Diethyl (3-oxopropyl)malonate

Base Information

• Chemical Name: Diethyl (3-oxopropyl)malonate
• CAS No.: 19515-61-8
• Molecular Formula: C10H16 O5
• Molecular Weight: 216.234
• Hs Code.: 2918300090
• European Community (EC) Number: 243-121-6
• UNII: 4X5K5KVC8U
• DSSTox Substance ID: DTXSID40173166
• Nikkaji Number: J242.839C
• Wikidata: Q83043244
• Mol file: 19515-61-8.mol

Synonyms:19515-61-8;diethyl 2-(3-oxopropyl)malonate;Diethyl (3-oxopropyl)malonate;diethyl 2-(3-oxopropyl)propanedioate;4X5K5KVC8U;1,3-DIETHYL 2-(3-OXOPROPYL)PROPANEDIOATE;EINECS 243-121-6;UNII-4X5K5KVC8U;SCHEMBL7337554;4,4-bis(ethoxycarbonyl)-butanal;DTXSID40173166;gamma,gamma-dicarbethoxybutyraldehyde;3-Oxopropylmalonic acid diethyl ester;AKOS000278819;FT-0666783;2-(3-oxo-propyl)-propanedioic acid diethyl ester;J-012640;PROPANEDIOIC ACID, 2-(3-OXOPROPYL)-, 1,3-DIETHYL ESTER

Chemical Property of Diethyl (3-oxopropyl)malonate

Chemical Property:

• Vapor Pressure: 0.000965mmHg at 25°C
• Boiling Point: 302.9°Cat760mmHg
• PKA: 12.46±0.59(Predicted)
• Flash Point: 130.4°C
• PSA: 69.67000
• Density: 1.09g/cm³
• LogP: 0.70790
• Storage Temp.: Refrigerator, Under Inert Atmosphere
• Solubility.: Chloroform, Methanol
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 9
• Exact Mass: 216.09977361
• Heavy Atom Count: 15
• Complexity: 206

Purity/Quality:

99% ^*data from raw suppliers

Diethyl2-(3-Oxopropyl)malonate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C(CCC=O)C(=O)OCC
• Uses: Diethyl 2-(3-Oxopropyl)malonate is used in the synthesis of methaprogerol analogs, as antiseptic agents. Also used in the synthesis of inhibitors of imidazole glycerol phosphate dehydratase.

Technology Process of Diethyl (3-oxopropyl)malonate

There total 11 articles about Diethyl (3-oxopropyl)malonate 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: 85.0%

acrolein (107-02-8,25068-14-8) + diethyl malonate (105-53-3) → diethyl 2-(3-oxo-propyl)malonate (19515-61-8)

Guidance literature:

With potassium carbonate; In dichloromethane; at 20 ℃;

DOI:10.1039/c2ob26423d

Reference yield:

Diethyl 2-bromomalonate (685-87-0) + acrolein (107-02-8,25068-14-8) → diethyl 2-(3-oxo-propyl)malonate (19515-61-8)

Guidance literature:

With tributyl-amine; In ethanol;

Reference yield:

acrolein (107-02-8,25068-14-8) + diethyl malonate (105-53-3) → diethyl 2-(3-oxo-propyl)malonate (19515-61-8) + 2-Allylidene-malonic acid diethyl ester (13654-26-7)

Guidance literature:

With potassium phosphate; In 1,4-dioxane; at 50 ℃; for 72h; Inert atmosphere;

DOI:10.1016/j.bioorg.2020.103846

upstream raw materials:

3-chloro-1,1-diethoxy-propane

sodium diethylmalonate

acrolein

diethyl malonate

Downstream raw materials:

Ethyl 2-ethoxycarbonyl-4-(1',3'-dioxolan-2'-yl)butanoate

(3-hydroxy-propyl)-malonic acid diethyl ester

(3S,5S,6R,9R,R_S)-3-benzyloxymethyl-9-hydroxymethyl-5-(p-tolyl)sulfinyl-1,7-dioxaspiro<5.5>undecane

[(3S,6R,9S,11S)-9-Benzyloxymethyl-11-((R)-toluene-4-sulfinyl)-1,7-dioxa-spiro[5.5]undec-3-yl]-methanol

Refernces

• 1、 Kryshtal,G.V. et al.. "-". . p. 107 - 109. Retrieved 1979.
• 2、 Kryshtal,Zhdankina,Astakhova,Zlotin. "Reactions of CH-acids with α,β-unsaturated aldehydes in ionic liquids". . p. 647 - 651. Retrieved 2004.
• 3、 Laszlo, Pierre,Pennetreau, Pascal. "CATALYSIS OF THE MICHAEL REACTION". . p. 2645 - 2648. Retrieved 1985.
• 4、 Chandan, Nandkishor,Thompson, Amber L.,Moloney, Mark G.. "Rapid synthesis of substituted pyrrolines and pyrrolidines by nucleophilic ring closure at activated oximes". supporting information. p. 7863 - 7868. Retrieved 2013/07/05.