2,2-dimethyl-3(R)-hydroxy-5(R)-isopropylenecyclohexanone

Base Information

• Chemical Name: 2,2-dimethyl-3(R)-hydroxy-5(R)-isopropylenecyclohexanone
• CAS No.: 97643-04-4
• Molecular Formula: C₁₁H₁₈O₂
• Molecular Weight: 182.263
• Mol file: 97643-04-4.mol

Synonyms:2,2-dimethyl-3(R)-hydroxy-5(R)-isopropylenecyclohexanone

Chemical Property of 2,2-dimethyl-3(R)-hydroxy-5(R)-isopropylenecyclohexanone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of 2,2-dimethyl-3(R)-hydroxy-5(R)-isopropylenecyclohexanone

There total 5 articles about 2,2-dimethyl-3(R)-hydroxy-5(R)-isopropylenecyclohexanone 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: 61.0%

(1R,4R,6R)-4-isopropenyl-1-methyl-7-oxabicyclo[4.1.0]heptan-2-one (36616-60-1) + methyl iodide (74-88-4) → 2,2-dimethyl-3(R)-hydroxy-5(R)-isopropylenecyclohexanone (97643-04-4)

Guidance literature:

With ammonia; lithium; at -33 - 20 ℃; for 3h;

DOI:10.1080/00397910500180295

Reference yield:

2,3-epoxy-5-isopropenyl-2-methylcyclohexanone (677326-54-4) + methyl iodide (74-88-4) → (R)-Carvone (6485-40-1,2244-16-8) + 2,2-dimethyl-3(R)-hydroxy-5(R)-isopropylenecyclohexanone (97643-04-4) + (3R,5R)-3-hydroxy-2-methyl-5-(1-methylethenyl)cyclohexanone (97643-05-5)

Guidance literature:

With ammonia; lithium; Yield given. Multistep reaction. Yields of byproduct given; 1.) ether, -33 deg C, 70 min, 2.) -33 deg C, 15 min;

DOI:10.1021/jo00219a011

Reference yield:

(3R,5R)-3-hydroxy-2-methyl-5-(1-methylethenyl)cyclohexanone (97643-05-5) + methyl iodide (74-88-4) → 2,2-dimethyl-3(R)-hydroxy-5(R)-isopropylenecyclohexanone (97643-04-4)

Guidance literature:

In tetrahydrofuran;

DOI:10.1039/a904646a

upstream raw materials:

2,3-epoxy-5-isopropenyl-2-methylcyclohexanone

methyl iodide

(1R,4R,6R)-4-isopropenyl-1-methyl-7-oxabicyclo[4.1.0]heptan-2-one

(3R,5R)-3-hydroxy-2-methyl-5-(1-methylethenyl)cyclohexanone

Downstream raw materials:

(1R,3R,5R)-5-isopropenyl-1,2,2-trimethylcyclohexane-1,3-diol

(S)-1-Allyl-5-(2-hydroxy-2-methyl-pent-4-enyl)-2,6,6-trimethyl-5-trimethylsilanyloxy-cyclohex-2-enol

(3S,5S)-3-Benzyl-5-isopropenyl-2,2-dimethyl-3-trimethylsilanyloxy-cyclohexanone

(3S,5S,6R)-5-Isopropenyl-2,2,6-trimethyl-3-(2-oxo-propyl)-3-trimethylsilanyloxy-cyclohexanone

Refernces

• 1、 Mehta, Goverdhan,Chattopadhyay, Shital K.,Umarye, Jayant D.. "A new carvone based construction of the ring-A of taxoids". . p. 4881 - 4884. Retrieved 2007/10/03.
• 2、 McChesney, James D.,Thompson, Thomas N.. "Stereochemistry of the Reductive Alkylation of α,β-Epoxy Ketones". . p. 3473 - 3481. Retrieved 2007/10/02.