cis-3a,4,9,9a-Tetrahydro-2,2-dimethylnaphtho(2,3-d)-1,3-dioxol-5-ol

Base Information

• Chemical Name: cis-3a,4,9,9a-Tetrahydro-2,2-dimethylnaphtho(2,3-d)-1,3-dioxol-5-ol
• CAS No.: 52187-19-6
• Molecular Formula: C₁₃H₁₆O₃
• Molecular Weight: 220.268
• European Community (EC) Number: 257-722-6
• DSSTox Substance ID: DTXSID30966564
• Mol file: 52187-19-6.mol

Synonyms:52187-19-6;cis-3a,4,9,9a-Tetrahydro-2,2-dimethylnaphtho(2,3-d)-1,3-dioxol-5-ol;2,2-Dimethyl-3a,4,9,9a-tetrahydronaphtho[2,3-d][1,3]dioxol-5-ol;344314-18-7;2,2-dimethyl-3a,4,9,9a-tetrahydrobenzo[f][1,3]benzodioxol-5-ol;EINECS 257-722-6;DTXSID30966564;2,2-Dimethyl-3a,4,9,9a-tetrahydro-2H-naphtho[2,3-d][1,3]dioxol-5-ol;Naphtho[2,3-d]-1,3-dioxol-5-ol, 3a,4,9,9a-tetrahydro-2,2-dimethyl-

Chemical Property of cis-3a,4,9,9a-Tetrahydro-2,2-dimethylnaphtho(2,3-d)-1,3-dioxol-5-ol

Chemical Property:

• Vapor Pressure: 3.18E-05mmHg at 25°C
• Boiling Point: 345°Cat760mmHg
• PKA: 9.93±0.40(Predicted)
• Flash Point: 162.4°C
• PSA: 38.69000
• Density: 1.162g/cm³
• LogP: 2.01090
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 220.109944368
• Heavy Atom Count: 16
• Complexity: 276

Purity/Quality:

99.9% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1(OC2CC3=C(CC2O1)C(=CC=C3)O)C

Technology Process of cis-3a,4,9,9a-Tetrahydro-2,2-dimethylnaphtho(2,3-d)-1,3-dioxol-5-ol

There total 8 articles about cis-3a,4,9,9a-Tetrahydro-2,2-dimethylnaphtho(2,3-d)-1,3-dioxol-5-ol 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: 73.0%

(-)-(6R,7S)-5,6,7,8-tetrahydro-1,6,7-naphthalenetriol (147331-60-0) + 2,2-dimethoxy-propane (77-76-9) → (-)-(6R,7S)-6,7-(isopropylidenedioxy)-5,6,7,8-tetrahydro-1-naphthol (685510-21-8,52187-19-6)

Guidance literature:

With toluene-4-sulfonic acid; at 20 ℃; for 2h;

DOI:10.1016/j.tetasy.2004.01.029

Reference yield:

5,8-dihydro-1-naphthyl acetate (51927-56-1) → (-)-(6R,7S)-6,7-(isopropylidenedioxy)-5,6,7,8-tetrahydro-1-naphthol (685510-21-8,52187-19-6)

Guidance literature:

Multi-step reaction with 4 steps

1.1: OsO₄; N-methylmorpholine N-oxide / 2-methyl-propan-2-ol; H₂O; acetone / 18 h

1.2: 86 percent / sodium thiosulfate; Florisil / 2-methyl-propan-2-ol; H₂O; acetonitrile / 3 h

2.1: 26 percent / 4-dimethylaminopyridine; dicyclohexylcarbodiimide / CH₂Cl₂ / 20 °C

3.1: 95 percent / KOH / methanol / 2 h

4.1: 73 percent / p-TsOH / 2 h / 20 °C

With dmap; potassium hydroxide; osmium(VIII) oxide; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; dicyclohexyl-carbodiimide; In methanol; dichloromethane; water; acetone; tert-butyl alcohol;

DOI:10.1016/j.tetasy.2004.01.029

Reference yield:

5,8-dihydro-1-naphthyl acetate (51927-56-1) → (+)-(6S,7R)-6,7-(isopropylidenedioxy)-5,6,7,8-tetrahydro-1-naphthol (52187-19-6)

Guidance literature:

Multi-step reaction with 4 steps

1.1: OsO₄; N-methylmorpholine N-oxide / 2-methyl-propan-2-ol; H₂O; acetone / 18 h

1.2: 86 percent / sodium thiosulfate; Florisil / 2-methyl-propan-2-ol; H₂O; acetonitrile / 3 h

2.1: 23 percent / 4-dimethylaminopyridine; dicyclohexylcarbodiimide / CH₂Cl₂ / 20 °C

3.1: 93 percent / KOH / methanol / 2 h

4.1: p-TsOH / 20 °C

With dmap; potassium hydroxide; osmium(VIII) oxide; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; dicyclohexyl-carbodiimide; In methanol; dichloromethane; water; acetone; tert-butyl alcohol;

DOI:10.1016/j.tetasy.2004.01.029

upstream raw materials:

(-)-(6R,7S)-5,6,7,8-tetrahydro-1,6,7-naphthalenetriol

2,2-dimethoxy-propane

5,8-dihydro-1-naphthyl acetate

(+/-)-cis-1-acetoxy-5,6,7,8-tetrahydro-6,7-naphthalenediol

Refernces