rel-(2R,6R)-2-[(R)-3-Furanylhydroxymethyl]-2,6-dimethylcyclohexanone

Base Information

• Chemical Name: rel-(2R,6R)-2-[(R)-3-Furanylhydroxymethyl]-2,6-dimethylcyclohexanone
• CAS No.: 136587-14-9
• Molecular Formula: C₁₃H₁₈O₃
• Molecular Weight: 222.284
• DSSTox Substance ID: DTXSID701158368
• Mol file: 136587-14-9.mol

Synonyms:DTXSID701158368;rel-(2R,6R)-2-[(R)-3-Furanylhydroxymethyl]-2,6-dimethylcyclohexanone;136587-14-9

Chemical Property of rel-(2R,6R)-2-[(R)-3-Furanylhydroxymethyl]-2,6-dimethylcyclohexanone

Chemical Property:

• XLogP3: 2.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 222.125594432
• Heavy Atom Count: 16
• Complexity: 276

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1CCCC(C1=O)(C)C(C2=COC=C2)O
• Isomeric SMILES: C[C@@H]1CCC[C@](C1=O)(C)[C@@H](C2=COC=C2)O

Technology Process of rel-(2R,6R)-2-[(R)-3-Furanylhydroxymethyl]-2,6-dimethylcyclohexanone

There total 3 articles about rel-(2R,6R)-2-[(R)-3-Furanylhydroxymethyl]-2,6-dimethylcyclohexanone 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: 8.0%

furan-3-carboxaldehyde (498-60-2) + 2,6-dimethyl-1-(trimethylsiloxy)cyclohexene (63547-53-5) → (2RS,6SR)-2-<(RS)-3-furylhydroxymethyl>-2,6-dimethylcyclohexanone (136657-25-5) + (2RS,6RS)-2-<(RS)-3-furylhydroxymethyl>-2,6-dimethylcyclohexanone (136657-24-4) + (2RS,6SR)-2-<(SR)-3-furylhydroxymethyl>-2,6-dimethylcyclohexanone (136657-26-6) + (2RS,6RS)-2-<(SR)-3-furylhydroxymethyl>-2,6-dimethylcyclohexanone (136587-14-9)

Guidance literature:

With titanium tetrachloride; In dichloromethane; at -78 ℃; for 0.0166667h; Product distribution; other substrates, other reaction times; stereoselectivity;

DOI:10.1021/jo00025a025

Reference yield:

furan-3-carboxaldehyde (498-60-2) + 2,6-dimethylcyclohexanone (2816-57-1) → (2RS,6SR)-2-<(RS)-3-furylhydroxymethyl>-2,6-dimethylcyclohexanone (136657-25-5) + (2RS,6SR)-2-<(SR)-3-furylhydroxymethyl>-2,6-dimethylcyclohexanone (136657-26-6) + (2RS,6RS)-2-<(SR)-3-furylhydroxymethyl>-2,6-dimethylcyclohexanone (136587-14-9)

Guidance literature:

With lithium diisopropyl amide; Yield given. Multistep reaction. Yields of byproduct given; 1) ether, hexane, -78 deg C, 15 min, 1) 60 min;

DOI:10.1021/jo00025a025

Reference yield:

furan-3-carboxaldehyde (498-60-2) + 2,6-dimethylcyclohexanone (2816-57-1) → (2RS,6SR)-2-<(RS)-3-furylhydroxymethyl>-2,6-dimethylcyclohexanone (136657-25-5) + (2RS,6RS)-2-<(RS)-3-furylhydroxymethyl>-2,6-dimethylcyclohexanone (136657-24-4) + (2RS,6SR)-2-<(SR)-3-furylhydroxymethyl>-2,6-dimethylcyclohexanone (136657-26-6) + (2RS,6RS)-2-<(SR)-3-furylhydroxymethyl>-2,6-dimethylcyclohexanone (136587-14-9)

Guidance literature:

With lithium diisopropyl amide; Yield given. Multistep reaction. Yields of byproduct given; 1) ether, hexane, -78 deg C, 15 min, 2) 60 min;

DOI:10.1021/jo00025a025

upstream raw materials:

furan-3-carboxaldehyde

2,6-dimethylcyclohexanone

2,6-dimethyl-1-(trimethylsiloxy)cyclohexene

Downstream raw materials:

dl-pyroangolensolide

(1RS,5RS,8aRS)-1-(3-furyl)-5,8a-dimethyl-5-(benzylseleno)-1,5,6,7,8,8a-hexahydro-3H-2-benzopyran-3-one

(1RS,4SR,8aRS)-2-(3-furyl)-5,8a-dimethyl-4-(benzylseleno)-3,4,6,7,8,8a-hexahydro-1H-2-benzopyran-3-one

(1RS,5SR,8aRS)-1-(3-furyl)-5,8a-dimethyl-1,5,6,7,8,8a-hexahydro-3H-2-benzopyran-3-one