40665-94-9

Usage

Uses

Used in Pharmaceutical Industry:
Dimethyl 3-(3-chlorophenoxy)-2-oxopropylphosphonate is used as a key intermediate for the synthesis of [application type] (+)-cloprostenol and α-pentanorbenzo analogs of prostaglandins for [application reason] their potential therapeutic applications in treating various medical conditions.
Dimethyl 3-(3-chlorophenoxy)-2-oxopropylphosphonate plays a vital role in the development of new drugs and therapies, contributing to the advancement of healthcare and improving the quality of life for patients suffering from different health issues. Its use in the pharmaceutical industry underscores its importance in the development of innovative and effective treatments.

InChI:InChI=1/C11H14ClO5P/c1-15-18(14,16-2)8-10(13)7-17-11-5-3-4-9(12)6-11/h3-6H,7-8H2,1-2H3

Upstream product

• 52094-98-1 ethyl (3-chlorophenoxy)acetate 
• 756-79-6 dimethyl methane phosphonate 
• 63501-50-8 dimethyl 3-(3-chlorophenoxy)-2-semicarbazonopropylphosphonate 
• 108-43-0 3-monochlorophenol 
• 74411-14-6 methyl 2-(3-chlorophenoxy)acetate 

Downstream Products

• 53872-62-1 Cloprostenol 
• 129368-04-3 {(1S,2S)-2-[(E)-4-(3-Chloro-phenoxy)-3-oxo-but-1-enyl]-5-oxo-cyclopentyl}-acetic acid methyl ester 
• 122437-71-2 7-{(1S,2S)-2-[(E)-4-(3-Chloro-phenoxy)-3-oxo-but-1-enyl]-5-oxo-cyclopentyl}-heptanoic acid methyl ester 
• 95645-73-1 methyl 1-homo-3,4-cis-didehydro-9,15-diketo-16-(m-chlorophenoxy)-17,18,19,20-tetranorprostenoate 
• 129367-86-8 11-{(1S,2S)-2-[(E)-4-(3-Chloro-phenoxy)-3-oxo-but-1-enyl]-5-oxo-cyclopentyl}-undecanoic acid methyl ester 
• 116206-45-2 Methyl 2-<3-oxo-4-(3-chlorophenoxy)-1E-butenyl>phenylacetate 
• 53872-62-1 [3aα,4α(E),5β,6aα]-(+/-)-4-[4-(3-chlorophenoxy)-3-oxo-1-butenyl]-hexahydro-5-hydroxy-2H-cyclopenta[b]-furan-2-one 
• 95645-72-0 methyl 4,5,17,18,19,20-hexanor-11-deoxy-3,17,dioxa-3,6-inter-(4-chloro-o-phenylene)-16-m-chlorophenoxy-(13E)-15-ketoprostenoate 
• 62515-35-9 (1SR,5RS,6RS,7RS)-6-<4-(3-Chlorophenoxy)-3-oxo-1(E)-butenyl>-7-trimethylsilyloxy-2-oxabicyclo<3.3.0>octan-3-one 
• 62524-96-3 16-(3-chlorophenoxy)-17,18,19,20-tetranor-15-dehydroprostaglandin F_2α 9-acetate methyl ester 11-(tetrahydropyran-2-yl ether) 
• 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 
• 129368-00-9 2β-<3-hydroxy-4-(m-chlorophenoxy)-trans-1-butenyl>-5α-hydroxycyclopentyl-1α-acetic acid γ-lactone 

Relevant academic research and scientific papers

The optically pure sodium alcoholate dextrorotary chlorine forefront of the method for the preparation of

The invention relates to a preparation method of optically pure dextro cloprostenol sodium. The method comprises the following steps: using the combination of ketonic acid and S-phenylethylamine resolving agent, and carrying out chiral resolution to obtain S-propenylphosphonate with the structural formula of R-ketonic acid; then separating to obtain R-chlorone and preparing to obtain R-cloprostenol sodium. The preparation method has the benefits that the optically pure dextro cloprostenol sodium in the invention is called D-cloprostenol sodium for short, the using amount only needs one third of cloprostenol sodium being a racemic modification in current market, and the pesticide effect is obviously better than cloprostenol sodium with three times of using amount.

Synthesis of (±) travoprost and its analogs

A new synthetic approach for the antiglaucoma agent, travoprost (1) has been developed in four steps from key intermediate (2). Key transformations include Horner-Wadsworth-Emmons reaction and separation of diastereomers to obtain (±) travoprost (1) and its analogs.

Use of 9-deoxy prostaglandin derivatives to treat glaucoma

Disclosed are 9-deoxyprostaglandins which are useful in the treatment of glaucoma and ocular hypertension. Some of these 9-deoxyprostaglandins are novel. Also disclosed are ophthalmic, pharmaceutical compositions comprising such prostaglandins.

PROSTANOIDS. XXX. SYNTHESIS OF THE ANALOGS OF 11-DEOXYPROSTA-GLANDINS E AND F

A practical approach to 11-deoxyprostaglandins is developed on the basis of the chemo- and stereoselective reduction of the readily obtainable methyl 9,15-diketo-16-aryloxyprostenoates.

PROSTANOIDS. XIX. THE SYNTHESIS OF 14C-LABELED CLOPROSTENOL

A 1:3400 mixture of 2-14C-labelled methyl bromoacetate with the nonradioactive ester gave labelled dimethoxy-2-oxo-3-(m-chlorophenoxy)phosphonate which was used for the synthesis of 16-14C-labelled cloprostenol by the Corey strategy.

Tertiary alcohols

Tertiary alcohols of the formula: STR1 wherein Y1 represents a carbonyl or hydroxymethylene group, and either (i) A1 represents a direct bond and R1 represents a phenyl group which may optionally carry one or more substituents selected from halogen atoms, straight- or branched-chain alkyl or alkoxy groups, each containing from 1 to 4 carbon atoms, and the trifluoromethyl group, or (ii) A1 represents a straight- or branched-chain alkylene group containing from 1 to 10 carbon atoms and R1 represents a hydrogen atom, or a phenyl, phenoxy or phenylthio group each of which may optionally carry one or more substituents selected from halogen atoms, straight- or branched-chain alkyl or alkoxy groups, each containing from 1 to 4 carbon atoms, and the trifluoromethyl group, are new compounds of use in the field of mammalian reproduction and also of use in the control of insects and acarines.

Phosphonates containing protected ketone group

The disclosure relates to novel protected ketone derivatives, for example dimethyl 3-(3-chlorophenoxy)-2-semicarbazonopropylphosphonate, for use as intermediates in the synthesis of known prostaglandin analogues, and to a process for their manufacture.

16-Phenoxy and phenylthio prostaglandin derivatives

The present invention relates to compounds of the formula: STR1 wherein A represents a grouping of the formula: STR2 B represents an oxygen or sulphur atom, R1 and R2, which may be the same or different, each represent a hydrogen or halogen atom, a trifluoromethyl group, or a straight- or branched-chain alkyl or alkoxy group containing from 1 to 4 carbon atoms, R represents a group of the formula --COOR3, in which R3 represents a hydrogen atom or a straight- or branched-chain alkyl group containing from 1 to 12 carbon atoms, or a group of the formula --CH2 OR4, in which R4 represents a hydrogen atom or an alkylcarbonyl group containing from 2 to 5 carbon atoms and the double bonds depicted in positions C2 -C3, C5 -C6 and C13 -C14 are trans, cis and trans respectively, the cyclodextrin clathrates thereof and, when R3 in the group --COOR3 represents a hydrogen atom, non-toxic salts thereof. These compounds exhibit characteristics of prostaglandin-like activity.