26054-46-6

Basic information

• Product Name: (+)-(1R,5S)-2-Oxabicyclo[3.3.0]oct-6-en-3-one
• Synonyms: 2H-Cyclopenta[b]furan-2-one, 3,3a,6,6a-tetrahydro-, (3aR,6aS)-rel-;(3aS,6aR)-rel-3,3a,6,6a-Tetrahydro-2H-cyclopenta[b]furan-2-one;cis-2-Hydroxy-4-cyclopentene-1-acetic acid lactone;(3aR,6aS)-rel-3,3a,6,6a-Tetrahydro-2H-cyclopenta[b]furan-2-one
• CAS NO: 26054-46-6
• Molecular Formula: C₇H₈O₂
• Molecular Weight: 124.14
• Mol File: 26054-46-6.mol
• Article Data: 72

Chemical Properties

• Boiling Point: 263.1°Cat760mmHg
• Flash Point: 104°C
• Appearance: /
• Density: 1.196g/cm³
• Vapor Pressure: 0.0105mmHg at 25°C
• Refractive Index: 1.522
• Storage Temp.: 2-8°C
• CAS DataBase Reference: (+)-(1R,5S)-2-Oxabicyclo[3.3.0]oct-6-en-3-one(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-(1R,5S)-2-Oxabicyclo[3.3.0]oct-6-en-3-one(26054-46-6)
• EPA Substance Registry System: (+)-(1R,5S)-2-Oxabicyclo[3.3.0]oct-6-en-3-one(26054-46-6)

Safety Data

• Hazardous Substances Data: 26054-46-6(Hazardous Substances Data)

Usage

General Description

"(+)-(1R,5S)-2-Oxabicyclo[3.3.0]oct-6-en-3-one" is a chemical compound, specifically known as a bicyclic ketone. Without additional context, its specific usage is difficult to identify, but generally, such compounds are used in a variety of chemical and pharmacological applications, such as synthetics and intermediates in pharmaceuticals. The nomenclature "(+)-(1R,5S)" refers to the stereochemistry of the molecule, which highlights its three-dimensional structure. The "2-Oxabicyclo[3.3.0]oct-6-en-3-one" part of the name specifies its bicyclic nature, meaning it contains two rings, and "oxa" indicates one of those rings contains an oxygen atom. The "en" and "one" parts of the name indicate a double bond and a ketone group (C=O), respectively.

InChI:InChI=1/C7H8O2/c8-7-4-5-2-1-3-6(5)9-7/h1-2,5-6H,3-4H2/t5-,6-/m0/s1

Upstream product

• 13259-28-4 (rac)-6-endo-bicyclo<3.2.0>hept-2-en-6-ol 
• 54483-50-0 methyl 2S-methylsulfonyloxy-4-cyclopentene-1S-acetate 
• 925211-06-9 bicyclo(3.2.0)hept-2-en-6-one 
• 71155-05-0 (1R,5S)-bicyclo[3.2.0]hept-2-en-6-one 
• 49826-01-9 methyl 2R-methylsulfonyloxy-4-cyclopentene-1R-acetate 
• 13259-28-4 (+/-)-exo-bicyclo<3.2.0>hept-2-en-6-ol 
• 34638-25-0 (1R,5S)-2-oxabicyclo[3.3.0]oct-6-en-3-one 
• 65529-50-2 (3aR,4R,6R,6aR)-4-hydroxy-6-iodohexahydro-2H-cyclopenta[b]furan-2-one 
• 5307-99-3 (+/-)-7,7-dichlorobicyclo[3.2.0]hept-2-en-6-one 
• 13173-09-6 bicyclo[3.2.0]hept-2-en-6-one 
• 29783-26-4 cis-4-cyclopentene-1,3-diol 
• 37517-41-2 (+/-)-cis-4-(2'R*-tetrahydropyranyloxy)-2-cyclopentenol 
• 13756-54-2 rac-bicyclo[3.2.0]hept-2-en-6-one 
• 1373502-35-2 (1S,5R,6S)-bicyclo[3.2.0]hept-2-en-6-yl 2-chloroacetate 

Downstream Products

• 90156-85-7 7α-formyloxy-8β-formyloxymethylene-cis-2-oxabicyclo<3.3.0>octan-3-one 
• 143741-40-6 ((3R,3aR,6aR)-2-Oxo-3,3a,6,6a-tetrahydro-2H-cyclopenta[b]furan-3-yl)-acetic acid methyl ester 
• 80040-30-8 ((1S,5R)-5-Hydroxy-cyclopent-2-enyl)-acetic acid 
• 54483-30-6 (1aS,2aR,5aR,5bR)-hexahydro-4H-oxireno[3,4]cyclopenta[1,2-b]furan-4-one 
• 65529-50-2 (3aR,4R,6R,6aR)-4-hydroxy-6-iodohexahydro-2H-cyclopenta[b]furan-2-one 
• 49862-47-7 ((1R,5S)-5-Hydroxy-cyclopent-2-enyl)-acetic acid 
• 59829-44-6 (1S,2S,4R,6S)-8-oxo-3,7-dioxatricyclo<4.3.0.0^2,4>nonane 
• 80735-00-8 (1S,2R,4S,6S)-8-oxo-3,7-dioxatricyclo<4.3.0.0^2,4>nonane 
• 87727-90-0 (-)-8-bromo-2-oxabicyclo<3.3.0>oct-6-en-3-one 
• 750641-60-2 (3aS,4S,6aS)-4-Bromo-3,3a,4,6a-tetrahydro-cyclopenta[b]furan-2-one 
• 34638-26-1 2-Oxabicyclo[3,3,0]oct-6-en-3-ol 
• 54483-54-4 (+)-2β-hydroxyethyl-3-cyclopenten-1β-ol 
• 117957-61-6 (3aSR,5R,6aR)-(+)-5-Hydroxy-hexahydro-2H-cyclopentafuran-2-on 
• 104319-65-5 (3aS,4R,6R,6aR)-4-hydroxy-6-iodohexahydro-2H-cyclopenta[b]furan-2-one 

Relevant articles and documents

Total synthesis of prostaglandins E2 and F2-alpha (dl) via a tricarbocyclic intermediate.

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A unified strategy to prostaglandins: chemoenzymatic total synthesis of cloprostenol, bimatoprost, PGF2α, fluprostenol, and travoprost guided by biocatalytic retrosynthesis

Development of efficient and stereoselective synthesis of prostaglandins (PGs) is of utmost importance, owing to their valuable medicinal applications and unique chemical structures. We report here a unified synthesis of PGs cloprostenol, bimatoprost, PGF2α, fluprostenol, and travoprost from the readily available dichloro-containing bicyclic ketone6aguided by biocatalytic retrosynthesis, in 11-12 steps with 3.8-8.4% overall yields. An unprecedented Baeyer-Villiger monooxygenase (BVMO)-catalyzed stereoselective oxidation of6a(99% ee), and a ketoreductase (KRED)-catalyzed diastereoselective reduction of enones12(87?:?13 to 99?:?1 dr) were utilized in combination for the first time to set the critical stereochemical configurations under mild conditions. Another key transformation was the copper(ii)-catalyzed regioselectivep-phenylbenzoylation of the secondary alcohol of diol10(9.3?:?1 rr). This study not only provides an alternative route to the highly stereoselective synthesis of PGs, but also showcases the usefulness and great potential of biocatalysis in construction of complex molecules.

Divorce in the two-component BVMO family: The single oxygenase for enantioselective chemo-enzymatic Baeyer-Villiger oxidations

Two-component flavoprotein monooxygenases consist of a reductase and an oxygenase enzyme. The proof of functionality of the latter without its counterpart as well as the mechanism of flavin transfer remains unanswered beyond doubt. To tackle this question, we utilized a reductase-free reaction system applying purified 2,5-diketocamphane-monooxygenase I (2,5-DKCMO), a FMN-dependent type II Baeyer-Villiger monooxygenase, and synthetic nicotinamide analogues (NCBs) as dihydropyridine derivatives for FMN reduction. This system demonstrated the stand-alone quality of the oxygenase, as well as the mechanism of FMNH2transport by free diffusion. The efficiency of this reductase-free system strongly relies on the balance of FMN reduction and enzymatic (re)oxidation, since reduced FMN in solution causes undesired side reactions, such as hydrogen peroxide formation. Design of experiments allowed us to (i) investigate the effect of various reaction parameters, underlining the importance to balance the FMN/FMNH2cycle, (ii) optimize the reaction system for the enzymatic Baeyer-Villiger oxidation of rac-bicyclo[3.2.0]hept-2-en-6-one,rac-camphor, andrac-norcamphor. Finally, this study not only demonstrates the reductase-independence of 2,5-DKCMO, but also revisits the terminology of two-component flavoprotein monooxygenases for this specific case.

Genome mining reveals new bacterial type I Baeyer-Villiger monooxygenases with (bio)synthetic potential

Baeyer-Villiger monooxygenases (BVMOs) are oxidorreductases that catalyze the oxidation of ketones in a very selective manner. By genome mining we detected seven putative type I BVMOs in Bradyrhizobium diazoefficiens USDA 110. As we established the phylogenetic relationships among them and with other type I BVMOs, we found out that they belong to different clades of the phylogenetic tree. Thus, we decided to clone and heterologously express five of them. Three of them, each one from a divergent phylogenetic group, were obtained as soluble proteins, allowing us to proceed with their biocatalytic assessment and enzymatic characterization. As to substrate scope and selectivity, we observed a complementary behavior among the three BVMOs. BVMO2 was the more versatile biocatalyst in whole-cell systems while BVMO4 and BVMO5 showed a narrow substrate profile with preference for linear ketones and particular regioselectivity for (±)-cis-bicyclo[3.2.0]hept-2-en-6-one.