3699-66-9

Usage

Uses

Used in Pharmaceutical and Chemical Research:
TRIETHYL 2-PHOSPHONOPROPIONATE is used as a reactant in intramolecular conjugate addition for the synthesis of floresolide B, enantioselective synthesis of spiroindane di-methyl acetic acid, and in stereoselective intramolecular Diels-Alder reactions. It plays an important role in Horner-Wadsworth-Emmons reactions and chemoenzymatic one-pot synthesis of gamma-butyrolactones. It is also used in the preparation of 3-[2]furyl-2-methyl-acrylic acid ethyl ester by reacting with furfural.
Used in Insecticide Studies:
TRIETHYL 2-PHOSPHONOPROPIONATE is used in studies involving insecticides and their efficacy on various bacteria, contributing to the development of more effective pest control methods.
Used in Virology:
TRIETHYL 2-PHOSPHONOPROPIONATE acts as inhibitors of Epstein-Barr virus transmission and infections, potentially aiding in the development of antiviral treatments and prevention strategies.

Purification Methods

Purify it by fractional distillation with high reflux ratio, preferably using a spinning band column. [Kosolapoff & Powell J Am Chem Soc 72 4198 1950, Kresze et al. Justus Liebigs Ann Chem 756 112 1972, Beilstein 4 IV 3617.]

InChI:InChI=1/C9H19O5P/c1-5-12-9(10)8(4)15(11,13-6-2)14-7-3/h8H,5-7H2,1-4H3/t8-/m0/s1

Upstream product

• 2303-76-6 sodium diethyl phosphite 
• 535-11-5 Ethyl 2-bromopropionate 
• 122-52-1 triethyl phosphite 
• 123-11-5 4-methoxy-benzaldehyde 
• 101834-91-7 chloro-2 phosphono-2 propionate de triethyle 
• 101834-92-8 bromo-2 phosphono-2 propionate de triethyle 
• 814-49-3 diethyl chlorophosphate 
• 105-37-3 Ethyl propionate 
• 589-57-1 diethyl phosphorylchloridite 
• 78-40-0 triethyl phosphate 
• 811-49-4 ethyllithium 
• 105-58-8 Diethyl carbonate 
• 78-38-6 ethylphosphonic acid diethyl ester 
• 867-13-0 diethoxyphosphoryl-acetic acid ethyl ester 

Downstream Products

• 5962-41-4 2-Phosphono-propionsaeure 
• 52094-41-4 3,3-Dicyclohexyl-2-methyl-acrylic acid ethyl ester 
• 38701-07-4 2-Methyl-4-aethyl-4-phenyl-butadien-(2,3)-carbonsaeureaethylester 
• 36858-88-5 α,γ-Dimethyl-γ-phenyl-allencarbonsaeure 
• 125346-88-5 4-methyl-1-(1'-carbethoxy)ethylidene-3-cyclohexene 
• 64739-80-6 Aethyl-2-diaethylphosphono-2-phenylselenylpropionat 
• 10067-38-6 (E)-2-Methyl-6-(4-methyl-cyclohex-3-enyl)-hepta-2,6-dienoic acid ethyl ester 
• 6323-97-3 1-aminoethanephosphonic acid 
• 14182-67-3 2-methyl-4-phenyl-but-2-enoic acid ethyl ester 
• 138344-84-0 (E)-ethyl 2-methyl-4-phenylbut-3-enoate 
• 5717-44-2 α,γ-Dimethyl-γ-phenyl-allencarbonsaeure-ethylester 
• 5717-41-9 ethyl 2-methylbuta-2,3-dienoate 
• 21016-46-6 2,4-dimethyl-pent-2-enioc acid ethyl ester 
• 21016-47-7 ethyl (Z)-2,4-dimethylpent-2-enoate 

Relevant academic research and scientific papers

Copper-Catalyzed Dehydrogenative Diels-Alder Reaction

A practical and effective copper-catalyzed dehydrogenative Diels-Alder reaction of gem-diesters and ketone with dienes has been established. The active dienophiles were generated in situ via a radical-based dehydrogenation process, which reacted with a wide variety of dienes to afford various polysubstituted cyclohexene derivatives in good to excellent yields.

Ravynic acid, an antibiotic polyeneyne tetramic acid from: Penicillium sp. elucidated through synthesis

A new antibiotic natural product, ravynic acid, has been isolated from a Penicillium sp. of fungus, collected from Ravensbourne National Park. The 3-acylpolyenyne tetramic acid structure was definitively elucidated via synthesis. Highlights of the synthetic method include the heat induced formation of the 3-acylphosphorane tetramic acid and a selective Wittig cross-coupling to efficiently prepare the natural compounds carbon skeleton. The natural compound was shown to inhibit the growth of Staphylococcus aureus down to concentrations of 2.5 g mL-1.

Synthesis and characterization of novel phosphonocarboxylate inhibitors of RGGT

Phosphonocarboxylate (PC) analogs of the anti-osteoporotic drugs, bisphosphonates, represent the first class of selective inhibitors of Rab geranylgeranyl transferase (RabGGTase, RGGT), an enzyme implicated in several diseases including ovarian, breast and skin cancer. Here we present the synthesis and biological characterization of an extended set of this class of compounds, including lipophilic derivatives of the known RGGT inhibitors. From this new panel of PCs, we have identified an inhibitor of RGGT that is of similar potency as the most active published phosphonocarboxylate, but of higher selectivity towards prenyl pyrophosphate synthases. New insights into structural requirements are also presented, showing that only PC analogs of the most potent 3rd generation bisphosphonates inhibit RGGT. In addition, the first phosphonocarboxylate-derived GGPPS weak inhibitor is reported.

Total synthesis of (±)-merrilactone A

The total synthesis of racemic merrilactone A (a neurotrophic agent) is described, featuring simultaneous and stereospecific creation of the C4 and C5 Stereocenters via a notable silyloxyfuran Nazarov cyclization. Full details of the successful synthetic strategy are given, as well as several examples of the interesting reactivity of intermediates that were prepared and studied during the execution of the total synthesis. A detailed investigation of the Lewis acid-catalyzed Nazarov cyclization of silyloxyfurans was conducted, including a systematic study of substrate scope and limitations. In addition, experiments were conducted that suggest the participation of Lewis acidic silicon species in the Nazarov cyclization.

Synthetic studies aimed at the elucidation of the stereostructure of the aggregation pheromone, 2-methyl-6-(4′-methylenebicyclo[3.1.0]hexyl)hept-2-en-1-ol, produced by the male stink bug Erysarcoris lewisi

The male-produced aggregation pheromone of the stink bug Erysarcoris lewisi Distant was shown to be one of the two diastereomers of (2Z,6R)-2-methyl-6-(4′-methylenebicyclo[3.1.0]hexyl)hept-2-en-1-ol by synthesizing and bioassaying (2E,6R)-, (2E,6S)-, (2Z,6R)-, and (2Z,6S)-isomers. These were synthesized from the enantiomers of citronellal by employing an intramolecular α-ketocarbene addition to a double bond and the E-selective or Z-selective olefination of a formyl group as the key steps. A reliable method was developed for the preparation of ethyl 2-(di-o-tolylphosphono)propanoate, Ando's reagent for Z-selective olefination.

Synthesis of spiro[4.5]decane and bicyclo[4.3.0]nonane ring systems by self-cyclization of (Z)- and (E)-2-(trimethylsilylmethyl)pentadienal derivative

The two title carbon frameworks were synthesized utilizing a new type of iron-induced cyclization reaction of 2-(trimethylsilylmethyl)pentadienal. 2-Methylspiro[4.5]dec-2-en-1-one was obtained from (Z)- and (E)-4- cyclohexylidene-2-(trimethylsilylmethyl)but-2-enal. It was found that the (Z)-substrate isomerized to (E)-intermediate followed by cyclization to afford the initial product, 2-methylenespiro[4.5]dec-3-en-1-ol, which was isomerized to the above product. The cyclization of 4-(4-alkyl)cyclohexylidene-2- (trimethylsilylmethyl)but-2-enal proceeded stereoselectively. While, (E)-3-(cyclohex-1-en-1-yl)-2-(trimethylsilylmethyl)prop-2-en-1-al cyclized immediately affording 8-methylenebicyclo[4.3.0]non-9-en-7-ol. The corresponding (Z)-isomer gave several cyclization products as a complex mixture.

Synthesis and biological evaluation of cycloalkylidene carboxylic acids as novel effectors of Ras/Raf interaction

The protooncogenes Ras and Raf play important roles in signal transduction pathways regulated by mitogen-activated protein kinases. Mutations of Ras that arrest the protein in its active state are frequently implicated in tumor formation. We used Ras and Raf proteins in the yeast two-hybrid system to search for natural or synthesized substances capable of modulating Ras/Raf interaction by specifically binding to one of the interacting partners. We found that cycloalkylidene carboxylic acids enhanced Ras/Raf interaction by acting on the cysteine-rich domain of Raf. Several analogues of the active substance 2-cyclohexylidene propanoic acid were synthesized and the importance of the semicyclic double bond in the stabilization of Ras/Raf interaction was demonstrated. Variation of the size and the substituents of the cyclic system as well as the length of the carboxylic acid resulted in enhanced Ras/Raf interaction.

A useful synthesis of diethyl 1-substituted vinylphosphonates

A variety of diethyl 1-substituted vinylphosphonates 8 has been conveniently synthesized by piperidine catalyzed decarboxylative condensation of 2-diethoxyphosphorylalkanoic acids and 2-diethoxyphosphorylalkenoic acids 7 with formaldehyde.

Nazarov cyclization of 4-cycloalkylidene-5-(trimethylsilyl)pent-1-en-3-one derivatives. Synthesis of spiro[4.5]decane, Spiro[4.4]nonane, and Their derivatives

Spiro[4.5]decane and spiro[4.4]nonane ring systems were synthesized by FeCl3-induced Nazarov cyclization of α-(trimethylsilylmethyl)divinyl ketone derivatives. It was found that the double bond position of the product is controlled by the presence/absence of α'-substituent, while trimethylsilyl group is essential to obtain the products in good yields. Spiro[4.4]nonanes having exo-methylene group underwent rearrangement to bicyclo[4.3.0]nonanes. (C) 2000 Elsevier Science Ltd.

Synthesis and SAR of 1-alkyl-2-phenylethylamine derivatives designed from N,N-dipropyl-4-methoxy-3-(2-phenylethoxy)phenylethylamine to discover σ1 ligands

The synthesis and structure-activity relationships (SAR) of 1-alkyl-2- phenylethylamine derivatives 5-8 designed from N,N-dipropyl-2-[4-methoxy-3- (2-phenylethoxy)phenyl]ethylamine hydrochloride (1, NE-100) are presented. The SAR between compound 1 and 1-alkyl-2-phenylethylamine derivatives suggested that the alkyl group on the 1-position carbon of 2-[4-methoxy-3-(2- phenylethyl)phenyl]ethylamine derivatives played the role of one of the propyl groups on the aminic nitrogen of compound 1. (-)-N-Propyl-1-butyl-2- [4-methoxy-3-(2-phenylethoxy)phenyl]ethylamine hydrochloride ((-)-6d, NE-537) and (-)-N-propyl-1-(3-methybutyl)-2-[4-methoxy-3-(2- phenylethoxy)phenyl]ethylamine hydrochloride ((-)-6i, NE-535), typical compounds in this series, have potent and selective σ1 affinity.