(1R,6R,7S,8S)-8-Isopropyl-5-methylene-12-oxa-tricyclo[5.3.2.0^1,6]dodec-2-en-10-one

Base Information

• Chemical Name: (1R,6R,7S,8S)-8-Isopropyl-5-methylene-12-oxa-tricyclo[5.3.2.0^1,6]dodec-2-en-10-one
• CAS No.: 69239-67-4
• Molecular Formula: C₁₅H₂₀O₂
• Molecular Weight: 232.323
• Mol file: 69239-67-4.mol

Synonyms:

Chemical Property of (1R,6R,7S,8S)-8-Isopropyl-5-methylene-12-oxa-tricyclo[5.3.2.0^1,6]dodec-2-en-10-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,6R,7S,8S)-8-Isopropyl-5-methylene-12-oxa-tricyclo[5.3.2.0^1,6]dodec-2-en-10-one

There total 28 articles about (1R,6R,7S,8S)-8-Isopropyl-5-methylene-12-oxa-tricyclo[5.3.2.0^1,6]dodec-2-en-10-one 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: 81.0%

(1S*,2R*,7R*,8R*,10S*)-10-Isopropyl-3-methylene-11-oxatricyclo<5,3,2,02,7>-5-dodecen-8-ol (111537-80-5,127590-20-9,127997-12-0) → (1S*,2R*,7R*,8R*,10S*)-10-Isopropyl-3-methylene-11-oxatricyclo<5,3,2,02,7>-5-dodecen-8-one (69239-67-4,69289-32-3,81873-24-7,111613-79-7,111613-80-0,112709-49-6,112709-50-9,112709-51-0,120964-65-0,130550-47-9)

Guidance literature:

With dipyridinium dichromate; 3 A molecular sieve; In dichloromethane; for 3h; Ambient temperature;

DOI:10.1016/S0040-4020(01)87817-0

Reference yield:

(1S*,2R*,7R*,8R*)-11-Oxatricyclo<5,3,2,02,7>-4,9-dodecadien-8-ol (127940-49-2) → (1S*,2R*,7R*,8R*,10S*)-10-Isopropyl-3-methylene-11-oxatricyclo<5,3,2,02,7>-5-dodecen-8-one (69239-67-4,69289-32-3,81873-24-7,111613-79-7,111613-80-0,112709-49-6,112709-50-9,112709-51-0,120964-65-0,130550-47-9)

Guidance literature:

Multi-step reaction with 14 steps

1: 92 percent / 1.) (COCl)2/DMSO; 2.) Et₃N / CH₂Cl₂ / 1.) -78 deg C; 2.) -20 deg C

2: 75 percent / CuCN / diethyl ether / -78 - 0 °C

3: 91 percent / Li/NH₃ / tetrahydrofuran; 2-methyl-propan-2-ol / -78 - 0 °C

4: 2,6-lutidine / CH₂Cl₂ / 0 - 5 °C

5: C₅H₅N*HBr*Br₂ / tetrahydrofuran / Ambient temperature

6: DBU / acetonitrile / Heating

7: O₂, methylene blue / methanol / 5 - 10 °C / Irradiation

8: LiAlH₄ / tetrahydrofuran / 0 - 5 °C

9: 72 percent / MnO₂ / CHCl₃ / Ambient temperature

10: 92 percent / H₂ / 10percent Pd/C / ethanol / Ambient temperature

11: 30 percent / n-BuLi / tetrahydrofuran / Ambient temperature

12: 79 percent / MeOCON^(1-)SO₂N⁽¹⁺⁾Et₃ / benzene / 75 - 80 °C

13: TBAF / tetrahydrofuran / Ambient temperature

14: PDC, MS 3A / CH₂Cl₂ / Ambient temperature

With 2,6-dimethylpyridine; manganese(IV) oxide; lithium aluminium tetrahydride; dipyridinium dichromate; n-butyllithium; oxalyl dichloride; Burgess Reagent; tetrabutyl ammonium fluoride; ammonia; hydrogen; oxygen; methylene blue; lithium; pyridinium hydrobromide perbromide complex; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; chloroform; acetonitrile; tert-butyl alcohol; benzene;

DOI:10.1016/S0040-4039(01)93470-7

Reference yield:

(1S*,2R*,7R*)-11-Oxatricyclo<5,3,2,02,7>-4,9-dodecadien-8-one (127940-50-5) → (1S*,2R*,7R*,8R*,10S*)-10-Isopropyl-3-methylene-11-oxatricyclo<5,3,2,02,7>-5-dodecen-8-one (69239-67-4,69289-32-3,81873-24-7,111613-79-7,111613-80-0,112709-49-6,112709-50-9,112709-51-0,120964-65-0,130550-47-9)

Guidance literature:

Multi-step reaction with 13 steps

1: 75 percent / CuCN / diethyl ether / -78 - 0 °C

2: 91 percent / Li/NH₃ / tetrahydrofuran; 2-methyl-propan-2-ol / -78 - 0 °C

3: 2,6-lutidine / CH₂Cl₂ / 0 - 5 °C

4: C₅H₅N*HBr*Br₂ / tetrahydrofuran / Ambient temperature

5: DBU / acetonitrile / Heating

6: O₂, methylene blue / methanol / 5 - 10 °C / Irradiation

7: LiAlH₄ / tetrahydrofuran / 0 - 5 °C

8: 72 percent / MnO₂ / CHCl₃ / Ambient temperature

9: 92 percent / H₂ / 10percent Pd/C / ethanol / Ambient temperature

10: 30 percent / n-BuLi / tetrahydrofuran / Ambient temperature

11: 79 percent / MeOCON^(1-)SO₂N⁽¹⁺⁾Et₃ / benzene / 75 - 80 °C

12: TBAF / tetrahydrofuran / Ambient temperature

13: PDC, MS 3A / CH₂Cl₂ / Ambient temperature

With 2,6-dimethylpyridine; manganese(IV) oxide; lithium aluminium tetrahydride; dipyridinium dichromate; n-butyllithium; Burgess Reagent; tetrabutyl ammonium fluoride; ammonia; hydrogen; oxygen; methylene blue; lithium; pyridinium hydrobromide perbromide complex; 1,8-diazabicyclo[5.4.0]undec-7-ene; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; chloroform; acetonitrile; tert-butyl alcohol; benzene;

DOI:10.1016/S0040-4039(01)93470-7

upstream raw materials:

(1S*,2R*,7R*,8R*,10S*)-10-Isopropyl-3-methylene-11-oxatricyclo<5,3,2,0^2,7>-5-dodecen-8-ol

(1S*,2R*,7R*,8R*)-11-Oxatricyclo<5,3,2,0^2,7>-4,9-dodecadien-8-ol

(1S*,2R*,7R*)-11-Oxatricyclo<5,3,2,0^2,7>-4,9-dodecadien-8-one

(1S*,2R*,7R*,8R*,10S*)-10-Isopropyl-11-oxatricyclo<5,3,2,0^2,7>-4-dodecen-8-ol

Downstream raw materials:

(1R,6R,7S,8S)-8-Isopropyl-5-methylene-12-oxa-tricyclo[5.3.2.0^1,6]dodec-2-en-10-one