(3S,8aα)-2,3,4,5,6,7,8,8a-Octahydro-3α,8,8-trimethyl-1H-3aα,6α-methanoazulen-7β-ol

Base Information

• Chemical Name: (3S,8aα)-2,3,4,5,6,7,8,8a-Octahydro-3α,8,8-trimethyl-1H-3aα,6α-methanoazulen-7β-ol
• CAS No.: 86703-03-9
• Molecular Formula: C₁₅H₂₆O
• Molecular Weight: 222.371
• Mol file: 86703-03-9.mol

Synonyms:

Chemical Property of (3S,8aα)-2,3,4,5,6,7,8,8a-Octahydro-3α,8,8-trimethyl-1H-3aα,6α-methanoazulen-7β-ol

Chemical Property:

• PSA: 20.23000
• LogP: 3.46730

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,8aα)-2,3,4,5,6,7,8,8a-Octahydro-3α,8,8-trimethyl-1H-3aα,6α-methanoazulen-7β-ol

There total 21 articles about (3S,8aα)-2,3,4,5,6,7,8,8a-Octahydro-3α,8,8-trimethyl-1H-3aα,6α-methanoazulen-7β-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:

tricyclo<7.2.1.01,6>dodec-6-en-8-one → (+/-)-jinkohol II (86703-03-9)

Guidance literature:

Multi-step reaction with 20 steps

1: 1.) KOBu-t / 1) tert-butyl alcohol, benzene; 2) tert-butyl alcohol, benzene, reflux, 2 h, room temperature, 6 h

2: NaBH₄ / ethanol / 2 h / Ambient temperature

3: 98 percent / NaH, tetrabutylammonium iodide / tetrahydrofuran / 1) 0 deg C --> room temperature, 1 h; 2) room temperature, 24 h

4: 1.) BH₃*THF, 2.) aq. NaOH, aq. H₂O₂ / 1) THF, 0 deg C --> room temperature; room temperature, 5 h; 2) THF, cooling, 3 h

5: 100 percent / pyridinium chlorochromate / CH₂Cl₂ / 1 h / Ambient temperature

6: 1.) aq. NaOH / 1) ethanol, 0 deg C, 30 min; 2) ethanol, room temperature, 7 h

7: 1.) O₃; 2) aq. H₂O₂, dil. H₂SO₄ / 1) -78 deg C, ethyl acetate; 2) acetic acid, overnight

8: 70 percent / diethyl ether

9: 78 percent / KOBu-t / benzene; 2-methyl-propan-2-ol / 6 h / Heating

10: 1.) NaH, 2.) PhSeCl, 3.) aq. H₂O₂ / 1) THF, 0 deg C, 25 min; 2) THF, 15 min; 3) CH₂Cl₂, 5 deg C, 10 min, 5 deg C --> room temperature, 15 min

11: 1) CuI / 1) diethyl ether, 0 deg C, 5 min; 2) diethyl ether, 30 min

12: 84 percent / 1,4-diazobicyclo<2.2.2>octane / xylene / 7 h / 85 °C

13: 93 percent / diisobutylaluminium hydride / hexane; tetrahydrofuran / 1) -78 deg C, 1 h; 2) room temperature, 1 h

14: 1.) NaH, imidazole / 1) THF, reflux, 2 h; 2) THF, reflux, 45 min; 3) THF, reflux, 30 min

15: 91 percent / tributyltin hydride, azoisobutyronitrile / toluene / 11 h / Heating

16: H₂ / Pd/C / ethanol / 2 h

17: pyridinium dichromate / CH₂Cl₂ / 2 h

18: 88 percent

19: 76 percent / Et₃N, MeSO₂Cl / CH₂Cl₂

20: 1.) BH₃*THF, 2.) aq. NaOH, aq. H₂O₂ / 1) THF, 0 deg C, 30 min, room temperature, 2 h; 2) THF, 30 min

With 1,4-diaza-bicyclo[2.2.2]octane; 1H-imidazole; sodium hydroxide; sodium tetrahydroborate; copper(l) iodide; dipyridinium dichromate; Phenylselenyl chloride; borane-THF; 2,2'-azobis(isobutyronitrile); sulfuric acid; potassium tert-butylate; hydrogen; dihydrogen peroxide; tri-n-butyl-tin hydride; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; ozone; methanesulfonyl chloride; triethylamine; pyridinium chlorochromate; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; ethanol; hexane; dichloromethane; toluene; xylene; tert-butyl alcohol; benzene;

Reference yield:

(4aR,7S,8S)-9,9-Dimethyl-2,3,4,5,6,7,8,9-octahydro-4a,7-methano-benzocyclohepten-8-ol → (+/-)-jinkohol II (86703-03-9)

Guidance literature:

Multi-step reaction with 18 steps

1: 98 percent / NaH, tetrabutylammonium iodide / tetrahydrofuran / 1) 0 deg C --> room temperature, 1 h; 2) room temperature, 24 h

2: 1.) BH₃*THF, 2.) aq. NaOH, aq. H₂O₂ / 1) THF, 0 deg C --> room temperature; room temperature, 5 h; 2) THF, cooling, 3 h

3: 100 percent / pyridinium chlorochromate / CH₂Cl₂ / 1 h / Ambient temperature

4: 1.) aq. NaOH / 1) ethanol, 0 deg C, 30 min; 2) ethanol, room temperature, 7 h

5: 1.) O₃; 2) aq. H₂O₂, dil. H₂SO₄ / 1) -78 deg C, ethyl acetate; 2) acetic acid, overnight

6: 70 percent / diethyl ether

7: 78 percent / KOBu-t / benzene; 2-methyl-propan-2-ol / 6 h / Heating

8: 1.) NaH, 2.) PhSeCl, 3.) aq. H₂O₂ / 1) THF, 0 deg C, 25 min; 2) THF, 15 min; 3) CH₂Cl₂, 5 deg C, 10 min, 5 deg C --> room temperature, 15 min

9: 1) CuI / 1) diethyl ether, 0 deg C, 5 min; 2) diethyl ether, 30 min

10: 84 percent / 1,4-diazobicyclo<2.2.2>octane / xylene / 7 h / 85 °C

11: 93 percent / diisobutylaluminium hydride / hexane; tetrahydrofuran / 1) -78 deg C, 1 h; 2) room temperature, 1 h

12: 1.) NaH, imidazole / 1) THF, reflux, 2 h; 2) THF, reflux, 45 min; 3) THF, reflux, 30 min

13: 91 percent / tributyltin hydride, azoisobutyronitrile / toluene / 11 h / Heating

14: H₂ / Pd/C / ethanol / 2 h

15: pyridinium dichromate / CH₂Cl₂ / 2 h

16: 88 percent

17: 76 percent / Et₃N, MeSO₂Cl / CH₂Cl₂

18: 1.) BH₃*THF, 2.) aq. NaOH, aq. H₂O₂ / 1) THF, 0 deg C, 30 min, room temperature, 2 h; 2) THF, 30 min

With 1,4-diaza-bicyclo[2.2.2]octane; 1H-imidazole; sodium hydroxide; copper(l) iodide; dipyridinium dichromate; Phenylselenyl chloride; borane-THF; 2,2'-azobis(isobutyronitrile); sulfuric acid; potassium tert-butylate; hydrogen; dihydrogen peroxide; tri-n-butyl-tin hydride; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; ozone; methanesulfonyl chloride; triethylamine; pyridinium chlorochromate; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; ethanol; hexane; dichloromethane; toluene; xylene; tert-butyl alcohol; benzene;

Reference yield:

7,7-dimethyltricyclo<7.2.1.01,6>dodec-5-en-8-one → (+/-)-jinkohol II (86703-03-9)

Guidance literature:

Multi-step reaction with 19 steps

1: NaBH₄ / ethanol / 2 h / Ambient temperature

2: 98 percent / NaH, tetrabutylammonium iodide / tetrahydrofuran / 1) 0 deg C --> room temperature, 1 h; 2) room temperature, 24 h

3: 1.) BH₃*THF, 2.) aq. NaOH, aq. H₂O₂ / 1) THF, 0 deg C --> room temperature; room temperature, 5 h; 2) THF, cooling, 3 h

4: 100 percent / pyridinium chlorochromate / CH₂Cl₂ / 1 h / Ambient temperature

5: 1.) aq. NaOH / 1) ethanol, 0 deg C, 30 min; 2) ethanol, room temperature, 7 h

6: 1.) O₃; 2) aq. H₂O₂, dil. H₂SO₄ / 1) -78 deg C, ethyl acetate; 2) acetic acid, overnight

7: 70 percent / diethyl ether

8: 78 percent / KOBu-t / benzene; 2-methyl-propan-2-ol / 6 h / Heating

9: 1.) NaH, 2.) PhSeCl, 3.) aq. H₂O₂ / 1) THF, 0 deg C, 25 min; 2) THF, 15 min; 3) CH₂Cl₂, 5 deg C, 10 min, 5 deg C --> room temperature, 15 min

10: 1) CuI / 1) diethyl ether, 0 deg C, 5 min; 2) diethyl ether, 30 min

11: 84 percent / 1,4-diazobicyclo<2.2.2>octane / xylene / 7 h / 85 °C

12: 93 percent / diisobutylaluminium hydride / hexane; tetrahydrofuran / 1) -78 deg C, 1 h; 2) room temperature, 1 h

13: 1.) NaH, imidazole / 1) THF, reflux, 2 h; 2) THF, reflux, 45 min; 3) THF, reflux, 30 min

14: 91 percent / tributyltin hydride, azoisobutyronitrile / toluene / 11 h / Heating

15: H₂ / Pd/C / ethanol / 2 h

16: pyridinium dichromate / CH₂Cl₂ / 2 h

17: 88 percent

18: 76 percent / Et₃N, MeSO₂Cl / CH₂Cl₂

19: 1.) BH₃*THF, 2.) aq. NaOH, aq. H₂O₂ / 1) THF, 0 deg C, 30 min, room temperature, 2 h; 2) THF, 30 min

With 1,4-diaza-bicyclo[2.2.2]octane; 1H-imidazole; sodium hydroxide; sodium tetrahydroborate; copper(l) iodide; dipyridinium dichromate; Phenylselenyl chloride; borane-THF; 2,2'-azobis(isobutyronitrile); sulfuric acid; potassium tert-butylate; hydrogen; dihydrogen peroxide; tri-n-butyl-tin hydride; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; ozone; methanesulfonyl chloride; triethylamine; pyridinium chlorochromate; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; ethanol; hexane; dichloromethane; toluene; xylene; tert-butyl alcohol; benzene;

upstream raw materials:

(+/-)-prezizaene

(+/-)-prezizanol

(+/-)-norprezizanone

Refernces

• 1、 -. "(+)- Or (-)-7-hydroxymethyl-2,6,6-trimethyltricyclo[6,2,1,01,5 ]undecane". . . Retrieved 2008/06/13.