19740-86-4

Basic information

• Product Name: (endo,endo)-9-oxabicyclo[4.2.1]nonane-2,5-diol
• Synonyms: (endo,endo)-9-oxabicyclo[4.2.1]nonane-2,5-diol;Einecs 243-264-4
• CAS NO: 19740-86-4
• Molecular Formula: C₈H₁₄O₃
• Molecular Weight: 158.19496
• EINECS: 243-264-4
• Mol File: 19740-86-4.mol

Chemical Properties

• Boiling Point: 325.3°Cat760mmHg
• Flash Point: 150.6°C
• Appearance: /
• Density: 1.258g/cm³
• Vapor Pressure: 1.79E-05mmHg at 25°C
• Refractive Index: 1.544
• PKA: 13.96±0.40(Predicted)
• CAS DataBase Reference: (endo,endo)-9-oxabicyclo[4.2.1]nonane-2,5-diol(CAS DataBase Reference)
• NIST Chemistry Reference: (endo,endo)-9-oxabicyclo[4.2.1]nonane-2,5-diol(19740-86-4)
• EPA Substance Registry System: (endo,endo)-9-oxabicyclo[4.2.1]nonane-2,5-diol(19740-86-4)

Safety Data

• Hazardous Substances Data: 19740-86-4(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
(endo,endo)-9-oxabicyclo[4.2.1]nonane-2,5-diol is used as a building block for the synthesis of various organic compounds. Its unique structure and reactivity make it a valuable component in creating complex organic molecules.
Used in Medicinal Chemistry:
In the pharmaceutical industry, (endo,endo)-9-oxabicyclo[4.2.1]nonane-2,5-diol is used as a key intermediate in the development of new drugs. Its bicyclic structure and functional groups contribute to the design and synthesis of novel pharmaceuticals with potential therapeutic applications.
Used in Natural Product Synthesis:
(endo,endo)-9-oxabicyclo[4.2.1]nonane-2,5-diol is also employed in the synthesis of natural products, which are often derived from plants, animals, or microorganisms. Its unique structure allows for the creation of complex natural compounds with potential biological activities.
Used in Stereochemical Research:
Due to its interesting stereochemistry and conformational flexibility, (endo,endo)-9-oxabicyclo[4.2.1]nonane-2,5-diol is used as a model compound in the study of organic chemical reactions and stereochemical effects. This research can lead to a better understanding of the relationship between molecular structure and biological activity, which is crucial for the development of new drugs and materials.

InChI:InChI=1/C8H14O3/c9-5-1-2-6(10)8-4-3-7(5)11-8/h5-10H,1-4H2/t5-,6+,7-,8+

Upstream product

• 1552-12-1 1,5-cis,cis-cyclooctadiene 

Relevant articles and documents

Transannular O -heterocyclization: A useful tool for the total synthesis of Murisolin and 16,19- cis -Murisolin

Transannular O-heterocyclization is applied as a key step in a total synthesis. This highly stereoselective and metal-free transformation introduces four stereocenters in one step. It was chosen to be the pivotal step in the synthesis of Murisolin and 16,19-cis-Murisolin, two annonaceous acetogenins. The efficiency of this synthesis is further illustrated by a stereodivergent late-stage separation of both synthetic routes.

Synthesis of enantiopure 9-oxabicyclononanediol derivatives by lipase-catalyzed transformations and determination of their absolute configuration

Mixtures of endo,endo-9-oxabicyclo[4.2.1]nonane-2,5-diol (meso-2) and endo,endo-9-oxabicyclo[3.3.1]nonane-2,6-diol [(±)-3] were prepared from cycloocta-1,5-diene (1) upon 09174874200 treatment with peracids by transannular O-heterocyclization and subsequent saponification of the formed diol monoesters such as (±)-4 and (±)-5. The corresponding diacetates, meso-6 and (±)-7, were formed by acetylation of either meso-2 and (±)-3 or (±)-4 and (±)-5 with acetic anhydride/pyridine. These diacetates were enantioselectively hydrolyzed by microbial enzymes such as the lipases from Candida antarctica (CAL) or Candida rugosa (CRL). The corresponding enantiomers were formed by lipase-catalyzed acetylation of the diols meso-2 and (±)-3 with vinyl acetate. The skeletal isomers can also be separated in this way because the enantiopure monoacetates 4 were formed from the meso-compounds 2 or 6, while one enantiomer of the racemic diacetate (±)-7 [or the diol (±)-3] was transformed into the enantiopure diol 3 (or the enantiopure diacetate 7, respectively) via the corresponding enantiomers of the monoacetate 5. The other enantiomer remained untouched in both cases. The lipases reacted enantioselectively to give the R isomer. Cycloocta-1,5-diene (1) was also used to synthesize 2-oxa-6-thiatricyclo[3.3.1. 13,7]decane-4,8-diol [(±)-11] in a four-step sequence. This racemic diol was also acetylated selectively (R isomer) with vinyl acetate and CRL. Reductive desulfuration of (±)-11 gave exo,exo-9-oxabicyclo[3.3.1]nonane-2,6-diol [(±)-12], which was acetylated selectively (S isomer) with CRL under the same conditions. The similarity in size and particularly in shape is responsible for the observed stereoselectivity of the lipases for the racemic endo,endo compounds (±)-3 and (±)-7 on the one hand and the exo,exo compound (±)-12 on the other hand. The absolute configuration and crystal packing of the products was determined by X-ray structural analysis. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.

Selectivity of Candida rugosa lipase in simultaneous separation of skeletal isomers, desymmetrization, and kinetic racemate cleavage of 9-oxabicyclononanediols

The diols 2 and 3, available in one step from cycloocta-1,5-diene, are selectively acetylated at the (R)-centers using Candida rugosa lipase to give the corresponding enantiopure compounds. In contrast, the (S,S)-enantiomer of 11 is transformed under iden