(1α,3aβ,4β,8aα)-3a,4,5,8a-Tetrahydro-4,8a-dimethyl-1-(phenylmethoxy)-6(1H)-azulenone

Base Information

• Chemical Name: (1α,3aβ,4β,8aα)-3a,4,5,8a-Tetrahydro-4,8a-dimethyl-1-(phenylmethoxy)-6(1H)-azulenone
• CAS No.: 68241-54-3
• Molecular Formula: C₁₉H₂₂O₂
• Molecular Weight: 282.382

Synonyms:(1α,3aβ,4β,8aα)-3a,4,5,8a-Tetrahydro-4,8a-dimethyl-1-(phenylmethoxy)-6(1H)-azulenone

Chemical Property of (1α,3aβ,4β,8aα)-3a,4,5,8a-Tetrahydro-4,8a-dimethyl-1-(phenylmethoxy)-6(1H)-azulenone

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of (1α,3aβ,4β,8aα)-3a,4,5,8a-Tetrahydro-4,8a-dimethyl-1-(phenylmethoxy)-6(1H)-azulenone

There total 29 articles about (1α,3aβ,4β,8aα)-3a,4,5,8a-Tetrahydro-4,8a-dimethyl-1-(phenylmethoxy)-6(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:

Methanesulfonic acid (3S,3aS,8R,8aR)-3-benzyloxy-3a,8-dimethyl-6-oxo-3,3a,4,5,6,7,8,8a-octahydro-azulen-4-yl ester (82010-19-3) → (1α,3aβ,4β,8aα)-3a,4,5,8a-Tetrahydro-4,8a-dimethyl-1-(phenylmethoxy)-6(1H)-azulenone (68241-54-3)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In benzene; for 0.25h; Yield given; Ambient temperature;

DOI:10.1021/ja00379a030

Reference yield:

benzyl bromide (100-39-0) → (1α,3aβ,4β,8aα)-3a,4,5,8a-Tetrahydro-4,8a-dimethyl-1-(phenylmethoxy)-6(1H)-azulenone (68241-54-3)

Guidance literature:

Multi-step reaction with 16 steps

1: 87 percent / NaH, Bu₄NI / tetrahydrofuran; hexamethylphosphoric acid triamide / 1.) 0 deg C, 30 min, 2.) room temperature, 1 h, 3.) 50 deg C, 12 h

2: p-toluenesulfonic acid / methanol / 2 h / Ambient temperature

3: 89 percent / 10percent aq. KOH / methanol / 21 h / 55 °C

4: 64 percent / p-toluenesulfonyl chloride, DBU / toluene / 1.) 0 deg C, 15 min, 2.) ambient temperature, 1 h

5: 92 percent / DBU / toluene / 3 h / Heating

6: i-Bu₂AlH / toluene / 0.5 h / -78 °C

7: benzene / 1 h / Ambient temperature

8: 85 percent / Collins reagent / CH₂Cl₂ / 0.5 h / 0 °C

9: 99 percent / 10percent aq. HCl / tetrahydrofuran / 12 h / Ambient temperature

10: 1.5percent KOH / methanol / 8 h / Ambient temperature

11: p-toluenesulfonic acid / CH₂Cl₂ / 1 h / 0 °C

12: 365 mg / NaBH₄ / methanol / 1.) 0 deg C, 2 h, 2.) room temperature, 3 h

13: 96 percent / pyridine / 2 h / Ambient temperature

14: 344 mg / p-toluenesulfonic acid / methanol / 1.) 0 deg c, 1 h, 2.) room temperature, 2 h

15: 342 mg / Jones reagent / acetone / 0.25 h / 0 °C

16: DBU / benzene / 0.25 h / Ambient temperature

With hydrogenchloride; potassium hydroxide; sodium tetrahydroborate; jones reagent; Collins oxidation agent; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; p-toluenesulfonyl chloride; In tetrahydrofuran; pyridine; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; acetone; toluene; benzene;

DOI:10.1021/ja00379a030

Reference yield:

(1S,4S,4aS,7S,7aR)-7-Benzyloxy-1,4,7a-trimethyl-1,3,4,4a,7,7a-hexahydro-cyclopenta[c]pyran-3-ol (71686-31-2) → (1α,3aβ,4β,8aα)-3a,4,5,8a-Tetrahydro-4,8a-dimethyl-1-(phenylmethoxy)-6(1H)-azulenone (68241-54-3)

Guidance literature:

Multi-step reaction with 10 steps

1: benzene / 1 h / Ambient temperature

2: 85 percent / Collins reagent / CH₂Cl₂ / 0.5 h / 0 °C

3: 99 percent / 10percent aq. HCl / tetrahydrofuran / 12 h / Ambient temperature

4: 1.5percent KOH / methanol / 8 h / Ambient temperature

5: p-toluenesulfonic acid / CH₂Cl₂ / 1 h / 0 °C

6: 365 mg / NaBH₄ / methanol / 1.) 0 deg C, 2 h, 2.) room temperature, 3 h

7: 96 percent / pyridine / 2 h / Ambient temperature

8: 344 mg / p-toluenesulfonic acid / methanol / 1.) 0 deg c, 1 h, 2.) room temperature, 2 h

9: 342 mg / Jones reagent / acetone / 0.25 h / 0 °C

10: DBU / benzene / 0.25 h / Ambient temperature

With hydrogenchloride; potassium hydroxide; sodium tetrahydroborate; jones reagent; Collins oxidation agent; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; pyridine; methanol; dichloromethane; acetone; benzene;

DOI:10.1021/ja00379a030

upstream raw materials:

(1S,2S,5R)-2-Benzyloxy-1-methyl-5-((R)-1-methyl-3-oxo-butyl)-cyclopent-3-enecarbaldehyde

Methanesulfonic acid (3S,3aS,8R,8aR)-3-benzyloxy-3a,8-dimethyl-6-oxo-3,3a,4,5,6,7,8,8a-octahydro-azulen-4-yl ester

benzyl bromide

(1S,4S,4aS,7S,7aR)-7-Benzyloxy-1,4,7a-trimethyl-1,3,4,4a,7,7a-hexahydro-cyclopenta[c]pyran-3-ol

Downstream raw materials:

(1α,3aβ,4β,8aα)-3a,4,5,8a-Tetrahydro-4,8a-dimethyl-1-(phenylmethoxy)-6(1H)-azulenol

(1aα,4β,4aβ,7α,7aα,7bα)-3,4,4a,7,7a,7b-hexahydro-4,7a-dimethyl-7-(phenylmethoxy)azuleno<4,5-b>oxiren-2(1aH)-one

(1aα,4β,4aβ,7α,7aα,7bα)-1a,2,3,4,4a,7,7a,7b-octahydro-4,7a-dimethyl-7-(phenylmethoxy)azuleno<4,5-b>oxiren-2-ol

(3aβ,4β,4aα,5α,7aβ,8β,9aβ)-3a,4,4a,5,7a,8,9,9a-octahydro-4-hydroxy-4a,8-dimethyl-5-(phenylmethoxy)azuleno<6,5-b>furan-2(3H)-one

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