Tetramethyl 3,3-dimethylcyclopropane-1,1,2,2-tetracarboxylate

Base Information

• Chemical Name: Tetramethyl 3,3-dimethylcyclopropane-1,1,2,2-tetracarboxylate
• CAS No.: 92157-77-2
• Molecular Formula: C₁₃H₁₈O₈
• Molecular Weight: 302.281
• NSC Number: 98395
• DSSTox Substance ID: DTXSID20294848
• Wikidata: Q82034418

Synonyms:92157-77-2;tetramethyl 3,3-dimethylcyclopropane-1,1,2,2-tetracarboxylate;NSC98395;Oprea1_715271;CBDivE_000433;DTXSID20294848;HMS1577N03;NSC-98395;SR-01000195372;SR-01000195372-1;Tetramethyl 3,3-dimethyl-1,1,2,2-cyclopropanetetracarboxylate

Chemical Property of Tetramethyl 3,3-dimethylcyclopropane-1,1,2,2-tetracarboxylate

Chemical Property:

• Vapor Pressure: 7.74E-05mmHg at 25°C
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 8
• Exact Mass: 302.10016753
• Heavy Atom Count: 21
• Complexity: 428

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1(C(C1(C(=O)OC)C(=O)OC)(C(=O)OC)C(=O)OC)C

Technology Process of Tetramethyl 3,3-dimethylcyclopropane-1,1,2,2-tetracarboxylate

There total 6 articles about Tetramethyl 3,3-dimethylcyclopropane-1,1,2,2-tetracarboxylate 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: 83.0%

2,4-Bis-methoxycarbonyl-3,3-dimethyl-pentanedioic acid dimethyl ester (110622-26-9) → tetramethyl ester of 3,3-dimethylcyclopropane-1,1,2,2-tetracarboxylic acid (92157-77-2)

Guidance literature:

With sodium iodide; In methanol; at 45 ℃; electrolysis, 220 mA/cm², 5.5 F/mole, Pt anode, iron cathode;

DOI:10.1007/BF00953888

Reference yield:

2,4-Bis-methoxycarbonyl-3,3-dimethyl-pentanedioic acid dimethyl ester (110622-26-9) → dimethyl isopropylidenemalonate (22035-53-6) + tetramethyl ester of 3,3-dimethylcyclopropane-1,1,2,2-tetracarboxylic acid (92157-77-2)

Guidance literature:

With sodium iodide; In methanol; at 30 ℃; electrolysis (Pt vs. Fe) with current density of 220 mA/cm², amount 2F;

DOI:10.1007/BF01184531

Reference yield:

3,6,6-trimethyl-5-methylcarbamoyl-2,4-dioxo-3-aza-bicyclo[3.1.0]hexane-1-carboxylic acid methyl ester (92848-50-5) → tetramethyl ester of 3,3-dimethylcyclopropane-1,1,2,2-tetracarboxylic acid (92157-77-2)

Guidance literature:

Multi-step reaction with 2 steps

1: aq. NaOH

With sodium hydroxide;

DOI:10.1021/ja00891a027

upstream raw materials:

diazomethane

3,3-Dimethyl-cyclopropan-1,1,2,2-tetracarbonsaeure

2,4-Bis-methoxycarbonyl-3,3-dimethyl-pentanedioic acid dimethyl ester

dimethyl isopropylidenemalonate

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