54713-44-9

Basic information

• Product Name: [1,1'-Biphenyl]-4-carboxylic acid, 4-[4-(3-chlorophenoxy)-3-hydroxy-1-butenyl]hexahydro-2-oxo-2H-cyclop enta[b]furan-5-yl ester, [3aR-[3aa,4a(1E,3R*),5b,6aa]]
• Synonyms: [1,1'-Biphenyl]-4-carboxylic acid, 4-[4-(3-chlorophenoxy)-3-hydroxy-1-butenyl]hexahydro-2-oxo-2H-cyclop enta[b]furan-5-yl ester, [3aR-[3aa,4a(1E,3R*),5b,6aa]];[3aR-[3aalpha,4alpha(1E,3R*),5beta,6aalpha]]-[1,1'-Biphenyl]-4-carboxylic acid 4-[4-(3-chlorophenoxy)-3-hydroxy-1-butenyl]hexahydro-2-oxo-2H-cyclopenta[b]furan-5-yl ester;[1,1'-Biphenyl]-4-carboxylic acid, 4-[4-(3-chlorophenoxy)-3-hydroxy-1-butenyl]hexahydro-2-oxo-2H-cyclopenta[b]furan-5-yl ester, [3aR-[3a,4(1E,3R*),5,6a]]-;[3aR-[3a,4(1E,3R*),5,6a]]-[1,1'-Biphenyl]-4-carboxylicacid,4-[4-(3-chlorophenoxy)-3-hydroxy-1-butenyl]hexahydro-2-oxo-2H-cyclopenta[b]furan-5-yl ester;[1,1'-Biphenyl]-4-carboxylicacid,4-[4-(3-chlorophenoxy)-3-hydroxy-1-butenyl]hexahydro-2-oxo-2H-cyclopenta[b]furan-5-ylester,[3aR-[3α,4α(1E,3R*),5,6aα]]- (9CI);[3aR-[3a,4(1E,3R*),5,6a]]- [1,1'-Biphenyl]-4-carboxylic acid,4-[4-(3-chlorophenoxy)-3-hydroxy-1-bute
• CAS NO: 54713-44-9
• Molecular Formula: C₃₀H₂₇ClO₆
• Molecular Weight: 518.98478
• Mol File: 54713-44-9.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 726.3±60.0 °C(Predicted)
• Appearance: /
• Density: 1.35±0.1 g/cm3(Predicted)
• PKA: 13.32±0.20(Predicted)
• CAS DataBase Reference: [1,1'-Biphenyl]-4-carboxylic acid, 4-[4-(3-chlorophenoxy)-3-hydroxy-1-butenyl]hexahydro-2-oxo-2H-cyclop enta[b]furan-5-yl ester, [3aR-[3aa,4a(1E,3R*),5b,6aa]](CAS DataBase Reference)
• NIST Chemistry Reference: [1,1'-Biphenyl]-4-carboxylic acid, 4-[4-(3-chlorophenoxy)-3-hydroxy-1-butenyl]hexahydro-2-oxo-2H-cyclop enta[b]furan-5-yl ester, [3aR-[3aa,4a(1E,3R*),5b,6aa]](54713-44-9)
• EPA Substance Registry System: [1,1'-Biphenyl]-4-carboxylic acid, 4-[4-(3-chlorophenoxy)-3-hydroxy-1-butenyl]hexahydro-2-oxo-2H-cyclop enta[b]furan-5-yl ester, [3aR-[3aa,4a(1E,3R*),5b,6aa]](54713-44-9)

Safety Data

• Hazardous Substances Data: 54713-44-9(Hazardous Substances Data)

Usage

Description

[1,1'-Biphenyl]-4-carboxylic acid, 4-[4-(3-chlorophenoxy)-3-hydroxy-1-butenyl]hexahydro-2-oxo-2H-cyclopent a[b]furan-5-yl ester, [3aR-[3aa,4a(1E,3R),5b,6aa]] is a complex organic compound with a unique molecular structure. It is characterized by its biphenyl core, a chlorophenoxy group, and a hexahydro-2-oxo-2H-cyclopent a[b]furan-5-yl ester moiety. [1,1'-Biphenyl]-4-carboxylic acid, 4-[4-(3-chlorophenoxy)-3-hydroxy-1-butenyl]hexahydro-2-oxo-2H-cyclop enta[b]furan-5-yl ester, [3aR-[3aa,4a(1E,3R),5b,6aa]] is known for its potential applications in the pharmaceutical industry, particularly in the synthesis of prostaglandin analogues.

Uses

Used in Pharmaceutical Industry:
[1,1'-Biphenyl]-4-carboxylic acid, 4-[4-(3-chlorophenoxy)-3-hydroxy-1-butenyl]hexahydro-2-oxo-2H-cyclopent a[b]furan-5-yl ester, [3aR-[3aa,4a(1E,3R),5b,6aa]] is used as a reagent in the synthesis of (+)-cloprostenol, a synthetic analogue of prostoglandin F2α. Prostaglandins are a group of naturally occurring lipid compounds that have various physiological effects, including the promotion of smooth muscle contraction, vasodilation, and regulation of inflammation. [1,1'-Biphenyl]-4-carboxylic acid, 4-[4-(3-chlorophenoxy)-3-hydroxy-1-butenyl]hexahydro-2-oxo-2H-cyclop enta[b]furan-5-yl ester, [3aR-[3aa,4a(1E,3R),5b,6aa]] plays a crucial role in the development of new drugs targeting these physiological processes.
Used in Synthesis of Prostaglandin Analogues:
In the field of medicinal chemistry, [1,1'-Biphenyl]-4-carboxylic acid, 4-[4-(3-chlorophenoxy)-3-hydroxy-1-butenyl]hexahydro-2-oxo-2H-cyclopent a[b]furan-5-yl ester, [3aR-[3aa,4a(1E,3R),5b,6aa]] is utilized as a key intermediate in the synthesis of prostaglandin F2α analogues. These analogues have potential applications in treating various medical conditions, such as cardiovascular diseases, inflammation, and reproductive disorders. [1,1'-Biphenyl]-4-carboxylic acid, 4-[4-(3-chlorophenoxy)-3-hydroxy-1-butenyl]hexahydro-2-oxo-2H-cyclop enta[b]furan-5-yl ester, [3aR-[3aa,4a(1E,3R),5b,6aa]]'s unique structure allows for the development of new drugs with improved efficacy and reduced side effects.

Upstream product

• 54324-79-7 (3aR,4R,5R,6aS)-4-((E)-4-(3-chlorophenoxy)-3-oxobut-1-enyl)-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl [1,1′-biphenyl]-4-carboxylate 
• 38754-71-1 (3aR,4R,5R,6aS)-4-formyl-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl biphenyl-4-carboxylate 
• 108-43-0 3-monochlorophenol 
• 52094-98-1 ethyl (3-chlorophenoxy)acetate 
• 31752-99-5 (-)-Corey lactone 5-(4-phenylbenzoate) 
• 87422-39-7 (3aR,6aS)-3,3-dichloro-3,3a,6,6a-tetrahydro-2H-cyclopenta[b]furan-2-one 
• 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 
• 130325-32-5 Formic acid (3aR,4S,5R,6aS)-4-formyloxymethyl-2-oxo-hexahydro-cyclopenta[b]furan-5-yl ester 
• 32233-40-2 (3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one 
• 14002-51-8 4-biphenyl-carboxylic acid chloride 
• 40665-94-9 dimethyl 3-(3-chlorophenoxy)-2-oxopropylphosphonate 

Downstream Products

• 54276-21-0 (+)-cloprostenol 
• 109323-20-8 (3aR,4R,5R,6aS)-4-((3R,E)-4-(3-chlorophenoxy)-3-(1-ethoxyethoxy)but-1-enyl)-5-(1-ethoxyethoxy)hexahydro-2Hcyclopenta[b]furan-2-ol 

Relevant articles and documents

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.

N-(Methanesulfonyl)-16-phenoxyprostaglandincarboxamides: Tissue-Selective, Uterine Stimulants

In an effort to develop tissue-selective prostaglandin analogues resistant to the metabolic inactivating pathways of the natural materials, hybrid compounds modified both at C-1 with a sulfonimide moiety and in the n-amylcarbinol side chain with substituted phenoxy groups were synthesized and evaluated in a variety of in vitro and in vivo models.Several of these analogues exhibited potent, tissue-selective, uterine stimulant activity, a finding subsequently confirmed in clinical studies with one member of this series, N-(methanesulfonyl)-16-phenoxy-ω-tetranor-PGE2-carboxamide (CP-34089/ZK-57671, sulprostone).