Hypnophilin

Base Information

• Chemical Name: Hypnophilin
• CAS No.: 80677-96-9
• Molecular Formula: C₁₅H₂₀O₃
• Molecular Weight: 248.322
• UNII: KZ0A93H82W
• DSSTox Substance ID: DTXSID301345614
• Nikkaji Number: J152.459C
• Metabolomics Workbench ID: 140375
• ChEMBL ID: CHEMBL506567
• Mol file: 80677-96-9.mol

Synonyms:hypnophilin

Chemical Property of Hypnophilin

Chemical Property:

• PSA: 49.83000
• LogP: 1.69610
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 248.14124450
• Heavy Atom Count: 18
• Complexity: 494

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(CC2CC34C(O3)C(=O)C(=C)C4(C2C1O)C)C
• Isomeric SMILES: C[C@]12[C@H]3[C@@H](C[C@@]14[C@H](O4)C(=O)C2=C)CC([C@@H]3O)(C)C

Technology Process of Hypnophilin

There total 69 articles about Hypnophilin 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: 52.4%

11α-hydroxy-3-methylene-2β,10,10-trimethyl-1α,8α-tricyclo<6.3.0.02,6>undec-5-en-4-one (76461-63-7,127000-12-8) → (+/-)-hypnophilin (80677-96-9,110611-15-9)

Guidance literature:

With water; dihydrogen peroxide; potassium carbonate; In dichloromethane; for 42h; Ambient temperature;

DOI:10.1021/ja00223a026

Reference yield:

1-bromo-3-<(tert-butyldimethylsilyl)oxy>-2,2-dimethylpropane (111849-25-3) → (+/-)-hypnophilin (80677-96-9,110611-15-9)

Guidance literature:

Multi-step reaction with 11 steps

2: 79.1 percent / NaOAc, pyridinium chlorochromate (PCC) / CH₂Cl₂ / 0.83 h / Ambient temperature

3: 97.7 percent / n-BuLi / tetrahydrofuran; hexane / 0.67 h

4: 83.5 percent / NaOAc, pyridinium chlorochromate (PCC) / CH₂Cl₂ / 4 h / Ambient temperature

5: 75.2 percent / trimethylortoformate, / p-toluenesulfonic acid / benzene / 1., room temperature, overnight 2.) reflux, 5 h

6: 85.3 percent / n-Bu₄NF_.3H₂O / tetrahydrofuran / 6 h / Ambient temperature

7: 84.9 percent / NaOAc, pyridinium chlorochromate (PCC) / CH₂Cl₂ / 0.75 h / Ambient temperature

8: 60.6 percent / samarium(II) iodide / tetrahydrofuran; various solvent(s) / -78 - -10 °C

9: 1.) diisopropylamine, n-BuLi / 1.) THF, hexane, 1 h, 0 deg C 2.) THF, hexane, dimethyltetrahydropyrimidinone

10: 72.4 percent / DDQ, 2,6-lutidine / benzene / 20 h / Heating

11: 52.4 percent / water, K₂CO₃, 30percent H₂O₂ / CH₂Cl₂ / 42 h / Ambient temperature

With 2,6-dimethylpyridine; n-butyllithium; tetrabutyl ammonium fluoride; water; dihydrogen peroxide; sodium acetate; potassium carbonate; diisopropylamine; pyridinium chlorochromate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; trimethyl orthoformate; samarium diiodide; toluene-4-sulfonic acid; In tetrahydrofuran; hexane; dichloromethane; benzene;

DOI:10.1021/ja00223a026

Reference yield:

trans-5-(2-hydroxyethyl)-3-<3-<(tert-butyldimethylsilyl)oxy>-2,2-dimethylpropyl>-1-methylcyclopent-1-ene → (+/-)-hypnophilin (80677-96-9,110611-15-9)

Guidance literature:

Multi-step reaction with 10 steps

1: 79.1 percent / NaOAc, pyridinium chlorochromate (PCC) / CH₂Cl₂ / 0.83 h / Ambient temperature

2: 97.7 percent / n-BuLi / tetrahydrofuran; hexane / 0.67 h

3: 83.5 percent / NaOAc, pyridinium chlorochromate (PCC) / CH₂Cl₂ / 4 h / Ambient temperature

4: 75.2 percent / trimethylortoformate, / p-toluenesulfonic acid / benzene / 1., room temperature, overnight 2.) reflux, 5 h

5: 85.3 percent / n-Bu₄NF_.3H₂O / tetrahydrofuran / 6 h / Ambient temperature

6: 84.9 percent / NaOAc, pyridinium chlorochromate (PCC) / CH₂Cl₂ / 0.75 h / Ambient temperature

7: 60.6 percent / samarium(II) iodide / tetrahydrofuran; various solvent(s) / -78 - -10 °C

8: 1.) diisopropylamine, n-BuLi / 1.) THF, hexane, 1 h, 0 deg C 2.) THF, hexane, dimethyltetrahydropyrimidinone

9: 72.4 percent / DDQ, 2,6-lutidine / benzene / 20 h / Heating

10: 52.4 percent / water, K₂CO₃, 30percent H₂O₂ / CH₂Cl₂ / 42 h / Ambient temperature

With 2,6-dimethylpyridine; n-butyllithium; tetrabutyl ammonium fluoride; water; dihydrogen peroxide; sodium acetate; potassium carbonate; diisopropylamine; pyridinium chlorochromate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; trimethyl orthoformate; samarium diiodide; toluene-4-sulfonic acid; In tetrahydrofuran; hexane; dichloromethane; benzene;

DOI:10.1021/ja00223a026

upstream raw materials:

(+)-Praehypnophilin

(3aR,3bS,4S,6aS)-(-)-3,3a,3b,4,5,6,6a,7-octahydro-4-hydroxy-3a,5,5-trimethylcyclopenta<4.5>pentalen-2-one

(3RS,3aR,3bR,4R,6aS)-3,3a,3b,4,5,6,6a,7-Octahydro-4-hydroxy-3-(hydroxymethyl)-3a,5,5-trimethyl-2H-cyclopentapentalen-2-on

(1R,3aR,6R,6aR)-(+)-6-(Benzoyloxy)-3,3a,4,5,6,6a-hexahydro-1,5,5-trimethyl-2(1H)-pentalenon

Refernces

• 1、 Paquette, Leo A.,Geng, Feng. "Applications of the squarate ester cascade to the expeditious synthesis of hypnophilin, coriolin, and ceratopicanol". . p. 9199 - 9203. Retrieved 2007/10/03.
• 2、 Weinges, Klaus,Dietz, Uwe,Oeser, Thomas,Irngartinger, Hermann. "Synthese von enantiomerenreinem (-)-Hypnophilin". . p. 685 - 687. Retrieved 2007/10/02.