Cannithrene 1

Base Information

• Chemical Name: Cannithrene 1
• CAS No.: 71135-80-3
• Molecular Formula: C15H14O3
• Molecular Weight: 242.27
• UNII: 3B8HAG9WGE
• DSSTox Substance ID: DTXSID30701477
• Nikkaji Number: J39.977I
• Wikidata: Q82633145
• Mol file: 71135-80-3.mol

Synonyms:Cannithrene 1;Cannabidihydrophenanthrene;3B8HAG9WGE;71135-80-3;9,10-Dihydro-7-methoxy-3,5-phenanthrenediol;UNII-3B8HAG9WGE;3,5-Phenanthrenediol, 9,10-dihydro-7-methoxy-;7-Methoxy-9,10-dihydrophenanthrene-3,5-diol;SCHEMBL21582166;DTXSID30701477

Chemical Property of Cannithrene 1

Chemical Property:

• PSA: 49.69000
• LogP: 2.87200
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 242.094294304
• Heavy Atom Count: 18
• Complexity: 294

Purity/Quality:

Cannithrene1 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC2=C(C(=C1)O)C3=C(CC2)C=CC(=C3)O
• Uses: Cannithrene 1 is a natural product from Cannabis sativa. It is structurally similar to orchid phytoalexin, an antimicrobial.

Technology Process of Cannithrene 1

There total 15 articles about Cannithrene 1 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: 56.0%

cannabispiradienone-A (71135-79-0) → cannithrene-1 (71135-80-3)

Guidance literature:

With hydrogenchloride; In acetic acid; at 20 ℃; for 48h;

Reference yield:

6,8-dimethoxy-3,4-dihydro-2H-naphthalen-1-one (883-07-8) → cannithrene-1 (71135-80-3)

Guidance literature:

Multi-step reaction with 7 steps

1: 77 percent / BCl₃ / CH₂Cl₂ / 1.) -78 deg. C; 2.) room temperature, 0.5 h

2: 95 percent / K₂CO₃ / acetone / 24 h / Heating

3: 100 percent / NaOMe

4: 100 percent / triethylamine / benzene / 168 h

5: NaOEt / ethanol / 3 h

6: 60 percent / NaH / tetrahydrofuran / 24 h

7: 1.) pyridinium bromide perbromide 2.) H₂ / 2.) 10 percent Pd/C / 1.) acetic acid, 0.5 h; 2.) ethanol, 16 h

With hydrogen; sodium methylate; sodium ethanolate; pyridinium hydrobromide perbromide; boron trichloride; sodium hydride; potassium carbonate; triethylamine; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; acetone; benzene;

DOI:10.1139/v85-367

Reference yield:

4-(3,5-dimethoxyphenyl)butanoic acid (91555-31-6) → cannithrene-1 (71135-80-3)

Guidance literature:

Multi-step reaction with 8 steps

1: 87 percent / polyphosphoric acid / 4 h / 100 - 110 °C

2: 77 percent / BCl₃ / CH₂Cl₂ / 1.) -78 deg. C; 2.) room temperature, 0.5 h

3: 95 percent / K₂CO₃ / acetone / 24 h / Heating

4: 100 percent / NaOMe

5: 100 percent / triethylamine / benzene / 168 h

6: NaOEt / ethanol / 3 h

7: 60 percent / NaH / tetrahydrofuran / 24 h

8: 1.) pyridinium bromide perbromide 2.) H₂ / 2.) 10 percent Pd/C / 1.) acetic acid, 0.5 h; 2.) ethanol, 16 h

With PPA; hydrogen; sodium methylate; sodium ethanolate; pyridinium hydrobromide perbromide; boron trichloride; sodium hydride; potassium carbonate; triethylamine; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; acetone; benzene;

DOI:10.1139/v85-367

upstream raw materials:

cannabispiradienone-A

5-Benzyloxy-7-methoxy-1,9,10,10a-tetrahydro-2H-phenanthren-3-one

O-methylcannabispiradienone

6,8-dimethoxy-3,4-dihydro-2H-naphthalen-1-one

Refernces

• 1、 Crombie, Leslie,Tuchinda, Patoomratana,Powell, Michael J.. "Total Synthesis of the Spirans of Cannabis: Cannabispiradienone, Cannabispirenone-A and -B, Cannabispirone, α- and β-Cannabispiranols and the Dihydrophenanthrene Cannithrene-1". . p. 1477 - 1484. Retrieved 2007/10/02.