Ethyl (triphenylphosphoranylidene)acetate

Base Information

• Chemical Name: Ethyl (triphenylphosphoranylidene)acetate
• CAS No.: 1099-45-2
• Deprecated CAS: 103603-89-0,21382-83-2
• Molecular Formula: C22H21O2P
• Molecular Weight: 348.381
• Hs Code.: 29310095
• European Community (EC) Number: 214-151-7
• NSC Number: 72406
• UNII: WX75SQL8ZF
• DSSTox Substance ID: DTXSID7061485
• Nikkaji Number: J728.507H,J217.213E
• Wikipedia: Triphenylcarbethoxymethylenephosphorane
• Wikidata: Q7843270
• Mol file: 1099-45-2.mol

Synonyms:1099-45-2;(Carbethoxymethylene)triphenylphosphorane;Ethyl (triphenylphosphoranylidene)acetate;Ethyl 2-(triphenylphosphoranylidene)acetate;(Ethoxycarbonylmethylene)triphenylphosphorane;Triphenylcarbethoxymethylenephosphorane;Acetic acid, (triphenylphosphoranylidene)-, ethyl ester;MFCD00009183;Carbethoxytriphenylphosphonium methylide;Carboethoxymethylidenetriphenylphosphorane;Ethyl (triphenylphosphoranilidene)acetate;ethyl (triphenylphosphoranylidene) acetate;ethyl 2-(triphenyl-lambda5-phosphanylidene)acetate;Carbethoxymethylidenetriphenylphosphorane;NSC 72406;WX75SQL8ZF;ethoxycarbonylmethylenetriphenylphosphorane;Phosphorane, (carboxymethylene)triphenyl-, ethyl ester;[(Ethoxycarbonyl)methylene]triphenylphosphorane;(Triphenylphosphoranylidene)acetic Acid Ethyl Ester;EINECS 214-151-7;NSC-72406;Carboethoxymethylenetriphenylphosphorane;Ethyl (triphenylphosphanylidene)acetate;ethyl(triphenylphosphoranylidene)acetate;Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl ester;((Ethoxycarbonyl)methylene)triphenylphosphorane;((Ethoxycarbonyl)ethylidene)triphenylphosphorane;[(Ethoxycarbonyl)ethylidene]triphenylphosphorane;carbethoxymethylene triphenylphosphorane;NSC-167159;ethyl triphenylphosphoranylidene-acetate;Ethyl (triphenylphosphoranyliden)acetate;Phosphorane, ethyl ester;UNII-WX75SQL8ZF;(TRIPHENYLCARBETHOXYMETHYLENE)PHOSPHORANE;SCHEMBL65066;DTXSID7061485;HMS3886A10;AMY24781;BCP28332;CS-M0973;NSC72406;carbethoxymethylenetriphenylphosphorane;carboethoxymethylentriphenylphosphorane;s5511;(carbethoxymethylene)triphenylphosphine;ethyl triphenylphosphoranylideneacetate;ethyl(triphenylphosphoranyliden)acetate;AKOS005146272;carbethoxymethylene-triphenylphosphorane;carbethoxymethylenetriphenyl phosphorane;carboethoxymethylene triphenylphosphoran;(Carbethoxymethylene)triphenylphosphoran;(carboethoxymethylene)triphenylphosphine;AB00967;CCG-268011;(carbethoxymethylen)-triphenylphosphorane;carbethoxy methylene triphenylphosphorane;carbethoxymethylene triphenyl phosphorane;Carboethoxymethylene triphenylphosphorane;ethoxycarbonylmethylenetriphenylphosphoran;ethyl (triphenylphosphanylidene)-acetate;ethyl 2-triphenylphosphoranylideneacetate;ethyl(triphenyl-phosphoranylidene)acetate;ethyl(triphenylphosphoranylidene)-acetate;(carbethoxy methylene)triphenylphosphorane;(carbethoxymethylene) triphenylphosphorane;(carbethoxymethylene)-triphenylphosphorane;(carbethoxymethylene)triphenyl phosphorane;(carbethoxymethylene)triphenyl-phosphorane;carbethoxy methylene triphenyl phosphorane;carboethoxy-methylenetriphenyl phosphorane;ethyl 2-(triphenylphosphanylidene)acetate;(carbethoxymethylidene)triphenylphosphorane;(carboethoxy-methylene)triphenylphosphorane;(carboethoxymethylene) triphenylphosphorane;(carboethoxymethylene)-triphenylphosphorane;(carboethoxymethylene)triphenylphospho-rane;(carboethoxyrnethylene)triphenylphosphorane;AS-12884;Carboethoxymethylidene triphenylphosphorane;ethyl (triphenylphosphoranylidene)-acetate;SY003933;(carbethoxymethylene) triphenyl-phosphorane;(carbethoxymethylene)-triphenyl phosphorane;(carbethoxymethylene)-triphenyl-phosphorane;Ethoxycarbonyl(triphenylphosphonio)methanide;ethoxycarbonylmethylene triphenylphosphorane;ethoxycarbonylmethylene-triphenylphosphorane;ethoxycarbonylmethylidenetriphenylphosphorane;ethyl 2-tri(phenyl)phosphoranylideneacetate;(carbethoxy methylene)-triphenyl phosphorane;(ethoxycarbonylmethylen)-triphenylphosphorane;Ethoxycarbonylmethylene triphenyl phosphorane;ethoxycarbonylmethylene-triphenyl-phosphorane;(ethoxycarbonylmethylene)-triphenylphosphorane;ethoxycarbonyl-methylene-triphenyl-phosphorane;ethyl 2-(triphenyl phosphoranylidene)acetate;ethyl 2-(triphenylphosphoranylidene)-acetate;FT-0623464;T1944;(ethoxy-carbonylmethylene)-triphenylphosphorane;(ethoxycarbonylmethylene)-triphenyl-phosphorane;EN300-19609;(2-Ethoxy-2-oxoethylidene)triphenylphosphorane;(Carbethoxymethylene)triphenylphosphorane, 95%;(ethoxycarbonyl methylene) triphenyl phosphorane;[(ethoxycarbonyl)methylene]triphenyl phosphorane;Ethyl(triphenyl-lambda5-phosphanylidene)acetate;triphenylphosphoranylideneacetic acid ethyl ester;(CARBOETHOXYMETHYLENE)TRIPHENYLPHOSPHORANE;(triphenylphosphanylidene)acetic acid ethyl ester;Ethyl (triphenyl-lambda5-phosphanylidene)acetate;triphenylphosphoranylidene acetic acid ethyl ester;(triphenyl-phosphanylidene)acetic acid ethyl ester;A802115;triphenyl-phosphoranylidene acetic acid ethyl ester;(triphenyl phosphoranylidene)acetic acid ethyl ester;(triphenyl-phosphanylidene)-acetic acid ethyl ester;(triphenylphosphoranylidene)-acetic acid ethyl ester;Q7843270;W-111711;(triphenyl-phosphoranylidene)-acetic acid ethyl ester;2-(triphenylphosphoranylidene)acetic acid ethyl ester;(Triphenyl-I>>5-phosphanylidene)-acetic acid ethyl ester;Z104474440;(triphenyl-lambda-5-phosphanylidene)acetic acid ethyl ester;(triphenyl-lambda5-phosphanylidene)acetic acid ethyl ester;(TRIPHENYL-LAMBDA5-PHOSPHANYLIDENE)-ACETIC ACID ETHYL ESTER

Chemical Property of Ethyl (triphenylphosphoranylidene)acetate

Chemical Property:

• Appearance/Colour: white or slight yellow powder
• Vapor Pressure: 9.18E-10mmHg at 25°C
• Melting Point: 125-127ºC
• Refractive Index: 1.6
• Boiling Point: 490.4 ºC at 760 mmHg
• Flash Point: 263.5 ºC
• PSA: 36.11000
• Density: 1.15 g/cm³
• LogP: 3.34580
• Storage Temp.: 2-8°C
• Sensitive.: Air Sensitive
• Solubility.: Chloroform, THF
• Water Solubility.: Insoluble
• XLogP3: 4.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 6
• Exact Mass: 348.12791691
• Heavy Atom Count: 25
• Complexity: 414

Purity/Quality:

99% ^*data from raw suppliers

(Carbethoxymethylene)triphenylphosphorane ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T,Xi,Xn
• Statements: 36/37/38-25-20/21/22
• Safety Statements: 22-24/25-45-37/39-26-36

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Phosphorus Compounds
• Canonical SMILES: CCOC(=O)C=P(C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3
• General Description: Ethyl (triphenylphosphoranylidene)acetate, also known as (carbethoxymethylene)triphenylphosphorane or (ethoxycarbonylmethylidene)triphenylphosphorane, is a phosphorane ylide commonly used in organic synthesis, particularly in Wittig-type reactions for the formation of carbon-carbon double bonds. It serves as a reagent for the introduction of carbethoxy-substituted alkenes, as demonstrated in studies involving the synthesis of cinnamic ester derivatives and reactions with thienylacrylonitriles. Its reactivity is influenced by the nature of substituents and reaction conditions, leading to diverse products such as cyclopropane derivatives, ylides, or pyran derivatives. While not directly highlighted for biological activity in the provided abstracts, its role as a synthetic intermediate underscores its utility in constructing pharmacologically relevant scaffolds.

Technology Process of Ethyl (triphenylphosphoranylidene)acetate

There total 44 articles about Ethyl (triphenylphosphoranylidene)acetate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

(carbethoxymethyl)triphenylphosphonium bromide (1530-45-6) → ethyl (triphenylphosphoranylidene)acetate (1099-45-2)

Guidance literature:

With sodium hydroxide; In water; at 20 ℃; for 5h;

Reference yield: 99.0%

P-(carboethoxymethyl)triphenylphosphonium cation (42809-80-3) → ethyl (triphenylphosphoranylidene)acetate (1099-45-2)

Guidance literature:

With sodium hydroxide; In dichloromethane; water; at 20 ℃; for 0.5h;

DOI:10.1002/chem.201800313

Reference yield: 89.5%

(ethoxycarbonylmethyl)triphenylphosphonium chloride (17577-28-5) → ethyl (triphenylphosphoranylidene)acetate (1099-45-2)

Guidance literature:

With potassium hydroxide; In water;

DOI:10.1016/j.jorganchem.2006.11.002

upstream raw materials:

diazoacetic acid ethyl ester

triphenylphosphine

sorbic Acid

(2,2-diethoxyvinylidene)triphenylphosphorane

Downstream raw materials:

ethyl (E)-3-(4-methylphenyl)acrylate

ethyl 3-methylhex-2-enoate

(N',N'-Dimethyl-hydrazinocarbonyl)-(triphenyl-λ⁵-phosphanylidene)-acetic acid ethyl ester

ethyl 3-oxo-5-phenyl-2-triphenylphosphoranylidenepent-4-ynoate

Refernces

Synthesis and in?vitro antitumour activity of crassalactone D, its stereoisomers and novel cinnamic ester derivatives

10.1016/j.ejmech.2017.03.088

The research presents a comprehensive study on the synthesis and in vitro antitumor activity of crassalactone D, its stereoisomers, and novel cinnamic ester derivatives. The purpose of the study was to develop a new one-pot synthesis method for these compounds starting from D-glucose and evaluate their cytotoxic effects against various human tumor cell lines. The conclusions drawn from the research indicate that many of the synthesized compounds exhibited potent cytotoxicities, with some showing higher potency than the commercial antitumor agent doxorubicin. The study also highlighted the importance of stereochemistry at the C-4 and C-7 positions, as well as the nature of the substituent at the C-4 position in the aromatic ring of the cinnamoate moiety, for biological activity. The chemicals used in the process included D-glucose, (methoxycarbonylmethylene)triphenylphosphorane (MCMP), (ethoxycarbonylmethylene)triphenylphosphorane (ECMP), cinnamoyl chloride, 4-nitrocinnamoyl chloride, 4-methoxycinnamic acid, and 4-fluorocinnamic acid, among others. The synthesized products were assessed for their in vitro antiproliferative activity, and the results were supported by flow cytometry and Western blot analysis, providing insights into the apoptotic mechanisms triggered by the compounds.

An Evaluation of Certain Chain-Extended Analogues of 9-β-D-Arabinofuranosyladenine for Antiviral and Cardiovascular Activity

10.1021/jm00364a033

The research aimed to synthesize and test nucleoside derivatives modified and chain-extended at the 5'-position for their biological activity, particularly against herpes simplex virus type 1 and their effects on coronary vasodilation. The study concluded that while none of the compounds showed marked antiviral activity, compounds 7 and 8 exhibited some selectivity against the virus. Additionally, compounds 5 and 8 showed weak coronary vasodilation effects in dogs. The chemicals used in the process included various nucleoside derivatives such as M-benz-amido-9-(2,3-di-O-benzoyl-~-~-arabino-pentodialdo-1,4-furanosyl)adenine and its analogues, as well as reagents like N,N'-dicyclohexylcarbodiimide, dichloroacetic acid, (carbethoxymethylene)triphenylphosphorane, and lithium aluminum hydride, among others, for the synthesis and biological evaluations of these compounds.

The reactions of triphenylphosphine alkylenes with 3(2-thienyl)acrylonitriles

10.1080/10426500307778

The research investigates the reactions of triphenylphosphine alkylenes with 3(2-thienyl)acrylonitriles, aiming to explore the formation of various products under different reaction conditions and the influence of the substituents on the reaction outcomes. Key chemicals involved include ethyl 3-(2-thienyl)acrylocyanoacetate (1b), various ylides such as (methoxycarbonylmethylene)triphenylphosphorane (2a), (ethoxycarbonylmethylene)triphenylphosphorane (2b), (benzoylmethylene)triphenylphosphorane (2c), and (cyanomethylene)triphenylphosphorane (14). The study found that the initial Michael addition of ylides to the exocyclic methide carbon in 1b leads to diverse products depending on the nature of the ylide and reaction conditions. For instance, reactions with 2a and 2b in the presence of triethylamine yielded cyclopropane derivatives and new ylides, while the reaction with 2c in ethyl acetate containing benzoic acid produced a pyran derivative. The reaction of (cyanomethylene)triphenylphosphorane (14) with 1b resulted in a cyclopropane derivative, whereas with malonitrile 1a, it produced a ylide and a propene derivative. The research concludes that the substituents on the ylides and the reaction conditions significantly affect the reaction pathways and products, highlighting the versatility of these reactions in synthesizing complex organic compounds with potential biological activities.