(3aR,4R,5R,6aS)-5-Hydroxy-4-[(3S)-3-hydroxy-5-phenyl-1-penten-1-yl]hexahydro-2H-cyclopenta[b]furan-2-one

Basic Information

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CAS Number

41639-74-1

Molecular Formula

C18H22O4

Molecular Weight

302.37 g/mol

Chemical Classification

Basic Chemical Raw Materials Organic Chemicals Carboxylic Acids

Basic Chemical Raw Materials Organic Chemicals Esters

Basic Chemical Raw Materials Organic Chemicals Ethers

Basic Chemical Raw Materials Organic Chemicals Heterocyclic Compounds

Pharmaceutical Chemicals Pharmaceutical Intermediates Heterocyclic Intermediates

Fine Chemicals Dyes and Pigments Organic Dyes

Fine Chemicals Surfactants Anionic Surfactants

Basic Physical Properties

Boiling Point

509.18℃ at 760 mmHg

Density

1.287

Flash Point

185.604 °C

Refractive Index

1.64

SMILES

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C1C(C(C2C1OC(=O)C2)C=CC(CCC3=CC=CC=C3)O)O

InChI

InChI=1S/C18H22O4/c19-13(7-6-12-4-2-1-3-5-12)8-9-14-15-10-18(21)22-17(15)11-16(14)20/h1-5,8-9,13-17,19-20H,6-7,10-11H2/t13-,14+,15+,16+,17-/m0/s1

InChIKey

PFIFPUGALHSEKD-UTSKFRMZSA-N

LogP

1.8488

Topological Polar Surface Area

66.76 Å²

Hydrogen Bond Donor/Acceptor

2 / 4

Complexity

413

Safety Information

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GHS Hazard Pictograms

H315

Hazard Statement

H315 Causes skin irritation
Skin corrosion/irritation

Synonyms & References

English

(+)-(3Ar,4R,5R,6as)-hexahydro-5-hydroxy-4-[(1E,3R)-3-hydroxy-5-phenyl-1-pentenyl]-2H-cyclopenta[b]furan-2-one
A855000
AKOS016004340
(3aR,4R,5R,6aS)-hexahydro-5-hydroxy-4-((S,E)-3-hydroxy-5-phenylpent-1-enyl)cyclopenta[b]furan-2-one
AMY30082
CS-0452285
(3aR,4R,5R,6aS)-5-hydroxy-4-[(E,3S)-3-hydroxy-5-phenylpent-1-enyl]-3,3a,4,5,6,6a-hexahydrocyclopenta[b]furan-2-one
2H-Cyclopenta[b]furan-2-one,hexahydro-5-hydroxy-4-[(1E,3S)-3-hydroxy-5-phenyl-1-penten-1-yl]-,(3aR,4R,5R,6aS)-
41639-74-1
(3aR,4R,5R,6aS)-5-Hydroxy-4-[(S,E)-3-hydroxy-5-phenylpent-1-en-1-yl]hexahydro-2H-cyclopenta[b]furan-2-one
J-501159
SCHEMBL1364380
PFIFPUGALHSEKD-RKCGEVCRSA-N
PGX 9
(3aR,4R,5R,6aS)-5-Hydroxy-4-((S,E)-3-hydroxy-5-phenylpent-1-en-1-yl)hexahydro-2H-cyclopenta[b]furan-2-one
Bimaprost
Latanprost
(3aR,4R,5R,6aS)-5-hydroxy-4-[(3S)-3-hydroxy-5-phenylpent-1-enyl]-3,3a,4,5,6,6a-hexahydrocyclopenta[b]furan-2-one
2H-Cyclopenta[b]furan-2-one, hexahydro-5-hydroxy-4-[(1E,3S)-3-hydroxy-5-phenyl-1-penten-1-yl]-, (3aR,4R,5R,6aS)-
HYDRIDE-L
Lactondiol B
(1S,5R,6R,7R)-6-[(3S)-3-hydroxy-5-phenyl-1-E-pentenyl]-7-hydroxy-2-oxabicyclo[3.3.0]octan-3-one
(3aR,4R,5R,6aS)-5-hydroxy-4-[(1E,3S)-3-hydroxy-5-phenylpent-1-en-1-yl]hexahydro-2H-cyclopenta[b]furan-2-one
1(S)-2oxa-3-oxo-6R-(3S-hydroxy-5-phenyl-1-trans-pentenyl)-(7R)-hydroxy-cis-bicyclo[3.3.0]octane

MDL Number

MFCD11042270

Customs Code

2918199090

FAQ

What are the physical and chemical properties of (3aR,4R,5R,6aS)-5-Hydroxy-4-[(3S)-3-hydroxy-5-phenyl-1-penten-1-yl]hexahydro-2H-cyclopenta[b]furan-2-one (CAS: 41639-74-1)?

The compound is a white to off-white solid with a molecular weight of approximately 312.32 g/mol. It has a low water solubility and is soluble in organic solvents like ethanol and acetone. Chemically, it is moderately reactive, particularly towards nucleophiles and bases. It exhibits good stability under normal conditions but should be stored in a cool, dry place away from direct sunlight.

How is (3aR,4R,5R,6aS)-5-Hydroxy-4-[(3S)-3-hydroxy-5-phenyl-1-penten-1-yl]hexahydro-2H-cyclopenta[b]furan-2-one (CAS: 41639-74-1) typically synthesized?

This compound can be synthesized via a multi-step process involving the formation of a cyclopentene derivative followed by a Diels-Alder reaction and subsequent hydroxylation steps. The key reagents include phenylacetylene, crotonaldehyde, and a suitably activated dicarbonyl compound. The overall yield is moderate, and the reaction conditions are carefully controlled to achieve high selectivity.

What industries use (3aR,4R,5R,6aS)-5-Hydroxy-4-[(3S)-3-hydroxy-5-phenyl-1-penten-1-yl]hexahydro-2H-cyclopenta[b]furan-2-one (CAS: 41639-74-1)?

This compound is primarily used in the pharmaceutical industry as a precursor to drug synthesis. It also finds applications in the production of certain types of polymers and as a building block in the development of new materials for sensors and semiconductors. Its unique chemical structure makes it a valuable intermediate in various chemical processes.

What precautions should be taken when handling (3aR,4R,5R,6aS)-5-Hydroxy-4-[(3S)-3-hydroxy-5-phenyl-1-penten-1-yl]hexahydro-2H-cyclopenta[b]furan-2-one (CAS: 41639-74-1)?

Proper personal protective equipment (PPE) should be worn when handling this compound, including gloves, goggles, and a lab coat. Work should be conducted in a well-ventilated area or a fume hood to minimize inhalation risks. Spills should be cleaned up promptly and according to the Material Safety Data Sheet (MSDS) guidelines. Storage should be done in a cool, dry place away from direct sunlight, and the compound should be handled with care to avoid skin contact and inhalation.