(3S,5aR,6aS,7aS)-5,5a,6,6a,7,7a-hexahydro-3,6,6,7a-tetramethyl-3-(3-phenylpropyl)bicyclo[4.1.0]hept-1⁽⁶⁾eno[3,4-b][1,4]oxazin-2(3H)-one

Base Information

• Chemical Name: (3S,5aR,6aS,7aS)-5,5a,6,6a,7,7a-hexahydro-3,6,6,7a-tetramethyl-3-(3-phenylpropyl)bicyclo[4.1.0]hept-1⁽⁶⁾eno[3,4-b][1,4]oxazin-2(3H)-one
• CAS No.: 1266681-16-6
• Molecular Formula: C₂₂H₂₉NO₂
• Molecular Weight: 339.478
• Mol file: 1266681-16-6.mol

Synonyms:(3S,5aR,6aS,7aS)-5,5a,6,6a,7,7a-hexahydro-3,6,6,7a-tetramethyl-3-(3-phenylpropyl)bicyclo[4.1.0]hept-1⁽⁶⁾eno[3,4-b][1,4]oxazin-2(3H)-one

Chemical Property of (3S,5aR,6aS,7aS)-5,5a,6,6a,7,7a-hexahydro-3,6,6,7a-tetramethyl-3-(3-phenylpropyl)bicyclo[4.1.0]hept-1⁽⁶⁾eno[3,4-b][1,4]oxazin-2(3H)-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,5aR,6aS,7aS)-5,5a,6,6a,7,7a-hexahydro-3,6,6,7a-tetramethyl-3-(3-phenylpropyl)bicyclo[4.1.0]hept-1⁽⁶⁾eno[3,4-b][1,4]oxazin-2(3H)-one

There total 6 articles about (3S,5aR,6aS,7aS)-5,5a,6,6a,7,7a-hexahydro-3,6,6,7a-tetramethyl-3-(3-phenylpropyl)bicyclo[4.1.0]hept-1⁽⁶⁾eno[3,4-b][1,4]oxazin-2(3H)-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: 99.0%

(3S,5aR,6aS,7aS)-3-cinnamyl-5,5a,6,6a,7,7a-hexahydro-3,6,6,7a-tetramethylbicyclo[4.1.0]hept-1(6)eno[3,4-b][1,4]oxazin-2(3H)-one → (3S,5aR,6aS,7aS)-5,5a,6,6a,7,7a-hexahydro-3,6,6,7a-tetramethyl-3-(3-phenylpropyl)bicyclo[4.1.0]hept-1(6)eno[3,4-b][1,4]oxazin-2(3H)-one (1266681-16-6)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In methanol; at 20 ℃; for 6h;

DOI:10.1021/jo1022537

Reference yield:

cis-3α,4α-caranediol (57457-02-0) → (3S,5aR,6aS,7aS)-5,5a,6,6a,7,7a-hexahydro-3,6,6,7a-tetramethyl-3-(3-phenylpropyl)bicyclo[4.1.0]hept-1(6)eno[3,4-b][1,4]oxazin-2(3H)-one (1266681-16-6)

Guidance literature:

Multi-step reaction with 5 steps

1: acetic acid; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / acetonitrile / 15 h / 20 °C

2: dmap; dicyclohexyl-carbodiimide / dichloromethane / 24 h / 0 - 20 °C

3: palladium 10% on activated carbon; hydrogen / methanol / 17 h / 20 °C

4: tetrabutylammomium bromide; potassium hydroxide / water; toluene / 0.33 h / 20 °C

5: palladium 10% on activated carbon; hydrogen / methanol / 6 h / 20 °C

With dmap; palladium 10% on activated carbon; tetrabutylammomium bromide; hydrogen; acetic acid; dicyclohexyl-carbodiimide; potassium hydroxide; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In methanol; dichloromethane; water; toluene; acetonitrile;

DOI:10.1021/jo1022537

Reference yield:

C21H27NO5 → (3S,5aR,6aS,7aS)-5,5a,6,6a,7,7a-hexahydro-3,6,6,7a-tetramethyl-3-(3-phenylpropyl)bicyclo[4.1.0]hept-1(6)eno[3,4-b][1,4]oxazin-2(3H)-one (1266681-16-6)

Guidance literature:

Multi-step reaction with 3 steps

1: palladium 10% on activated carbon; hydrogen / methanol / 17 h / 20 °C

2: tetrabutylammomium bromide; potassium hydroxide / water; toluene / 0.33 h / 20 °C

3: palladium 10% on activated carbon; hydrogen / methanol / 6 h / 20 °C

With palladium 10% on activated carbon; tetrabutylammomium bromide; hydrogen; potassium hydroxide; In methanol; water; toluene;

DOI:10.1021/jo1022537

upstream raw materials:

(5aR,6aS,7aS)-5,5a,6,6a,7,7a-hexahydro-3,6,6,7a-tetramethylbicyclo[4.1.0]hept-1⁽⁶⁾eno[3,4-b][1,4]oxazin-2(3H)-one

(+)-Δ³-carene

cis-3α,4α-caranediol

(1R,4S,6S)-4-hydroxy-4,7,7-trimethylbicyclo[4.1.0]heptan-3-one