1,2-Dehydro-a-cyperone

Base Information

• Chemical Name: 1,2-Dehydro-a-cyperone
• CAS No.: 17081-85-5
• Molecular Formula: C₁₅H₂₀O
• Molecular Weight: 216.323
• Nikkaji Number: J2.378.710E
• Wikidata: Q105347917
• Mol file: 17081-85-5.mol

Synonyms:1,2-dehydro-alpha-cyperone;1,2-Dehydro-a-cyperone;1,4,11-Selinatrien-3-one;1,4,11-Eudesmatrien-3-one;CHEBI:191680;(+)-Eudesma-1,4,11-trien-3-one;1,4a-dimethyl-7-prop-1-en-2-yl-5,6,7,8-tetrahydronaphthalen-2-one;(4aS-cis)-5,6,7,8-Tetrahydro-1,4a-dimethyl-7-(1-methylethenyl)-2(4aH)-naphthalenone

Chemical Property of 1,2-Dehydro-a-cyperone

Chemical Property:

• XLogP3: 4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 216.151415257
• Heavy Atom Count: 16
• Complexity: 411

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1=C2CC(CCC2(C=CC1=O)C)C(=C)C

Technology Process of 1,2-Dehydro-a-cyperone

There total 1 articles about 1,2-Dehydro-a-cyperone 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: 8.0%

(4aS,7R,8aS)-1,4a-dimethyl-7-isopropenyl-3,4,4a,5,6,7,8,8a-octahydro-2-(trimethylsilyloxy)-naphthalene (141871-28-5) → eudesma-4,11-dien-3-one (473-08-5) + (4aS,7R)-1,4a-dimethyl-7-isopropenyl-5,6,7,8-tetrahydronaphthalene-2-(4aH)-one (17081-85-5)

Guidance literature:

With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In benzene; for 1h; Ambient temperature;

DOI:10.1016/S0040-4020(01)92253-7

Reference yield:

(4aS,7R)-1,4a-dimethyl-7-isopropenyl-5,6,7,8-tetrahydronaphthalene-2-(4aH)-one (17081-85-5) → 2-[(2R,4aS,7R,8S)-4a,8-Dimethyl-7-(2-nitro-phenylselanyl)-2,3,4,4a,7,8-hexahydro-naphthalen-2-yl]-propan-2-ol (176665-72-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 94 percent / Oxone, 18-crown-6, NaHCO₃ / CH₂Cl₂; acetone; H₂O / 3.5 h / 0 °C

2: 1.) t-BuOK, 2.) CaCl₂, NaBH₄ / 1.) DMSO, room temperature, 45 min, 2.) EtOH, THF, -25 deg C, 1.5 h

3: 91 percent / LAH / tetrahydrofuran / 1 h / Ambient temperature

4: 91 percent / n-Bu₃P / tetrahydrofuran / 20 h / Ambient temperature

With Oxone; sodium tetrahydroborate; lithium aluminium tetrahydride; 18-crown-6 ether; tributylphosphine; potassium tert-butylate; sodium hydrogencarbonate; calcium chloride; In tetrahydrofuran; dichloromethane; water; acetone;

DOI:10.1021/jo9602534

Reference yield:

(4aS,7R)-1,4a-dimethyl-7-isopropenyl-5,6,7,8-tetrahydronaphthalene-2-(4aH)-one (17081-85-5) → (1R,4R,6R,8aR)-6-(1-Hydroxy-1-methyl-ethyl)-4,8a-dimethyl-1,2,3,4,6,7,8,8a-octahydro-naphthalen-1-ol (176776-01-5)

Guidance literature:

Multi-step reaction with 5 steps

1: 94 percent / Oxone, 18-crown-6, NaHCO₃ / CH₂Cl₂; acetone; H₂O / 3.5 h / 0 °C

2: 1.) t-BuOK, 2.) CaCl₂, NaBH₄ / 1.) DMSO, room temperature, 45 min, 2.) EtOH, THF, -25 deg C, 1.5 h

3: 1.) TMEDA, BuLi, 2.) (Me₂N)2P(O)Cl, 3.) Li, EtMH₂

4: 1.) NBS, 2.) KOH / 1.) dioxane, H₂O, 5-10 deg C, 30 min, 2.) MeOH, room temperature, 1 h

5: 1.) NaOEt, benzeneselenol, 2.) Raney Ni / 1.) EtOH, reflux, 7 h, 2.) room temperature, 1 h

With Oxone; potassium hydroxide; sodium tetrahydroborate; N-Bromosuccinimide; n-butyllithium; Phosphodiamidic Monochloride; 18-crown-6 ether; N,N,N,N,-tetramethylethylenediamine; potassium tert-butylate; sodium ethanolate; Benzeneselenol; lithium; nickel; sodium hydrogencarbonate; calcium chloride; In dichloromethane; water; acetone;

DOI:10.1021/jo9602534

upstream raw materials:

(4aS,7R,8aS)-1,4a-dimethyl-7-isopropenyl-3,4,4a,5,6,7,8,8a-octahydro-2-(trimethylsilyloxy)-naphthalene

Downstream raw materials:

(1R,4R,6R,8aR)-6-(1-Hydroxy-1-methyl-ethyl)-4,8a-dimethyl-1,2,3,4,6,7,8,8a-octahydro-naphthalen-1-ol

2-[(2R,4aS,7R,8S)-4a,8-Dimethyl-7-(2-nitro-phenylselanyl)-2,3,4,4a,7,8-hexahydro-naphthalen-2-yl]-propan-2-ol