(S)-5,5a,6,7-Tetrahydro-8-hydroxy-3,5a,9-trimethylnaphtho[1,2-b]furan-2(4H)-one

Base Information

• Chemical Name: (S)-5,5a,6,7-Tetrahydro-8-hydroxy-3,5a,9-trimethylnaphtho[1,2-b]furan-2(4H)-one
• CAS No.: 17453-65-5
• Molecular Formula: C₁₅H₁₈O₃
• Molecular Weight: 246.306
• Mol file: 17453-65-5.mol

Synonyms:Eudesma-3,5,7(11)-trien-12-oicacid, 3,6-dihydroxy-, g-lactone (8CI); Naphtho[1,2-b]furan-2(4H)-one,5,5a,6,7-tetrahydro-8-hydroxy-3,5a,9-trimethyl-, (S)-; Santonene, dihydro-(7CI); 1,2-Dihydrosantonene; Dihydrosantonene

Chemical Property of (S)-5,5a,6,7-Tetrahydro-8-hydroxy-3,5a,9-trimethylnaphtho[1,2-b]furan-2(4H)-one

Chemical Property:

• PSA: 46.53000
• LogP: 3.53970

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (S)-5,5a,6,7-Tetrahydro-8-hydroxy-3,5a,9-trimethylnaphtho[1,2-b]furan-2(4H)-one

There total 4 articles about (S)-5,5a,6,7-Tetrahydro-8-hydroxy-3,5a,9-trimethylnaphtho[1,2-b]furan-2(4H)-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:

santonin (481-06-1) → (5aS)-8-hydroxy-3,5a,9-trimethyl-5,5a,6,7-tetrahydro-4H-naphtho[1,2-b]furan-2-one (17453-65-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 80 percent / hydrogen / Reaney nickel / benzene / 1 h / 20 °C

2: 61 percent / TsOH / benzene / 10 h / Heating

3: 30 percent / LDA; 1,2-dibromoethane; HMPT / tetrahydrofuran; hexane / 4 h / -15 °C

4: aq. H₂SO₄ / acetone / 4 h / Heating

With N,N,N,N,N,N-hexamethylphosphoric triamide; sulfuric acid; hydrogen; toluene-4-sulfonic acid; ethylene dibromide; lithium diisopropyl amide; Reaney nickel; In tetrahydrofuran; hexane; acetone; benzene; 1: Hydrogenation / 2: Cycloaddition / 3: Dehydrogenation / 4: Hydrolysis;

Reference yield:

3,3-ethylenedioxy-4,7α,11βH-eudesm-5-en-6,13-olide (202583-41-3) → (5aS)-8-hydroxy-3,5a,9-trimethyl-5,5a,6,7-tetrahydro-4H-naphtho[1,2-b]furan-2-one (17453-65-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 30 percent / LDA; 1,2-dibromoethane; HMPT / tetrahydrofuran; hexane / 4 h / -15 °C

2: aq. H₂SO₄ / acetone / 4 h / Heating

With N,N,N,N,N,N-hexamethylphosphoric triamide; sulfuric acid; ethylene dibromide; lithium diisopropyl amide; In tetrahydrofuran; hexane; acetone; 1: Dehydrogenation / 2: Hydrolysis;

Reference yield:

(+)-1,2-dihydro-α-santonin (18409-93-3) → (5aS)-8-hydroxy-3,5a,9-trimethyl-5,5a,6,7-tetrahydro-4H-naphtho[1,2-b]furan-2-one (17453-65-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 61 percent / TsOH / benzene / 10 h / Heating

2: 30 percent / LDA; 1,2-dibromoethane; HMPT / tetrahydrofuran; hexane / 4 h / -15 °C

3: aq. H₂SO₄ / acetone / 4 h / Heating

With N,N,N,N,N,N-hexamethylphosphoric triamide; sulfuric acid; toluene-4-sulfonic acid; ethylene dibromide; lithium diisopropyl amide; In tetrahydrofuran; hexane; acetone; benzene; 1: Cycloaddition / 2: Dehydrogenation / 3: Hydrolysis;

upstream raw materials:

3,3-ethylenedioxy-4α-eudesm-5,7(11)-dien-6,13-olide

3,3-ethylenedioxy-4,7α,11βH-eudesm-5-en-6,13-olide

(+)-1,2-dihydro-α-santonin

santonin