2,3,6,7-TetraMethoxy-9-phenanthreneMethanol

Base Information

• Chemical Name: 2,3,6,7-TetraMethoxy-9-phenanthreneMethanol
• CAS No.: 30062-15-8
• Molecular Formula: C19H20O5
• Molecular Weight: 328.365
• DSSTox Substance ID: DTXSID001259957
• Nikkaji Number: J2.813.345F
• Mol file: 30062-15-8.mol

Synonyms:30062-15-8;2,3,6,7-TetraMethoxy-9-phenanthreneMethanol;(2,3,6,7-Tetramethoxyphenanthren-9-yl)methanol;2,3,6,7-TETRAMETHOXY-9-(HYDROXYMETHYL)PHENANTHRENE;2,3,6,7-Tetramethoxyphenanthrene-9-methanol;SCHEMBL5308382;AMY9002;DTXSID001259957;BCP34534;MFCD30471695;s10111;9-Phenanthrenemethanol, 2,3,6,7-tetramethoxy-

Chemical Property of 2,3,6,7-TetraMethoxy-9-phenanthreneMethanol

Chemical Property:

• Melting Point: >143°C (dec.)
• PSA: 57.15000
• LogP: 3.51970
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 5
• Exact Mass: 328.13107373
• Heavy Atom Count: 24
• Complexity: 403

Purity/Quality:

99% ^*data from raw suppliers

2,?3,?6,?7-Tetramethoxy-9-phenanthrenemethanol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC2=CC(=C3C=C(C(=CC3=C2C=C1OC)OC)OC)CO
• Uses: 2,3,6,7-Tetramethoxy-9-phenanthrenemethanol is an intermediate in the synthesis of (+)-(S)-Tylophorine (T898200) is a major alkaloid of Tylophora indica.

Technology Process of 2,3,6,7-TetraMethoxy-9-phenanthreneMethanol

There total 1 articles about 2,3,6,7-TetraMethoxy-9-phenanthreneMethanol 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: 67.0%

2,3,6,7-tetramethoxy-9-(chloromethyl)phenanthrene (30062-19-2) + H-Pro-OBzl (41324-66-7) → 2,3,6,7-tetramethoxy-9-(hydroxymethyl)phenanthrene (30062-15-8) + (S)-N-<(2,3,6,7-tetramethoxy-9-phenanthryl)methyl>proline benzyl ester (30061-09-7)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; benzene; at 80 - 85 ℃;

DOI:10.1021/jo00171a014

Reference yield:

2,3,6,7-tetramethoxy-9-(hydroxymethyl)phenanthrene (30062-15-8) → (S)-(+)-tylophorine (482-20-2)

Guidance literature:

Multi-step reaction with 9 steps

1: phosphorus tribromide / chloroform / 4 h / 20 °C / Inert atmosphere

2: potassium carbonate / N,N-dimethyl-formamide / 20 °C

3: acetic acid / methanol / 3 h / 45 °C

4: potassium hydroxide / 1,4-dioxane; methanol / 3 h

5: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 20 °C / Reflux

6: tin(IV) chloride / dichloromethane / 6 h / Reflux

7: sodium tetrahydroborate / ethanol / 6 h / 0 - 20 °C

8: triethylsilane; trifluoroacetic acid / dichloromethane / 0.5 h / Reflux

9: lithium aluminium tetrahydride / tetrahydrofuran / 6 h / Reflux

With triethylsilane; sodium tetrahydroborate; lithium aluminium tetrahydride; oxalyl dichloride; phosphorus tribromide; tin(IV) chloride; potassium carbonate; acetic acid; N,N-dimethyl-formamide; trifluoroacetic acid; potassium hydroxide; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; dichloromethane; chloroform; N,N-dimethyl-formamide; 6: Friedel Crafts reaction;

DOI:10.1021/jf902543r

Reference yield:

2,3,6,7-tetramethoxy-9-(hydroxymethyl)phenanthrene (30062-15-8) → (R)-tylophorine (482-20-2,25908-92-3,101984-34-3,111408-21-0)

Guidance literature:

Multi-step reaction with 9 steps

1: phosphorus tribromide / chloroform / 4 h / 20 °C / Inert atmosphere

2: potassium carbonate / N,N-dimethyl-formamide / 20 °C

3: acetic acid / methanol / 3 h / 45 °C

4: potassium hydroxide / 1,4-dioxane; methanol / 3 h

5: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 20 °C / Reflux

6: tin(IV) chloride / dichloromethane / 6 h / Reflux

7: sodium tetrahydroborate / ethanol / 6 h / 0 - 20 °C

8: triethylsilane; trifluoroacetic acid / dichloromethane / 0.5 h / Reflux

9: lithium aluminium tetrahydride / tetrahydrofuran / 6 h / Reflux

With triethylsilane; sodium tetrahydroborate; lithium aluminium tetrahydride; oxalyl dichloride; phosphorus tribromide; tin(IV) chloride; potassium carbonate; acetic acid; N,N-dimethyl-formamide; trifluoroacetic acid; potassium hydroxide; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; dichloromethane; chloroform; N,N-dimethyl-formamide; 6: Friedel Crafts reaction;

DOI:10.1021/jf902543r

upstream raw materials:

2,3,6,7-tetramethoxy-9-(chloromethyl)phenanthrene

H-Pro-OBzl

Downstream raw materials:

(R)-tylophorine

(S)-(+)-tylophorine