4,7,7-trimethyl-3-exo-(1-naphthyl)bicyclo<2.2.1>heptan-2-exo-yl 3-oxo-4-phenylbutanoate

Base Information

• Chemical Name: 4,7,7-trimethyl-3-exo-(1-naphthyl)bicyclo<2.2.1>heptan-2-exo-yl 3-oxo-4-phenylbutanoate
• CAS No.: 110971-12-5
• Molecular Formula: C₃₀H₃₂O₃
• Molecular Weight: 440.582
• Mol file: 110971-12-5.mol

Synonyms:4,7,7-trimethyl-3-exo-(1-naphthyl)bicyclo<2.2.1>heptan-2-exo-yl 3-oxo-4-phenylbutanoate

Chemical Property of 4,7,7-trimethyl-3-exo-(1-naphthyl)bicyclo<2.2.1>heptan-2-exo-yl 3-oxo-4-phenylbutanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4,7,7-trimethyl-3-exo-(1-naphthyl)bicyclo<2.2.1>heptan-2-exo-yl 3-oxo-4-phenylbutanoate

There total 2 articles about 4,7,7-trimethyl-3-exo-(1-naphthyl)bicyclo<2.2.1>heptan-2-exo-yl 3-oxo-4-phenylbutanoate 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: 82.0%

methyl 3-oxo-4-phenylbutanoate (37779-49-0) + (4S)-3-exo-(1-naphthyl)-4,7,7-trimethylbicyclo[2.2.1]heptan-2-exo-ol (86835-18-9) → 4,7,7-trimethyl-3-exo-(1-naphthyl)bicyclo<2.2.1>heptan-2-exo-yl 3-oxo-4-phenylbutanoate (110971-12-5)

Guidance literature:

With dmap; In toluene; for 40h; Heating;

DOI:10.1021/ja00258a039

Reference yield:

phenylacetyl chloride (103-80-0) → 4,7,7-trimethyl-3-exo-(1-naphthyl)bicyclo<2.2.1>heptan-2-exo-yl 3-oxo-4-phenylbutanoate (110971-12-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 79.6 percent / LDA / tetrahydrofuran / -78 °C

2: 82 percent / 4-DMAP / toluene / 40 h / Heating

With dmap; lithium diisopropyl amide; In tetrahydrofuran; toluene;

DOI:10.1021/ja00258a039

Reference yield:

4,7,7-trimethyl-3-exo-(1-naphthyl)bicyclo<2.2.1>heptan-2-exo-yl 3-oxo-4-phenylbutanoate (110971-12-5) → 4,7,7-trimethyl-3-exo-(1-naphthyl)bicyclo<2.2.1>heptan-2-exo-yl 3(R)-hydroxy-4-phenylbutanoate + 4,7,7-trimethyl-3-exo-(1-naphthyl)bicyclo<2.2.1>heptan-2-exo-yl 3(S)-hydroxy-4-phenylbutanoate

Guidance literature:

With zinc(II) tetrahydroborate; In toluene; at -78 ℃; for 2.5h; Yield given;

DOI:10.1021/ja00258a039

upstream raw materials:

methyl 3-oxo-4-phenylbutanoate

(4S)-3-exo-(1-naphthyl)-4,7,7-trimethylbicyclo[2.2.1]heptan-2-exo-ol

phenylacetyl chloride