(+)-(4aS,5S)-5-benzoyloxy-3,4,4a,5,6,7-hexahydro-1,1,4a-trimethylnaphthalen-2(1H)-one

Base Information

• Chemical Name: (+)-(4aS,5S)-5-benzoyloxy-3,4,4a,5,6,7-hexahydro-1,1,4a-trimethylnaphthalen-2(1H)-one
• CAS No.: 110654-75-6
• Molecular Formula: C₂₀H₂₄O₃
• Molecular Weight: 312.409
• Mol file: 110654-75-6.mol

Synonyms:(+)-(4aS,5S)-5-benzoyloxy-3,4,4a,5,6,7-hexahydro-1,1,4a-trimethylnaphthalen-2(1H)-one

Chemical Property of (+)-(4aS,5S)-5-benzoyloxy-3,4,4a,5,6,7-hexahydro-1,1,4a-trimethylnaphthalen-2(1H)-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+)-(4aS,5S)-5-benzoyloxy-3,4,4a,5,6,7-hexahydro-1,1,4a-trimethylnaphthalen-2(1H)-one

There total 1 articles about (+)-(4aS,5S)-5-benzoyloxy-3,4,4a,5,6,7-hexahydro-1,1,4a-trimethylnaphthalen-2(1H)-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: 84.0%

(+)-(4aS,5S)-5-benzoyloxy-4,4a,5,6,7,8-hexahydro-4a-methylnaphthalen-2(3H)-one (32042-79-8,93903-43-6,126452-85-5,110715-79-2) + methyl iodide (74-88-4) → (+)-(4aS,5S)-5-benzoyloxy-3,4,4a,5,6,7-hexahydro-1,1,4a-trimethylnaphthalen-2(1H)-one (110654-75-6)

Guidance literature:

(+)-(4aS,5S)-5-benzoyloxy-4,4a,5,6,7,8-hexahydro-4a-methylnaphthalen-2(3H)-one; With potassium tert-butylate; In tert-butyl alcohol; at 20 ℃; for 15h;

methyl iodide; In tert-butyl alcohol; at 20 ℃; for 0.75h;

DOI:10.1016/S0040-4020(99)00627-4

Reference yield:

(+)-(4aS,5S)-5-benzoyloxy-3,4,4a,5,6,7-hexahydro-1,1,4a-trimethylnaphthalen-2(1H)-one (110654-75-6) → (1S,2S)-1,3,3-Trimethyl-2-[2-(2-oxo-cyclohex-3-enyl)-ethyl]-cyclohexanecarbaldehyde (97855-75-9)

Guidance literature:

Multi-step reaction with 17 steps

1: 93 percent / potassium hydroxide, hydrazine hydrate / bis-(2-hydroxy-ethyl) ether / 6 h / Heating

2: 95 percent / H₂ / Adam's catalyst / acetic acid

3: 90 percent / Florisil, PCC / CH₂Cl₂ / 2 h / Ambient temperature

4: 97 percent / PBB / acetic acid / 2 h / Ambient temperature

5: 97 percent / sodium hydroxide / dimethylformamide; H₂O / 0.5 h / Ambient temperature

6: lead tetra-acetate (LTA) / benzene / 0.17 h / Ambient temperature

7: NaBH₄ / methanol / 0.33 h / Ambient temperature

8: 98 percent / tributylphosphine / tetrahydrofuran / 0.33 h / Ambient temperature

9: 91 percent / hydrogen peroxide / tetrahydrofuran / 10 h / Ambient temperature

10: 1.) lithium aluminium hydride; 2.) sodium hydroxide / 1.) diethyl ether, rt, 30 min; 2.) water, 30 min.

11: 88 percent / Florisil, PCC / CH₂Cl₂ / 1 h / Ambient temperature

12: 98 percent / toluene-p-sulphonic acid / benzene / 0.33 h / Heating

13: 1. osmium tetraoxide; 2.) sodium periodate / 1.) diethyl ether, water, rt, 5 min; 2.) rt, 10 h.

14: 1.) lithium diisopropylamide (LDA) / 1.) THF, -78 deg C; 2.) THF, rt, 1 h.

15: 98 percent / H₂ / 10 percent palladium-charcoal / ethanol

17: 83 percent / 10 percent perchloric acid / tetrahydrofuran / 1 h / Ambient temperature

With lead(IV) acetate; potassium hydroxide; sodium hydroxide; sodium tetrahydroborate; florisil; sodium periodate; osmium(VIII) oxide; lithium aluminium tetrahydride; perchloric acid; tributylphosphine; hydrogen; dihydrogen peroxide; toluene-4-sulfonic acid; hydrazine hydrate; pyridinium chlorochromate; lithium diisopropyl amide; platinum(IV) oxide; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; acetic acid; N,N-dimethyl-formamide; diethylene glycol; benzene;

Reference yield:

(+)-(4aS,5S)-5-benzoyloxy-3,4,4a,5,6,7-hexahydro-1,1,4a-trimethylnaphthalen-2(1H)-one (110654-75-6) → 2-[2-((1S,2S)-2-[1,3]Dioxolan-2-yl-2,6,6-trimethyl-cyclohexyl)-ethyl]-cyclohexanone (110654-77-8)

Guidance literature:

Multi-step reaction with 15 steps

1: 93 percent / potassium hydroxide, hydrazine hydrate / bis-(2-hydroxy-ethyl) ether / 6 h / Heating

2: 95 percent / H₂ / Adam's catalyst / acetic acid

3: 90 percent / Florisil, PCC / CH₂Cl₂ / 2 h / Ambient temperature

4: 97 percent / PBB / acetic acid / 2 h / Ambient temperature

5: 97 percent / sodium hydroxide / dimethylformamide; H₂O / 0.5 h / Ambient temperature

6: lead tetra-acetate (LTA) / benzene / 0.17 h / Ambient temperature

7: NaBH₄ / methanol / 0.33 h / Ambient temperature

8: 98 percent / tributylphosphine / tetrahydrofuran / 0.33 h / Ambient temperature

9: 91 percent / hydrogen peroxide / tetrahydrofuran / 10 h / Ambient temperature

10: 1.) lithium aluminium hydride; 2.) sodium hydroxide / 1.) diethyl ether, rt, 30 min; 2.) water, 30 min.

11: 88 percent / Florisil, PCC / CH₂Cl₂ / 1 h / Ambient temperature

12: 98 percent / toluene-p-sulphonic acid / benzene / 0.33 h / Heating

13: 1. osmium tetraoxide; 2.) sodium periodate / 1.) diethyl ether, water, rt, 5 min; 2.) rt, 10 h.

14: 1.) lithium diisopropylamide (LDA) / 1.) THF, -78 deg C; 2.) THF, rt, 1 h.

15: 98 percent / H₂ / 10 percent palladium-charcoal / ethanol

With lead(IV) acetate; potassium hydroxide; sodium hydroxide; sodium tetrahydroborate; florisil; sodium periodate; osmium(VIII) oxide; lithium aluminium tetrahydride; tributylphosphine; hydrogen; dihydrogen peroxide; toluene-4-sulfonic acid; hydrazine hydrate; pyridinium chlorochromate; lithium diisopropyl amide; platinum(IV) oxide; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; acetic acid; N,N-dimethyl-formamide; diethylene glycol; benzene;

upstream raw materials:

(+)-(4aS,5S)-5-benzoyloxy-4,4a,5,6,7,8-hexahydro-4a-methylnaphthalen-2(3H)-one

methyl iodide

Downstream raw materials:

(-)-(4aS,8aS)-4,4a,5,6,7,8-hexahydro-2,5,5,8a-tetramethylnaphthalen-1(8aH)-one

(-)-Hispanolone

(+)-(4aS,8aS)-4-[2-(3-furyl)ethyl]-4a,5,6,7,8,8a-hexahydro-3,4a,8,8-tetramethylnaphthalen-2(1H)-one

(2ζ,4aS,8aS)-2,5,5,8a-Tetramethyl-3,4,4a,5,6,7,8,8a-octahydronaphthalen-1(2H)-one

Refernces

• 1、 Ihara, Masataka,Toyota, Masahiro,Fukumoto, Keiichiro,Kametani, Tetsuji. "An Enantioselective Total Synthesis of (+)-Atisirene by Intramolecular Double Michael Reaction". . p. 2151 - 2162. Retrieved 2007/10/02.