2-Methoxystypandrone

Base Information

• Chemical Name: 2-Methoxystypandrone
• CAS No.: 85122-21-0
• Molecular Formula: C₁₄H₁₂O₅
• Molecular Weight: 260.246
• DSSTox Substance ID: DTXSID10234258
• Nikkaji Number: J3.482.488F
• Wikidata: Q72486064
• Metabolomics Workbench ID: 45962
• ChEMBL ID: CHEMBL322776
• Mol file: 85122-21-0.mol

Synonyms:2-methoxy-6-acetyl-7-methyljuglone;1,4-Naphthalenedione,6-acetyl-5-hydroxy-2-methoxy-7-methyl;6-acetyl-5-hydroxy-2-methoxy-7-methyl-naphthalene-1,4-dione;2-Methoxystypandrone;

Chemical Property of 2-Methoxystypandrone

Chemical Property:

• Vapor Pressure: 7.31E-12mmHg at 25°C
• Boiling Point: 530.3°Cat760mmHg
• PKA: 6.65±0.20(Predicted)
• Flash Point: 206.5°C
• PSA: 80.67000
• Density: 1.37g/cm³
• LogP: 1.81250
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 260.06847348
• Heavy Atom Count: 19
• Complexity: 465

Purity/Quality:

98.5% ^*data from raw suppliers

2-Methoxystypandrone 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC2=C(C(=O)C=C(C2=O)OC)C(=C1C(=O)C)O

Technology Process of 2-Methoxystypandrone

There total 12 articles about 2-Methoxystypandrone 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: 93.0%

5-acetoxy-6-acetyl-2-methoxy-7-methylnaphthalene-1,4-dione (87686-85-9) → 2-Methoxystypandrone (85122-21-0)

Guidance literature:

With potassium hydroxide; water; In methanol; for 0.0166667h;

Reference yield:

2,3,5-trimethoxy-benzaldehyde (5556-84-3) → 2-Methoxystypandrone (85122-21-0)

Guidance literature:

Multi-step reaction with 10 steps

1: 78 percent / benzene / 119 h / Heating

2: 81 percent / trifluoroacetic acid / 21 h / Ambient temperature

3: 96 percent / potassium acetate / 1.5 h / Heating

4: lithium aluminium hydride / tetrahydrofuran / 2 h / Ambient temperature

5: 88 percent / hydrogen, aq. hydrochloric acid / palladized charcoal (10percent) / ethyl acetate

6: 95 percent / pyridine

7: 72 percent / boron trifluoride*diethyl ether / 1 h / 50 °C

8: 95 percent / pyridine

9: 38 percent / ammonium cerium(IV) nitrate / H₂O; acetonitrile / 1 h / Ambient temperature

10: 93 percent / potassium hydroxide, water / methanol / 0.02 h

With pyridine; hydrogenchloride; potassium hydroxide; lithium aluminium tetrahydride; ammonium cerium(IV) nitrate; boron trifluoride diethyl etherate; water; hydrogen; potassium acetate; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; water; ethyl acetate; acetonitrile; benzene;

Reference yield:

2,3,5-trimethoxybenzoic acid (36873-96-8) → 2-Methoxystypandrone (85122-21-0)

Guidance literature:

Multi-step reaction with 11 steps

1: 1) LiAlH₄, 2) manganese dioxide / 1) THF, reflux, 2 h, 2) benzene, reflux, 18 h

2: 78 percent / benzene / 119 h / Heating

3: 81 percent / trifluoroacetic acid / 21 h / Ambient temperature

4: 96 percent / potassium acetate / 1.5 h / Heating

5: lithium aluminium hydride / tetrahydrofuran / 2 h / Ambient temperature

6: 88 percent / hydrogen, aq. hydrochloric acid / palladized charcoal (10percent) / ethyl acetate

7: 95 percent / pyridine

8: 72 percent / boron trifluoride*diethyl ether / 1 h / 50 °C

9: 95 percent / pyridine

10: 38 percent / ammonium cerium(IV) nitrate / H₂O; acetonitrile / 1 h / Ambient temperature

11: 93 percent / potassium hydroxide, water / methanol / 0.02 h

With pyridine; hydrogenchloride; manganese(IV) oxide; potassium hydroxide; lithium aluminium tetrahydride; ammonium cerium(IV) nitrate; boron trifluoride diethyl etherate; water; hydrogen; potassium acetate; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; water; ethyl acetate; acetonitrile; benzene;

upstream raw materials:

5-acetoxy-6-acetyl-2-methoxy-7-methylnaphthalene-1,4-dione

1-hydroxy-5,6,8-trimethoxy-3-methyl-2-naphthyl methyl ketone

Acetic acid 2-acetyl-5,6,8-trimethoxy-3-methyl-naphthalen-1-yl ester

2,3,5-trimethoxy-benzaldehyde

Refernces

• 1、 Hughes, Andrew B.,Sargent, Melvyn V.. "Synthesis of 2-Methoxystypandrone: Comments on the Structure of Ventilaginone". . p. 449 - 452. Retrieved 2007/10/02.