Naphtho(2,3-b)furan, 4,4a,7,8,8a,9-hexahydro-6,9,9-trimethyl-, (4aR,8aS)-

Base Information

• Chemical Name: Naphtho(2,3-b)furan, 4,4a,7,8,8a,9-hexahydro-6,9,9-trimethyl-, (4aR,8aS)-
• CAS No.: 70546-62-2
• Molecular Formula: C₁₅H₂₀O
• Molecular Weight: 216.323
• DSSTox Substance ID: DTXSID40220826
• Nikkaji Number: J838.511D
• Wikidata: Q83098287
• Metabolomics Workbench ID: 171772
• ChEMBL ID: CHEMBL478782
• Mol file: 70546-62-2.mol

Synonyms:70546-62-2;Naphtho(2,3-b)furan, 4,4a,7,8,8a,9-hexahydro-6,9,9-trimethyl-, (4aR,8aS)-;CHEMBL478782;DTXSID40220826;Naphtho[2,3-b]furan, 4,4a,7,8,8a,9-hexahydro-6,9,9-trimethyl-, cis-()-

Chemical Property of Naphtho(2,3-b)furan, 4,4a,7,8,8a,9-hexahydro-6,9,9-trimethyl-, (4aR,8aS)-

Chemical Property:

• Vapor Pressure: 0.00826mmHg at 25°C
• Boiling Point: 276.1°Cat760mmHg
• Flash Point: 113.7°C
• Density: 0.98g/cm³
• XLogP3: 3.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 216.151415257
• Heavy Atom Count: 16
• Complexity: 315

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC2CC3=C(C(C2CC1)(C)C)OC=C3
• Isomeric SMILES: CC1=C[C@H]2CC3=C(C([C@H]2CC1)(C)C)OC=C3

Technology Process of Naphtho(2,3-b)furan, 4,4a,7,8,8a,9-hexahydro-6,9,9-trimethyl-, (4aR,8aS)-

There total 7 articles about Naphtho(2,3-b)furan, 4,4a,7,8,8a,9-hexahydro-6,9,9-trimethyl-, (4aR,8aS)- 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: 57.0%

(4aS,8aR)-6,9,9-Trimethyl-4a,7,8,8a,9,9a-hexahydro-4H-naphtho[2,3-b]furan-2-one (115819-66-4) → (+/-)-furodizin (70546-62-2,115889-38-8,129783-56-8)

Guidance literature:

With diisobutylaluminium hydride; In tetrahydrofuran;

DOI:10.1246/cl.1987.2079

Reference yield: 39.0%

(E)-1-Furan-3-yl-4,8-dimethyl-nona-2,7-dien-4-ol (178324-27-1) → (+/-)-furodizin (70546-62-2,115889-38-8,129783-56-8) + 3-((1S,6S)-6-Isopropenyl-3-methyl-cyclohex-2-enylmethyl)-furan + 3-((1S,6R)-6-Isopropenyl-3-methyl-cyclohex-2-enylmethyl)-furan + (4aR,8aR)-6,9,9-Trimethyl-4,4a,7,8,8a,9-hexahydro-naphtho[2,3-b]furan

Guidance literature:

With phosphoric acid; In water; toluene; at 100 ℃; for 0.333333h;

DOI:10.1007/bf01431820

Reference yield:

(4aS,8aR)-6-Methyl-3,4,4a,7,8,8a-hexahydro-1H-naphthalen-2-one (61530-97-0) → (+/-)-furodizin (70546-62-2,115889-38-8,129783-56-8)

Guidance literature:

Multi-step reaction with 5 steps

1: 78 percent / potassium t-butoxide / 2-methyl-propan-2-ol; benzene

2: 83 percent / lithium diisopropylamide

3: 80 percent / KOH / methanol

4: 83 percent / sodium acetate, acetic anhydride

5: 57 percent / diisobutylaluminum hydride / tetrahydrofuran

With potassium hydroxide; potassium tert-butylate; sodium acetate; acetic anhydride; diisobutylaluminium hydride; lithium diisopropyl amide; In tetrahydrofuran; methanol; tert-butyl alcohol; benzene;

DOI:10.1246/cl.1987.2079

upstream raw materials:

(4aS,8aR)-6,9,9-Trimethyl-4a,7,8,8a,9,9a-hexahydro-4H-naphtho[2,3-b]furan-2-one

(E)-1-Furan-3-yl-4,8-dimethyl-nona-2,7-dien-4-ol

1-Furan-3-yl-4,8-dimethyl-non-7-en-2-yn-4-ol

(4aS,8aR)-6-Methyl-3,4,4a,7,8,8a-hexahydro-1H-naphthalen-2-one