7459-46-3

Basic information

• Product Name: TRIETHYL 1,1,2-ETHANETRICARBOXYLATE
• Synonyms: 1,1,2-Tricarbethoxyethane;Ethane-1,1,2-tricarboxylic acid, triethyl ester;Triethyl ethane tricarboxylate;Triethyl ethane-1,2,2-tricarboxylate;LABOTEST-BB LT00452668;TRIETHYL 1,1,2-ETHANETRICARBOXYLATE;2-(Ethoxycarbonyl)butanedioic Acid Diethyl Ester;Diethyl 2-(Ethoxycarbonyl)butanedioate
• CAS NO: 7459-46-3
• Molecular Formula: C₁₁H₁₈O₆
• Molecular Weight: 246.26
• EINECS: 231-235-9
• Product Categories: C10 to C11;Carbonyl Compounds;Esters;Building Blocks;C10 to C11;Carbonyl Compounds;Chemical Synthesis;Organic Building Blocks
• Mol File: 7459-46-3.mol

Chemical Properties

• Boiling Point: 99 °C0.5 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: Clear colorless/Liquid
• Density: 1.074 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0011mmHg at 25°C
• Refractive Index: n20/D 1.429(lit.)
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Chloroform, Ethyl Acetate
• PKA: 11.78±0.59(Predicted)
• BRN: 1796294
• CAS DataBase Reference: TRIETHYL 1,1,2-ETHANETRICARBOXYLATE(CAS DataBase Reference)
• NIST Chemistry Reference: TRIETHYL 1,1,2-ETHANETRICARBOXYLATE(7459-46-3)
• EPA Substance Registry System: TRIETHYL 1,1,2-ETHANETRICARBOXYLATE(7459-46-3)

Safety Data

• Safety Statements: 23-24/25
• WGK Germany: 3
• Hazardous Substances Data: 7459-46-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Triethyl 1,1,2-ethanetricarboxylate is used as a synthetic intermediate for the preparation of Isobutylsuccinic Acid (I780660). This acid is further utilized in the synthesis of succinimide derivatives, which act as inhibitors of human leukocyte elastase, cathepsin G, and proteinase 3. These enzymes are involved in various inflammatory processes and diseases, making the synthesized succinimide derivatives potential therapeutic agents for treating such conditions.
Used in Organic Synthesis:
In addition to its applications in the pharmaceutical industry, Triethyl 1,1,2-ethanetricarboxylate can also be used as a versatile building block in the synthesis of various organic compounds. Its ester functionality allows for a range of chemical reactions, making it a valuable reagent in organic chemistry research and development.

InChI:InChI=1/C11H18O6/c1-4-15-9(12)7-8(10(13)16-5-2)11(14)17-6-3/h8H,4-7H2,1-3H3

Upstream product

• 56-23-5 tetrachloromethane 
• 15219-34-8 Oxalyl bromide 
• 78209-71-9 dibromosuccinic acid 
• 996-82-7 sodium diethylmalonate 
• 105-39-5 chloroacetic acid ethyl ester 
• 105-53-3 diethyl malonate 
• 95-92-1 oxalic acid diethyl ester 
• 123-25-1 succinic acid diethyl ester 
• 64-17-5 ethanol 
• 996-82-7 sodium diethylmalonate 
• 609-15-4 ethyl 2-chloro-3-oxo-butyrate 
• 13049-86-0 diethyl 2-(ethoxycarbonylmethylene)malonate 
• 42126-21-6 1-oxo-propane-1,2,3-tricarboxylic acid triethyl ester 
• 141-52-6 sodium ethanolate 

Downstream Products

• 49597-17-3 5-oxo-1-phenyl-2,5-dihydro-1H-pyrazole-3-carboxylic acid 
• 57420-27-6 2-piperonylsuccinic acid 
• 56416-10-5 2-Ethoxycarbonyl-2-(4-nitro-benzyl)-succinic acid diethyl ester 
• 103347-16-6 2-(4-Chloro-3-methoxy-benzyl)-2-ethoxycarbonyl-succinic acid diethyl ester 
• 175023-06-0 triethyl 1-<(2-nitrophenyl)acetyl>-1,1,2-ethanetricarboxylate 
• 674786-75-5 cis/trans-4-(perfluorooctyl)methyl-2-carboethoxymethyl-2-carboethoxy-4-hydroxy-butanoic acid γ-lactone 
• 141-52-6 sodium ethanolate 
• 6482-32-2 2-(hydroxymethyl)butane-1,4-diol 
• 96141-67-2 2-{3-[2-Bromo-5-(2,4-diamino-pyrimidin-5-ylmethyl)-3-methoxy-phenoxy]-propyl}-2-ethoxycarbonyl-succinic acid diethyl ester 
• 75887-69-3 1-<3,5-Dimethoxybenzyl>-aethan-1,1,2-tricarbonsaeure-triaethylester 
• 84763-36-0 Triethyl-1-(3-oxocyclohexyl)-1,1,2-ethantricarboxylat 
• 56416-11-6 2-(4-Chloro-benzyl)-2-ethoxycarbonyl-succinic acid diethyl ester 
• 162685-91-8 diethyl 5-oxo-1-[(R)-1-phenylethyl]pyrrolidine-3,3-dicarboxylate 

Relevant articles and documents

Synthesis and biological evaluation of N4-hydrazone derivatives of 5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one as novel anticancer agents with antimetastatic adjunct efficacy

To obtain new anticancer agents with antimetastatic adjunct efficacy, a series of novel N4-hydrazone derivatives of 5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one were designed and synthesized by an eight-step reaction, with appropriate yields. All the synthesized compounds were evaluated for their antiproliferative activity against A549 and MCF-7 cells and for antiplatelet aggregation activity in vitro. The results showed that compounds 25 and 35 not only showed potent antiproliferative activity against the A549 (IC50 = 15.3 and 21.4 μM) and MCF-7 (IC50 = 15.6 and 10.9 μM) cell lines but also showed certain antiplatelet aggregation activity (inhibition rates: 47.0% and 45.8%). These results indicated that the structural modification on the N4-hydrazone moiety of 5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one is promising to obtain novel anticancer compounds with antimetastatic adjunct efficacy. In addition, a molecular docking study was performed to investigate the possible targets, and these results indicated that compounds 25 and 35 have the potential to target EGFR, HER2, and P2Y12.

Design, synthesis and biological evaluation of 4-Aryl-5,7-dihydro- 6H-pyrrolo[2,3-d]pyrimidin-6-one derivatives as a PI3Kα inhibitor

A novel series of 4-aryl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one derivatives were designed as a phosphoinositide 3-kinase α (PI3Kα) inhibitor by scaffold hopping. The target compounds, characterized by 1H-NMR, 13C-NMR and high resolution (HR)-MS, were synthesized from diethyl malonate and ethyl chloroacetate by nucleophilic substitution, ring-closure, chlorination and Suzuki reaction, etc. The biological activities were evaluated with cytotoxic activity in vitro on Uppsala 87 Malignant Glioma (U87MG) and prostate cancer-3 (PC-3) by Cell Counting Kit-8 (CCK-8). The results showed that compound 9c displayed the higher inhibition than the positive control PI-103, and high PI3Kα inhibitory activity with IC50 of 113 ± 9 nM in the same order of magnitude as BEZ235. In addition, the Log Kow values and molecular docking studies were performed to further investigate the drug-like properties of target compounds and interactions between 9c and PI3Kα.

Discovery and optimization of 5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one derivatives as mTORC1/mTORC2 dual inhibitors

New potent mTORC1/mTORC2 dual inhibitors, 5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one derivatives, were obtained by optimizing functional groups on our previously reported PI3Kα inhibitor. All the target compounds were synthesized and structural optimization on the structure of the lead compound based on cytotoxic activity. The results showed that some of the target compounds exhibited moderate to high cytotoxic activity against cell line U87MG and PC-3. The activities against mTOR kinase were investigated and the compound 12q showed excellent activity with an IC50 value of 54 nM in the same level of the positive control BEZ235 with IC50 value of 55 nM under the same test conditions. The western blot and cell cycle results demonstrate that compound 12q is a candidate as an mTORC1/mTORC2 dual-target inhibitor. The theoretical calculations were also performed to better understanding the binding modes of the compound 12q in the mTOR active site.

A New Approach to the Synthesis of Diethyl 2,3-Diisobutylsuccinate, a Component of Titanium–Magnesium Catalysts for Propylene Polymerization

A procedure was developed for preparing 2,3-dialkyl-substituted succinates by condensation of a succinic acid diester with two isobutyraldehyde molecules, followed by esterification and hydrogenation of the sum of dienes. Diethyl 2,3-diisobutylsuccinate of 75%–99% purity was prepared by this procedure in a good yield. The use of the synthesized diethyl 2,3-diisobutylsuccinate as a stereoregulating component of titanium–magnesium catalysts allows synthesis of polypropylene with broad molecular-mass distribution. The catalysts prepared using >95% pure diethyl 2,3-diisobutylsuccinate demonstrated the best characteristics and allowed polypropylene synthesis with high isotacticity index in a high yield.

5. 7 - Dihydro - 6H - pyrrolo [2, 3 - d] pyrimidine -6 - ketone derivatives preparation method and application (by machine translation)

5. 7 - Dihydro - 6 H - pyrrolo [2, 3 - d] pyrimidine - 6 - ketone derivatives preparation method and application, which belongs to the new compound preparation and pharmaceutical application field, in particular to immune dysfunction and technical field of tumor diseases, in particular relates to a 5, 7 - dihydro - 6 H - pyrrolo [2, 3 - d] pyrimidine - 6 - ketone derivative compounds of the general formula I as the structure of the PI3K/mTOR inhibitor compound. The structure of the compound of the general formula I . The invention discloses the general formula I indicated by the 5, 7 - dihydro - 6 H - pyrrolo [2, 3 - d] pyrimidine - 6 - ketone derivatives of the preparation method, and also relates to the compounds in the immune disorders and neoplastic diseases, the compounds of the antiproliferative in the treatment of diseases related to the application of the medicament. (by machine translation)

Preparation method of 1,1,2-triethyl ethane triformate

The invention relates to a preparation method of 1,1,2-triethyl ethane triformate. The method mainly comprises the following steps: adding first inorganic alkaline into a first organic solvent, addingdiethyl malonate into a reaction system, adding a catalyst 1, generating heating reaction for a period of time, adding ethyl acetate, and generating heating reaction to obtain a final product. The product has a high value, can be applied to multiple fields, and is high in conversion rate, easy to separate and purify and high in reaction controllability, and the raw material cost is low.

Preparation method of tetrahydro-3-furanmethanol

The invention relates to the field of preparation of insecticides, in particular to a preparation method of tetrahydro-3-furanmethanol. The method comprises the steps as follows: 13.6 g of sodium ethoxide and 0.5 g of sodium iodide are dissolved in 120 mL of absolute ethyl alcohol, 32 g of diethyl malonate is dropwise added in an ice-water bath, the temperature is controlled at 20 DEG C or below,stirring is performed continuously for 1 h after addition, then 30.3 g of ethyl bromoacetate is slowly added, the temperature is increased to 50-60 DEG C after addition, stirring is performed for about 8 h, ethyl bromoacetate is detected to be used up through gas chromatography, a heating reaction is stopped, the system is cooled to the room temperature, 10 mL of a saturated ammonium chloride solution is added with stirring, the system is adjusted to be neutral or slightly acid, solvent ethyl alcohol is evaporated, residues are dissolved in 100 mL of water and 100 mL of ethyl acetate for extraction, solution separation is performed, an organic phase is separated, the solvent ethyl acetate is removed from the organic phase, reduced pressure distillation is performed through an oil pump, andthe first fraction point, namely, a triethyl 1,1,2-ethanetricarboxylate product, is collected. The process is simple, safety in actual production is guaranteed, and the product with higher yield is obtained.

Preparation method and applications of a class of electrophilic enol salts

The invention relates to a preparation method and applications of a class of electrophilic enol salts, and belongs to the technical field of metal organic catalysis, wherein an alkynyl terminated compound, a nitrogen oxide and a proton supplying agent are subjected to an addition reaction in an organic solvent by using a silver salt as a catalyst to obtain the electrophilic enol salt, and the electrophilic enol salt is used for preparing a functionalized carbonyl compound. According to the present invention, with the synthesis method, by using various commercially availaboe monovalent silver salts as the catalyst and using various alkynyl terminated compounds as the starting raw material, the alkynyl terminated compound can be added by the protonated nitrogen oxide so as to achieve the synthesis of the special enol salt; the obtained enol salt has characteristics of diverse structure, high tolerance of the functional group, and good yield; and the electrophilic enol salts with the characteristic of easy separation is synthesized.

3-tetrahydrofurfuryl alcohol intermediate synthesis method

The present invention discloses a 3-tetrahydrofurfuryl alcohol intermediate synthesis method, wherein under a condition of a weak base acid-binding agent, dialkyl malonate and halogenated alkyl acetate are adopted as raw materials and are subjected to a dehydration reaction in a solvent under the effects of a catalyst and a phase transfer catalyst, and post-treatment is performed to obtain 2-alkoxy acyl-dialkyl succinate. According to the present invention, the weak base acid-binding agent is used to replace metal sodium, sodium hydride, potassium hydride and other strong bases; and compared with the traditional methods, the method of the present invention has advantages of high yield, mild and easily-controlled reaction conditions, easy post-treatment and environmental protection, and is suitable for industrial large-scale production.

COMPOUNDS FOR IMPROVING MRNA SPLICING

Provided herein are compounds useful for improving mRNA splicing in a cell. Exemplary compounds provided herein are useful for improving mRNA splicing in genes comprising at least one exon ending in the nucleotide sequence CAA. Methods for preparing the compounds and methods of treating diseases of the central nervous system are also provided.