(3aβ(Z),4β,6aα,9aβ,9bβ)-(+/-)-3a,4,6a,7,8,9,9a,9b-octahydro-5-phenylselenenyl-4,7,7,9b-tetramethyl-3a-<3-(methoxymethyloxy)-3-methyl-1-butenyl>-5H-naphtho<1,8-de>-1,3-dioxin-6-one

Base Information

• Chemical Name: (3aβ(Z),4β,6aα,9aβ,9bβ)-(+/-)-3a,4,6a,7,8,9,9a,9b-octahydro-5-phenylselenenyl-4,7,7,9b-tetramethyl-3a-<3-(methoxymethyloxy)-3-methyl-1-butenyl>-5H-naphtho<1,8-de>-1,3-dioxin-6-one
• CAS No.: 124666-44-0
• Molecular Formula: C₂₈H₄₀O₅Se
• Molecular Weight: 535.583
• Mol file: 124666-44-0.mol

Synonyms:

Chemical Property of (3aβ(Z),4β,6aα,9aβ,9bβ)-(+/-)-3a,4,6a,7,8,9,9a,9b-octahydro-5-phenylselenenyl-4,7,7,9b-tetramethyl-3a-<3-(methoxymethyloxy)-3-methyl-1-butenyl>-5H-naphtho<1,8-de>-1,3-dioxin-6-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3aβ(Z),4β,6aα,9aβ,9bβ)-(+/-)-3a,4,6a,7,8,9,9a,9b-octahydro-5-phenylselenenyl-4,7,7,9b-tetramethyl-3a-<3-(methoxymethyloxy)-3-methyl-1-butenyl>-5H-naphtho<1,8-de>-1,3-dioxin-6-one

There total 16 articles about (3aβ(Z),4β,6aα,9aβ,9bβ)-(+/-)-3a,4,6a,7,8,9,9a,9b-octahydro-5-phenylselenenyl-4,7,7,9b-tetramethyl-3a-<3-(methoxymethyloxy)-3-methyl-1-butenyl>-5H-naphtho<1,8-de>-1,3-dioxin-6-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:

3-methyl-4-nitro-1-(2',6',6'-trimethylcyclohex-2-en-1-yl)butan-1-one (104751-86-2) → (3aβ(Z),4β,6aα,9aβ,9bβ)-(+/-)-3a,4,6a,7,8,9,9a,9b-octahydro-5-phenylselenenyl-4,7,7,9b-tetramethyl-3a-<3-(methoxymethyloxy)-3-methyl-1-butenyl>-5H-naphtho<1,8-de>-1,3-dioxin-6-one (124666-44-0)

Guidance literature:

Multi-step reaction with 13 steps

1: 98.3 percent / LiAlH₄, AlCl₃ / diethyl ether / 15 min, 0 deg C then 30 min, rt.

2: pyridine / 6 h / Ambient temperature

3: 3-chlorophenyl isocyanate, aq. ammonia / benzene; triethylamine / 0.5 h

4: 85 percent / hydrogen / Raney nickel W-2 / methanol; aq. acetic acid / 24 h / Ambient temperature

5: 71 percent / P₂O₅ / CHCl₃ / 2 h

6: 96 percent / n-butyl-lithium / tetrahydrofuran; hexane / 6 h / -78 °C

7: 92.7 percent / P₂O₅, methylal / CHCl₃ / 4 h / Ambient temperature

8: sodium hydroxide / methanol; H₂O / 6 h / Heating

9: pyridinium chlorochromate, sodium acetate, molecular sieves 4A / CH₂Cl₂ / 4 h / Ambient temperature

10: sodium / methanol / 6 h / Heating

11: 94 percent / hydrogen / Raney nickel W-2 / methanol / 4 h / 1551.4 Torr / Ambient temperature

12: diisopropylamine, butyllitium / hexane; tetrahydrofuran / 0.25 h / -78 °C

13: bromine / tetrahydrofuran / 0.17 h / -78 °C

With ammonium hydroxide; sodium hydroxide; lithium aluminium tetrahydride; n-butyllithium; aluminium trichloride; Dimethoxymethane; 4 A molecular sieve; hydrogen; bromine; sodium acetate; sodium; phosphorus pentoxide; diisopropylamine; pyridinium chlorochromate; m-chlorophenyl isocyanate; Raney nickel W-2; In tetrahydrofuran; pyridine; methanol; diethyl ether; hexane; dichloromethane; chloroform; water; acetic acid; triethylamine; benzene;

DOI:10.1016/0040-4020(89)80150-4

Reference yield:

2,6,6-trimethyl-α-(2-methyl-3-nitropropyl)-2-cyclohexene-1-methanol (104751-89-5) → (3aβ(Z),4β,6aα,9aβ,9bβ)-(+/-)-3a,4,6a,7,8,9,9a,9b-octahydro-5-phenylselenenyl-4,7,7,9b-tetramethyl-3a-<3-(methoxymethyloxy)-3-methyl-1-butenyl>-5H-naphtho<1,8-de>-1,3-dioxin-6-one (124666-44-0)

Guidance literature:

Multi-step reaction with 12 steps

1: pyridine / 6 h / Ambient temperature

2: 3-chlorophenyl isocyanate, aq. ammonia / benzene; triethylamine / 0.5 h

3: 85 percent / hydrogen / Raney nickel W-2 / methanol; aq. acetic acid / 24 h / Ambient temperature

4: 71 percent / P₂O₅ / CHCl₃ / 2 h

5: 96 percent / n-butyl-lithium / tetrahydrofuran; hexane / 6 h / -78 °C

6: 92.7 percent / P₂O₅, methylal / CHCl₃ / 4 h / Ambient temperature

7: sodium hydroxide / methanol; H₂O / 6 h / Heating

8: pyridinium chlorochromate, sodium acetate, molecular sieves 4A / CH₂Cl₂ / 4 h / Ambient temperature

9: sodium / methanol / 6 h / Heating

10: 94 percent / hydrogen / Raney nickel W-2 / methanol / 4 h / 1551.4 Torr / Ambient temperature

11: diisopropylamine, butyllitium / hexane; tetrahydrofuran / 0.25 h / -78 °C

12: bromine / tetrahydrofuran / 0.17 h / -78 °C

With ammonium hydroxide; sodium hydroxide; n-butyllithium; Dimethoxymethane; 4 A molecular sieve; hydrogen; bromine; sodium acetate; sodium; phosphorus pentoxide; diisopropylamine; pyridinium chlorochromate; m-chlorophenyl isocyanate; Raney nickel W-2; In tetrahydrofuran; pyridine; methanol; hexane; dichloromethane; chloroform; water; acetic acid; triethylamine; benzene;

DOI:10.1016/0040-4020(89)80150-4

Reference yield:

α-damascone (24720-09-0) → (3aβ(Z),4β,6aα,9aβ,9bβ)-(+/-)-3a,4,6a,7,8,9,9a,9b-octahydro-5-phenylselenenyl-4,7,7,9b-tetramethyl-3a-<3-(methoxymethyloxy)-3-methyl-1-butenyl>-5H-naphtho<1,8-de>-1,3-dioxin-6-one (124666-44-0)

Guidance literature:

Multi-step reaction with 14 steps

1: 90 percent / tetramethylguanidine / 2 h / Ambient temperature

2: 98.3 percent / LiAlH₄, AlCl₃ / diethyl ether / 15 min, 0 deg C then 30 min, rt.

3: pyridine / 6 h / Ambient temperature

4: 3-chlorophenyl isocyanate, aq. ammonia / benzene; triethylamine / 0.5 h

5: 85 percent / hydrogen / Raney nickel W-2 / methanol; aq. acetic acid / 24 h / Ambient temperature

6: 71 percent / P₂O₅ / CHCl₃ / 2 h

7: 96 percent / n-butyl-lithium / tetrahydrofuran; hexane / 6 h / -78 °C

8: 92.7 percent / P₂O₅, methylal / CHCl₃ / 4 h / Ambient temperature

9: sodium hydroxide / methanol; H₂O / 6 h / Heating

10: pyridinium chlorochromate, sodium acetate, molecular sieves 4A / CH₂Cl₂ / 4 h / Ambient temperature

11: sodium / methanol / 6 h / Heating

12: 94 percent / hydrogen / Raney nickel W-2 / methanol / 4 h / 1551.4 Torr / Ambient temperature

13: diisopropylamine, butyllitium / hexane; tetrahydrofuran / 0.25 h / -78 °C

14: bromine / tetrahydrofuran / 0.17 h / -78 °C

With ammonium hydroxide; sodium hydroxide; lithium aluminium tetrahydride; n-butyllithium; aluminium trichloride; Dimethoxymethane; 1,1,3,3-tetramethylguanidine; 4 A molecular sieve; hydrogen; bromine; sodium acetate; sodium; phosphorus pentoxide; diisopropylamine; pyridinium chlorochromate; m-chlorophenyl isocyanate; Raney nickel W-2; In tetrahydrofuran; pyridine; methanol; diethyl ether; hexane; dichloromethane; chloroform; water; acetic acid; triethylamine; benzene;

DOI:10.1016/0040-4020(89)80150-4

upstream raw materials:

diphenyl diselenide

(3aS,6aR,9aR,9bS)-3a-((Z)-3-Methoxymethoxy-3-methyl-but-1-enyl)-4,7,7,9b-tetramethyl-3a,6,6a,7,8,9,9a,9b-octahydro-naphtho[1,8-de][1,3]dioxin-6-ol

3-methyl-3-(tetrahydro-2H-pyran-2-yloxy)butyne

α-damascone