19419-67-1

Usage

Uses

Used in Fragrance Industry:
2,5β,9,9-Tetramethyl-6,7,8,9-tetrahydro-5H-benzocycloheptene is used as a key component in the synthesis of essential oils and pheromones. Its unique chemical structure and chiral properties make it an ideal candidate for creating complex and diverse fragrances, as well as pheromonal compounds that can be used in various applications, such as perfumery, aromatherapy, and pest control.
Used in Pharmaceutical Industry:
Due to its structural complexity and potential biological activities, 2,5β,9,9-Tetramethyl-6,7,8,9-tetrahydro-5H-benzocycloheptene may be utilized as a starting material or intermediate in the development of new pharmaceutical compounds. Its potential applications in this industry could include the treatment of various diseases and disorders, as well as the development of novel drug delivery systems.
Used in Chemical Research:
The unique structure and properties of 2,5β,9,9-Tetramethyl-6,7,8,9-tetrahydro-5H-benzocycloheptene make it an interesting subject for chemical research. It can be used as a model compound to study various aspects of organic chemistry, such as reaction mechanisms, stereochemistry, and the influence of molecular structure on reactivity and selectivity.
Used in Material Science:
The potential applications of 2,5β,9,9-Tetramethyl-6,7,8,9-tetrahydro-5H-benzocycloheptene in material science could include the development of novel materials with specific properties, such as improved stability, enhanced mechanical strength, or unique optical and electronic properties. Its incorporation into polymers, coatings, or other materials could lead to the creation of innovative products with a wide range of applications.

Upstream product

• 51599-87-2 (R)-5,5,9-Trimethyl-3-methylene-2,3,4,4a,5,6,7,8-octahydro-1H-benzocycloheptene 
• 60909-27-5 (10S, 11S)-himachala-2,4-diene 
• 1461-03-6 β-himachalene 
• 3853-83-6 α-himachalene 
• 403786-40-3 (6S,7R)-2,2,6-trimethyl-10-methylenebicyclo[5.4.0]undec-1⁽¹¹⁾-ene 
• 1413723-36-0 3,5,5,9-tetramethyl-8,9-dihydro-5H-benzo[7]annulen-6(7H)-one 
• 38142-58-4 (+/-)-ar-turmerone 
• 35944-26-4 12-bromolongibornane-4-one 
• 51704-14-4 (R)-5,5,9-Trimethyl-3-methylene-1,2,3,4,4a,5,6,8-octahydro-benzocyclohepten-7-one 
• 19419-75-1 (+)-Cyclo-ar-turmeron 

Relevant academic research and scientific papers

Enantioselective synthesis of the essential oil and pheromonal component ar-himachalene by a chiral pool and chirality induction approach

The enantioselective synthesis of both isomers of ar-himachalene has been achieved starting from enantiomerically pure citronellal and p-methyl α-methyl styrene as an application of a chiral pool and chirality induction approach, respectively. The key reactions involved in the synthesis include the Sharpless asymmetric dihydroxylation for the induction of chirality at benzylic carbon bearing the methyl group and the use of a hypervalent iodine reagent or trimethylsilyldiazomethane (TMSCHN2) for the six to seven membered ring expansion.

Synthesis and stereochemistry of the four himachalene-type sesquiterpenes isolated from the flea beetle (Aphthona flava) as pheromone candidates

Both the (1S,2R) and (1R,2S) isomers of 2,6,6-trimethylbicyclo[5.4.0]undec- 7-en-9-one (1) were synthesized by starting from (S)- and (R)-citronellal (5), respectively. The stereochemistry of (1R,2S)-(-)-1 was established by an X-ray analysis; it exhibits a CD spectrum similar to that of cholest-4-en-3-one, in agreement with its absolute configuration. The ketones (1S,2R)- and (1R,2S)-1 were converted into the en-antiomers of three other himachalene hydrocarbons, 2,2,6-trimethyl-10-methylenebicyclo[5.4.0]undec-1(11)-ene (2), 1,1,5,8-tetramethyl-1,2,3,4,5,6,5a-hepta hydro benzo [1,2-a]-[7]annulene (3), and 1,1,5,8-tetramethyl-1,2,3,4,5-pentahydrobenzo[a][7]annulene (ar-himachalene, 4). The stereochemistry of these himachalene-type sesquiterpenes isolated from flea beetles such as Aphthona flava and Phyllotreta cruciferae as their male-pheromone components was revised to (1S,2R)-1, (6R,7S)-2,(5R,5aS)-3, and (R)-4. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.

Five new cis-himachalane-type sesquiterpenes from the heartwood of Juniperus chinensis var. tsukusiensis

The following constituents were isolated from the heartwood of Juniperus chinensis vat. tsukusiensis: ar-himachalene (1), 2-himachalen-6-ol (2), 3- himachalen-6-ol (3), 2α,6α-epoxy-3-himachalene (4), 2α,6α- epoxyhimachalan-3β-ol (5), and chinensiol (6). Compounds 2-6 are new cis- himachalane-type sesquiterpenes, and their structures were elucidated on the basis of spectral and chemical evidence. Himachalane-type sesquiterpenes were isolated for the first time in Juniperus species.

NEW SESQUITERPENOIDS FROM THE OLEORESIN OF Abies alba

The structures of four new sesquiterpenoids from the oleoresin of Abies alba have been studied, On the basis of various spectral characteristics, the structures of (10S, 11S)-himachala-2,4-diene, (10S, 11S)-himachala-3(12),4-diene, humula-4,9-dien-8-ol, and (4S, 5S, 10S)-selina-6-en-4-ol have been proposed for the compounds isolated.The stereochemistry of the assymetric centers was determined by the conversion of these compounds into known sesquiterpenes and also by analysis of PMR spectra with a shift reagent.