(4-methyl-3-pentenyl)bicyclo[2.2.1]heptane is used as a pharmaceutical compound for its potential therapeutic properties. Its unique chemical structure allows it to interact with biological targets and modulate various biological pathways, making it a promising candidate for the development of new drugs.
Used in Fragrance Industry:
(1S-exo)-2-methyl-3-methylene-2-(4-methyl-3-pentenyl)bicyclo[2.2.1]heptane is used as a fragrance ingredient due to its unique and pleasant aroma. Its ability to create a distinct scent profile makes it valuable in the formulation of perfumes, colognes, and other fragrance products.
Used in Flavor Industry:
(1S-exo)-2-methyl-3-methylene-2-(4-methyl-3-pentenyl)bicyclo[2.2.1]heptane is used as a flavoring agent in the food and beverage industry. Its unique taste profile can enhance the flavor of various products, making it a valuable ingredient in the creation of new and innovative flavors.
Used in Agrochemical Industry:
(1S-exo)-2-methyl-3-methylene-2-(4-methyl-3-pentenyl)bicyclo[2.2.1]heptane is used as an agrochemical compound for its potential applications in pest control and crop protection. Its unique chemical structure allows it to target specific pests and diseases, making it a valuable tool in the development of new and effective agrochemical products.

InChI:InChI=1/C15H24/c1-11(2)6-5-9-15(4)12(3)13-7-8-14(15)10-13/h6,13-14H,3,5,7-10H2,1-2,4H3

Upstream product

• 77-42-9 (-)-(Z)-β-santalol 
• 131232-80-9 3-(2-Methyl-3-methylenebicyclo<2.2.1>hept-2-yl)propanal 
• 1530-33-2 isopropyltriphenylphosphonium bromide 
• 106708-91-2 (1S,2S)-3-methylidene-2-(4-methyl-3-pentenyl)bicyclo<2.2.1>heptane-2-methanol 
• 106708-92-3 (1S,2S)-3-methylidene-2-(4-methyl-3-pentenyl)bicyclo<2.2.1>heptane-2-carbaldehyde 
• 131726-03-9 (1R,3R,4S)-3-Methyl-3-(4-methyl-pent-3-enyl)-bicyclo[2.2.1]heptan-2-one 
• 74-95-3 1,1-dibromomethane 
• 172721-78-7 2-((1S,2R,4R)-2-Methyl-3-methylene-bicyclo[2.2.1]hept-2-yl)-ethanol 
• 172721-77-6 ((1S,2R,4R)-2-Methyl-3-methylene-bicyclo[2.2.1]hept-2-yl)-acetaldehyde 
• 172721-75-4 (1R,4S)-3-Methyl-bicyclo[2.2.1]hept-2-ene-2-carboxylic acid methyl ester 
• 88948-27-0 (1S,2R,3S)-3-(2,2-dimethylpropoxy)-4,7,7-trimethylbicyclo<2.2.1>hept-2-yl (1R,2S)-3-methylidenebicyclo<2.2.1>hept-5-ene-2-carboxylate 
• 18530-03-5 (+/-)-Isoepicampherenol 
• 79157-56-5 4-Methyl-1-(2-methyl-3-methylenbicyclo<2.2.1>hept-2-yl)-3-penten-2-on 
• 18530-02-4 (+/-)-Epicampherenon 

Downstream Products

• 77-42-9 (-)-(Z)-β-santalol 

Relevant academic research and scientific papers

A SESQUITERPENOID ANT REPELLENT FROM DYSOXYLUM SPECTABILE

(2S,3R)-2,3-Dimethyl-3-(4-methyl-3-pentenyl)-2-norbornanol was isolated as the ant repellent in an activity guided separation of the fruits of Dysoxylum spectabile.The structure of the alcohol was established by NMR.Other sesquiterpenes were recognized in a GCMS analysis of the steam distillate.

ASYMMETRIC DIELS-ALDER REACTION OF A CHIRAL ALLENIC ESTER: ENANTIOSELECTIVE SYNTHESIS OF (-)-β-SANTALENE

The Lewis-acid promoted Diels-Alder reaction of the allenic ester 10 provides the adduct 11 with excellent ?-facial selection leading to an efficient enantioselective synthesis of (-)-β-santalene and to the recovery of the chiral control element 7.

Diastereo- and enantio-controlled synthesis of sandalwood constituents (-)-β-santalene and (+)-epi-β-santalene starting from the same (+)-norcamphor

(-)-β-Santalene and (+)-epi-β-santalene, both occurring in East Indian sandalwood oil and having an enantiomeric core bicyclo[2.2.1]heptane framework, have been synthesized in diastereo- and enantio-controlled manner starting from the same (+)-norcamphor.

Site-Selective Rhodium(II) Acetate Mediated Intramolecular Metal-Carbene Insertions into C-H Bonds of Bicycloheptanes: Efficient Syntheses of (+)-Albene and (-)-β-Santalene

Treatment of α-diazo ketones 1a-d and 2a-d with catalytic amounts of rhodium(II) acetate led to selective carbene insertions into C-H bonds resulting in cyclopentane-annulated products in high yields.The highly selective insertion realized into the exo-methyl C-H bond of 1a has been utilized in the syntheses of (+)-albene (8) and (-)-β-santalene (11).

Total Syntheses of Sandalwood Fragrances: (Z)- and (E)-β-Santalol and Their Enantiomers, ent-β-Santalene

Via asymmetric Diels-Alder reactions, large scale preparations of enantiomerically pure norbornane-2-carboxylic acids were carried out.Oxidative degradation furnished 2-norbornanone and 3-methyl-2-norbornanone which gave the title compounds via stereoselective alkylations, subsequent Wittig reactions and reductions.

221. Asymmetric Diels-Alder Reactions of Neopentyl-Ether-Shielded Acrylates and Allenic Esters: Syntheses of (-)-Norbornenone and (-)-β-Santalene

Starting from (+)- or (-)-camphor, the antipodal alcohols 14 and 18, respectively, have been prepared; the corresponding acrylates 15 and 19 underwent TiCl2(i-PrO)2-mediated Diels-Alder additions to cyclopentadiene to give adducts 20a and 22a respectively, with 95percent endo- and 99.2percent ?-face selectivities.Adduct 22a was converted to enentiomerically pure norbornenone 26.Addition of 1,3-butadiene to acrylate 15 in the presence of TiCl4 afforded 3-cyclohexenyl carboxylate 29 with > 95.6percent stereodifferentiation.The TiCl2(i-PrO)2-promoted cycloaddition of cyclopentadiene to allenic ester 43 proceeding with 99percent face differentiation served as the key step for an efficient enantioselective synthesis of (-)-β-santalene ((-)-41) with concomitant recovery of the chiral control alcohol 14.

IDENTIFICATION OF TRANS-β-SANTALOL AND EPI-CIS-β-SANTALOL IN EAST INDIAN SANDALWOOD OIL

An analysis of East Indian sandalwood oil (Santalum album) has resulted in the isolation and identification of trans-β-santalol and epi-cis-β-santalol.Key Word Index- Santalum album; Santalaceae; East Indian sandalwood oil; trans-β-santalol; epi-cis-β-santalol.

Terpenes and Terpene Derivatives, XI. - Synthesis and Reductions of β-Santalenone hept-2-yl)-3-penten-2-one>

Starting from cyclopentadiene (2) and 2-butynoic acid (3), and via the acids 5 and 7, the allyl alcohol 9 has been prepared. 9 reacts with the dienol ether 10 to give β-santalenone 11.Reduction of 11 with LiAlH4/AlCl3 yields, depending on the reaction temperature various amounts of hydrocarbons 25, 26, and β-santalenone (1), of the ketone 27 and of the alcohol 28.With NaBH4 the alcohols 28 and 29 have been obtained.