40834-86-4

Basic information

• Product Name: 5-(benzoyloxy)-3,3a,4,5,6,6a-hexahydro-4-(3-oxo-1-octenyl)-2H-cyclopenta(b)furan-2-one
• Synonyms: 5-(benzoyloxy)-3,3a,4,5,6,6a-hexahydro-4-(3-oxo-1-octenyl)-2H-cyclopenta(b)furan-2-one;DN-BK;(3AR,4R,5R,6aS)-2-Oxo-4-((E)-3-oxooct-1-en-1-yl)-hexahydro-2H-cyclopenta[b]furan-5-yl benzoate;2H-Cyclopenta[b]furan-2-one, 5-(benzoyloxy)hexahydro-4-[(1E)-3-oxo-1-octen-1-yl]-, (3aR,4R,5R,6aS)-
• CAS NO: 40834-86-4
• Molecular Formula: C₂₂H₂₆O₅
• Molecular Weight: 370.44
• Mol File: 40834-86-4.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 546.8 °C at 760 mmHg
• Flash Point: 238.3 °C
• Appearance: /
• Density: 1.18 g/cm³
• Refractive Index: 1.554
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 5-(benzoyloxy)-3,3a,4,5,6,6a-hexahydro-4-(3-oxo-1-octenyl)-2H-cyclopenta(b)furan-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 5-(benzoyloxy)-3,3a,4,5,6,6a-hexahydro-4-(3-oxo-1-octenyl)-2H-cyclopenta(b)furan-2-one(40834-86-4)
• EPA Substance Registry System: 5-(benzoyloxy)-3,3a,4,5,6,6a-hexahydro-4-(3-oxo-1-octenyl)-2H-cyclopenta(b)furan-2-one(40834-86-4)

Safety Data

• Hazardous Substances Data: 40834-86-4(Hazardous Substances Data)

Usage

Description

5-(benzoyloxy)-3,3a,4,5,6,6a-hexahydro-4-(3-oxo-1-octenyl)-2H-cyclopenta(b)furan-2-one, also known as 3-Oxo-1-octenyl hydrobenzoate, is a synthetic organic compound characterized by its complex molecular structure. It is a derivative of furan, featuring a benzoyloxy group and a 3-oxo-1-octenyl side chain. This versatile chemical is known for its unique chemical properties and structure, which contribute to its wide range of potential applications across different industries.

Uses

Used in Pharmaceutical Synthesis:
5-(benzoyloxy)-3,3a,4,5,6,6a-hexahydro-4-(3-oxo-1-octenyl)-2H-cyclopenta(b)furan-2-one is used as an intermediate in the synthesis of pharmaceuticals for its ability to contribute to the development of new drug molecules. Its unique structure allows for the creation of compounds with specific therapeutic properties, making it a valuable component in medicinal chemistry.
Used in Flavoring Agents for the Food Industry:
In the food industry, 5-(benzoyloxy)-3,3a,4,5,6,6a-hexahydro-4-(3-oxo-1-octenyl)-2H-cyclopenta(b)furan-2-one is utilized as a flavoring agent. Its distinctive chemical composition endows it with the capacity to enhance the taste and aroma of various food products, contributing to a more appealing sensory experience for consumers.
Used in Chemical Research:
5-(benzoyloxy)-3,3a,4,5,6,6a-hexahydro-4-(3-oxo-1-octenyl)-2H-cyclopenta(b)furan-2-one is also employed in chemical research as a model compound for studying the properties and reactions of furan derivatives. Its complex structure provides a platform for understanding the behavior of similar compounds and for developing new synthetic pathways and methodologies in organic chemistry.
Used in Fragrance Industry:
In the fragrance industry, 5-(benzoyloxy)-3,3a,4,5,6,6a-hexahydro-4-(3-oxo-1-octenyl)-2H-cyclopenta(b)furan-2-one is used as a component in the creation of various scents. Its unique chemical makeup can contribute to the development of novel fragrances, offering new olfactory experiences in perfumes, cosmetics, and other scented products.
Used in Material Science:
5-(benzoyloxy)-3,3a,4,5,6,6a-hexahydro-4-(3-oxo-1-octenyl)-2H-cyclopenta(b)furan-2-one may also find applications in material science, where its chemical properties could be leveraged to develop new materials with specific characteristics. This could include uses in coatings, adhesives, or other industrial materials where unique properties are desired.

InChI:InChI=1/C22H26O5/c1-2-3-5-10-16(23)11-12-17-18-13-21(24)26-20(18)14-19(17)27-22(25)15-8-6-4-7-9-15/h4,6-9,11-12,17-20H,2-3,5,10,13-14H2,1H3

Upstream product

• 33803-58-6 1-(triphenylphosphoranylidene)-2-heptanone 
• 39746-01-5 (1S,5R,6R,7R)-6-formyl-7-benzoyloxy-2-oxabicyclo[3.3.0]octan-3-one 
• 36969-89-8 dimethyl 2-oxoheptylphosphonate 
• 61728-15-2 2-oxohexylphosphonic acid dimethyl ester 

Downstream Products

• 1056034-74-2 (3aR,4R,5R,6aS)-4-((E)-3-hydroxy-3-methyloct-1-enyl)-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl benzoate 
• 1151944-14-7 (3aR,4R,5R,6aS)-4-((E)-3,3-difluorooct-1-enyl)-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl benzoate 
• 40834-88-6 [3aR,4R(1E,3S),5R,6aS]-5-benzoyloxy-4-(3-hydroxyocten-1-yl)-hexahydro-2H-cyclopenta[b]furan-2-one 
• 587869-87-2 (5Z)-7-{(1RS,2SR,5RS)-2-[(1E,3SR)-3-(tert-butyldimethylsilanyloxy)oct-1-enyl]-5-(2-nitrophenylselanyl)cyclopent-3-enyl}hept-5-enoic acid methyl ester 
• 587869-81-6 (3aR,4R,5R,6aS)-benzoic acid 4-[(1E,3S)-3-(tert-butyl-dimethylsilanyloxy)-oct-1-enyl]-2-oxo-hexahydro-cyclopenta[b]furan-5-yl ester 
• 60203-57-8 prostaglandin J₂ 
• 733037-18-8 [3aR,4R(3S),5R,6aS]-5-benzoyloxy-4-(3-fluorooctyl)-hexahydro-2H-cyclopenta[b]furan-2-one 
• 69224-05-1 [3aR,4R(3R),5R,6aS]-5-benzoyloxy-4-(3-hydroxyoctyl)-hexahydro-2H-cyclopenta[b]furan-2-one 
• 851542-03-5 Benzoic acid (3aR,4R,5R,6aS)-4-[(E)-(R)-3-(tert-butyl-dimethyl-silanyloxy)-oct-1-enyl]-2-oxo-hexahydro-cyclopenta[b]furan-5-yl ester 
• 38873-82-4 (15R)-PGE2 
• 51705-58-9 [3aR,4R(1E,3R),5R,6aS]-5-benzoyloxy-4-(3-hydroxyocten-1-yl)-hexahydro-2H-cyclopenta[b]furan-2-one 
• 1010074-85-7 (3aR,4R,5R,6aS)-benzoic acid 4-[(1E)-3-hydroxy-oct-1-enyl]-2-oxo-hexahydro-cyclopenta[b]furan-5-yl ester 

Relevant articles and documents

15-ketone preparation method

The present invention relates to a drug intermediate 15-ketone preparation method in chemical field. The preparation method comprises the following steps: (1) (-)-Corey lactone benzoate, an oxidizing agent and a catalyst are added into a first organic solvent for oxidation to obtain a reaction solution A; (2) after a dilute acid is dropwise added into the reaction solution A obtained in the step (1), the solution is stirred and filtered, the filtrate is extracted directly with the first organic solvent, an organic phase is washed with water, dehydrated with a desiccant and filtered to obtain a (-)-Corey lactone benzoate aldehyde solution; (3) Wittig reagent is added into the (-)-Corey lactone benzoate aldehyde solution obtained in the step (2) for Wittig reaction to obtain a reaction solution B, the reaction solution B is concentrated, a second organic solvent is added, and after cooling and crystallization, a crystallization liquid is obtained; and (4) the crystallization liquid obtained in the step (3) is filtered, the filter cake is washed with a third organic solvent, the filter cake is dissolved by the first organic solvent for impurity removal, and after filteration and concentration, an oil matter is obtained. The drug intermediate 15-ketone preparation method has the advantages of good product quality and the like.

Enantio- and stereospecific syntheses of 15(R)-Me-PGD2, a potent and selective DP2-receptor agonist

(Chemical Equation Presented) The first total synthesis of 15(R)-Me-PGD2 3 is reported. The synthesis is based on the enantioselective and stereospecific syntheses of synthon 17 and its attachment to the five-membered ring by a olefin cross metathesis reaction. This approach permits the introduction of a side chain with a predetermined stereogenic center into the prostanoid ring, resulting in the synthesis of 15R-methyl prostaglandin D2 and allows rapid access to other prostanoids.

Synthesis of 15R-PGD2: A potential DP2 receptor agonist

The first total synthesis of 15R-PGD2 3 was accomplished. The approach used in this report is also an efficient method to produce 15R-PGE 2. 15R-PGD2, a potential DP2 receptor agonist, could be an important novel tool for defining the role of this receptor in inflammatory diseases.