(+)-(1R,2R,3S,4R,6R,7R)-1,6-Dimethyl-2-(1-naphthyl)-4-phenyltricyclo<4.3.1.0^3,7>decan-9-one

Base Information

• Chemical Name: (+)-(1R,2R,3S,4R,6R,7R)-1,6-Dimethyl-2-(1-naphthyl)-4-phenyltricyclo<4.3.1.0^3,7>decan-9-one
• CAS No.: 140185-87-1
• Molecular Formula: C₂₈H₂₈O
• Molecular Weight: 380.53

Synonyms:(+)-(1R,2R,3S,4R,6R,7R)-1,6-Dimethyl-2-(1-naphthyl)-4-phenyltricyclo<4.3.1.0^3,7>decan-9-one

Chemical Property of (+)-(1R,2R,3S,4R,6R,7R)-1,6-Dimethyl-2-(1-naphthyl)-4-phenyltricyclo<4.3.1.0^3,7>decan-9-one

Chemical Property:

Purity/Quality:

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• Pictogram(s):  
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Technology Process of (+)-(1R,2R,3S,4R,6R,7R)-1,6-Dimethyl-2-(1-naphthyl)-4-phenyltricyclo<4.3.1.0^3,7>decan-9-one

There total 7 articles about (+)-(1R,2R,3S,4R,6R,7R)-1,6-Dimethyl-2-(1-naphthyl)-4-phenyltricyclo<4.3.1.0^3,7>decan-9-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: 60.0%

styrene (100-42-5,25038-60-2,25247-68-1,28213-80-1,28325-75-9,79637-11-9,9003-53-6) + (+)-(1R,4R,8RS)-8-Bromo-1,8-dimethyl-6-(1-naphthyl)bicyclo<2.2.2>oct-5-en-2-one (140185-82-6,140385-24-6) → (+)-(1R,2R,3S,4R,6R,7R)-1,6-Dimethyl-2-(1-naphthyl)-4-phenyltricyclo<4.3.1.03,7>decan-9-one (140185-87-1)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In benzene; for 1h;

DOI:10.1021/jo00061a026

Reference yield:

(R)-Carvone (6485-40-1,2244-16-8) → (+)-(1R,2R,3S,4R,6R,7R)-1,6-Dimethyl-2-(1-naphthyl)-4-phenyltricyclo<4.3.1.03,7>decan-9-one (140185-87-1)

Guidance literature:

Multi-step reaction with 5 steps

1: 1) n-BuLi, 2) PCC, silica gel / 1) THF, RT, 6 h, 2) CH₂Cl₂, RT, 6 h

2: 83 percent / NBS / methanol; CH₂Cl₂ / 12 h / Ambient temperature

3: 75 percent / tBuOK, tBuOH / tetrahydrofuran / 12 h / Ambient temperature

4: 78 percent / boron tribromide / CH₂Cl₂ / 1 h / -60 °C

5: 60 percent / nBu₃SnH, AIBN / benzene / 1 h

With N-Bromosuccinimide; n-butyllithium; 2,2'-azobis(isobutyronitrile); potassium tert-butylate; tri-n-butyl-tin hydride; silica gel; boron tribromide; pyridinium chlorochromate; tert-butyl alcohol; In tetrahydrofuran; methanol; dichloromethane; benzene;

DOI:10.1021/jo00061a026

Reference yield:

(+)-(S)-5-<1-Bromo-2-methoxyprop-2-yl>-2-methyl-3-(1-naphthyl)cyclohex-2-en-1-one (140185-84-8,147666-31-7,147666-38-4) → (+)-(1R,2R,3S,4R,6R,7R)-1,6-Dimethyl-2-(1-naphthyl)-4-phenyltricyclo<4.3.1.03,7>decan-9-one (140185-87-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 75 percent / tBuOK, tBuOH / tetrahydrofuran / 12 h / Ambient temperature

2: 78 percent / boron tribromide / CH₂Cl₂ / 1 h / -60 °C

3: 60 percent / nBu₃SnH, AIBN / benzene / 1 h

With 2,2'-azobis(isobutyronitrile); potassium tert-butylate; tri-n-butyl-tin hydride; boron tribromide; tert-butyl alcohol; In tetrahydrofuran; dichloromethane; benzene;

DOI:10.1021/jo00061a026

upstream raw materials:

styrene

(+)-(1R,4R,8RS)-8-Bromo-1,8-dimethyl-6-(1-naphthyl)bicyclo<2.2.2>oct-5-en-2-one

1-Bromonaphthalene

(R)-Carvone

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