(+)-11,12-Epoxy-11,12-dihydrocembrene C

Base Information

• Chemical Name: (+)-11,12-Epoxy-11,12-dihydrocembrene C
• CAS No.: 69778-94-5
• Molecular Formula: C20H32O
• Molecular Weight: 288.46748
• Mol file: 69778-94-5.mol

Synonyms:(4E,6E,10E)-(1S,14S)-4-Isopropyl-1,7,11-trimethyl-15-oxa-bicyclo[12.1.0]pentadeca-4,6,10-triene;(+)-11,12-epoxycembrene;

Chemical Property of (+)-11,12-Epoxy-11,12-dihydrocembrene C

Chemical Property:

• PSA: 12.53000
• LogP: 5.97310

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (+)-11,12-Epoxy-11,12-dihydrocembrene C

There total 15 articles about (+)-11,12-Epoxy-11,12-dihydrocembrene C 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: 90.0%

(4E,6E,10E)-(1S,14S)-1-Iodomethyl-4-isopropyl-7,11-dimethyl-15-oxa-bicyclo[12.1.0]pentadeca-4,6,10-triene (309744-01-2) → (+)-11,12-epoxycembrene (69778-94-5)

Guidance literature:

With N,N,N,N,N,N-hexamethylphosphoric triamide; sodium cyanoborohydride; In tetrahydrofuran; at 60 ℃;

DOI:10.1016/S0040-4039(00)00982-5

Reference yield:

5-iodo-2-methylpent-2-ene (43161-11-1) → (+)-11,12-epoxycembrene (69778-94-5)

Guidance literature:

Multi-step reaction with 12 steps

1: 88 percent / NaH / dimethylformamide / 60 °C

2: 93 percent / m-CPBA / CH₂Cl₂ / 0 °C

3: 73 percent / LDA / tetrahydrofuran / -78 - 23 °C

4: 81 percent / LiClO₄ / benzene / Heating

5: K₂CO₃ / methanol / 23 °C

6: 72 percent / MnO₂ / hexane / 23 °C

7: TiCl₄; zinc powder / tetrahydrofuran / 6 h / Heating

8: OH^(1-)

9: 92 percent / LiAlH₄ / diethyl ether / 20 °C

10: 85 percent / Ti(O-iPr)4; D(-)-DET; t-BuOOH / CH₂Cl₂ / -20 °C

11: 90 percent / I₂; PPh₃; imidazole / pyridine; diethyl ether; acetonitrile / 0 °C

12: 90 percent / NaBH₃CN; HMPA / tetrahydrofuran / 60 °C

With 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; N,N,N,N,N,N-hexamethylphosphoric triamide; manganese(IV) oxide; lithium aluminium tetrahydride; diethyl (2S,3S)-tartrate; hydroxide; iodine; lithium perchlorate; titanium tetrachloride; sodium hydride; sodium cyanoborohydride; potassium carbonate; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; zinc; lithium diisopropyl amide; In tetrahydrofuran; pyridine; methanol; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; acetonitrile; benzene; 1: Condensation / 2: Epoxidation / 3: Wadsworth-Horner-Emmons coupling / 4: Rearrangement / 5: saponification / 6: Oxidation / 7: Cyclization / 8: Hydrolysis / 9: Reduction / 10: Sharpless epoxidation / 11: Iodination / 12: reductive dehalogenation;

DOI:10.1016/S0040-4039(00)00982-5

Reference yield:

6-hydroxy-7(9)-dehydro-6,7-dihydrogeranyl acetate (33766-43-7) → (+)-11,12-epoxycembrene (69778-94-5)

Guidance literature:

Multi-step reaction with 12 steps

1: 83 percent / Hg(OAc)2 / Heating

2: 90 percent / 110 °C / Thermolysis

3: 73 percent / LDA / tetrahydrofuran / -78 - 23 °C

4: 81 percent / LiClO₄ / benzene / Heating

5: K₂CO₃ / methanol / 23 °C

6: 72 percent / MnO₂ / hexane / 23 °C

7: TiCl₄; zinc powder / tetrahydrofuran / 6 h / Heating

8: OH^(1-)

9: 92 percent / LiAlH₄ / diethyl ether / 20 °C

10: 85 percent / Ti(O-iPr)4; D(-)-DET; t-BuOOH / CH₂Cl₂ / -20 °C

11: 90 percent / I₂; PPh₃; imidazole / pyridine; diethyl ether; acetonitrile / 0 °C

12: 90 percent / NaBH₃CN; HMPA / tetrahydrofuran / 60 °C

With 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; N,N,N,N,N,N-hexamethylphosphoric triamide; manganese(IV) oxide; lithium aluminium tetrahydride; diethyl (2S,3S)-tartrate; mercury(II) diacetate; hydroxide; iodine; lithium perchlorate; titanium tetrachloride; sodium cyanoborohydride; potassium carbonate; triphenylphosphine; zinc; lithium diisopropyl amide; In tetrahydrofuran; pyridine; methanol; diethyl ether; hexane; dichloromethane; acetonitrile; benzene; 1: Alkylation / 2: Claisen rearrangement / 3: Wadsworth-Horner-Emmons coupling / 4: Rearrangement / 5: saponification / 6: Oxidation / 7: Cyclization / 8: Hydrolysis / 9: Reduction / 10: Sharpless epoxidation / 11: Iodination / 12: reductive dehalogenation;

DOI:10.1016/S0040-4039(00)00982-5

upstream raw materials:

(4E,6E,10E)-(1S,14S)-1-Iodomethyl-4-isopropyl-7,11-dimethyl-15-oxa-bicyclo[12.1.0]pentadeca-4,6,10-triene

5-iodo-2-methylpent-2-ene

6-hydroxy-7⁽⁹⁾-dehydro-6,7-dihydrogeranyl acetate

Acetic acid (E)-3,7-dimethyl-6-vinyloxy-octa-2,7-dienyl ester

Refernces