Hydroxyanigorufone

Base Information

• Chemical Name: Hydroxyanigorufone
• CAS No.: 56252-02-9
• Molecular Formula: C19H12 O3
• Molecular Weight: 288.302
• Mol file: 56252-02-9.mol

Synonyms:Emenolone;Hydroxyanigorufone

Chemical Property of Hydroxyanigorufone

Chemical Property:

• Melting Point: 201-204℃
• PSA: 57.53000
• LogP: 4.30760

Purity/Quality:

99% ^*data from raw suppliers

Hydroxyanigorufone 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Hydroxyanigorufone

There total 12 articles about Hydroxyanigorufone 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: 90.0%

2-hydroxy-9-(4'-methoxyphenyl)-1H-phenalen-1-one (65874-44-4) → 2-hydroxy-9-(4-hydroxyphenyl)-1H-phenalen-1-one (56252-02-9)

Guidance literature:

With boron tribromide; In dichloromethane; at 25 ℃; for 1h; Inert atmosphere;

DOI:10.1021/acs.jnatprod.7b00709

Reference yield:

1-naphthaldehyde (66-77-3) → 2-hydroxy-9-(4-hydroxyphenyl)-1H-phenalen-1-one (56252-02-9)

Guidance literature:

Multi-step reaction with 8 steps

1.1: potassium tert-butylate / tetrahydrofuran / 1 h / 20 - 25 °C / Inert atmosphere

1.2: 12 h / 20 - 25 °C / Inert atmosphere

2.1: sodium hydroxide / tetrahydrofuran; water / 12 h / 40 °C / Inert atmosphere

2.2: 20 - 25 °C / Inert atmosphere

3.1: oxalyl dichloride / dichloromethane / 0.17 h / Inert atmosphere

3.2: 20 - 25 °C / Inert atmosphere

4.1: aluminum (III) chloride / dichloromethane / 0 - 25 °C / Inert atmosphere

5.1: tetrahydrofuran / -10 - 25 °C / Inert atmosphere

5.2: 3 h / Inert atmosphere; Reflux

6.1: N-benzyl-trimethylammonium hydroxide; tert.-butylhydroperoxide / methanol; water; toluene / 4 h / -5 °C / Inert atmosphere

7.1: toluene-4-sulfonic acid / toluene / Inert atmosphere

8.1: boron tribromide / dichloromethane / 1 h / 25 °C / Inert atmosphere

With tert.-butylhydroperoxide; aluminum (III) chloride; oxalyl dichloride; potassium tert-butylate; boron tribromide; N-benzyl-trimethylammonium hydroxide; toluene-4-sulfonic acid; sodium hydroxide; In tetrahydrofuran; methanol; dichloromethane; water; toluene; 1.1: |Wittig Olefination / 1.2: |Wittig Olefination / 4.1: |Friedel-Crafts Acylation;

DOI:10.1021/acs.jnatprod.7b00709

Reference yield:

(E)-ethyl 3-(naphthalen-1-yl)acrylate (98978-43-9) → 2-hydroxy-9-(4-hydroxyphenyl)-1H-phenalen-1-one (56252-02-9)

Guidance literature:

Multi-step reaction with 7 steps

1.1: sodium hydroxide / tetrahydrofuran; water / 12 h / 40 °C / Inert atmosphere

1.2: 20 - 25 °C / Inert atmosphere

2.1: oxalyl dichloride / dichloromethane / 0.17 h / Inert atmosphere

2.2: 20 - 25 °C / Inert atmosphere

3.1: aluminum (III) chloride / dichloromethane / 0 - 25 °C / Inert atmosphere

4.1: tetrahydrofuran / -10 - 25 °C / Inert atmosphere

4.2: 3 h / Inert atmosphere; Reflux

5.1: N-benzyl-trimethylammonium hydroxide; tert.-butylhydroperoxide / methanol; water; toluene / 4 h / -5 °C / Inert atmosphere

6.1: toluene-4-sulfonic acid / toluene / Inert atmosphere

7.1: boron tribromide / dichloromethane / 1 h / 25 °C / Inert atmosphere

With tert.-butylhydroperoxide; aluminum (III) chloride; oxalyl dichloride; boron tribromide; N-benzyl-trimethylammonium hydroxide; toluene-4-sulfonic acid; sodium hydroxide; In tetrahydrofuran; methanol; dichloromethane; water; toluene; 3.1: |Friedel-Crafts Acylation;

DOI:10.1021/acs.jnatprod.7b00709

upstream raw materials:

p-Coumaric Acid

1-naphthaldehyde

(E)-ethyl 3-(naphthalen-1-yl)acrylate

(E)-3-(naphthalen-1-yl)acrylic acid

Downstream raw materials:

2-methoxy-9-(4'-methoxyphenyl)phenalen-1-one

Refernces

• 1、 Wang, Ming-Zhong,Ku, Chuen-Fai,Si, Tong-Xu,Tsang, Siu-Wai,Lv, Xiao-Meng,Li, Xiao-Wan,Li, Zheng-Ming,Zhang, Hong-Jie,Chan, Albert S. C.. "Concise Synthesis of Natural Phenylphenalenone Phytoalexins and a Regioisomer". . p. 98 - 105. Retrieved 2018/02/07.