(Z)-Dehydroambliol-A

Base Information

• Chemical Name: (Z)-Dehydroambliol-A
• CAS No.: 133004-97-4
• Molecular Formula: C₂₀H₃₀O
• Molecular Weight: 286.458
• Mol file: 133004-97-4.mol

Synonyms:(Z)-Dehydroambliol-A

Chemical Property of (Z)-Dehydroambliol-A

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (Z)-Dehydroambliol-A

There total 17 articles about (Z)-Dehydroambliol-A 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:

methyl 2,2-dimethyl-6-oxocyclohexanecarboxylate (71135-95-0) → (Z)-Dehydroambliol-A (133004-97-4)

Guidance literature:

Multi-step reaction with 12 steps

2: 56 percent / LiI*2H₂O, 2,4,6-collidine / 19 h / Heating

3: 1.) O₃; 2.) NaBH₄ / methanol; 1.) -50 deg C, 0.25 h; 2.) -30 deg C, 1 h

4: pyridine / 18 h / Ambient temperature

5: 81 percent / CrO₃ / pyridine; CH₂Cl₂ / 1.5 h / Ambient temperature

6: 1.) 1.6 M n-BuLi / 1.) Et₂O, room temp., 3 h; 2.) THF, reflux, 4 h

7: 71 percent / Na, liq. NH₃ / tetrahydrofuran / 0.5 h

8: 75 percent / pyridine / 48 h / -20 °C

9: 90 percent / dibenzo-18-crown-6 / acetonitrile / a) room temp., 1 h; b) reflux, 18 h

10: 85 percent / 25 N NaOH / ethanol / 18 h / Heating

11: 77 percent / hexane; tetrahydrofuran / 2 h / 0 °C

12: 1.) NaH / benzene; 1.) 2 h; 2.) 3 h

With pyridine; 2,4,6-trimethyl-pyridine; chromium(VI) oxide; sodium hydroxide; sodium tetrahydroborate; n-butyllithium; ammonia; sodium; sodium hydride; ozone; lithium iodide; dibenzo-18-crown-6; In tetrahydrofuran; pyridine; ethanol; hexane; dichloromethane; acetonitrile;

DOI:10.1021/jo00009a033

Reference yield:

2-(2'-Methylene-6',6'-dimethylcyclohexyl)ethanol (84078-59-1) → (Z)-Dehydroambliol-A (133004-97-4)

Guidance literature:

Multi-step reaction with 5 steps

1: 75 percent / pyridine / 48 h / -20 °C

2: 90 percent / dibenzo-18-crown-6 / acetonitrile / a) room temp., 1 h; b) reflux, 18 h

3: 85 percent / 25 N NaOH / ethanol / 18 h / Heating

4: 77 percent / hexane; tetrahydrofuran / 2 h / 0 °C

5: 1.) NaH / benzene; 1.) 2 h; 2.) 3 h

With pyridine; sodium hydroxide; sodium hydride; dibenzo-18-crown-6; In tetrahydrofuran; ethanol; hexane; acetonitrile;

DOI:10.1021/jo00009a033

Reference yield:

2-allyl-3,3-dimethylcyclohexan-1-one (57074-03-0) → (Z)-Dehydroambliol-A (133004-97-4)

Guidance literature:

Multi-step reaction with 10 steps

1: 1.) O₃; 2.) NaBH₄ / methanol; 1.) -50 deg C, 0.25 h; 2.) -30 deg C, 1 h

2: pyridine / 18 h / Ambient temperature

3: 81 percent / CrO₃ / pyridine; CH₂Cl₂ / 1.5 h / Ambient temperature

4: 1.) 1.6 M n-BuLi / 1.) Et₂O, room temp., 3 h; 2.) THF, reflux, 4 h

5: 71 percent / Na, liq. NH₃ / tetrahydrofuran / 0.5 h

6: 75 percent / pyridine / 48 h / -20 °C

7: 90 percent / dibenzo-18-crown-6 / acetonitrile / a) room temp., 1 h; b) reflux, 18 h

8: 85 percent / 25 N NaOH / ethanol / 18 h / Heating

9: 77 percent / hexane; tetrahydrofuran / 2 h / 0 °C

10: 1.) NaH / benzene; 1.) 2 h; 2.) 3 h

With pyridine; chromium(VI) oxide; sodium hydroxide; sodium tetrahydroborate; n-butyllithium; ammonia; sodium; sodium hydride; ozone; dibenzo-18-crown-6; In tetrahydrofuran; pyridine; ethanol; hexane; dichloromethane; acetonitrile;

DOI:10.1021/jo00009a033

upstream raw materials:

4-(2',2'-Dimethyl-6'-methylidenecyclohexyl)butan-2-one

<3-(3-Furyl)propyl>triphenylphosphonium Bromide

methyl 2,2-dimethyl-6-oxocyclohexanecarboxylate

1-(2'-Cyanoethyl)-2-methylene-6,6-dimethylcyclohexane