1,1-Diethyl 3-oxocyclobutane-1,1-dicarboxylate

Base Information

• Chemical Name: 1,1-Diethyl 3-oxocyclobutane-1,1-dicarboxylate
• CAS No.: 99173-61-2
• Molecular Formula: C10H14O5
• Molecular Weight: 214.218
• DSSTox Substance ID: DTXSID10563393
• Wikidata: Q82447824
• Mol file: 99173-61-2.mol

Synonyms:1,1-Diethyl 3-oxocyclobutane-1,1-dicarboxylate;99173-61-2;diethyl 3-oxocyclobutane-1,1-dicarboxylate;1,1-Cyclobutanedicarboxylic acid, 3-oxo-, diethyl ester;MFCD20928423;SCHEMBL3147434;DTXSID10563393;RNEYQVYRVAVAIF-UHFFFAOYSA-N;ZDA17361;AKOS010209398;SB11001;AS-51533;SY098887;CS-0052769;diethyl 3-oxo-cyclobutane-1,1-dicarboxylate;1,1-Diethyl3-oxocyclobutane-1,1-dicarboxylate;P12892;3-Oxo-cyclobutane-1,1-dicarboxylic acid diethyl ester;3-oxocyclobutane-1,1-dicarboxylic acid diethyl ester

Chemical Property of 1,1-Diethyl 3-oxocyclobutane-1,1-dicarboxylate

Chemical Property:

• Boiling Point: 128 °C(Press: 4 Torr)
• PSA: 69.67000
• Density: 1.230±0.06 g/cm3(Predicted)
• LogP: 0.46190
• XLogP3: 0.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 6
• Exact Mass: 214.08412354
• Heavy Atom Count: 15
• Complexity: 266

Purity/Quality:

99% ^*data from raw suppliers

1,1-Diethyl3-oxocyclobutane-1,1-dicarboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1(CC(=O)C1)C(=O)OCC

Technology Process of 1,1-Diethyl 3-oxocyclobutane-1,1-dicarboxylate

There total 3 articles about 1,1-Diethyl 3-oxocyclobutane-1,1-dicarboxylate 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: 96.0%

diethyl 3-hydroxycyclobutane-1,1-dicarboxylate (99974-66-0) → diethyl 3-oxo-cyclobutane-1,1-dicarboxylate (99173-61-2)

Guidance literature:

diethyl 3-hydroxycyclobutane-1,1-dicarboxylate; With Dess-Martin periodane; In dichloromethane; at 20 ℃; for 2h;

With sodium hydrogencarbonate; sodium thiosulfate; In dichloromethane; water; for 0.666667h;

Reference yield:

diethyl 3-(benzyloxy)cyclobutane-1,1-dicarboxylate (54166-15-3) → diethyl 3-oxo-cyclobutane-1,1-dicarboxylate (99173-61-2)

Guidance literature:

Multi-step reaction with 2 steps

1: H₂ / 10percent Pd/C / ethanol / 760 Torr

2: 92 percent / sodium metaperiodate, RuO₄ / H₂O; CCl₄ / 24 h

With sodium periodate; ruthenium tetroxide; hydrogen; palladium on activated charcoal; In tetrachloromethane; ethanol; water;

DOI:10.1021/jm00172a036

Reference yield:

diethyl malonate (105-53-3) → diethyl 3-oxo-cyclobutane-1,1-dicarboxylate (99173-61-2)

Guidance literature:

Multi-step reaction with 3 steps

1: sodium ethylate; benzene / 170 °C

2: palladium; ethanol / Hydrogenation

3: CrO₃; pyridine

With pyridine; chromium(VI) oxide; ethanol; sodium ethanolate; palladium; benzene;

upstream raw materials:

diethyl 3-hydroxycyclobutane-1,1-dicarboxylate

diethyl 3-(benzyloxy)cyclobutane-1,1-dicarboxylate

diethyl malonate

Downstream raw materials:

(+/-)-1-amino-3-(phosphonomethylene)cyclobutanecarboxylic acid

3-aminocyclobutane-1,1,3-tricarboxylic acid

C₁₃H₁₉NO₂

C₆H₁₃NO₂

Refernces

• 1、 Tian, Wen,He, Ling. "Synthesis and anticancer activity of diam(m)ine platinum(II) complexes with 3-oxo-cyclobutane-1,1-dicarboxylate as the leaving group". . p. 8725 - 8733. Retrieved 2015/02/19.
• 2、 -. "COMPOUNDS AND COMPOSITIONS AS C-KIT KINASE INHIBITORS". Paragraph 0543-0551. . Retrieved 2013/03/26.