203319-31-7

Usage

Uses

Used in Organic Synthesis:
5-Cyclooctene-1,2-diol, (1R,2R)is used as a reagent in organic synthesis for its versatile chemical properties and ability to form various derivatives. Its presence in the synthesis process allows for the creation of a wide range of compounds with potential applications in different industries.
Used in Pharmaceutical Industry:
5-Cyclooctene-1,2-diol, (1R,2R)is used as a building block in the preparation of various pharmaceuticals. Its unique structure and functional groups make it suitable for the development of new drugs with specific therapeutic properties. The chiral nature of the compound also allows for the synthesis of enantiomerically pure drugs, which can have different biological activities.
Used in Agrochemical Industry:
5-Cyclooctene-1,2-diol, (1R,2R)is used as a building block in the preparation of agrochemicals, such as pesticides and herbicides. Its unique structure and functional groups can be utilized to create new compounds with improved efficacy and selectivity, leading to more effective and environmentally friendly agrochemicals.

Upstream product

• 37940-17-3 (Z)-(1R,8R)-10,10-dimethyl-9,11-dioxabicyclo[6.3.0]undec-4-ene 
• 203715-36-0 (5R,6R)-5,6-dihydroxydeca-1,9-diene 
• 1552-12-1 1,5-cis,cis-cyclooctadiene 
• 19740-90-0 (Z)-9-oxabicyclo[6.1.0]non-4-ene 
• 108-05-4 vinyl acetate 
• 31598-91-1 rac-(Z)-cyclooct-5-en-1,2-diol 
• 117468-07-2 rel-(1S,2S,5Z)-cyclooct-5-en-1,2-diol 
• 155236-98-9 (4R,5R)-4,5-dibut-3-enyl-2,2-dimethyl-1,3-dioxacyclopentane 
• 39139-91-8 trans-1,5,9-decatriene 

Downstream Products

• 29417-27-4 (1R,2R,6R)-9-oxabicyclo[3.3.1]-non-6-en-2-yl acetate 
• 37940-17-3 (Z)-(1R,8R)-10,10-dimethyl-9,11-dioxabicyclo[6.3.0]undec-4-ene 
• 917236-93-2 C₂₆H₃₀O₆ 
• 39840-97-6 (1R,2R,5R)-9-oxabicyclo[3.3.1]-non-6-en-2-ol 
• 10299-48-6 (1R,5R)-9-oxabicyclo[3.3.1]nona-2,6-diene 
• 272781-30-3 (1R,2R,5R,6S)-5-bromo-9-oxabicyclo[4.2.1]-nonan-2-ol 
• 272781-29-0 (1R,2R,5R,6S)-6-bromo-9-oxabicyclo[3.3.1]-nonan-2-ol 
• 272781-32-5 (1R,2R,3R)-9-oxabicyclo[3.3.1]non-6-en-2-yl N,N-dimethylthiocarbamate 
• 272781-27-8 (1R,4S,5S,8R)-4,5-dibromo-10,10-dimethyl-9,11-dioxabicyclo[6.3.0]undecane 
• 272781-28-9 (1R,4R,5R,8R)-4,5-dibromo-10,10-dimethyl-9,11-dioxabicyclo[6.3.0]undecane 

Relevant academic research and scientific papers

Microwave- Assisted kinetic resolution of homochiral (Z)-cyclooct-5-ene-1, 2-diol and (Z)-2- Acetoxycyclooct-4-enyl acetate using lipases

Over the last decade, the use of biocatalysts has become an attractive alternative to conventional chemical methods, especially for organic synthesis, due to their unusual properties. Among these enzymes, lipases are the most widely used, because they are cheap, easily available, cofactor-free, and have broad substrate specificity. Combined to microwave heating in non- Aqueous medium, recent results suggest that irradiation may influence the enzyme activity. This Communication reports the benefits of lipases and the microwave irradiation on the kinetic resolution of racemic homochiral (Z)-cyclooct-5-ene- 1,2-diol and (Z)-2- Acetoxycyclooct-4-enyl acetate. In order to best achieve the kinetic resolution, different parameters were studied including the type of lipase, the temperature, the impact of microwave power compared to conventional heating. Optimization of the reaction parameters lead to the obtainment of highly enriched or enantiopure diols and diesters in a clean, efficient and safe way.

An asymmetric synthesis of enantiopure chair and twist trans-cyclooctene isomers

A pair of enantiopure chair and twist trans-cyclooctenes isomers were prepared by regioselective Sharpless asymmetric dihydroxylation of the central olefin of (E)-1,5,9-dectriene triene, with subsequent ring-closing metathesis to form an enantiomerically pure cis-cyclooctene. Epoxidation and ring-opening with lithium diphenylphosphide gives after oxidation two diastereomeric hydroxyphosphine oxides. Separate syn-elimination of these diastereomers gives enantiomerically pure chair and twist trans-cyclooctenes. A discussion of the molecular motion required to achieve the chair and twist isomers is discussed with reference to the X-ray crystal structure obtained for the hydroxyphosphine oxide leading to the chair trans-cyclooctene.

Synthesis of optically active bicyclo[3.3.0]octane Skeleton using transannular reaction

Optically active 5-cyclooctene-1,2-diol derivatives prepared by an enzymatic procedure have been converted into bicyclo[3.3.0]octane derivatives by transannular reaction with complete inversion of the stereogenic center linked to the leaving group. Formal synthesis of (+)-iridomyrmecin has been achieved starting from (S,S)-5-cyclooctene-1,2-diol by using this process.