Methyl alpha-methyl-3-oxocyclohexaneacetate

Base Information

• Chemical Name: Methyl alpha-methyl-3-oxocyclohexaneacetate
• CAS No.: 82423-69-6
• Molecular Formula: C₁₀H₁₆O₃
• Molecular Weight: 184.235
• DSSTox Substance ID: DTXSID101280268
• Mol file: 82423-69-6.mol

Synonyms:Methyl alpha-methyl-3-oxocyclohexaneacetate;DTXSID101280268;82423-69-6

Chemical Property of Methyl alpha-methyl-3-oxocyclohexaneacetate

Chemical Property:

• XLogP3: 1.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 184.109944368
• Heavy Atom Count: 13
• Complexity: 210

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(C1CCCC(=O)C1)C(=O)OC

Technology Process of Methyl alpha-methyl-3-oxocyclohexaneacetate

There total 9 articles about Methyl alpha-methyl-3-oxocyclohexaneacetate 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: 87.0%

methyl 2-(3-trimethylsiloxycyclohex-2-enyl)propionate (77086-39-6) → methyl 2-(3-oxocyclohexyl)propionate (82423-69-6)

Guidance literature:

With hydrogenchloride; In diethyl ether; for 24h; Ambient temperature;

Reference yield: 54.0%

methanol (67-56-1) + C23H25NO4S → C16H21NO5S (1239945-49-3) + 3,1'-syn-3-<1'-(carbomethoxy)ethyl>-1-cyclohexanone (82423-69-6,89597-25-1,89597-44-4,136426-01-2,136426-02-3)

Guidance literature:

With chloro-trimethyl-silane; water; Reflux; Inert atmosphere;

DOI:10.1021/ol101418d

Reference yield: 19.0%

methyl 2-(3-trimethylsiloxycyclohex-2-enyl)propionate (77086-39-6) + allyl bromide (106-95-6) → methyl 2-(3-oxocyclohexyl)propionate (82423-69-6) + 2-(2-Allyl-3-oxo-cyclohexyl)-propionic acid methyl ester (89597-39-7,89673-91-6)

Guidance literature:

With tris(dimethylamino)sulfonium trimethylsilyldifluoride; In tetrahydrofuran; acetonitrile; 1) -78 deg C, 2h, 2) RT;

DOI:10.1021/jo00186a001

upstream raw materials:

methyl 2-(3-trimethylsiloxycyclohex-2-enyl)propionate

allyl bromide

3,1'-anti-3-<1'-(carbomethoxy)ethyl>-1-<(trimethylsilyl)oxy>-1-cyclohexene

cyclohexenone

Downstream raw materials:

(+/-)-Santonin-A

(+/-)-Santonin-B

(+/-)-Dihydrosantonin-A

(+/-)-Dihydrosantonin-B