39182-59-7

Basic information

• Product Name: Corey PG-lactone diol
• Synonyms: Corey PG-lactone diol;(3aR,4R,5R,6aS)-5-hydroxy-4-[(E,3R)-3-hydroxyoct-1-enyl]-3,3a,4,5,6,6a-hexahydrocyclopenta[b]furan-2-one
• CAS NO: 39182-59-7
• Molecular Formula: C₁₅H₂₄O₄
• Molecular Weight: 268.351
• Mol File: 39182-59-7.mol
• Article Data: 12

Chemical Properties

• Boiling Point: 430.072 °C at 760 mmHg
• Flash Point: 156.399 °C
• Appearance: /
• Density: 1.199 g/cm³
• Vapor Pressure: 3.35E-09mmHg at 25°C
• Refractive Index: 1.576
• PKA: 14.30±0.40(Predicted)
• CAS DataBase Reference: Corey PG-lactone diol(CAS DataBase Reference)
• NIST Chemistry Reference: Corey PG-lactone diol(39182-59-7)
• EPA Substance Registry System: Corey PG-lactone diol(39182-59-7)

Safety Data

• Hazardous Substances Data: 39182-59-7(Hazardous Substances Data)

Usage

General Description

Corey PG-lactone diol is a chemical compound that is commonly used as a building block in the synthesis of various polymers and materials. It is a type of polyester diol that contains propylene glycol segments and lactone rings. Corey PG-lactone diol provides excellent flexibility, low temperature flexibility, and chemical resistance, making it suitable for use in various applications such as adhesives, sealants, coatings, and elastomers. Corey PG-lactone diol can also be used as a reactive diluent in the formulation of polyurethane dispersions and other polymers, providing improved flexibility and durability to the final products.

InChI:InChI=1/C15H24O4/c1-2-3-4-5-10(16)6-7-11-12-8-15(18)19-14(12)9-13(11)17/h6-7,10-14,16-17H,2-5,8-9H2,1H3/b7-6+

Upstream product

• 60623-67-8 (-)-7α-Hydroxy-3-oxo-6β-<3-oxo-1(E)-octenyl>-cis-2-oxabicyclo<3.3.0>octane 
• 51705-58-9 [3aR,4R(1E,3R),5R,6aS]-5-benzoyloxy-4-(3-hydroxyocten-1-yl)-hexahydro-2H-cyclopenta[b]furan-2-one 
• 162897-38-3 (Z)-(1S,5R,6R,7R,1'R)-7-Benzoyloxy-6-(1'-hydroxyoct-2'-enyl)-2-oxabicyclo[3.3.0]octan-3-one 
• 162992-65-6 (Z)-(1S,5R,6R,7R,1'S)-7-Benzoyloxy-6-(1'-hydroxyoct-2'-enyl)-2-oxabicyclo[3.3.0]octan-3-one 
• 215033-22-0 (Z)-(1S,5R,6R,7R,1'R)-7-Benzoyloxy-6-(1'-benzoyloxyoct-2'-enyl)-2-oxabicyclo[3.3.0]octan-3-one 
• 215033-23-1 (Z)-(1S,5R,6R,7R,1'S)-7-Benzoyloxy-6-(1'-N-phenylcarbamoyloxyoct-2'-enyl)-2-oxabicyclo[3.3.0]octan-3-one 
• 215033-24-2 Benzoic acid (3aR,4R,5R,6aS)-4-{(E)-(R)-3-[((Z)-2-methyl-but-2-enyl)-diphenyl-silanyl]-oct-1-enyl}-2-oxo-hexahydro-cyclopenta[b]furan-5-yl ester 
• 31753-00-1 [1,1'-bisphenyl]-4-carboxylic acid (3aR,4R,5R,6aS)-hexahydro-2-oxo-4-[(1E)-3-oxo-1-octen-1-yl]-2H-cyclopenta[b]furan-5-yl ester 
• 5307-99-3 (+/-)-7,7-dichlorobicyclo[3.2.0]hept-2-en-6-one 
• 26054-46-6 (-)-(1S,5R)-2-oxabicyclo[3.3.0]oct-6-en-3-one 
• 542-92-7 cyclopenta-1,3-diene 
• 32233-40-2 (3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one 
• 87422-39-7 (3aR,6aS)-3,3-dichloro-3,3a,6,6a-tetrahydro-2H-cyclopenta[b]furan-2-one 
• 62961-72-2 Corey aldehyde 

Downstream Products

• 73089-64-2 (3'R)-3α,5α-Dihydroxy-2β-(3'-hydroxy-trans-1'-octenyl)cyclopentane-1α-acetic acid γ-lactone 3,3'-dibenzoate 
• 113517-83-2 (3aR,4R,5R,6aR)-5-(tert-Butyl-diphenyl-silanyloxy)-4-[(E)-(S)-3-(tert-butyl-diphenyl-silanyloxy)-oct-1-enyl]-6a-phenylsulfanyl-hexahydro-cyclopenta[b]pyrrol-2-one 
• 113517-91-2 (3aR,4R,5R,6aS)-5-(tert-Butyl-diphenyl-silanyloxy)-4-[(E)-(S)-3-(tert-butyl-diphenyl-silanyloxy)-oct-1-enyl]-1-(2,4-dimethoxy-benzyl)-6a-prop-1-ynyl-hexahydro-cyclopenta[b]pyrrol-2-one 
• 113517-90-1 (3aR,4R,5R,6aS)-5-(tert-Butyl-diphenyl-silanyloxy)-4-[(E)-(S)-3-(tert-butyl-diphenyl-silanyloxy)-oct-1-enyl]-1-(2,4-dimethoxy-benzyl)-6a-trimethylsilanylethynyl-hexahydro-cyclopenta[b]pyrrol-2-one 

Relevant articles and documents

Access to a Key Building Block for the Prostaglandin Family via Stereocontrolled Organocatalytic Baeyer–Villiger Oxidation

A new protocol for the construction of a crucial bicyclic lactone of prostaglandins using a stereocontrolled organocatalytic Baeyer–Villiger (B-V) oxidation was developed. The key B-V oxidation of a racemic cyclobutanone derivative with aqueous hydrogen peroxide has enabled an early-stage construction of a bicyclic lactone skeleton in high enantiomeric excess (up to 95 %). The generated bicyclic lactone is fully primed with two desired stereocenters and enabled the synthesis of the entire family of prostaglandins according to Corey′s route. Furthermore, the reactivity and enantioselectivity of B-V oxidation of racemic bicyclic cyclobutanones were evaluated and 90–99 % ee was obtained, representing one of the most efficient routes to chiral lactones. This study further facilitates the synthesis of prostaglandins and chiral lactone-containing natural products to promote drug discovery.

PROSTANOIDS. XXXII. SYNTHESIS OF (+)-PROSTAGLANDIN F2α

Natural prostaglandin F2α was obtained from cyclopentadiene monoxide.The key stages of the synthesis included the following: Optical resolution of (+/-)-trans-2-carboxymethylcyclopent-3-en-1-ol with the transformation of its (-)-enantiomer into (-)-cis-2-oxabicyclooct-6-en-3-one and then into (-)-7α-triethylsilyloxy-6β-triethylsilyloxymethyl-cis-2-oxabicyclooctan-3-one; selective oxidation of the latter by the DMSO-(COCl)2 system; condensation of the intermediate (-)-7α-triethylsilyloxy-6β-formyl-cis-2-oxabicyclooctan-3-one with dimethyl 2-oxoheptylphosphonate under the conditions of phase-transfer catalysis with the production of (-)-7α-hydroxy-6β-(3-oxo-1E-octenyl)-cis-2-oxabicyclooctan-3-one; conversion of the latter into (+)-PGF2α by standard methods.

TOTAL SYNTHESIS AND PROPERTIES OF PROSTAGLANDINS. X. SYNTHESIS OF γ-KETO ESTERS AND THEIR REACTION WITH SOME ALUMINUM- AND BORON-CONTAINING REAGENTS

The cuprate synthesis of the monotetrahydrofuryl-γ-keto ester from 2-methoxycarbonyl-4-trimethylsilyloxy-2-cyclopenten-1-one and the active diastereomer (SS + RR) of 3-(2-tetrahydrofuryloxy)iodooctenol is described.The stereoselectivity of the reaction of the mono- and bistetrahydrofuryl-γ-keto esters with some aluminum- and boron-containing reagents was investigated, and the possibility of the production of the corresponding lactones with good yields was demonstrated.The reaction of the γ-keto esters and lactones with lithium selectride gave the corresponding γ-lactol, which together with the γ-lactones is the basic raw material for the synthesis of prostaglandins.