58866-18-5

Usage

Uses

Used in Organic Synthesis:
(3aR,3bS,6aS,7aR)-decahydro-7H-cyclopenta[a]pentalen-7-one is used as a synthetic intermediate for the production of various organic compounds. Its unique structure and reactivity make it a valuable building block in the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Natural Product Isolation:
In the field of natural products, (3aR,3bS,6aS,7aR)-decahydro-7H-cyclopenta[a]pentalen-7-one is used for the isolation and purification of bioactive compounds from plant and animal sources. Its presence in some natural products aids researchers in identifying and characterizing novel bioactive molecules with potential therapeutic applications.
Used in Chemical Research:
(3aR,3bS,6aS,7aR)-decahydro-7H-cyclopenta[a]pentalen-7-one serves as a subject of study in chemical research, where its structure and reactivity are investigated to understand its potential applications and to develop new synthetic methods. This research can lead to the discovery of new reactions and the development of more efficient synthetic routes for the production of complex organic molecules.
Used in Pharmaceutical Industry:
(3aR,3bS,6aS,7aR)-decahydro-7H-cyclopenta[a]pentalen-7-one is used as a key component in the development of new pharmaceuticals. Its unique structure and reactivity can contribute to the design of novel drug candidates with improved efficacy and selectivity, potentially leading to the discovery of new treatments for various diseases.
Used in Agrochemical Development:
In the agrochemical industry, (3aR,3bS,6aS,7aR)-decahydro-7H-cyclopenta[a]pentalen-7-one is utilized for the development of new pesticides, herbicides, and other crop protection agents. Its unique properties can be harnessed to create more effective and environmentally friendly agrochemicals, contributing to sustainable agriculture practices.

Upstream product

• 58866-22-1 α,α'-dicyclopentenyl ketone 
• 61617-58-1 tricyclo<6.3.0.0^2,7>undecan-3-one 
• 142-29-0 cyclopentene 
• 96-22-0 pentan-3-one 
• 138622-57-8 decahydro<3aα,3bβ,6aβ,7aα>-7H-cyclopentapentalen-7-ol 
• 108686-36-8 tricyclo<6.3.0.0^2,6>undec-2(6)-en-7-one 
• 138622-65-8 C₁₄H₁₈O₄S 
• 138622-61-4 (2S,5R,6R)-5-(3-oxopropyl)-tricyclo<5.2.1.0^2,6>dec-8-en-3-one propylene ketal 
• 138622-64-7 C₁₃H₁₆O₂ 
• 138622-63-6 (2S,8S,9R)-tetracyclo<8.2.1.0^2,9.0^4,8>trideca-4,11-dien-3-one 
• 138622-66-9 (2S,4S,8S,9R)-tetracyclo<8.2.1.0^2,9.0^4,8>tridec-11-en-3-one 
• 118451-81-3 (1S,5S)-bicyclo<3.3.0>oct-3-en-2-one 

Relevant academic research and scientific papers

Ionic hydrogenation of oxyallyl intermediates: The reductive nazarov cyclization

Cyclization of tri- and tetrasubstituted dienones 1 under Lewis acidic conditions in the presence of triethylsilane led to formation of either silyl enol ethers 6 or cyclopentanones 7 in good to excellent yields, depending on work-up conditions. The proposed mechanism involves initial Nazarov cyclization to give oxyallyl intermediates 5, which are intercepted via intermolecular transfer of hydride. The reactions proceeded cleanly with as little as 2 equiv. of silane and in most cases catalytic amounts of Lewis acid could be used. Trapping with Et3SiD occurs at the less substituted terminus in unsymmetrical cases. (C) 2000 Elsevier Science Ltd.

The reductive Nazarov cyclization

Tri- and tetrasubstituted 1,4-dien-3-ones 1 were treated with Lewis acid in the presence of triethylsilane, furnishing either silyl enol ethers 4 or cyclopentanones 5 in good yields, depending upon work-up conditions. This reaction is presumed to occur th

Cyclobutane ring expansion in tricyclo2,7>undecan-3-ol. Potential application in the synthesis of triquinane and cyclopentacyclooctane derivatives

The acid catalysed rearrangement of tricyclo2,7>undecan-3-ol (2) gives 2,3,3b,4,5,6,6a,7-octahydro-1H-cyclopentapentalene (3) as the major product which is converted to decahydro-1H-cyclopentacyclooctane-4,8-dione (8).The other products of rearrangement are cis-anti-cis- and cis-syn-cis-decahydro-7H-cyclopentapentalen-7-ols (4 and 5), decahydro-9(endo)hydroxy- and decahydro-9(exo)hydroxy-4,8-methanoazulenes (6 and 7).

Synthesis of a New Ketone and Alcohol with C2 Symmetry; (S,S,S,S) Tricyclo3,7>undecan-2-one and (S,S,S,S) Tricyclo3,7>undecan-2-ol

Dissolving metal reduction of known enone 5 affords predominantly the racemic form of the title ketone (3) whereas catalytic reduction gives the meso isomer 6.Neither ketone 3 nor alcohol 4 could be satisfactorily resolved.Asymmetric synthesis of (-)-3 and (+)-4 (ee=91percent) was effected from ketone (+)-13.