1489-28-7

Usage

Bicyclic organic compound

It has a six-membered ring fused to a five-membered ring, which gives it a unique structure.

Physical state at room temperature

Colorless, viscous liquid
The compound is a colorless liquid with a viscous consistency.

Precursor in synthesis

It is used as a starting material in the synthesis of various pharmaceuticals and organic compounds.

Applications in perfumes and fragrances

Due to its pleasant aroma, it is used in the production of perfumes and fragrances.

Flavoring agent in the food industry

Its pleasant aroma also makes it suitable for use as a flavoring agent in the food industry.

Chemical intermediate

It is used as a chemical intermediate in the production of various products, such as rubber chemicals, antioxidants, and UV stabilizers.

Upstream product

• 7148-07-4 1-pyrrolidinocyclopent-1-ene 
• 78-94-4 methyl vinyl ketone 
• 5111-69-3 5-methoxyindane 
• 64-17-5 ethanol 
• 141-52-6 sodium ethanolate 
• 141-97-9 ethyl acetoacetate 
• 1489-27-6 2-(3-oxobutyl)cyclopentanone 
• 111602-11-0 ethoxy-1 methyl-3 oxa-2 bicyclo<4,3,0>nonene 
• 107-21-1 ethylene glycol 
• 75066-62-5 3-Oxo-5-(2-oxocyclopentyl)-2-(triphenylphosphoranyliden)pentananilid 
• 40050-12-2 2-oxo-1-(3-oxobutyl)cyclopentanecarbaldehyde 
• 4668-91-1 (+/-)-cis-bicyclo<4.3.0>nonan-3-one 
• 19980-43-9 1-(trimethylsilyloxy)cyclopentene 
• 6053-92-5 hexahydro-cyclopenta[b]pyran-2-one 

Downstream Products

• 18366-35-3 4,4-Dimethyl-1,2,4,6,7,7a-hexahydro-inden-5-one 
• 41596-98-9 5-(1-Phenylsulfanyl-cyclopropyl)-2,3,5,6,7,7a-hexahydro-1H-inden-5-ol 
• 30270-46-3 Phenyl-1-bicyclo<4.3.0>nonan-cis 
• 119971-63-0 (1S^*,4S^*,5R^*,8R^*)-Tricyclo<6.3.0.0^1,4>undecan-5-yl p-bromobenzoate 
• 119594-92-2 (+/-)-trans-bicyclo<4.3.0>nonan-3-one 
• 4668-91-1 (+/-)-cis-bicyclo<4.3.0>nonan-3-one 
• 22578-06-9 5.5-Difluor-cis-hydrindan 

Relevant academic research and scientific papers

Tridemethylisovelleral, a potent cytotoxic agent

The synthesis and in vitro cytotoxicity toward various tumor cell lines of (±)-tridemethylisovelleral, an analogue of the bioactive fungal sesquiterpene (+)-isovelleral retaining the bicyclo[4,1,0]hept-2-en-1,2- dicarbaldehyde system but lacking the three methyl groups, is reported. The cytotoxicity of tridemethylisovelleral toward several tumor cell lines was found to be comparable with those of established antitumor drugs, and significantly higher than that of isovelleral.

Dehydrogenation of polycyclic ketones using trichloromethyl cation in superacid

In HF/SbF3/CCl4 bicyclic cyclohexanones are dehydrogenated to enones and dienones, superelectrophilic trichloromethyl cation CCl3+ reacting as a strong hydride acceptor. Dehydrogenation is also observed with steroidal enones.

Use of the bifunctional reagent (Z)-4-iodo-1-(tributylstannyl)but-1-ene: A new cyclohexenone annulation method

A new cyclohexenone annulation method, based on the use of the bifunctional reagent (Z)-4-iodo-1-(tributylstannyl)but-l-ene (6) and exemplified by conversion of the substrate 8 into the annulated products 13 and 18 and of the starting materials 19-23 into the products 34-38, respectively, is described.

Cascade Radical Cyclization-Fragmentation-Transannular-Ring Expansion Reactions Involving Oximes. A New Approach to the Synthesis of Angular Triquinanes

Treatment of the acetylene-substituted cyclobutanone oxime ether (13) with (Me3Si)3SiH leads, in one pot, to the 5,6-bicyclic enone oxime (14) in 70percent yield.It is suggested that the formation of (14) from (13) proceeds by way of a novel double ring e

A new method for the preparation of Michael adducts and cyclic enones using lithium chloride-hexamethylphosphoramide system

A new procedure using lithium chloride in hexamethylphosphoramide was found to be useful for the synthesis of Michael-type adducts and cyclic enones. Selectivity for the two products could be controlled by altering the reaction temperature employed. The urea-type solvents were also examined instead of hexamethylphosphoramide.

Cascade radical reactions in synthesis. A new radical mediated double ring expansion-cyclisation process oxime ethers

Treatment of the acetylene substituted cyclobutanone oxime ether (1) with (Me3Si)3SiH leads, in one pot, to the bicycle (2, 70%) by way of a novel double ring expansion-cyclisation process involving aminyl radical intermediates.

A Method for the Cyclic Enone Synthesis Using Lithium Chloride-Hexamethylphosphoramide System

Cyclic enones were obtained from the reactions of β-keto esters with acyclic α,β-unsaturated ketones by using lithium chloride in hexamethylphosphoramide.The products were brought via the Michael addition, decarboxylation, and the aldol condensation.

A New Annulation Reagent, 2-Oxo-3-alkenylphosphonates. Reactions with Carbonyl-Stabilized Carboanions or Silyl Enol Ethers Leading to Cyclohexanones

The reactions of 2-oxo-3-alkenylphosphonates with carbonyl-stabilized carbanions directly lead to 2-cyclohexen-1-ones through a sequence of Michael reaction and intramolecular Horner-Emmons olefination.On the other hand, the Lewis acid-mediated reactions with silyl enol ethers produce 1,5-diketones as Michael adducts, which then undergo cyclization on treatment with sodium hydride or triethylamine/zinc (II) bromide to afford 2-cyclohexen-1-ones or 2-phosphinyl-2-cyclohexen-1-ones, respectively.

Organotin Triflate as Practical Catalyst for Michael Addition of Enol Silyl Ethers

Dibutyltin bis(triflate) is a mild Lewis acid which catalyzes clean Michael addition of enol silyl ethers.The new catalyst allows to employ various labile acceptors such as methyl vinyl ketone and 2-cyclopentenone which do not undergo smooth reaction with

Organotin triflates as functional Lewis acids. A new entry to simple and efficient Robinson annulation

An efficient Robinson annulation has been established through the Michael addition of enol silyl ethers to α-enones catalyzed by dibutyltinbis(triflate) followed by the MeONa-mediated intramolecular aldol condensation of the adducts.