Cyclohexanone, 2,3-dimethyl-2-(3-oxobutyl)-, (2S,3R)-

Base Information

• Chemical Name: Cyclohexanone, 2,3-dimethyl-2-(3-oxobutyl)-, (2S,3R)-
• CAS No.: 184653-52-9
• Molecular Formula: C₁₂H₂₀O₂
• Molecular Weight: 196.29
• DSSTox Substance ID: DTXSID80452563
• Nikkaji Number: J1.613.773A
• Wikidata: Q82273274
• Mol file: 184653-52-9.mol

Synonyms:184653-52-9;Cyclohexanone, 2,3-dimethyl-2-(3-oxobutyl)-, (2S,3R)-;DTXSID80452563;2alpha,3alpha-Dimethyl-2-(3-oxobutyl)cyclohexane-1-one

Chemical Property of Cyclohexanone, 2,3-dimethyl-2-(3-oxobutyl)-, (2S,3R)-

Chemical Property:

• PSA: 34.14000
• LogP: 2.75100
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 196.146329876
• Heavy Atom Count: 14
• Complexity: 245

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1CCCC(=O)C1(C)CCC(=O)C
• Isomeric SMILES: C[C@@H]1CCCC(=O)[C@@]1(C)CCC(=O)C

Technology Process of Cyclohexanone, 2,3-dimethyl-2-(3-oxobutyl)-, (2S,3R)-

There total 8 articles about Cyclohexanone, 2,3-dimethyl-2-(3-oxobutyl)-, (2S,3R)- 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:

2-methyl-2-vinyl-1,3-dioxolane (26924-35-6) + (R)-(2,3-dimethylcyclohex-1-enyloxy)trimethylsilane (184422-45-5) → (2S,3R)-2,3-Dimethyl-2-(3-oxo-butyl)-cyclohexanone (184653-52-9)

Guidance literature:

With titanium(IV) isopropylate; titanium tetrachloride; In dichloromethane; at -78 ℃;

DOI:10.1016/0957-4166(96)00370-9

Reference yield:

methyl vinyl ketone (78-94-4,25038-87-3) + [(R)-2,3-Dimethyl-cyclohex-(E)-ylidene]-((S)-1-phenyl-ethyl)-amine → (2S,3R)-2,3-Dimethyl-2-(3-oxo-butyl)-cyclohexanone (184653-52-9) + (R)-2,3-Dimethyl-6-(3-oxo-butyl)-cyclohexanone

Guidance literature:

methyl vinyl ketone; [(R)-2,3-Dimethyl-cyclohex-(E)-ylidene]-((S)-1-phenyl-ethyl)-amine; In tetrahydrofuran; at 20 ℃; for 72h;

With acetic acid; In tetrahydrofuran; at 20 ℃; for 1.5h; Title compound not separated from byproducts;

DOI:10.1016/S0957-4166(01)00089-1

Reference yield:

(2RS,3R)-2,3-dimethylcyclohexanone (234078-11-6) → (2S,3R)-2,3-Dimethyl-2-(3-oxo-butyl)-cyclohexanone (184653-52-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 82 percent / p-toluenesulfonic acid / benzene / 5 h / Heating

2.1: tetrahydrofuran / 72 h / 20 °C

2.2: aq. AcOH / tetrahydrofuran / 1.5 h / 20 °C

With toluene-4-sulfonic acid; In tetrahydrofuran; benzene; 2.1: Michael addition;

DOI:10.1016/S0957-4166(01)00089-1

upstream raw materials:

2-methyl-2-vinyl-1,3-dioxolane

(R)-(2,3-dimethylcyclohex-1-enyloxy)trimethylsilane

(4aS,5R)-3,4,4a,5,6,7-hexahydro-4a,5-dimethyl-2H-1-benzopyran-2-one

methyllithium

Refernces

• 1、 Cuesta, Xavier,Gonzalez, Asensio,Bonjoch, Josep. "First stereoselective synthesis of (4aS,5R)-4,4a,5,6,7,8-hexahydro-4a,5- dimethyl-2(3H)-naphthalenone". . p. 3365 - 3370. Retrieved 2007/10/03.