Frontalin

Base Information

• Chemical Name: Frontalin
• CAS No.: 28401-39-0
• Deprecated CAS: 22625-04-3,22625-18-9,57917-95-0,1315057-62-5,1354213-53-8
• Molecular Formula: C8H14 O2
• Molecular Weight: 142.198
• Hs Code.: 2932999099
• UNII: 9T71ZVB55P
• DSSTox Substance ID: DTXSID9041994
• Nikkaji Number: J40.438A
• Wikidata: Q27889410
• Metabolomics Workbench ID: 144321
• Mol file: 28401-39-0.mol

Synonyms:frontalin

Chemical Property of Frontalin

Chemical Property:

• Vapor Pressure: 2.25mmHg at 25°C
• Boiling Point: 167.3°Cat760mmHg
• Flash Point: 53.4°C
• PSA: 18.46000
• Density: 1.056g/cm³
• LogP: 1.69200
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 142.099379685
• Heavy Atom Count: 10
• Complexity: 157

Purity/Quality:

99% ^*data from raw suppliers

FRONTALIN 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC12CCCC(O1)(OC2)C
• Isomeric SMILES: C[C@@]12CCC[C@@](O1)(OC2)C

Technology Process of Frontalin

There total 3 articles about Frontalin 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:

3-(2-methyl-[1,3]dioxolan-2-yl)-propan-1-ol (29021-98-5) → 1,5-Dimethyl-6,8-dioxabicyclo[3.2.1]octane (28401-39-0,57917-96-1,60478-96-8,84024-93-1)

Guidance literature:

Multi-step reaction with 8 steps

1: 86 percent / pyridinium chlorochromate, sodium acetate / CH₂Cl₂ / 0.75 h / 25 °C

2: 1.) sodium hydride / 1.) ether, 25 deg C, 45 min, 2.) 3 h

3: 98 percent / hydrogen / 5percent Pd-C / methanol / 12 h / 25 °C

4: 93 percent / lithium aluminum hydride / diethyl ether / 2 h / 0 °C

5: 95 percent / pyridine

6: 1.) sodium iodide, 2.) DBU / 1.) DMF, 50 deg C, 3.5 h, 2.) 80 deg C, 3.5 h

7: 95 percent / m-chloroperbenzoic acid

8: 69 percent / 2M sulfuric acid / tetrahydrofuran / 5 h / 25 °C

With pyridine; lithium aluminium tetrahydride; sulfuric acid; hydrogen; sodium acetate; sodium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; 3-chloro-benzenecarboperoxoic acid; pyridinium chlorochromate; sodium iodide; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; dichloromethane;

Reference yield:

hept-6-en-2-one (21889-88-3) → 1,5-Dimethyl-6,8-dioxabicyclo[3.2.1]octane (28401-39-0,57917-96-1,60478-96-8,84024-93-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 55 percent / (CH₃)3SO⁽¹⁺⁾*I^(1-), NaH / dimethylsulfoxide / 1 h / 60 °C

2: 5percent H₂SO₄ / tetrahydrofuran

3: 50 percent / copper(II)chloride / palladium chloride / 1,2-dimethoxy-ethane

With sulfuric acid; trimethylsulfoxonium iodide; sodium hydride; copper dichloride; palladium dichloride; In tetrahydrofuran; 1,2-dimethoxyethane; dimethyl sulfoxide;

DOI:10.1246/cl.1985.1849

Reference yield:

hept-6-en-2-one (21889-88-3) → (1S)-(-)-Frontalin (28401-39-0)

Guidance literature:

Multi-step reaction with 10 steps

2: 32 percent / Pichia miso IAM 4682 (growing cells) / H₂O / 48 h / 30 °C / enantiomer selective hydrolysis, method for obtaining optically active cyanohydrin acetates

3: 652 mg / p-TsOH / ethanol / Heating; several hours

4: p-TsOH / CH₂Cl₂ / 5 h / Ambient temperature

5: 1) KOH / 1) EtOH-H₂O, reflux, 40 h, 2) Et₂O

6: 88 percent / LiAlH₄ / tetrahydrofuran / 1 h / Ambient temperature

7: 187 mg / acetone / 10 h / Ambient temperature

8: 1) Hg(OAc)2, 2) NaBH₄, 3N NaOH / 1) THF, r.t., 10 min,

9: 189 mg / pyridinium chlorochromate, Molecular Sieves 3A / CH₂Cl₂ / 0 °C

10: 80 mg / 2N HCl / pentane / 1 h / Ambient temperature

With hydrogenchloride; potassium hydroxide; sodium hydroxide; sodium tetrahydroborate; lithium aluminium tetrahydride; 3 A molecular sieve; Pichia miso IAM 4682 (growing cells); mercury(II) diacetate; toluene-4-sulfonic acid; pyridinium chlorochromate; In tetrahydrofuran; ethanol; dichloromethane; water; acetone; pentane;

DOI:10.1016/S0040-4020(01)89493-X

upstream raw materials:

3-(2-methyl-[1,3]dioxolan-2-yl)-propan-1-ol

hept-6-en-2-one

Downstream raw materials:

trans-2,6-dimethyl-2-hydroxymethyltetrahydropyran

cis-2,6-dimethyl-2-hydroxymethyltetrahydropyran