(1S,6R)-6-Methyl-3-phenylselanyl-bicyclo[4.2.0]octan-2-one

Base Information

• Chemical Name: (1S,6R)-6-Methyl-3-phenylselanyl-bicyclo[4.2.0]octan-2-one
• CAS No.: 105539-68-2
• Molecular Formula: C₁₅H₁₈OSe
• Molecular Weight: 293.267
• Mol file: 105539-68-2.mol

Synonyms:

Chemical Property of (1S,6R)-6-Methyl-3-phenylselanyl-bicyclo[4.2.0]octan-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,6R)-6-Methyl-3-phenylselanyl-bicyclo[4.2.0]octan-2-one

There total 26 articles about (1S,6R)-6-Methyl-3-phenylselanyl-bicyclo[4.2.0]octan-2-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:

(1S,6S)-5,5-(ethylenedioxy)bicyclo<4.2.0>octane-1-carboxamide (105539-65-9,105616-16-8) → (1S,6R)-6-Methyl-3-phenylselanyl-bicyclo[4.2.0]octan-2-one (105539-68-2,105616-29-3)

Guidance literature:

Multi-step reaction with 6 steps

1: 89 percent / KOH / ethane-1,2-diol / 10 h / 125 - 130 °C

2: 86 percent / LiAlH₄ / diethyl ether / 1 h / Ambient temperature

3: 95 percent / pyridine / 24 h / 0 °C

4: 81 percent / lithium triethylborohydride / tetrahydrofuran / 14 h / Ambient temperature

5: 90 percent / HCl / diethyl ether / 12 h

6: ethyl acetate / 0.33 h

With hydrogenchloride; potassium hydroxide; lithium aluminium tetrahydride; lithium triethylborohydride; In tetrahydrofuran; pyridine; diethyl ether; ethylene glycol; ethyl acetate;

DOI:10.1021/jo00376a033

Reference yield:

(1R,6R)-5,5-(ethylenedioxy)bicyclo<4.2.0>octane-1-carboxamide (105539-65-9,105616-16-8) → (1R,6S)-6-Methyl-3-phenylselanyl-bicyclo[4.2.0]octan-2-one (105539-68-2,105616-29-3)

Guidance literature:

Multi-step reaction with 6 steps

1: 86 percent / KOH / ethane-1,2-diol / 10 h / 125 - 130 °C

2: 82 percent / LiAlH₄ / diethyl ether / 1 h / Ambient temperature

3: 96 percent / pyridine / 24 h / 0 °C

4: 81 percent / lithium triethylborohydride / tetrahydrofuran / 14 h / Ambient temperature

5: 87 percent / HCl / diethyl ether / 12 h

6: ethyl acetate / 0.33 h

With hydrogenchloride; potassium hydroxide; lithium aluminium tetrahydride; lithium triethylborohydride; In tetrahydrofuran; pyridine; diethyl ether; ethylene glycol; ethyl acetate;

DOI:10.1021/jo00376a033

Reference yield:

(1R,6R)-5,5-(ethylenedioxy)-N-((S)-1-phenylethyl)bicyclo<4.2.0>octane-1-carboxamide (105539-64-8,105616-15-7) → (1R,6S)-6-Methyl-3-phenylselanyl-bicyclo[4.2.0]octan-2-one (105539-68-2,105616-29-3)

Guidance literature:

Multi-step reaction with 7 steps

1: 95 percent / Li, NH₃ / tetrahydrofuran; H₂O

2: 86 percent / KOH / ethane-1,2-diol / 10 h / 125 - 130 °C

3: 82 percent / LiAlH₄ / diethyl ether / 1 h / Ambient temperature

4: 96 percent / pyridine / 24 h / 0 °C

5: 81 percent / lithium triethylborohydride / tetrahydrofuran / 14 h / Ambient temperature

6: 87 percent / HCl / diethyl ether / 12 h

7: ethyl acetate / 0.33 h

With hydrogenchloride; potassium hydroxide; lithium aluminium tetrahydride; ammonia; lithium; lithium triethylborohydride; In tetrahydrofuran; pyridine; diethyl ether; water; ethylene glycol; ethyl acetate;

DOI:10.1021/jo00376a033

upstream raw materials:

Phenylselenyl chloride

(1R,6S)-6-methylbicyclo<4.2.0>-octan-2-one

(1R,6R)-5,5-(ethylenedioxy)bicyclo<4.2.0>octane-1-carboxamide

(1R,6R)-5,5-(ethylenedioxy)bicyclo<4.2.0>octane-1-carboxylic acid

Downstream raw materials:

C₁₇H₂₂O₂Se

(1R, 2S)-grandisol

(1R,2S)-2-isopropenyl-1-methylcyclobutaneacetic acid

C₁₇H₂₂O₂Se