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8-oxabicyclo[4.3.0]non-3-en-9-one is a complex organic compound with the molecular formula C9H12O2. It is a cyclic ketone with a unique structure, featuring a seven-membered ring that includes an oxygen atom, forming an oxa-bridge. 8-oxabicyclo[4.3.0]non-3-en-9-one is known for its potential applications in the synthesis of various pharmaceuticals and natural products due to its reactive ketone group and strained ring system. It can be used as a building block in organic synthesis, particularly in the preparation of complex molecules that require a bicyclo[4.3.0]nonane core. The compound's name reflects its structure, with "8-oxa" indicating the presence of an oxygen atom in the ring, and "bicyclo[4.3.0]non-3-en-9-one" describing the ring size, the position of the double bond, and the ketone functional group.

2744-05-0

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2744-05-0 Usage

Check Digit Verification of cas no

The CAS Registry Mumber 2744-05-0 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 2,7,4 and 4 respectively; the second part has 2 digits, 0 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 2744-05:
(6*2)+(5*7)+(4*4)+(3*4)+(2*0)+(1*5)=80
80 % 10 = 0
So 2744-05-0 is a valid CAS Registry Number.

2744-05-0Relevant academic research and scientific papers

Simple Preparation of Rhodococcus erythropolis DSM 44534 as Biocatalyst to Oxidize Diols into the Optically Active Lactones

Martinez-Rojas, Enriqueta,Olejniczak, Teresa,Neumann, Konrad,Garbe, Leif-Alexander,Boraty?ski, Filip

, p. 623 - 627 (2016)

In the current study, we present a green toolbox to produce ecological compounds like lactone moiety. Rhodococcus erythropolis DSM 44534 cells have been used to oxidize both decane-1,4-diol (2a) and decane-1,5-diol (3a) into the corresponding γ- (2b) and δ-decalactones (3b) with yield of 80% and enantiomeric excess (ee)?=?75% and ee?=?90%, respectively. Among oxidation of meso diols, (?)-(1S,5R)-cis-3-oxabicyclo[4.3.0]non-7-en-2-one (5a) with 56% yield and ee?=?76% as well as (?)-(2R,3S)-cis-endo-3-oxabicyclo[2.2.1]dec-7-en-2-one (6a) with 100% yield and ee?=?90% were formed. It is worth mentioning that R. erythropolis DSM 44534 grew in a mineral medium containing ethanol as the sole source of energy and carbon Chirality 28:623–627, 2016.

Microbial alcohol dehydrogenase screening for enantiopure lactone synthesis: Down-stream process from microtiter plate to bench bioreactor

Boratyński,Pannek,Walczak,Janik-Polanowicz,Huszcza,Szczepańska,Martinez-Rojas,Olejniczak

, p. 1637 - 1646 (2015/02/05)

One-pot conversion with whole cells of bacteria was performed for biooxidation of meso monocyclic (3a-b) and bicyclic diols (3c-e) into corresponding chiral lactones of bicyclo[4.3.0]nonane structure (2a-b) as well as exo- and endo-bridged lactones with the structure of [2.2.1] (3c-d) and [2.2.2] (3e). Micrococcus sp. DSM 30771 was selected as biocatalyst with significant alcohol dehydrogenase activity. Among tested strains, microbial oxidation of meso diols 3a-e catalyzed by Micrococcus sp. afforded enantiomerically pure ((+)-(2S,3R)-2c (ee = 99%), (+)-(2S,3R)-2e (ee = 99%)) or enriched ((+)-(1S,5R)-2a (ee = 90%), (-)-(1S,5R)-2b (ee = 86%), (+)-(2S,3R)-2d (ee = 80%)) lactone moieties. Comparative study with respect to microbial cultivation as well as biooxidation was undertaken to verify agreement of secondary metabolite biosynthesis in different scales: from MTP (4 mL), across shake flask (100 mL) till bioreactor (4 L). The results from biotransformations showed quite similar dependence in oxidation of all substrates 3a-e in MTP and flasks as well, thereby confirmed the validity and reasonable approach of using MTP for preliminary studies.

Syntheses stereoselectives des γ-lactones bicycliques condensees

Canonne, P.,Akssira, M.

, p. 3695 - 3704 (2007/10/02)

A highly stereoselective synthesis of trans/trans and cis/trans bicyclic γ-lactones is described using bicyclic dicarboxylic anhydrides.

REDUCTION DES ANHYDRIDES BICYCLIQUES CONDENSES PAR LE BROMURE DE CYCLOPENTYLMAGNESIUM

Canonne, P.,Akssira, M.

, p. 1297 - 1300 (2007/10/02)

Greatly different product distributions were observed in the reactions of cyclopentyl- and isopropylmagnesium bromides with cyclohexane-, cyclohex-4-ene- and cyclobutane-1,2 dicarboxylic anhydrides.Cyclopentylmagnesium bromide yielded reduction products with high stereoselectivity whereas the isopropylmagnesium bromide provided the corresponding trans diastereomeric ketoacids via an addition enolization process.

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