(4S,4aR,5R)-4-Isopropenyl-4a,5-dimethyl-1,4,4a,5,6,7-hexahydronaphthalen-1-one

Base Information

• Chemical Name: (4S,4aR,5R)-4-Isopropenyl-4a,5-dimethyl-1,4,4a,5,6,7-hexahydronaphthalen-1-one
• CAS No.: 115356-19-9
• Molecular Formula: C₁₅H₂₀O
• Molecular Weight: 216.323
• Mol file: 115356-19-9.mol

Synonyms:(4S,4aR,5R)-4-Isopropenyl-4a,5-dimethyl-1,4,4a,5,6,7-hexahydronaphthalen-1-one

Chemical Property of (4S,4aR,5R)-4-Isopropenyl-4a,5-dimethyl-1,4,4a,5,6,7-hexahydronaphthalen-1-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S,4aR,5R)-4-Isopropenyl-4a,5-dimethyl-1,4,4a,5,6,7-hexahydronaphthalen-1-one

There total 1 articles about (4S,4aR,5R)-4-Isopropenyl-4a,5-dimethyl-1,4,4a,5,6,7-hexahydronaphthalen-1-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:

nardosinone (23720-80-1) → (4S,4aR,5R)-4-Isopropenyl-4a,5-dimethyl-1,4,4a,5,6,7-hexahydronaphthalen-1-one (115356-19-9)

Guidance literature:

Multi-step reaction with 2 steps

1: H₂ / Pd/CaCO₃ / methanol / 1 h / Ambient temperature

2: POCl₃ / pyridine / 0.5 h / Ambient temperature

With hydrogen; trichlorophosphate; Lindlar's catalyst; In pyridine; methanol;

DOI:10.1016/0031-9422(88)80303-0

Reference yield:

(4S,4aR,5R)-4-Isopropenyl-4a,5-dimethyl-1,4,4a,5,6,7-hexahydronaphthalen-1-one (115356-19-9) → (2RS,4aR,5R)-4-(1-Hydroxy-1-methylethyl)-4a,5-dimethyl-2-(phenylseleno)-3,4,4a,5,6,7-hexahydronaphthalen-1(2H)-one

Guidance literature:

Multi-step reaction with 5 steps

1: 69 percent / m-CPBA / CH₂Cl₂

2: 42 percent / LiBEt₃H

3: 84 percent / LiAlH₄ / tetrahydrofuran / 1.) 0 deg C, 5 min, 2.) reflux, 4 h

4: 98 percent / PDC, molecular sieves 4 Angstroem / CH₂Cl₂ / 2 h / Ambient temperature

5: 66 percent / LHMDS, HMPA / tetrahydrofuran / 1.) 0 deg C, 1 h, 2.) 3 h

With N,N,N,N,N,N-hexamethylphosphoric triamide; lithium aluminium tetrahydride; dipyridinium dichromate; 4 A molecular sieve; lithium triethylborohydride; 3-chloro-benzenecarboperoxoic acid; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jo00071a025

Reference yield:

(4S,4aR,5R)-4-Isopropenyl-4a,5-dimethyl-1,4,4a,5,6,7-hexahydronaphthalen-1-one (115356-19-9) → kanshone A (115356-18-8)

Guidance literature:

Multi-step reaction with 6 steps

1: 69 percent / m-CPBA / CH₂Cl₂

2: 42 percent / LiBEt₃H

3: 84 percent / LiAlH₄ / tetrahydrofuran / 1.) 0 deg C, 5 min, 2.) reflux, 4 h

4: 98 percent / PDC, molecular sieves 4 Angstroem / CH₂Cl₂ / 2 h / Ambient temperature

5: 66 percent / LHMDS, HMPA / tetrahydrofuran / 1.) 0 deg C, 1 h, 2.) 3 h

6: 60 percent / pyridine, 30percent H₂O₂ / tetrahydrofuran / 0.67 h / Ambient temperature

With pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; lithium aluminium tetrahydride; dipyridinium dichromate; 4 A molecular sieve; dihydrogen peroxide; lithium triethylborohydride; 3-chloro-benzenecarboperoxoic acid; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jo00071a025

upstream raw materials:

nardosinone

Downstream raw materials:

kanshone A