1,4-Methanonaphthalen-5-ol,1,4,4a,5,6,7,8,8a-octahydro-8-methylene-,(1S,4R,4aS,5R,8aR)-(9CI)

Base Information

• Chemical Name: 1,4-Methanonaphthalen-5-ol,1,4,4a,5,6,7,8,8a-octahydro-8-methylene-,(1S,4R,4aS,5R,8aR)-(9CI)
• CAS No.: 612481-34-2
• Molecular Formula: C12H16O
• Molecular Weight: 176.25
• Mol file: 612481-34-2.mol

Synonyms:1,4-Methanonaphthalen-5-ol,1,4,4a,5,6,7,8,8a-octahydro-8-methylene-,(1S,4R,4aS,5R,8aR)-(9CI)

Chemical Property of 1,4-Methanonaphthalen-5-ol,1,4,4a,5,6,7,8,8a-octahydro-8-methylene-,(1S,4R,4aS,5R,8aR)-(9CI)

Chemical Property:

• PSA: 20.23000
• LogP: 2.13560

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 1,4-Methanonaphthalen-5-ol,1,4,4a,5,6,7,8,8a-octahydro-8-methylene-,(1S,4R,4aS,5R,8aR)-(9CI)

There total 7 articles about 1,4-Methanonaphthalen-5-ol,1,4,4a,5,6,7,8,8a-octahydro-8-methylene-,(1S,4R,4aS,5R,8aR)-(9CI) 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: 100.0%

Acetic acid (1S,4R,4aS,5R,8aR)-8-methylene-1,4,4a,5,6,7,8,8a-octahydro-1,4-methano-naphthalen-5-yl ester (612481-19-3) → (1S,4R,4aS,5R,8aR)-8-Methylene-1,4,4a,5,6,7,8,8a-octahydro-1,4-methano-naphthalen-5-ol (612481-34-2)

Guidance literature:

With potassium carbonate; In methanol; at 0 ℃;

DOI:10.1016/S0040-4039(03)01643-5

Reference yield:

norbornenoquinone (51175-59-8) → (1S,4R,4aS,5R,8aR)-8-Methylene-1,4,4a,5,6,7,8,8a-octahydro-1,4-methano-naphthalen-5-ol (612481-34-2)

Guidance literature:

Multi-step reaction with 7 steps

1: 78 percent / LiAlH₄ / diethyl ether / 0 °C

2: 82 percent / PCC / CH₂Cl₂ / 0 °C

3: 83 percent / DIBAL-H / CH₂Cl₂ / -78 °C

4: 85 percent / Lipase PS (amano) / tetrahydrofuran / 20 °C

5: 80 percent / PDC / CH₂Cl₂ / 0 °C

6: 76 percent / Zn; TiCl₄ / CH₂Cl₂ / 0 °C

7: 100 percent / K₂CO₃ / methanol / 0 °C

With lithium aluminium tetrahydride; dipyridinium dichromate; Lipase PS (Amano); titanium tetrachloride; diisobutylaluminium hydride; potassium carbonate; pyridinium chlorochromate; zinc; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; 6: Lombardo methylenation;

DOI:10.1016/S0040-4039(03)01643-5

Reference yield:

endo-tricyclo[6.2.1.02,7]undec-9-ene-3,6-dione (32061-93-1) → (1S,4R,4aS,5R,8aR)-8-Methylene-1,4,4a,5,6,7,8,8a-octahydro-1,4-methano-naphthalen-5-ol (612481-34-2)

Guidance literature:

Multi-step reaction with 5 steps

1: 83 percent / DIBAL-H / CH₂Cl₂ / -78 °C

2: 85 percent / Lipase PS (amano) / tetrahydrofuran / 20 °C

3: 80 percent / PDC / CH₂Cl₂ / 0 °C

4: 76 percent / Zn; TiCl₄ / CH₂Cl₂ / 0 °C

5: 100 percent / K₂CO₃ / methanol / 0 °C

With dipyridinium dichromate; Lipase PS (Amano); titanium tetrachloride; diisobutylaluminium hydride; potassium carbonate; zinc; In tetrahydrofuran; methanol; dichloromethane; 4: Lombardo methylenation;

DOI:10.1016/S0040-4039(03)01643-5

upstream raw materials:

Acetic acid (1S,4R,4aS,5R,8aR)-8-methylene-1,4,4a,5,6,7,8,8a-octahydro-1,4-methano-naphthalen-5-yl ester

norbornenoquinone

endo-tricyclo[6.2.1.0^2,7]undec-9-ene-3,6-dione

meso-1,4,4a,5,6,8,8a-Octahydro-5,8-dihydroxy-endo-1,4-methanonaphthalene