Dehydromiltirone

Base Information

• Chemical Name: Dehydromiltirone
• CAS No.: 116064-77-8
• Molecular Formula: C19H20 O2
• Molecular Weight: 280.367
• UNII: RPP9EW3OBQ
• DSSTox Substance ID: DTXSID50151273
• Nikkaji Number: J323.572F
• Wikidata: Q72461889
• Mol file: 116064-77-8.mol

Synonyms:dehydromiltirone

Chemical Property of Dehydromiltirone

Chemical Property:

• Vapor Pressure: 2.17E-07mmHg at 25°C
• Melting Point: 71-75℃ (hexane )
• Boiling Point: 423.8°Cat760mmHg
• Flash Point: 180.5°C
• PSA: 34.14000
• Density: 1.116g/cm³
• LogP: 4.18590
• XLogP3: 4.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 280.146329876
• Heavy Atom Count: 21
• Complexity: 536

Purity/Quality:

98% ^*data from raw suppliers

1,2-Didehydromiltirone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)C1=CC2=C(C3=C(C=C2)C(CC=C3)(C)C)C(=O)C1=O
• Uses: Dehydromiltirone displays inhibitory effect against acetylcholinesterase (AChE) and butyrylcholinesterase (BChE).

Technology Process of Dehydromiltirone

There total 20 articles about Dehydromiltirone 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: 78.0%

miltirone (27210-57-7) → 1,2-didehydromiltirone (116064-77-8)

Guidance literature:

With toluene-4-sulfonic acid; In toluene; at 110 ℃; for 12h; Inert atmosphere; Reflux;

DOI:10.1016/j.tetlet.2018.05.073

Reference yield: 57.0%

1,2-Dihydro-1,1-dimethyl-7-isopropylphenanthren-6-ol (126979-91-7) → 1,2-didehydromiltirone (116064-77-8)

Guidance literature:

With dipotassium hydrogenphosphate; potassiuim nitrosodisulfonate; In water; acetone; for 4h;

DOI:10.1021/jo00298a029

Reference yield:

2-(1-methylethyl)phenol (88-69-7) → 1,2-didehydromiltirone (116064-77-8)

Guidance literature:

Multi-step reaction with 13 steps

1: 87 percent / 20percent aq. NaOH / 2 h / Heating

2: 53 percent / AlCl₃ / nitrobenzene / Ambient temperature

3: 53 percent / Zn, HgCl₂, conc. HCl / H₂O; toluene / 24 h / Heating

4: 81 percent / P₂O₅, H₃PO₄ / CH₂Cl₂ / 0.33 h / 70 - 80 °C

5: 69 percent / Zn / tetrahydrofuran / 2 h

6: 62 percent / Pd-black / 2 h / 280 - 300 °C

7: 1) Mg / 1) Et₂O, 30 min 2) Et₂O, 3h

8: P₂O₅, H₃PO₄ / 0.5 h / 60 - 70 °C

9: 80 percent / pyridinium chlorochromate / CH₂Cl₂ / 96 h / Ambient temperature

10: 82 percent / NaBH₄ / ethanol / 1 h / Ambient temperature

11: 42 percent / CH₃SO₂Cl, Et₃N / CH₂Cl₂ / 0 °C

12: 77 percent / NaH, EtSH / dimethylformamide / 3 h / 150 °C

13: 57 percent / potassium nitrosodisulfonate, potassium hydrogen phosphate / H₂O; acetone / 4 h

With hydrogenchloride; sodium hydroxide; sodium tetrahydroborate; dipotassium hydrogenphosphate; aluminium trichloride; potassiuim nitrosodisulfonate; phosphoric acid; phosphorus pentoxide; sodium hydride; magnesium; methanesulfonyl chloride; triethylamine; pyridinium chlorochromate; ethanethiol; mercury dichloride; zinc; palladium; In tetrahydrofuran; ethanol; dichloromethane; water; nitrobenzene; N,N-dimethyl-formamide; acetone; toluene;

DOI:10.1021/jo00298a029

upstream raw materials:

1,2-Dihydro-1,1-dimethyl-7-isopropylphenanthren-6-ol

7-Isopropyl-5,6-dimethoxy-1,1-dimethyl-2,3,9,10-tetrahydro-1H-phenanthren-4-one

7-Isopropyl-5,6-dimethoxy-1,1-dimethyl-1,2-dihydro-phenanthrene

7‐isopropyl‐5,6‐dimethoxy‐1,1‐dimethyl‐2,3‐dihydrophenanthren‐4 (1H)‐one