4β,4aβ,7β,7aβ-Tetramethyl-4a,5,6,7,7a,8-hexahydro-4H-indeno[5,6-b]furan

Base Information

• Chemical Name: 4β,4aβ,7β,7aβ-Tetramethyl-4a,5,6,7,7a,8-hexahydro-4H-indeno[5,6-b]furan
• CAS No.: 49776-70-7
• Molecular Formula: C15H22O
• Molecular Weight: 218.33
• Mol file: 49776-70-7.mol

Synonyms:deoxopinguisone;(4S,4aS,7R,7aS)-4,4a,7,7a-Tetramethyl-4a,5,6,7,7a,8-hexahydro-4H-indeno[5,6-b]furan;

Chemical Property of 4β,4aβ,7β,7aβ-Tetramethyl-4a,5,6,7,7a,8-hexahydro-4H-indeno[5,6-b]furan

Chemical Property:

• PSA: 13.14000
• LogP: 4.38170

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 4β,4aβ,7β,7aβ-Tetramethyl-4a,5,6,7,7a,8-hexahydro-4H-indeno[5,6-b]furan

There total 24 articles about 4β,4aβ,7β,7aβ-Tetramethyl-4a,5,6,7,7a,8-hexahydro-4H-indeno[5,6-b]furan 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: 69.0%

r-4,c-4a,c-7,c-7a-tetramethyl-4,4a,5,6,7,7a,8,8a-octahydroindeno<5,6-b>furan-2-one (100692-79-3) → (+/-)-deoxopinguisone (49776-70-7,100762-43-4)

Guidance literature:

With sulfuric acid; diisobutylaluminium hydride; In tetrahydrofuran; hexane; -20 deg C, 5 min; 0 deg C, 30 min;

DOI:10.1246/bcsj.59.2521

Reference yield:

r-1,c-5,c-6-trimethylspirononane-3,2'-<1,3>dioxolan>-9-one (100692-68-0) → (+/-)-deoxopinguisone (49776-70-7,100762-43-4)

Guidance literature:

Multi-step reaction with 13 steps

1: 1) diisopropylamine, n-BuLi / 1) THF, hexane, 10 min, 0 deg C; -78 deg C, 15 min; 2) THF, hexane, -78 deg C, 1 h; RT, 1 h

2: 95 percent / NaIO₄ / methanol; H₂O / Ambient temperature

3: 78 percent / CaCO₃ / toluene / 90 deg C, 12 h; reflux, 6 h

4: 90 percent / diethyl ether / 0.5 h / 0 °C

5: 87 percent / sodium acetate, piridinium chlorochromate / CH₂Cl₂ / 2.5 h / Ambient temperature

6: 33 percent / NH₃, t-BuOH, Li / tetrahydrofuran / Ambient temperature

8: 86 percent / tributyltin hydride / toluene / 6 h / Heating

9: 97 percent / aq. HCl / H₂O; acetone / 4 h / Ambient temperature

10: 1) diisopropylamine, n-Buli, hexamethylphosphoric triamide / 1) THF, -78 deg C; 30 min, 0 deg C; 2) THF, 0 deg C, 4 h

11: 1) K₂CO₃, 2) aq. HCl / methanol; H₂O / Ambient temperature

12: TsOH / benzene / 48 h / Heating

13: 69 percent / 1) DIBAH; 2) aq. sulfuric acid / hexane; tetrahydrofuran / -20 deg C, 5 min; 0 deg C, 30 min

With hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium periodate; n-butyllithium; sulfuric acid; ammonia; tri-n-butyl-tin hydride; sodium acetate; lithium; diisobutylaluminium hydride; potassium carbonate; toluene-4-sulfonic acid; diisopropylamine; pyridinium chlorochromate; calcium carbonate; tert-butyl alcohol; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; acetone; toluene; benzene;

DOI:10.1246/bcsj.59.2521

Reference yield:

r-1,c-5,c-6-trimethylspironon-8-ene-3,2'-<1,3>dioxolane> (100692-73-7) → (+/-)-deoxopinguisone (49776-70-7,100762-43-4)

Guidance literature:

Multi-step reaction with 11 steps

1: 1) CrO₃, 3,5-dimethylpyrazole; 2) aq. NaOH / 1) CH₂Cl₂, 15 min, -20 deg C; 2) CH₂Cl₂, 4 h, -20 deg C; 1 h, 0 deg C

2: 90 percent / diethyl ether / 0.5 h / 0 °C

3: 87 percent / sodium acetate, piridinium chlorochromate / CH₂Cl₂ / 2.5 h / Ambient temperature

4: 33 percent / NH₃, t-BuOH, Li / tetrahydrofuran / Ambient temperature

6: 86 percent / tributyltin hydride / toluene / 6 h / Heating

7: 97 percent / aq. HCl / H₂O; acetone / 4 h / Ambient temperature

8: 1) diisopropylamine, n-Buli, hexamethylphosphoric triamide / 1) THF, -78 deg C; 30 min, 0 deg C; 2) THF, 0 deg C, 4 h

9: 1) K₂CO₃, 2) aq. HCl / methanol; H₂O / Ambient temperature

10: TsOH / benzene / 48 h / Heating

11: 69 percent / 1) DIBAH; 2) aq. sulfuric acid / hexane; tetrahydrofuran / -20 deg C, 5 min; 0 deg C, 30 min

With 3,5-dimethyl-1H-pyrazole; chromium(VI) oxide; hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium hydroxide; n-butyllithium; sulfuric acid; ammonia; tri-n-butyl-tin hydride; sodium acetate; lithium; diisobutylaluminium hydride; potassium carbonate; toluene-4-sulfonic acid; diisopropylamine; pyridinium chlorochromate; tert-butyl alcohol; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; acetone; toluene; benzene;

DOI:10.1246/bcsj.59.2521

upstream raw materials:

r-4,c-4a,c-7,c-7a-tetramethyl-4,4a,5,6,7,7a,8,8a-octahydroindeno<5,6-b>furan-2-one

r-1,c-5,c-6,c-9-tetramethylbicyclo<4.3.0>nonan-3-one

r-1,c-5,c-6-trimethylspironon-8-ene-3,2'-<1,3>dioxolane>

r-1,c-5,c-6-trimethylspirononane-3,2'-<1,3>dioxolan>-9-one

Refernces

• 1、 Uyehara, Tadao,Kabasawa, Yasuhiro,Kato, Tadahiro. "PHOTOCHEMICAL REARRANGEMENT APPROACH TO THE TOTAL SYNTHESIS OF (+/-)-PINGUISONE AND (+/-)-DEOXOPINGUISONE". . p. 2343 - 2346. Retrieved 2007/10/02.