168416-22-6

Basic information

• Product Name: <(R,S)-2-<13CD3>>-2,2,6-trimethylcyclohexanone
• Synonyms: <(R,S)-2-<13CD3>>-2,2,6-trimethylcyclohexanone
• CAS NO: 168416-22-6
• Molecular Weight: 144.191
• Mol File: 168416-22-6.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: <(R,S)-2-<13CD3>>-2,2,6-trimethylcyclohexanone(CAS DataBase Reference)
• NIST Chemistry Reference: <(R,S)-2-<13CD3>>-2,2,6-trimethylcyclohexanone(168416-22-6)
• EPA Substance Registry System: <(R,S)-2-<13CD3>>-2,2,6-trimethylcyclohexanone(168416-22-6)

Safety Data

• Hazardous Substances Data: 168416-22-6(Hazardous Substances Data)

Upstream product

• 2816-57-1 2,6-dimethylcyclohexanone 
• 20710-47-8 [13C₂H₃] methyl iodide 

Downstream Products

• 168416-28-2 ethyl (R,S)-(2E,4E,6Z,8E)-3,7-dimethyl-9-(6-<13CD3>-2,6,6-trimethylcyclohex-1-en-1-yl)nonatetraenoate 
• 168416-26-0 C₁₄⁽¹³⁾CH₂₁⁽²⁾H₃O₂ 
• 168416-25-9 (R,S)-5,6-dihydro-4-methyl-6-<6-<13CD3>-2,6,6-trimethylcyclohex-1-en-1-yl>-2H-pyran-2-one 
• 168416-27-1 (R,S)-(2Z,4E)-3-methyl-5-(6-<13CD3>-2,6,6-trimethylcyclohex-1-en-1-yl)-2,4-pentadienenal 
• 168416-24-8 <(R,S)-6-<13CD3>>-2,6,6-trimethyl-1-cyclohexene-1-aldehyde 

Relevant articles and documents

Synthesis of 1-[13CD3]-9-cis-retinoic acid

1-[13CD3]-9-cis-Retinoic acid was prepared in 8 steps from 2,6-dimethylcyclohexanone. Alkylation of 2,6-dimethylcyclohexanone under LiHMDS/MnBr2/13CD3I gave the corresponding labeled 2-[13CD3]-2,2,6-trimethylcyclohexanone 4 in good yield. Further functionalization of 4 to 6-[13CD3]-β-cyclocitral 6 proceeded through a Shapiro reaction. Aldehyde 6 was condensed with ethyl 3,3-dimethylacrylate to afford the corresponding bicyclic pyranone 7. Reduction of 7 to lactol 8, followed by acid-catalyzed ring opening gave the 9-cis-aldehyde 9. Wittig-Horner olefination and saponification afforded the title compound in good overall yield and in excellent isotopic purity.