5alpha-(tert-Butyldimethylsiloxy)-2-cyclohexen-1-one

Base Information

• Chemical Name: 5alpha-(tert-Butyldimethylsiloxy)-2-cyclohexen-1-one
• CAS No.: 199613-48-4
• Molecular Formula: C12H22O2Si
• Molecular Weight: 226.391
• DSSTox Substance ID: DTXSID30456233
• Nikkaji Number: J904.418C
• Wikidata: Q82278523
• Mol file: 199613-48-4.mol

Synonyms:199613-48-4;5alpha-(tert-Butyldimethylsiloxy)-2-cyclohexen-1-one;SCHEMBL4495874;DTXSID30456233;(5S)-5-[tert-butyl(dimethyl)silyl]oxycyclohex-2-en-1-one

Chemical Property of 5alpha-(tert-Butyldimethylsiloxy)-2-cyclohexen-1-one

Chemical Property:

• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 226.138906475
• Heavy Atom Count: 15
• Complexity: 274

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)[Si](C)(C)OC1CC=CC(=O)C1
• Isomeric SMILES: CC(C)(C)[Si](C)(C)O[C@H]1CC=CC(=O)C1

Technology Process of 5alpha-(tert-Butyldimethylsiloxy)-2-cyclohexen-1-one

There total 32 articles about 5alpha-(tert-Butyldimethylsiloxy)-2-cyclohexen-1-one 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: 95.0%

(1R,5S)-3-oxo-5-(tert-butyldimethylsilyloxy)cyclohexyl acetate (373640-23-4) → 5-tert-butyl-dimethylsilyloxy-(5S)-2-cyclohexenone (199613-48-4)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; for 2h;

DOI:10.1021/jo016141g

Reference yield: 91.0%

(1S,3S,5R)-1-hydroxy-3-(p-toluenesulfonyloxy)-5-(tert-butyldimethylsilyloxy)cyclohexane → 5-tert-butyl-dimethylsilyloxy-(5S)-2-cyclohexenone (199613-48-4)

Guidance literature:

(1S,3S,5R)-1-hydroxy-3-(p-toluenesulfonyloxy)-5-(tert-butyldimethylsilyloxy)cyclohexane; With 2-azatricyclo[3.3.1.1^3,7]dec-2-yloxidanyl; [bis(acetoxy)iodo]benzene; In aq. phosphate buffer; acetonitrile; at 0 - 20 ℃; for 2h; pH=7.4;

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 20 ℃; for 1.5h; Inert atmosphere;

DOI:10.1055/s-0036-1588878

Reference yield: 90.0%

(1RS,3S)-1-hydroxy-3-(tert-butyldimethylsiloxy)bicyclo<3.1.0>hexane (199613-50-8) → 5-tert-butyl-dimethylsilyloxy-(5S)-2-cyclohexenone (199613-48-4)

Guidance literature:

(1RS,3S)-1-hydroxy-3-(tert-butyldimethylsiloxy)bicyclo<3.1.0>hexane; With pyridine; iron(III) chloride; In N,N-dimethyl-formamide;

With sodium acetate; In methanol;

DOI:10.1016/S0040-4039(01)01014-0

upstream raw materials:

(R)-3-(tert-Butyl-dimethyl-silanyloxy)-5-chloro-cyclohexanone

(1RS,3S)-1-hydroxy-3-(tert-butyldimethylsiloxy)bicyclo<3.1.0>hexane

(1R,5S)-3-oxo-5-(tert-butyldimethylsilyloxy)cyclohexyl acetate

tert-butyldimethylsilyl chloride

Refernces

• 1、 Ochi, Yuji,Yokoshima, Satoshi,Fukuyama, Tohru. "Total Synthesis of Lycopalhine A". . p. 96 - 114. Retrieved 2016/12/24.
• 2、 Nicolaou,Yee, Hwee Lim,Piper, Jared L.,Papageorgiou, Charles D.. "Total syntheses of 2,2′-epi-cytoskyrin A, rugulosin, and the alleged structure of rugulin". . p. 4001 - 4013. Retrieved 2008/02/04.