34638-25-0

Basic information

• Product Name: 3,3A,6,6A-TETRAHYDROCYCLOPENTA[B]FURAN-2-ONE
• Synonyms: 3,3A,6,6A-TETRAHYDROCYCLOPENTA[B]FURAN-2-ONE
• CAS NO: 34638-25-0
• Molecular Formula: C₇H₈O₂
• Molecular Weight: 124.14
• Mol File: 34638-25-0.mol

Chemical Properties

• Boiling Point: 263.139°C at 760 mmHg
• Flash Point: 104.019°C
• Appearance: /
• Density: 1.196g/cm³
• Vapor Pressure: 0.01mmHg at 25°C
• Refractive Index: 1.522
• CAS DataBase Reference: 3,3A,6,6A-TETRAHYDROCYCLOPENTA[B]FURAN-2-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 3,3A,6,6A-TETRAHYDROCYCLOPENTA[B]FURAN-2-ONE(34638-25-0)
• EPA Substance Registry System: 3,3A,6,6A-TETRAHYDROCYCLOPENTA[B]FURAN-2-ONE(34638-25-0)

Safety Data

• Hazardous Substances Data: 34638-25-0(Hazardous Substances Data)

Usage

Uses

Used in Polymer and Resin Production:
3,3A,6,6A-TETRAHYDROCYCLOPENTA[B]FURAN-2-ONE is used as a key component in the production of polymers and resins for its ability to enhance the properties of these materials, such as strength, durability, and resistance to various environmental factors.
Used in Adhesive Manufacturing:
In the adhesive industry, 3,3A,6,6A-TETRAHYDROCYCLOPENTA[B]FURAN-2-ONE is used as a solvent or a component in the formulation of adhesives, contributing to improved bonding strength and flexibility.
Used in Coating, Ink, and Paint Production:
3,3A,6,6A-TETRAHYDROCYCLOPENTA[B]FURAN-2-ONE is used as a solvent in the production of coatings, inks, and paints, providing a smooth application and enhancing the final product's performance characteristics.
Used in the Food Industry:
3,3A,6,6A-TETRAHYDROCYCLOPENTA[B]FURAN-2-ONE is used as a flavoring agent in the food industry, adding unique taste profiles to various food products while maintaining the quality and safety standards.
Used in Pharmaceutical Manufacturing:
In the pharmaceutical industry, 3,3A,6,6A-TETRAHYDROCYCLOPENTA[B]FURAN-2-ONE is used in the manufacturing process of various drugs, serving as a starting material for the synthesis of other organic compounds that possess therapeutic properties.
Used in Organic Synthesis:
3,3A,6,6A-TETRAHYDROCYCLOPENTA[B]FURAN-2-ONE is used as a starting material in organic synthesis, enabling the creation of a wide range of chemical compounds with diverse applications across various industries.

InChI:InChI=1/C7H8O2/c8-7-4-5-2-1-3-6(5)9-7/h1-2,5-6H,3-4H2/t5-,6-/m1/s1

Upstream product

• 925211-06-9 bicyclo(3.2.0)hept-2-en-6-one 
• 124938-45-0 C₇H₉ClHgO₂ 
• 3234-54-6 vinyl crotonate 
• 606490-73-7 2-(5-Hydroxy-cyclopent-2-enyl)-N,N-dimethyl-acetamide 
• 3377-92-2 vinyl pivalate 
• 769-78-8 vinyl benzoate 
• 60176-77-4 (1S,4R)-4-hydroxy-2-cyclopentenyl acetate 
• 13173-09-6 bicyclo[3.2.0]hept-2-en-6-one 
• 542-92-7 cyclopenta-1,3-diene 
• 71155-04-9 (1S,5R)-(-)-bicyclo[3.2.0]hept-2-en-6-one 
• 71155-05-0 (1R,5S)-bicyclo[3.2.0]hept-2-en-6-one 
• 124938-38-1 (3aS,6aR)-2-ethoxy-3,3a,6,6a-tetrahydro-2H-cyclopentafuran 
• 26054-46-6 cis-(±)-2-oxabicyclo[3.3.0]oct-6-en-3-one 
• 13259-28-4 (rac)-6-endo-bicyclo<3.2.0>hept-2-en-6-ol 

Downstream Products

• 88420-92-2 2-[1-Phenylsulfanyl-meth-(E)-ylidene]-3,3a,6,6a-tetrahydro-2H-cyclopenta[b]furan 
• 434313-66-3 3-hydroxymethylene-3,3a,6,6a-tetrahydrocyclopentafuran-2-one 
• 78646-91-0 4-(2-oxo-3,3a,6,6a-tetrahydro-2H-cyclopentafuran-3-ylidenemethoxy)-2-phenylbut-2-en-4-olide 
• 78646-92-1 4-(2-oxo-3,3a,6,6a-tetrahydro-2H-cyclopentafuran-3-ylidenemethoxy)-2,3-diphenylbut-2-en-4-olide 
• 32233-40-2 (3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one 
• 101208-17-7 (3aR,4S,5R,6aS)-5-(benzoyloxy)hexahydro-4-[(triphenylmethoxy)methyl]-2H-cyclopenta[b]furan-2-one 
• 26054-46-6 (-)-(1S,5R)-2-oxabicyclo[3.3.0]oct-6-en-3-one 
• 76704-05-7 <3aS(3aα,4α,5β,6aα)>-(+)-5-hydroxy-4-hydroxymethyl-hexahydro-2H-cyclopentafuran-2-one 
• 143741-39-3 (3R,3aR,6aR)-3-Butyl-3,3a,6,6a-tetrahydro-cyclopenta[b]furan-2-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 
• 104220-79-3 (3aR,4R,5R,6aR)-5-Iodo-4-(1-methoxy-1-methyl-ethoxy)-hexahydro-cyclopenta[b]furan-2-one 

Relevant articles and documents

Towards practical baeyer-villiger-monooxygenases: Design of cyclohexanone monooxygenase mutants with enhanced oxidative stability

Baeyer-Villiger monooxygenases (BVMOs) catalyze the conversion of ketones and cyclic ketones into esters and lactones, respectively. Cyclohexanone monooxygenase (CHMO) from Acinetobacter sp. NCIMB 9871 is known to show an impressive substrate scope as wel

Kinetic resolution of racemic 2-substituted 3-cyclopenten-1-ols by lipase-catalyzed transesterifications: A rational strategy to improve enantioselectivity

The effect of the acyl group of acylating agents on the enantioselectivity in the Pseudomonas cepacia lipase-catalyzed acylations of racemic alcohols has been studied. 2-[(N,N-Dimethylcarbamoyl)-methyl]-3-cyclopenten-1-ol (1) and 2-[2-(tert-butyldimethylsilyloxy)ethyl]-3-cyclopenten-1-ol (4) were resolved with a variety of enantioselectivities. In the case of alcohol 1, the enantiomeric ratio (the E value) was increased by changing the acylating agent from vinyl acetate (E = 30) to vinyl butyrate (E = 156) and dropped substantially with longer acyl donors. With vinyl chloroacetate, the reaction rate was fast and the enantioselectivity was high (E = 89), whereas the resolution with vinyl trifluoroacetate resulted in a very poor enantioselectivity (E = 4). The bulky acylating agent, vinyl pivalate, gave a moderate enantioselectivity (E = 15). In the case of alcohol 4, the enantioselectivities were excellent (E > 142) except vinyl pivalate (E = 12). It is indicated that the acyl group transiently attached at the active site of the lipase acts as a stereochemical controller. The solvent effect is also described briefly. A clear correlation was observed between the E values and the log P values of the organic solvents; the smaller the log P value of the solvent, the higher the E value.

Lewis acidic Sn(IV) centers - Grafted onto MCM-41 - As catalytic sites for the Baeyer-Villiger oxidation with hydrogen peroxide

Sn(IV) centers have been grafted onto mesoporous MCM-41 using different RnSnX4-n precursors. For a successful incorporation of the tin, one or two alkyl substituents are beneficial. The calcined samples are able to activate a carbonyl bond for nucleophilic attack as it could be shown by in situ IR spectroscopy. The resulting catalysts are active for the Baeyer-Villiger oxidation of various substrates with hydrogen peroxide and achieve good conversions and selectivities. Chemoselective oxidations toward unsaturated lactones are obtained from unsaturated ketones. The Lewis acidity and the catalytic performance of the grafted Sn(IV) centers are very similar to the directly synthesized Sn-MCM-41, but lower than those of the Sn-Beta zeolite.

Aerobic Baeyer–Villiger Oxidation Catalyzed by a Flavin-Containing Enzyme Mimic in Water

Direct incorporation of molecular oxygen into small organic molecules has attracted much attention for the development of new environmentally friendly oxidation processes. In line with this approach, bioinspired systems mimicking enzyme activities are of particular interest since they may perform catalysis in aqueous media. Demonstrated herein is the incorporation of a natural flavin cofactor (FMN) into the specific microenvironment of a water-soluble polymer which allows the efficient reduction of the FMN by NADH in aqueous solution. Once reduced, this artificial flavoenzyme can then activate molecular dioxygen under aerobic conditions and result in the Baeyer–Villiger reaction at room temperature in water.

Preparation method corey lactone diol

The invention provides a preparation method of corey lactone diol, which has the advantages of easily available raw materials. The method has the characteristics of mild reaction conditions, simple operation, simple synthetic route, high chemical yield, low cost and the like, and is suitable for industrial production.

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.

Genome Mining of Oxidation Modules in trans-Acyltransferase Polyketide Synthases Reveals a Culturable Source for Lobatamides

Bacterial trans-acyltransferase polyketide synthases (trans-AT PKSs) are multimodular megaenzymes that biosynthesize many bioactive natural products. They contain a remarkable range of domains and module types that introduce different substituents into growing polyketide chains. As one such modification, we recently reported Baeyer–Villiger-type oxygen insertion into nascent polyketide backbones, thereby generating malonyl thioester intermediates. In this work, genome mining focusing on architecturally diverse oxidation modules in trans-AT PKSs led us to the culturable plant symbiont Gynuella sunshinyii, which harbors two distinct modules in one orphan PKS. The PKS product was revealed to be lobatamide A, a potent cytotoxin previously only known from a marine tunicate. Biochemical studies show that one module generates glycolyl thioester intermediates, while the other is proposed to be involved in oxime formation. The data suggest varied roles of oxygenation modules in the biosynthesis of polyketide scaffolds and support the importance of trans-AT PKSs in the specialized metabolism of symbiotic bacteria.

A synthesis method of the branch stands lactone diol

The invention discloses a method for the branch stands lactone diol (( -) - Corey lactone diol) synthetic method, synthesis method of the invention is to dicyclopentadiene as raw materials, by depolymerization, cyclization, oxidation, dechlorination, open-loop, split, Prins reaction, hydrolysis reaction to obtain the target product. The invention discloses a synthetic route, raw material economic, high separation efficiency, and is suitable for industrial production.

Flavinium and Alkali-Metal Assembly on Sulfated Chitin: A Heterogeneous Supramolecular Catalyst for H2O2-Mediated Oxidation

Heterogeneous multiple-catalyst assemblies were developed in which the flavinium cation and Na or Li cations were easily immobilized on a chitin-derived anionic polymeric scaffold through noncovalent ionic interactions. The supramolecular flavinium catalysts were successfully employed in the environmentally friendly heterogeneous Baeyer–Villiger oxidation and sulfoxidation by H2O2. Owing to the cooperative catalytic effect of flavinium, alkali metal, and sulfated chitin, the supramolecular flavinium assembly showed higher catalytic activity for the Baeyer–Villiger oxidation of cyclic ketones than the corresponding homogeneous flavinium catalyst. Because the ionic assembly was stable under the reaction conditions, the catalyst could be readily recovered by simple filtration and reused.