(3α,3aα,8α,8aα)-octahydro-3a,8-dimethyl-5-(3-methyl-2-butenyl)-3-(phenylmethoxy)-4(1H)-azulenone

Base Information

• Chemical Name: (3α,3aα,8α,8aα)-octahydro-3a,8-dimethyl-5-(3-methyl-2-butenyl)-3-(phenylmethoxy)-4(1H)-azulenone
• CAS No.: 82042-02-2
• Molecular Formula: C₂₄H₃₄O₂
• Molecular Weight: 354.533

Synonyms:(3α,3aα,8α,8aα)-octahydro-3a,8-dimethyl-5-(3-methyl-2-butenyl)-3-(phenylmethoxy)-4(1H)-azulenone

Chemical Property of (3α,3aα,8α,8aα)-octahydro-3a,8-dimethyl-5-(3-methyl-2-butenyl)-3-(phenylmethoxy)-4(1H)-azulenone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3α,3aα,8α,8aα)-octahydro-3a,8-dimethyl-5-(3-methyl-2-butenyl)-3-(phenylmethoxy)-4(1H)-azulenone

There total 14 articles about (3α,3aα,8α,8aα)-octahydro-3a,8-dimethyl-5-(3-methyl-2-butenyl)-3-(phenylmethoxy)-4(1H)-azulenone 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:

(S)-2-{(1R,4R,5R)-4-Hydroxy-5-methyl-5-[(R)-1-(tetrahydro-pyran-2-yloxy)-ethyl]-cyclopent-2-enyl}-propionic acid (81987-61-3) → (3α,3aα,8α,8aα)-octahydro-3a,8-dimethyl-5-(3-methyl-2-butenyl)-3-(phenylmethoxy)-4(1H)-azulenone (82042-02-2)

Guidance literature:

Multi-step reaction with 14 steps

2: H₂ / PtO₂ / ethyl acetate / 2.5 h / Ambient temperature

3: LiAlH₄ / diethyl ether / 2 h / Ambient temperature

4: pyridine / 12 h / 0 - 5 °C

5: dimethylsulfoxide / 2 h / 90 °C

6: 88 percent / NaH, Bu₄NI / tetrahydrofuran; hexamethylphosphoric acid triamide / 1.) 0 deg C, 30 min, 2.) room temperature, 1 h, 3.) 50 deg C, 10 h

7: i-Bu₂AlH₄ / toluene / 1 h / -78 °C

8: NaBH₄ / methanol / 2 h / Ambient temperature

9: 94 percent / p-toluenesulfonic acid / methanol / 2 h / Ambient temperature

10: pyridine / 18 h / 0 - 5 °C

11: Jones reagent / acetone / 0.25 h

12: 95 percent / NaI / acetone / 16 h / Ambient temperature

13: 88 percent / LiN(SiMe₃)2 / tetrahydrofuran; hexamethylphosphoric acid triamide / 1.) -78 deg C, 1 h, 2.) -20 deg C, 3 h, 3.) 0 deg C, 2 h

14: diisopropylamine, n-BuLi, hexamethylphosphoramide / tetrahydrofuran; hexane / 1.) -78 deg C, 30 min, 2.) -20 deg C, 3 h

With N,N,N,N,N,N-hexamethylphosphoric triamide; sodium tetrahydroborate; lithium aluminium tetrahydride; n-butyllithium; jones reagent; hydrogen; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; diisopropylamine; sodium iodide; lithium hexamethyldisilazane; platinum(IV) oxide; In tetrahydrofuran; pyridine; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; hexane; dimethyl sulfoxide; ethyl acetate; acetone; toluene;

DOI:10.1021/ja00379a029

Reference yield:

methyl α,5-dimethyl-4-hydroxy-5-<1-<(tetrahydro-2H-pyran-2-yl)oxy>ethyl>-2-cyclopentene-1-acetate (82041-93-8) → (3α,3aα,8α,8aα)-octahydro-3a,8-dimethyl-5-(3-methyl-2-butenyl)-3-(phenylmethoxy)-4(1H)-azulenone (82042-02-2)

Guidance literature:

Multi-step reaction with 13 steps

1: H₂ / PtO₂ / ethyl acetate / 2.5 h / Ambient temperature

2: LiAlH₄ / diethyl ether / 2 h / Ambient temperature

3: pyridine / 12 h / 0 - 5 °C

4: dimethylsulfoxide / 2 h / 90 °C

5: 88 percent / NaH, Bu₄NI / tetrahydrofuran; hexamethylphosphoric acid triamide / 1.) 0 deg C, 30 min, 2.) room temperature, 1 h, 3.) 50 deg C, 10 h

6: i-Bu₂AlH₄ / toluene / 1 h / -78 °C

7: NaBH₄ / methanol / 2 h / Ambient temperature

8: 94 percent / p-toluenesulfonic acid / methanol / 2 h / Ambient temperature

9: pyridine / 18 h / 0 - 5 °C

10: Jones reagent / acetone / 0.25 h

11: 95 percent / NaI / acetone / 16 h / Ambient temperature

12: 88 percent / LiN(SiMe₃)2 / tetrahydrofuran; hexamethylphosphoric acid triamide / 1.) -78 deg C, 1 h, 2.) -20 deg C, 3 h, 3.) 0 deg C, 2 h

13: diisopropylamine, n-BuLi, hexamethylphosphoramide / tetrahydrofuran; hexane / 1.) -78 deg C, 30 min, 2.) -20 deg C, 3 h

With N,N,N,N,N,N-hexamethylphosphoric triamide; sodium tetrahydroborate; lithium aluminium tetrahydride; n-butyllithium; jones reagent; hydrogen; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; diisopropylamine; sodium iodide; lithium hexamethyldisilazane; platinum(IV) oxide; In tetrahydrofuran; pyridine; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; hexane; dimethyl sulfoxide; ethyl acetate; acetone; toluene;

DOI:10.1021/ja00379a029

Reference yield:

methyl α,5-dimethyl-4-hydroxy-5-<1-<(tetrahydro-2H-pyran-2-yl)oxy>ethyl>cyclopentane-1-ethanol (82041-98-3) → (3α,3aα,8α,8aα)-octahydro-3a,8-dimethyl-5-(3-methyl-2-butenyl)-3-(phenylmethoxy)-4(1H)-azulenone (82042-02-2)

Guidance literature:

Multi-step reaction with 11 steps

1: pyridine / 12 h / 0 - 5 °C

2: dimethylsulfoxide / 2 h / 90 °C

3: 88 percent / NaH, Bu₄NI / tetrahydrofuran; hexamethylphosphoric acid triamide / 1.) 0 deg C, 30 min, 2.) room temperature, 1 h, 3.) 50 deg C, 10 h

4: i-Bu₂AlH₄ / toluene / 1 h / -78 °C

5: NaBH₄ / methanol / 2 h / Ambient temperature

6: 94 percent / p-toluenesulfonic acid / methanol / 2 h / Ambient temperature

7: pyridine / 18 h / 0 - 5 °C

8: Jones reagent / acetone / 0.25 h

9: 95 percent / NaI / acetone / 16 h / Ambient temperature

10: 88 percent / LiN(SiMe₃)2 / tetrahydrofuran; hexamethylphosphoric acid triamide / 1.) -78 deg C, 1 h, 2.) -20 deg C, 3 h, 3.) 0 deg C, 2 h

11: diisopropylamine, n-BuLi, hexamethylphosphoramide / tetrahydrofuran; hexane / 1.) -78 deg C, 30 min, 2.) -20 deg C, 3 h

With N,N,N,N,N,N-hexamethylphosphoric triamide; sodium tetrahydroborate; n-butyllithium; jones reagent; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; diisopropylamine; sodium iodide; lithium hexamethyldisilazane; In tetrahydrofuran; pyridine; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane; dimethyl sulfoxide; acetone; toluene;

DOI:10.1021/ja00379a029

upstream raw materials:

(3α,3aα,8α,8aα)-octahydro-3a,8-dimethyl-3-(phenylmethoxy)-4(1H)-azulenone

prenyl bromide

methyl α,5-dimethyl-4-hydroxy-5-<1-<(tetrahydro-2H-pyran-2-yl)oxy>ethyl>cyclopentane-1-ethanol

<1α(S<*>),2β(S<*>),5β>-1-<2-(3-hydroxy-1-methylpropyl)-1-methyl-5-(phenylmethoxy)cyclopentyl>ethanol

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