2-Epi-(-)-shyobunone

Base Information

• Chemical Name: 2-Epi-(-)-shyobunone
• CAS No.: 72258-67-4
• Molecular Formula: C₁₅H₂₄O
• Molecular Weight: 220.355
• Mol file: 72258-67-4.mol

Synonyms:

Chemical Property of 2-Epi-(-)-shyobunone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-Epi-(-)-shyobunone

There total 21 articles about 2-Epi-(-)-shyobunone 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: 62.0%

1,1-Ethylenedioxy-6β-isopropyl-2β-isopropenyl-3β-methyl-3α-vinylcyclohexane (74211-90-8) → (+/-)-Shyobunone (21698-44-2,39020-72-9,58437-65-3,58437-66-4,64141-34-0,65794-23-2,65830-01-5,69427-51-6,69427-52-7,72258-66-3,72258-67-4,74243-52-0)

Guidance literature:

With toluene-4-sulfonic acid; In water; acetone; for 12h; Ambient temperature;

Reference yield: 9.5%

(1S,2S,6S)-2-Isopropenyl-6-isopropyl-3-methyl-3-vinyl-cyclohexanol (35727-45-8,35727-46-9,69350-61-4,72258-63-0,72258-64-1,72258-65-2,74924-06-4,74924-07-5,74924-08-6) → 3-Epi-(-)-shyobunone (65830-01-5) + 2-Epi-(-)-shyobunone (72258-67-4) + (-)-Shyobunone (72258-66-3)

Guidance literature:

With jones reagent; In acetone; for 0.5h;

DOI:10.1021/jo01310a040

Reference yield:

1-methylcyclobutene (1489-60-7) → 2-Epi-(-)-shyobunone (72258-67-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 71 percent / CH₂Cl₂ / -78 °C / Irradiation

2: 70 percent / NaBH₄ / methanol / 16 h / Ambient temperature

3: xylene / 1 h / 190 °C

4: 7.6 percent / Jones reagent / acetone / 0.5 h

With sodium tetrahydroborate; jones reagent; In methanol; dichloromethane; acetone; xylene;

DOI:10.1021/jo01310a040

upstream raw materials:

8c-isopropyl-1,5-dimethyl-(1rH,2tH,5tH,6cH)-tricyclo[4.4.0.0^2,5]decan-7t-ol

1,1-Ethylenedioxy-6β-isopropyl-2β-isopropenyl-3β-methyl-3α-vinylcyclohexane

piperitone

6β-Isopropyl-3β-methyl-3α-vinylcyclohexanone

Refernces

• 1、 Williams, John R.,Callahan, James F.. "Photocycloaddition of Methylcyclobutene and (-)-Piperitone: Synthesis of (-)-Shyobunone and Related Sesquiterpenes". . p. 4475 - 4478. Retrieved 2007/10/02.