Methyl 2,2-dimethyl-3-oxocyclobutanecarboxylate

Base Information

• Chemical Name: Methyl 2,2-dimethyl-3-oxocyclobutanecarboxylate
• CAS No.: 78685-51-5
• Molecular Formula: C8H12O3
• Molecular Weight: 156.17900
• Hs Code.: 2916200090
• European Community (EC) Number: 873-841-1
• Mol file: 78685-51-5.mol

Synonyms:78685-51-5;METHYL 2,2-DIMETHYL-3-OXOCYCLOBUTANECARBOXYLATE;methyl 2,2-dimethyl-3-oxocyclobutane-1-carboxylate;Cyclobutanecarboxylic acid, 2,2-dimethyl-3-oxo-, methyl ester;SCHEMBL15549635;GYEUKBYFWMJNSM-UHFFFAOYSA-N;MFCD21332873;AKOS025291194;PB31192;AS-51541;CS-0049193;FT-0738135;P12907;EN300-1664924;METHYL2,2-DIMETHYL-3-OXOCYCLOBUTANECARBOXYLATE

Chemical Property of Methyl 2,2-dimethyl-3-oxocyclobutanecarboxylate

Chemical Property:

• PSA: 43.37000
• LogP: 0.77460
• XLogP3: 0.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 156.078644241
• Heavy Atom Count: 11
• Complexity: 205

Purity/Quality:

99% ^*data from raw suppliers

Methyl2,2-Dimethyl-3-oxocyclobutanecarboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of Methyl 2,2-dimethyl-3-oxocyclobutanecarboxylate

There total 1 articles about Methyl 2,2-dimethyl-3-oxocyclobutanecarboxylate 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: 66.0%

1-chloro-1-(dimethylamino)-2-methyl-1-propene (26189-59-3) + acrylic acid methyl ester (292638-85-8,9003-21-8,96-33-3) → 2,2-dimethyl-3-oxo-cyclobutanecarboxylic acid methyl ester (78685-51-5,527751-17-3)

Guidance literature:

1-chloro-1-(dimethylamino)-2-methyl-1-propene; acrylic acid methyl ester; With zinc trifluoromethanesulfonate; at 35 ℃; for 6h; Neat (no solvent); Microwave irradiation;

With water; In tetrahydrofuran; for 1h;

DOI:10.1021/jo102257k

Reference yield: 91.0%

2,2-dimethyl-3-oxo-cyclobutanecarboxylic acid methyl ester (78685-51-5,527751-17-3) → 2,2-dimethyl-3-oxocyclobutanecarboxylic acid (3183-43-5)

Guidance literature:

2,2-dimethyl-3-oxo-cyclobutanecarboxylic acid methyl ester; With water; lithium hydroxide; In tetrahydrofuran; at 23 ℃; for 18h; Inert atmosphere;

With hydrogenchloride; In tetrahydrofuran; at 0 ℃; for 0.0833333h;

DOI:10.1021/jo102257k

Reference yield:

2,2-dimethyl-3-oxo-cyclobutanecarboxylic acid methyl ester (78685-51-5,527751-17-3) → tert-butyl ((1S,3S)-3-((2-((3-chlorophenethyl)amino)-5-cyanopyrimidin-4-yl)amino)-2,2-dimethylcyclobutyl)carbamate

Guidance literature:

Multi-step reaction with 6 steps

1.1: sodium hydroxide; water / methanol / 2 h / 50 °C

2.1: triethylamine; diphenyl phosphoryl azide / toluene / 4 h / 0 - 100 °C / Reflux

2.2: 15 h / Reflux

3.1: hydroxylamine hydrochloride; sodium carbonate / water; methanol / 20 °C

4.1: ammonia; hydrogen / methanol / 20 °C

5.1: N-ethyl-N,N-diisopropylamine / 1,4-dioxane / 5 h / 125 °C / Microwave irradiation

6.1: chiral column: OJ / methanol; carbon dioxide; diethylamine / 35 °C / Supercritical conditions; Resolution of racemate; liquid CO₂

With diphenyl phosphoryl azide; hydroxylamine hydrochloride; ammonia; water; hydrogen; sodium carbonate; triethylamine; N-ethyl-N,N-diisopropylamine; sodium hydroxide; In 1,4-dioxane; methanol; carbon dioxide; water; diethylamine; toluene;

upstream raw materials:

1-chloro-1-(dimethylamino)-2-methyl-1-propene

acrylic acid methyl ester

Downstream raw materials:

2,2-dimethyl-3-oxocyclobutanecarboxylic acid

tert-butyl (2,2-dimethyl-3-oxocyclobutyl)carbamate

tert-butyl (3-hydroxy-2,2-dimethylcyclobutyl)carbamate

3-amino-2,2-dimethylcyclobutanol

Refernces

• 1、 -. "HETEROARYLDIHYDROPYRIMIDINE DERIVATIVES AND METHODS OF TREATING HEPATITIS B INFECTIONS". Page/Page column 79. . Retrieved 2019/01/17.
• 2、 O'Brien, Jeannette M.,Kingsbury, Jason S.. "A Practical synthesis of 3-Acyl cyclobutanones by [2 〈 2] annulation. Mechanism and utility of the zn(II)-Catalyzed condensation of r-Chloroenamines with electron-deficient alkenes". experimental part. p. 1662 - 1672. Retrieved 2011/05/12.