5927-18-4

Basic information

• Product Name: Trimethyl phosphonoacetate
• Synonyms: TriMethyl phosphonoacetate, 98% 25GR;Dimethylphosphonoacetic Acid Methyl Ester Methyl Dimethylphosphonoacetate Phosphonoacetic Acid Trimethyl Ester;TriMethyl phosphonoacetat;Aceticacid, 2-(diMethoxyphosphinyl)-, Methyl ester;Dibenzyloxyphosphoiyl three Methyl acetate;(Carboxymethyl)phosphonic acid trimethyl ester;NSC 84262;Dimethyl methoxycarbonylmethanephosphonate for synthesis
• CAS NO: 5927-18-4
• Molecular Formula: C₅H₁₁O₅P
• Molecular Weight: 182.11
• EINECS: 227-663-0
• Product Categories: Horner-Emmons Reaction;Synthetic Organic Chemistry;Wittig & Horner-Emmons Reaction;C-C Bond Formation;Horner-Wadsworth-Emmons Reagents;Olefination
• Mol File: 5927-18-4.mol
• Article Data: 7

Chemical Properties

• Melting Point: 242 °C
• Boiling Point: 118 °C0.85 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: Clear colorless to light yellow/Liquid
• Density: 1.125 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.000577mmHg at 25°C
• Refractive Index: n20/D 1.437(lit.)
• Storage Temp.: Store below +30°C.
• Water Solubility: Slightly miscible with water.
• BRN: 1865177
• CAS DataBase Reference: Trimethyl phosphonoacetate(CAS DataBase Reference)
• NIST Chemistry Reference: Trimethyl phosphonoacetate(5927-18-4)
• EPA Substance Registry System: Trimethyl phosphonoacetate(5927-18-4)

Safety Data

• Safety Statements: 23-24/25
• WGK Germany: 3
• F: 9
• TSCA: Yes
• Hazardous Substances Data: 5927-18-4(Hazardous Substances Data)

Usage

Chemical Properties

clear colorless to light yellow liquid

Uses

Trimethyl phosphonoacetate is used in the preparation of sarin A by intramolecular Mannich-type reactions. It is involved in the Horner-Wadsworth-Emmons olefination with aldehydes and ketones to give acrylic esters. It is also involved in oxa-Michael reactions, prenylation of oxindoles and heterocyclization reactions.

Application

Trimethyl phosphonoacetate is an important Wittig-horner reagent, which can be used to manufacture important intermediates of natural compounds such as vitamins, drugs, insect pheromones, etc.Reactant involved in:Intramolecular Mannich-type reactions to produce the sarain A diazatricyclic coreOrganocatalytic oxa-Michael reactionsPrenylation and geranylation of oxindolesIntramolecular Horner-Wadsworth-Emmons reactionsOlefin cross-metathesis / heterocyclization

InChI:InChI=1/C5H11O5P/c1-8-5(6)4-11(7,9-2)10-3/h4H2,1-3H3

Synthetic route

methanol (67-56-1) + bis-(2,2,2-trifluoroethyl)(methoxycarbonylmethyl)phosphonate (88738-78-7) → trimethyl phosphonoacetate (5927-18-4) + methyl methyl(2,2,2-trifluoroethyl)phosphonoacetate (681123-85-3)

Conditions	Yield
With triethylamine at 20℃; for 0.5h;	A 7% B 88%

bromoacetic acid methyl ester (96-32-2) + phosphorous acid trimethyl ester (121-45-9) → trimethyl phosphonoacetate (5927-18-4)

Conditions	Yield
at 100℃; for 12h;	74%

methyl chloroacetate (96-34-4) + phosphorous acid trimethyl ester (121-45-9) → trimethyl phosphonoacetate (5927-18-4)

Conditions	Yield
Heating;	70%

methyl diazoacetate (6832-16-2) + Dimethyl phosphite (868-85-9) → trimethyl phosphonoacetate (5927-18-4)

Conditions	Yield
With copper acetylacetonate In benzene Heating;	60%

methanol (67-56-1) + ethyl diphenylphosphonoacetate (16139-79-0) → ethyl 2-(dimethoxyphosphoryl)acetate (311-46-6) + trimethyl phosphonoacetate (5927-18-4) + methyl methylphenylphosphonoacetate (625396-69-2) + ethyl methylphenylphosphonoacetate (625396-71-6, 852573-54-7)

Conditions	Yield
With sodium hydroxide at 20℃; for 0.666667h;	A 2% B 13% C 32% D 7%

methanol (67-56-1) + phosphonoacetic acid (4408-78-0) → trimethyl phosphonoacetate (5927-18-4)

Conditions	Yield
(i) PCl5, (ii) /BRN= 1098229/, Et3N; Multistep reaction;

methanol (67-56-1) + (2-chloro-2-ethoxy-vinyl)-phosphonic acid dichloride (42451-44-5) → trimethyl phosphonoacetate (5927-18-4)

Conditions	Yield
In diethyl ether

methyl chloroacetate (96-34-4) + Dimethyl phosphite (868-85-9) → trimethyl phosphonoacetate (5927-18-4)

Conditions	Yield
With potassium carbonate at 20 - 30℃;

2-methylnicotinaldehyde (60032-57-7) + trimethyl phosphonoacetate (5927-18-4) → methyl (E)/(Z)-3-(2-methyl-3-pyridyl)propenoate (137146-28-2, 137146-29-3)

Conditions	Yield
With potassium carbonate In water for 4h; Ambient temperature;	100%

2-methylbut-2-enal (497-03-0) + trimethyl phosphonoacetate (5927-18-4) → methyl (2E,4E)-4-methyl-2,4-hexadienoate (57258-50-1)

Conditions	Yield
Stage #1: trimethyl phosphonoacetate With sodium hydride In benzene at 20℃; for 1.33333h; Stage #2: 2-methylbut-2-enal In benzene for 0.5h; Heating;	100%
With sodium hydride 1.) THF, 2.) RT, 9 h; Multistep reaction;
With sodium hydride In benzene at 65℃; for 4h;	37.82 g

trimethyl phosphonoacetate (5927-18-4) + 1,3-Diphenylpropanone → 4-Phenyl-3-(phenylmethyl)-2-butenoic acid methyl ester (157731-51-6)

Conditions	Yield
With N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium In diethyl ether; hexane 1.) -20 deg C, 20 min, 2.) r.t., 50 h;	100%

trimethyl phosphonoacetate (5927-18-4) + 4-methoxy-benzaldehyde (123-11-5) → 3-(4-methoxy-phenyl)acrylic acid methyl ester (3901-07-3)

Conditions	Yield
Stage #1: trimethyl phosphonoacetate With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Metallation; Stage #2: 4-methoxy-benzaldehyde In tetrahydrofuran; hexane at -78 - 20℃; Condensation; Horner-Wadsworth-Emmons reaction;	100%
Stage #1: trimethyl phosphonoacetate With n-butyllithium In tetrahydrofuran at -78℃; Stage #2: 4-methoxy-benzaldehyde In tetrahydrofuran at -78 - 20℃; Horner-Wadsworth-Emmons reaction;
In tetrahydrofuran; hexane for 1h; Horner-Wadsworth-Emmons Olefination; Cooling with ice;

furfural (98-01-1) + trimethyl phosphonoacetate (5927-18-4) → methyl 3-(2-furyl)acrylate (58293-85-9)

Conditions	Yield
With sodium hydride In tetrahydrofuran at 0℃;	100%
Stage #1: trimethyl phosphonoacetate With sodium hydride In tetrahydrofuran at 0℃; Metallation; Stage #2: furfural In tetrahydrofuran for 0.166667h; Condensation;	90%
With 2,8,9-tris(2-methylpropyl)-2,5,8,9-tetraaza-1-phosphabicyclo[3.3.3]undecane In tetrahydrofuran at 20℃; for 2.2h; Inert atmosphere; optical yield given as %de; stereoselective reaction;	84%

chloro-trimethyl-silane (75-77-4) + trimethyl phosphonoacetate (5927-18-4) → methyl 2-(bis((trimethylsilyl)oxy)phosphoryl)acetate (67605-34-9)

Conditions	Yield
at 80℃; for 96h; Inert atmosphere;	100%
In chlorobenzene at 130℃; for 8h;
at 80℃; for 96h; Inert atmosphere;

trimethyl phosphonoacetate (5927-18-4) + (1S,3aS,5S,7aR)-3a-hydroxy-5-cyclohexyl-7a-methylperhydroindene-1-carboxaldehyde (178379-71-0) → methyl (1R,3aS,5S,7aR)-5-cyclohexyl-3a-hydroxy-7a-methylperhydroindene-1-yl-(E)-acrylate (392235-25-5)

Conditions	Yield
Stage #1: trimethyl phosphonoacetate With sodium hydride In tetrahydrofuran at 0℃; for 1h; Stage #2: (1S,3aS,5S,7aR)-3a-hydroxy-5-cyclohexyl-7a-methylperhydroindene-1-carboxaldehyde In tetrahydrofuran at 20℃; for 2h; Horner-Emmons reaction; Further stages.;	100%

3-Quinuclidinone (3731-38-2) + trimethyl phosphonoacetate (5927-18-4) → 2-(1-azabicyclo[2.2.2]oct-3-ylidene)acetic acid methyl ester (94764-01-9)

Conditions	Yield
Stage #1: trimethyl phosphonoacetate With sodium hydride In tetrahydrofuran; mineral oil at 0 - 20℃; for 1h; Wittig Olefination; Inert atmosphere; Stage #2: 3-Quinuclidinone In tetrahydrofuran; mineral oil at 20℃; Wittig Olefination; Inert atmosphere;	100%
Stage #1: trimethyl phosphonoacetate With sodium In methanol at 0℃; for 1h; Stage #2: 3-Quinuclidinone In methanol at 0℃; for 0.5h; Horner-Wadsworth-Emmons reaction; Stage #3: In methanol at 50℃; for 18h;
Stage #1: trimethyl phosphonoacetate With sodium hydride In tetrahydrofuran at 0 - 20℃; Stage #2: 3-Quinuclidinone In tetrahydrofuran at 0 - 20℃; Wadsworth-Emmons reaction;
Stage #1: trimethyl phosphonoacetate With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 1h; Stage #2: 3-Quinuclidinone In tetrahydrofuran; mineral oil at 20℃; for 18h;

trimethyl phosphonoacetate (5927-18-4) + 4-(2-oxo-2-quinolin-3-yl-ethyl)-piperidine-1-carboxylic acid tert-butyl ester (669075-94-9) → 4-(3-methoxycarbonyl-2-quinolin-3-ylallyl)piperidine-1-carboxylic acid tert-butyl ester (669075-95-0)

Conditions	Yield
With sodium hexamethyldisilazane In tetrahydrofuran for 4h; Heating;	100%

furan-3-carboxaldehyde (498-60-2) + trimethyl phosphonoacetate (5927-18-4) → Methyl 3-(3'-furanyl)prop-2-en-1-oate (99595-62-7)

Conditions	Yield
With sodium hydride In tetrahydrofuran at 0℃;	100%

3-thiophene carboxaldehyde (498-62-4) + trimethyl phosphonoacetate (5927-18-4) → 3-Thiophen-3-yl-acrylic Acid Methyl Ester (75754-85-7)

Conditions	Yield
With sodium hydride In tetrahydrofuran at 0℃;	100%
Stage #1: trimethyl phosphonoacetate With sodium hydride In tetrahydrofuran for 1h; Stage #2: 3-thiophene carboxaldehyde In tetrahydrofuran at 20℃; for 18h;	94%
Stage #1: trimethyl phosphonoacetate With sodium hydride In tetrahydrofuran; mineral oil at 20℃; for 2h; Inert atmosphere; Stage #2: 3-thiophene carboxaldehyde In tetrahydrofuran; mineral oil at 20℃; Inert atmosphere;	81%

3-(4-methoxyphenoxy)-3-perfluoropentyl-prop-2-enal + trimethyl phosphonoacetate (5927-18-4) → methyl (EE)-5-(4-methoxyphenoxy)-5-perfluoropentyl-2,4-pentadienoate

Conditions	Yield
With sodium hydride In methanol at 20℃; for 2h; Wadsworth-Emmons reaction;	100%

trimethyl phosphonoacetate (5927-18-4) + 4-Carboxybenzaldehyde (619-66-9) → methyl (E)-4-carboxyl cinnamate (115974-97-5)

Conditions	Yield
Stage #1: trimethyl phosphonoacetate; 4-Carboxybenzaldehyde With potassium carbonate In water at 0 - 20℃; for 1.5h; Stage #2: In water pH=1; Acidic aqueous solution;	100%
With potassium carbonate In water at 0 - 20℃; pH=Ca. 2;	95%

trimethyl phosphonoacetate (5927-18-4) + m-formylphenyl benzoic acid (619-21-6) → (E)-3-(methoxy-3-oxoprop-1-en-1-yl)benzoic acid (115974-96-4)

Conditions	Yield
Stage #1: trimethyl phosphonoacetate; m-formylphenyl benzoic acid With potassium carbonate In water at 0 - 20℃; for 17h; Stage #2: In water pH=1; Acidic aqueous solution;	100%
With potassium carbonate In water at 0 - 20℃; pH=Ca. 2;	93%

trimethyl phosphonoacetate (5927-18-4) + 2-ethoxy-4-nitro-benzaldehyde (1134-43-6) → ethyl 4-nitro-2-ethoxycinnamate (863885-81-8)

Conditions	Yield
Stage #1: trimethyl phosphonoacetate With sodium hydride In tetrahydrofuran at 0℃; for 0.5h; Inert atmosphere; Stage #2: 2-ethoxy-4-nitro-benzaldehyde In tetrahydrofuran at 20℃; for 4h; Wittig-Horner Reaction; Inert atmosphere;	100%
Stage #1: trimethyl phosphonoacetate With sodium hydride In tetrahydrofuran at 0℃; Stage #2: 2-ethoxy-4-nitro-benzaldehyde In tetrahydrofuran at 0 - 20℃; for 15h;	99%
With sodium hydride In tetrahydrofuran at 0 - 20℃; for 15h;

trimethyl phosphonoacetate (5927-18-4) + 4-(4-hydroxyphenyl)cyclohexan-1-one (105640-07-1) → [4-(4-hydroxyphenyl)cyclohexylidene]acetic acid methyl ester (701232-66-8)

Conditions	Yield
Stage #1: trimethyl phosphonoacetate With sodium hydride In mineral oil at 0 - 20℃; for 0.5h; Inert atmosphere; Stage #2: 4-(4-hydroxyphenyl)cyclohexan-1-one In tetrahydrofuran; mineral oil at 20℃; for 0.416667h; Inert atmosphere;	100%
With sodium hydride In tetrahydrofuran; mineral oil at 0 - 20℃; for 2.83333h; Inert atmosphere;	100%
Stage #1: trimethyl phosphonoacetate With sodium hydride In tetrahydrofuran; mineral oil at 0℃; Inert atmosphere; Stage #2: 4-(4-hydroxyphenyl)cyclohexan-1-one In tetrahydrofuran; mineral oil at 25℃; for 5h;	97%

trimethyl phosphonoacetate (5927-18-4) + (2R)-2-(1,1-dimethylethoxycarbonylamino)-2-cyclohexylethanal (171560-20-6) → (R)-4-tert-butoxycarbonylamino-4-cyclohexyl-but-2-enoic acid methyl ester (876761-53-4)

Conditions	Yield
Stage #1: trimethyl phosphonoacetate With sodium hydride In tetrahydrofuran; mineral oil at 5℃; for 1h; Inert atmosphere; Stage #2: (2R)-2-(1,1-dimethylethoxycarbonylamino)-2-cyclohexylethanal In tetrahydrofuran; mineral oil at 0 - 20℃;	100%
Stage #1: trimethyl phosphonoacetate With sodium hydride In tetrahydrofuran at 0 - 20℃; for 0.5h; Stage #2: (2R)-2-(1,1-dimethylethoxycarbonylamino)-2-cyclohexylethanal In tetrahydrofuran at 0 - 20℃; for 0.333333h;

p-benzyloxybenzaldehyde (4397-53-9) + trimethyl phosphonoacetate (5927-18-4) → (E)-methyl 3-(4-(benzyloxy)phenyl)acrylate (84184-51-0)

Conditions	Yield
Stage #1: trimethyl phosphonoacetate With sodium hydride In tetrahydrofuran; mineral oil at 0℃; Stage #2: p-benzyloxybenzaldehyde In tetrahydrofuran; mineral oil at 20℃;	100%

pyridine-4-carbaldehyde (872-85-5) + trimethyl phosphonoacetate (5927-18-4) → (E)-methyl 3-(pyridine-4-yl)prop-2-enoate (81124-49-4)

Conditions	Yield
With potassium tert-butylate In tetrahydrofuran at 0 - 20℃; for 5h;	100%

tert-butoxycarbonylamino-[4-(4-formylphenoxy)-phenyl]-acetic acid (918337-11-8) + trimethyl phosphonoacetate (5927-18-4) → 3-{4-[4-(tert-butoxycarbonylaminocarboxymethyl)-phenoxy]-phenyl}-acrylic acid methyl ester (918337-12-9)

Conditions	Yield
Stage #1: trimethyl phosphonoacetate With sodium hydride In tetrahydrofuran at 0 - 5℃; for 0.0833333h; Stage #2: tert-butoxycarbonylamino-[4-(4-formylphenoxy)-phenyl]-acetic acid In tetrahydrofuran at 0 - 20℃; for 0.5h; Stage #3: With hydrogenchloride; citric acid In tetrahydrofuran; water pH=~ 2;	100%

trimethyl phosphonoacetate (5927-18-4) + 2-(trifluoromethoxy)benzaldehyde (94651-33-9) → methyl (2E)-3-[2-(trifluoromethoxy)phenyl]prop-2-enoate (1202578-19-5)

Conditions	Yield
Stage #1: trimethyl phosphonoacetate With sodium hydride In tetrahydrofuran at 0℃; Inert atmosphere; Stage #2: 2-(trifluoromethoxy)benzaldehyde In tetrahydrofuran at 20℃; Inert atmosphere;	100%

trimethyl phosphonoacetate (5927-18-4) + C13H19NO2 → C16H23NO3

Conditions	Yield
With sodium hydride In tetrahydrofuran at 20℃; Horner-Wadsworth-Emmons Olefination;	100%

trimethyl phosphonoacetate (5927-18-4) + 2-methylphenyl aldehyde (529-20-4) → methyl (E)-3-(2-methylphenyl)-2-propenoate (70625-62-6, 75950-75-3, 130451-86-4)

Conditions	Yield
Stage #1: trimethyl phosphonoacetate With sodium hydride In tetrahydrofuran; paraffin oil at 0 - 20℃; for 0.5h; Inert atmosphere; Stage #2: 2-methylphenyl aldehyde In tetrahydrofuran; paraffin oil at -78 - 20℃; Inert atmosphere;	100%
With sodium methylate In methanol; N,N-dimethyl-formamide Wittig-Horner Reaction;

trimethyl phosphonoacetate (5927-18-4) + 3-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester (101385-93-7) → tert-butyl 3-(2-methoxy-2-oxoethylidene)pyrrolidine-1-carboxylate (441773-67-7)

Conditions	Yield
Stage #1: trimethyl phosphonoacetate With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 0.333333h; Stage #2: 3-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester In tetrahydrofuran; mineral oil at 0 - 20℃; for 16h;	100%
Stage #1: trimethyl phosphonoacetate With potassium tert-butylate In tetrahydrofuran at 0℃; for 2.5h; Stage #2: 3-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester In tetrahydrofuran at 0℃; for 1h;	92.8%

trimethyl phosphonoacetate (5927-18-4) + m-tolyl aldehyde (620-23-5) → (E)-methyl 3-methylcinnamate (82444-40-4, 118315-74-5, 95416-56-1)

Conditions	Yield
Stage #1: trimethyl phosphonoacetate With sodium hydride In tetrahydrofuran; paraffin oil at 0 - 20℃; for 0.5h; Inert atmosphere; Stage #2: m-tolyl aldehyde In tetrahydrofuran; paraffin oil at -78 - 20℃; Inert atmosphere;	100%

piperonal (120-57-0) + trimethyl phosphonoacetate (5927-18-4) → methyl (2E)-3-(1,3-benzodioxol-5-yl)acrylate (40918-96-5)

Conditions	Yield
Stage #1: trimethyl phosphonoacetate With sodium hydride In tetrahydrofuran; paraffin oil at 0 - 20℃; for 0.5h; Inert atmosphere; Stage #2: piperonal In tetrahydrofuran; paraffin oil at -78 - 20℃; Inert atmosphere;	100%

trimethyl phosphonoacetate (5927-18-4) + 4-methyl-benzaldehyde (104-87-0) → 3-p-tolyl-acrylic acid methyl ester (20754-20-5)

Conditions	Yield
Stage #1: trimethyl phosphonoacetate With sodium hydride In tetrahydrofuran; paraffin oil at 0 - 20℃; for 0.5h; Inert atmosphere; Stage #2: 4-methyl-benzaldehyde In tetrahydrofuran; paraffin oil at -78 - 20℃; Inert atmosphere;	100%

trimethyl phosphonoacetate (5927-18-4) + 2-(8-phenyloctyl) benzaldehyde (96964-45-3) → methyl 3-<2-(8-phenyloctyl)phenyl>propenoate (145950-31-8)

Conditions	Yield
	99%

trimethyl phosphonoacetate (5927-18-4) + (2S,3S)-3-(tert-Butyl-diphenyl-silanyl)-oxirane-2-carbaldehyde (178391-54-3) → (E)-3-[(2S,3S)-3-(tert-Butyl-diphenyl-silanyl)-oxiranyl]-acrylic acid methyl ester

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium chloride In acetonitrile for 0.5h; Ambient temperature;	99%

trimethyl phosphonoacetate (5927-18-4) + 4-methoxy-1-naphthaldehyde (15971-29-6) → methyl-3-(4-methoxy-1-naphthyl)-E-propenoate

Conditions	Yield
Stage #1: trimethyl phosphonoacetate With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane at 0℃; for 0.25h; Stage #2: 4-methoxy-1-naphthaldehyde In dichloromethane at 20℃; for 36h;	99%
Stage #1: trimethyl phosphonoacetate With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane at 0℃; for 0.25h; Stage #2: 4-methoxy-1-naphthaldehyde In dichloromethane at 0 - 20℃; for 36h;	99%
With sodium hydride In N,N-dimethyl-formamide at 20℃; for 2h; Horner-Wadsworth-Emmons reaction;	89%

Upstream product

• 67-56-1 methanol 
• 4408-78-0 phosphonoacetic acid 
• 96-34-4 methyl chloroacetate 
• 868-85-9 Dimethyl phosphite 
• 16139-79-0 ethyl diphenylphosphonoacetate 
• 88738-78-7 bis-(2,2,2-trifluoroethyl)(methoxycarbonylmethyl)phosphonate 
• 6832-16-2 methyl diazoacetate 
• 42451-44-5 (2-chloro-2-ethoxy-vinyl)-phosphonic acid dichloride 
• 96-32-2 bromoacetic acid methyl ester 
• 121-45-9 phosphorous acid trimethyl ester 

Downstream Products

• 1189-09-9 methyl geranate 
• 3675-00-1 methyl (E,E)-farnesoate 
• 2482-39-5 2-decenoic acid methyl ester 
• 75128-90-4 (2Z)-decenoic acid methyl ester 
• 7367-85-3 methyl (E)-dec-2-enoate 
• 10485-70-8 methyl 3,7,11-trimethyldodeca-2,6,10-trienoate 
• 13894-63-8 methyl (E)-hex-2-enoate 
• 13894-64-9 methyl (Z)-hex-2-enoate 
• 1577-28-2 cis-2-hexenoic acid 
• 13419-69-7 (E)-2-Hexenoic acid 
• 124939-60-2 (propene-2 oate de methyle) yl-4 cyclohexene trans 
• 120264-02-0 (propene-2 oate de methyle) yl-4 cyclohexene cis 
• 6722-00-5 Ro 11-0976 
• 42489-46-3 (2E,4E,6E,8E,10E,12E)-3,7,11-Trimethyl-13-(2,6,6-trimethyl-cyclohex-1-enyl)-trideca-2,4,6,8,10,12-hexaenoic acid methyl ester 

Relevant articles and documents

Composition on the basis of phosphonoacetic acid. Synthesis and antiviral activity

A manufacturable technology for the production of an antiviral composition containing phosphonoacetic acid, involing PH-alkylation of dimethyl phosphite with methyl chloroacetate under phase-transfer conditions and subsequent in situ hydrolysis of the intermediate product, was developed. The composition showed expressed antiviral effect against herpesviral infections caused by herpes simplex virus 1 and 2 and cytomegalovirus. The composition in the effective concentration range was found to exhibit no cytotoxic effect on VERO green monkey kidney and M-19 human diploid cell cultures. The resulting data suggest potential uses of the composition as an antiviral agent in practical medicine and as an antiviral additive to synthetic detergents for sanitation in health care and food production facilities.

Intramolecular cyclopropanation reactions en route to novel P- heterocycles

The first examples of intramolecular cyclopropanation reactions on a phosphonate template catalyzed by Rh2(OAc)4 are described. These reactions proceed in excellent yield and give mixtures of the P-heterocycles cis-2a-d and trans-2a-d with moderate levels of diastereoselectivity. The diastereoselectivity of this transformation is dependent upon the size of the alkyl group R contained in the alkyl α-diazodiallylphosphonoacetate starting materials 1a-d.

INSERTION OF CARBENES INTO P-H BONDS. 5. SYNTHESIS OF NEW PHOSPHONATES AND PHOSPHINATES IN REACTIONS CATALYSED BY Cu, Pd, Rh, Ni COMPLEXES

Cu(OTf)2 and Cu(acac)2 were found to be the most effective catalysts in the reaction of diazo compounds Ph2CN2 (1a), EtOC(O)CHN2 (1b), MeOC(O)CHN2 (1c), MeC(O)CN2C(O)OMe (1d), ClCH2C(O)CHN2 (1e) and CH2N2 (1f) with hydrophosphoryl compounds (MeO)2P(O)H (2a), (t-BuO)2P(O)H (2b), Ph(MeO)P(O)H (2c), (EtO)2P(O)H (2d) and P(O)H (2e) resulting in P-C bond formations.Cu, Pd and Rh acetates and Ni(acac)2 have a much lower efficiency.Chlorines in Cl3CC(O)CH2P(O)(OMe)2 (3k) and Cl2CHC(O)CH2P(O)(OMe)2 (3l) are reduced in the copper catalysed Atherton-Todd reaction.Key words: Catalyst; diazo compound; hydrophosphoryl compound; insertion; phosphonate; phosphinate.