(1R)-2-endo-[(1R)-4-methylcyclohex-3-en-1-ylcarbonyl]-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ol

Base Information

• Chemical Name: (1R)-2-endo-[(1R)-4-methylcyclohex-3-en-1-ylcarbonyl]-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ol
• CAS No.: 465500-08-7
• Molecular Formula: C₁₈H₂₈O₂
• Molecular Weight: 276.419
• Mol file: 465500-08-7.mol

Synonyms:(1R)-2-endo-[(1R)-4-methylcyclohex-3-en-1-ylcarbonyl]-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ol

Chemical Property of (1R)-2-endo-[(1R)-4-methylcyclohex-3-en-1-ylcarbonyl]-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R)-2-endo-[(1R)-4-methylcyclohex-3-en-1-ylcarbonyl]-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ol

There total 2 articles about (1R)-2-endo-[(1R)-4-methylcyclohex-3-en-1-ylcarbonyl]-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ol 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: 91.0%

(1R)-2-endo-propenoyl-1,7,7-trimethylbicyclo[2.2.1]-heptan-2-ol (465500-02-1) + isoprene (78-79-5,9003-31-0) → ((1R,2R,4R)-2-Hydroxy-1,7,7-trimethyl-bicyclo[2.2.1]hept-2-yl)-((R)-3-methyl-cyclohex-3-enyl)-methanone + (1R)-2-endo-[(1R)-4-methylcyclohex-3-en-1-ylcarbonyl]-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ol (465500-08-7)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at -25 ℃; for 20h;

DOI:10.1021/ja025906e

Reference yield: 91.0%

(1R)-2-endo-propenoyl-1,7,7-trimethylbicyclo[2.2.1]-heptan-2-ol (465500-02-1) + isoprene (78-79-5,9003-31-0) → (1R)-2-endo-[(1R)-4-methylcyclohex-3-en-1-ylcarbonyl]-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ol (465500-08-7)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at -25 ℃; for 16h; optical yield given as %de; diastereoselective reaction; Inert atmosphere;

DOI:10.1021/jo9023039

Reference yield: 75.0%

n-butyllithium (109-72-8,29786-93-4) + (1R)-2-endo-[(1R)-4-methylcyclohex-3-en-1-ylcarbonyl]-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ol (465500-08-7) → butyl-[(1R)-4-methylcyclohex-3-enyl]ketone + (1R,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one (464-49-3,68546-28-1)

Guidance literature:

n-butyllithium; (1R)-2-endo-[(1R)-4-methylcyclohex-3-en-1-ylcarbonyl]-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ol; In tetrahydrofuran; hexane; at 0 ℃; for 1.5h;

With ammonium cerium(IV) nitrate; In water; acetonitrile; at 0 ℃; for 0.166667h;

DOI:10.1021/ja025906e

upstream raw materials:

(1R)-2-endo-propenoyl-1,7,7-trimethylbicyclo[2.2.1]-heptan-2-ol

isoprene

Downstream raw materials:

(1R,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one

methyl-[(1R)-4-methylcyclohex-3-enyl]ketone

(+)-(1R)-4-methyl-cyclohex-3-enecarboxylic acid

(1R)-2-endo-(E)-p-chlorocinnamoyl-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ol