3779-29-1

Basic information

• Product Name: Diethyl 1,1-cyclobutanedicarboxylate
• Synonyms: 1,1-CYCLOBUTANEDICARBOXYLIC ACID DIETHYL ESTER;1,1-DICARBOETHOXYCYCLOBUTANE;AKOS BBS-00006459;CYCLOBUTANE-1,1-DICARBOXYLIC ACID DIETHYL ESTER;CYCLOBUTANE-1,1-DICARBOXYLIC ACID DIMETHYL ESTER;DIETHYL 2,2-TRIMETHYLENEMALONATE;DIETHYL CYCLOBUTANE-1,1-DICARBOXYLATE;DIETHYL 1,1-CYCLOBUTANEDICARBOXYLATE
• CAS NO: 3779-29-1
• Molecular Formula: C₁₀H₁₆O₄
• Molecular Weight: 200.23
• EINECS: 223-239-4
• Product Categories: Pharmaceutical Intermediates;Cyclobutanes & Cyclobutenes;Simple 4-Membered Ring Compounds;Cycloalkanes;Intermediates & Fine Chemicals;Pharmaceuticals;Building Blocks;C10 to C11;Carbonyl Compounds;Chemical Synthesis;Esters;Organic Building Blocks;NULL
• Mol File: 3779-29-1.mol
• Article Data: 18

Chemical Properties

• Boiling Point: 104-105 °C12 mm Hg(lit.)
• Flash Point: 89°C
• Appearance: Colourless oil
• Density: 1.05 g/mL at 20 °C(lit.)
• Vapor Pressure: 0.0907mmHg at 25°C
• Refractive Index: 1.4360
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Chloroform, Dichloromethane, Methanol,
• Water Solubility: Insoluble in water.
• BRN: 2050195
• CAS DataBase Reference: Diethyl 1,1-cyclobutanedicarboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: Diethyl 1,1-cyclobutanedicarboxylate(3779-29-1)
• EPA Substance Registry System: Diethyl 1,1-cyclobutanedicarboxylate(3779-29-1)

Safety Data

• Statements: 36/37/38
• Safety Statements: 23-24/25
• WGK Germany: 3
• TSCA: Yes
• Hazardous Substances Data: 3779-29-1(Hazardous Substances Data)

Usage

Chemical Properties

Colourless Oil

Uses

Different sources of media describe the Uses of 3779-29-1 differently. You can refer to the following data:
1. Diethyl 1,1-cyclobutanedicarboxylate is used as a pharmaceutical intermediate. Used as intermediate in the production of Carboplatin.
2. Diethyl cyclobutane-1,1-dicarboxylate may be used in chemical synthesis studies.
3. Intermediate in the production of Carboplatin

Preparation

The preparation of diethyl 1,1-cyclobutanedicarboxylate is as follows:The major product is tetraethy1 1,1,5,5-pentanetetra-carboxylate II with diethyl malonate. To eliminate this side reaction, II was independently prepared by the addition of hydrogen bromide to diethyl allylmalonate (I) and then cyclized to II by treatment with sodium ethylate. The over-all yield from I is about 50%.

InChI:InChI=1/C10H16O4/c1-3-13-8(11)10(6-5-7-10)9(12)14-4-2/h3-7H2,1-2H3

Upstream product

• 18719-43-2 diethyl (3-chloropropyl)malonate 
• 10149-21-0 diethyl 2-(3-bromopropane)malonate 
• 141-52-6 sodium ethanolate 
• 64-17-5 ethanol 
• 5445-51-2 cyclobutane-1,1'-dicarboxylic acid 
• 5469-66-9 propane-1,3-diol ditosylate 
• 105-53-3 diethyl malonate 
• 996-82-7 sodium diethylmalonate 
• 109-64-8 1,3-dibromo-propane 
• 5162-44-7 1-bromo-4-butene 
• 28438-55-3 2-(3-Ethylsulfanyl-propyl)-malonic acid diethyl ester 
• 142-28-9 1,3-Dichloropropane 
• 109-70-6 1.3-chlorobromopropane 

Downstream Products

• 4415-82-1 cyclobutanemethanol 
• 4399-47-7 Bromocyclobutane 
• 77500-75-5 6-Phenyl-7-(pyridine-3-carbonyl)-6,7-diaza-spiro[3.4]octane-5,8-dione 
• 77500-73-3 6-(4-Nitro-benzoyl)-7-phenyl-6,7-diaza-spiro[3.4]octane-5,8-dione 
• 77500-74-4 6-(3,5-Dinitro-benzoyl)-7-phenyl-6,7-diaza-spiro[3.4]octane-5,8-dione 
• 57742-93-5 ethyl 1-formylcyclobutanecarboxylate 
• 1259489-92-3 N-Boc-2-azaspiro[3,3]heptane 
• 665-04-3 2-azaspiro[3.3]heptane 
• 28114-87-6 spiro<3.3>heptane-3-carboxylic acid 
• 64775-97-9 spiro[3.3]heptane-2,2-dicarboxylic acid 
• 1610455-66-7 C₁₃H₁₅ClO₂ 
• 1387563-26-9 C₁₃H₁₆O₃ 
• 114671-90-8 1-(hydroxymethyl)cyclobutanecarboxylic acid 
• 1610455-70-3 N-(4-cyano-2,3,5,6-tetrafluorophenyl)-1-((1,3-dioxoisoindolin-2-yl)methyl)cyclobutanecarboxamide 

Relevant articles and documents

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Preparation method of 1, 1-cycloalkane dicarboxylic acid and derivatives thereof

The invention discloses a preparation method of 1, 1-cycloalkane dicarboxylic acid and derivatives thereof, which at least comprises the following steps of: forming a mixed system from malonic acid or derivatives thereof, dihalogenated hydrocarbon, tert-butyl alcohol salt and a solvent in a reactor; AND according to the method, the raw material conversion rate and the product selectivity are improved, and side reactions are hardly generated.

Discovery of potent c-MET inhibitors with new scaffold having different quinazoline, pyridine and tetrahydro-pyridothienopyrimidine headgroups

Cellular mesenchymal-epithelial transition factor (c-MET) is closely linked to human malignancies, which makes it an important target for treatment of cancer. In this study, a series of 3-methoxy-N-phenylbenzamide derivatives, N-(3-(tert-butyl)-1-phenyl-1H-pyrazol-5-yl) benzamide derivatives and N1-(3-fluoro-4-methoxyphenyl)-N3-(4-fluorophenyl) malonamide derivatives were designed and synthesized, some of them were identified as c-MET inhibitors. Among these compounds with new scaffolds having different quinazoline, pyridine and tetrahydro-pyridothienopyrimidine head groups, compound 11c, 11i, 13b, 13h exhibited both potent inhibitory activities against c-MET and high anticancer activity against tested cancer cell lines in vitro. In addition, kinase selectivity assay further demonstrated that both 13b and 13h are potent and selective c-MET inhibitors. Molecular docking supported that they bound well to c-MET and VEGFR2, which demonstrates that they are potential c-MET RTK inhibitors for cancer therapy.