Regiolone

Base Information

• Chemical Name: Regiolone
• CAS No.: 137494-04-3
• Molecular Formula: C₁₀H₁₀O₃
• Molecular Weight: 178.188
• Mol file: 137494-04-3.mol

Synonyms:1(2H)-Naphthalenone,3,4-dihydro-4,8-dihydroxy-,(R);(-)-isosclerone;

Chemical Property of Regiolone

Chemical Property:

• PSA: 57.53000
• LogP: 1.40210

Purity/Quality:

99% ^*data from raw suppliers

Regiolone 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Regiolone

There total 15 articles about Regiolone 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: 50.0%

5-hydroxynaphtho-1,4-quinone (481-39-0) → (3S,4R)-3,4,8-trihydroxy-1-tetralone (149341-67-3) + (-)-(4S)-4,8-dihydroxy-α-tetralone (54712-38-8,51114-98-8,62332-73-4,137494-04-3) + (3R,4R)-3,4-dihydro-3,4,8-trihydroxy-1(2H)-naphthalenone (36134-66-4,81339-27-7,112924-86-4,149341-67-3)

Guidance literature:

With Paraconiothyrium variabile resting cells; In aq. phosphate buffer; at 25 ℃; for 48h;

DOI:10.1016/j.tetlet.2012.12.038

Reference yield: 40.0%

benzyl 8-(benzyloxy)-1,2,3,4-tetrahydro-4-hydroxy-1-oxonaphthalene-2-carboxylate → isosclerone (51114-98-8,54712-38-8,62332-73-4,137494-04-3)

Guidance literature:

benzyl 8-(benzyloxy)-1,2,3,4-tetrahydro-4-hydroxy-1-oxonaphthalene-2-carboxylate; With hydrogen; palladium on activated charcoal; In tetrahydrofuran; under 760 Torr;

In tetrahydrofuran; water; at 50 ℃; for 5h;

DOI:10.1002/hlca.200390014

Reference yield: 34.3%

preussomerin A (129240-52-4) → (-)-(4S)-4,8-dihydroxy-α-tetralone (54712-38-8,51114-98-8,62332-73-4,137494-04-3)

Guidance literature:

With hydrogenchloride; In acetone; at 100 ℃; for 12h; seald tube;

DOI:10.1021/jo00014a007

upstream raw materials:

juglone

2,2-dimethoxy-propane

5-acetoxy-2,3-dihydro-[1,4]naphthoquinone

1,4,5-trihydroxynaphthalene

Downstream raw materials:

5-hydroxynaphtho-1,4-quinone

(-)-(4S)-4,8-dihydroxy-α-tetralone

cis-3,4-dihydro-2,4,8-trihydroxynaphthalen-1(2H)-one

2,4,8-trihydroxy-1-tetralone

Refernces

• 1、 Yang, Li,Ma, Xiao-Yan,Ruan, Xiao,Jiang, De-An,Pan, Cun-De,Wang, Qiang. "Enantioselective separation of 4,8-DHT and phytotoxicity of the enantiomers on various plant species". . . Retrieved 2016.
• 2、 -. "4,8-dihydroxy-1-Tetralone chemical synthesis method". Paragraph 0020; 0021. . Retrieved 2016/10/08.
• 3、 Prado, Soizic,Buisson, Didier,Ndoye, Idrissa,Vallet, Marine,Nay, Bastien. "One-step enantioselective synthesis of (4S)-isosclerone through biotranformation of juglone by an endophytic fungus". . p. 1189 - 1191. Retrieved 2013/03/28.