(1S,2R)-5,7,8-trimethoxy-2,3-dimethyl-1-(2,4,5-trimethoxyphenyl)-1,2-dihydronaphthalene

Base Information

• Chemical Name: (1S,2R)-5,7,8-trimethoxy-2,3-dimethyl-1-(2,4,5-trimethoxyphenyl)-1,2-dihydronaphthalene
• CAS No.: 86702-02-5
• Molecular Formula: C₂₄H₃₀O₆
• Molecular Weight: 414.499
• DSSTox Substance ID: DTXSID901007036
• Nikkaji Number: J473.396G
• Wikidata: Q27107289
• Mol file: 86702-02-5.mol

Synonyms:magnoshinin;magnoshinin, (trans)-isomer

Chemical Property of (1S,2R)-5,7,8-trimethoxy-2,3-dimethyl-1-(2,4,5-trimethoxyphenyl)-1,2-dihydronaphthalene

Chemical Property:

• Vapor Pressure: 3.52E-10mmHg at 25°C
• Refractive Index: 1.532
• Boiling Point: 514.4 °C at 760 mmHg
• Flash Point: 202.3 °C
• PSA: 55.38000
• Density: 1.103 g/cm³
• LogP: 4.92310
• XLogP3: 4.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 7
• Exact Mass: 414.20423867
• Heavy Atom Count: 30
• Complexity: 580

Purity/Quality:

99% ^*data from raw suppliers

Magnoshinin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1C(C2=C(C=C1C)C(=CC(=C2OC)OC)OC)C3=CC(=C(C=C3OC)OC)OC
• Isomeric SMILES: C[C@@H]1[C@H](C2=C(C=C1C)C(=CC(=C2OC)OC)OC)C3=CC(=C(C=C3OC)OC)OC

Technology Process of (1S,2R)-5,7,8-trimethoxy-2,3-dimethyl-1-(2,4,5-trimethoxyphenyl)-1,2-dihydronaphthalene

There total 8 articles about (1S,2R)-5,7,8-trimethoxy-2,3-dimethyl-1-(2,4,5-trimethoxyphenyl)-1,2-dihydronaphthalene 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: 99.0%

(1R,2S)-2-Bromomethyl-5,7,8-trimethoxy-3-methyl-1-(2,4,5-trimethoxy-phenyl)-1,2-dihydro-naphthalene → magnoshinin (86702-02-5,115812-31-2)

Guidance literature:

With tri-n-butyl-tin hydride; In toluene; for 12h; Heating;

DOI:10.1055/s-2001-16086

Reference yield:

asaraldehyde (4460-86-0,14374-62-0) → magnoshinin (86702-02-5,115812-31-2)

Guidance literature:

Multi-step reaction with 8 steps

1.1: NaOEt / ethanol / 21 h / Heating

2.1: 3.16 g / K₂CO₃ / acetone / 20 h / Heating

3.1: LDA / tetrahydrofuran / 0.17 h / -70 °C

3.2: tetrahydrofuran / 1 h / -70 °C

4.1: TFA / 1 h / 20 °C

4.2: 0.798 mg / K₂CO₃ / acetone / 3.5 h / Heating

5.1: 100 percent / LiAlH₄ / tetrahydrofuran / 0.5 h / 0 °C

6.1: PBr₃ / tetrahydrofuran / 1 h / -78 °C

6.2: 72 percent / LiAlH₄ / tetrahydrofuran / 1.92 h

7.1: 49 percent / PBr₃ / tetrahydrofuran / 1 h / 60 °C

8.1: 99 percent / n-Bu₃SnH / toluene / 12 h / Heating

With lithium aluminium tetrahydride; tri-n-butyl-tin hydride; sodium ethanolate; phosphorus tribromide; potassium carbonate; trifluoroacetic acid; lithium diisopropyl amide; In tetrahydrofuran; ethanol; acetone; toluene; 1.1: Stobbe condensation;

DOI:10.1055/s-2001-16086

Reference yield:

2-[1-(2,4,5-Trimethoxy-phenyl)-meth-(E)-ylidene]-succinic acid diethyl ester (367248-68-8) → magnoshinin (86702-02-5,115812-31-2)

Guidance literature:

Multi-step reaction with 6 steps

1.1: LDA / tetrahydrofuran / 0.17 h / -70 °C

1.2: tetrahydrofuran / 1 h / -70 °C

2.1: TFA / 1 h / 20 °C

2.2: 0.798 mg / K₂CO₃ / acetone / 3.5 h / Heating

3.1: 100 percent / LiAlH₄ / tetrahydrofuran / 0.5 h / 0 °C

4.1: PBr₃ / tetrahydrofuran / 1 h / -78 °C

4.2: 72 percent / LiAlH₄ / tetrahydrofuran / 1.92 h

5.1: 49 percent / PBr₃ / tetrahydrofuran / 1 h / 60 °C

6.1: 99 percent / n-Bu₃SnH / toluene / 12 h / Heating

With lithium aluminium tetrahydride; tri-n-butyl-tin hydride; phosphorus tribromide; trifluoroacetic acid; lithium diisopropyl amide; In tetrahydrofuran; toluene;

DOI:10.1055/s-2001-16086

upstream raw materials:

asaraldehyde

(E)-3-ethoxycarbonyl-4-(2,4,5-trimethoxyphenyl)but-3-enoic acid

2-[1-(2,4,5-Trimethoxy-phenyl)-meth-(E)-ylidene]-succinic acid diethyl ester

2-[Hydroxy-(2,4,5-trimethoxy-phenyl)-methyl]-3-[1-(2,4,5-trimethoxy-phenyl)-meth-(E)-ylidene]-succinic acid diethyl ester

Downstream raw materials:

3-Methyl-4-(2,4,5-trimethoxy-phenyl)-4-(2,3,5-trimethoxy-phenyl)-butan-2-one

3,4,6-Trimethoxy-2-[2-methyl-3-oxo-1-(2,4,5-trimethoxy-phenyl)-butyl]-benzaldehyde

Refernces