1,4-Naphthalenedione, 2-(phenylthio)-

Base Information

• Chemical Name: 1,4-Naphthalenedione, 2-(phenylthio)-
• CAS No.: 57341-12-5
• Molecular Formula: C16H10O2S
• Molecular Weight: 266.32

Synonyms:

Chemical Property of 1,4-Naphthalenedione, 2-(phenylthio)-

Chemical Property:

Purity/Quality:

Safty Information:

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MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 1,4-Naphthalenedione, 2-(phenylthio)-

There total 10 articles about 1,4-Naphthalenedione, 2-(phenylthio)- 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%

thiophenol (108-98-5) + [1,4]naphthoquinone (130-15-4) → 2-phenylsulfanyl-[1,4]naphthoquinone (57341-12-5)

Guidance literature:

With aluminum oxide; In neat (no solvent); at 20 ℃; for 0.5h; regioselective reaction;

Reference yield: 81.0%

diphenyldisulfane (882-33-7) + [1,4]naphthoquinone (130-15-4) → 2-phenylsulfanyl-[1,4]naphthoquinone (57341-12-5)

Guidance literature:

With 1,3-bis-(diphenylphosphino)propane; H₃N*C₂H₆O₆S₂; tetrabutylammonium tetrafluoroborate; silver(I) acetate; In dimethyl sulfoxide; at 20 ℃; for 48h; Reagent/catalyst; Solvent; Time; Temperature; Concentration;

DOI:10.1021/acs.joc.5b00247

Reference yield: 52.0%

racemic methyl phenyl sulfoxide (1193-82-4) + 3,4-dihydronaphthalene-1(2H)-one (529-34-0) → 2-phenylsulfanyl-[1,4]naphthoquinone (57341-12-5)

Guidance literature:

With iodine; at 80 ℃; for 12h; Inert atmosphere;

upstream raw materials:

2-phenylsulfanyl-naphthalene-1,4-diol

thiophenol

[1,4]naphthoquinone

N,N-diethylbenzamide

Downstream raw materials:

cis-5-hydroxy-6-phenylsulphanyl-6b,9a-dihydrofuro<3,2-b>naphtho<2,1-d>furan-8(9H)-one

2-(2-Oxo-cyclobutyl)-3-phenylsulfanyl-[1,4]naphthoquinone

1,3-dimethoxy-9,10-anthraquinone

1-hydroxy-3-methoxy-9,10-anthraquinone

Refernces

Regioselective Addition Reaction of Lithium Enolates to Thio-Substituted 1,4-Naphthoquinones. Convenient Synthesis of a Naphthofuran-4,9-dione Ring System

10.1246/cl.1988.1415

The research investigates the regioselective addition of lithium enolates to thio-substituted 1,4-naphthoquinones, aiming to develop a convenient synthesis route for naphthofuran-4,9-dione ring systems, which are biologically important naturally-occurring quinones. Key chemicals used include 2-phenylthio-1,4-naphthoquinone (1a), 2-ethylthio-1,4-naphthoquinone (1b), lithium enolates (2a-c), and HMPA. The study found that the addition of lithium enolates to thio-substituted 1,4-naphthoquinones selectively occurred at the 1,4-position, yielding 2-(2-oxoalkyl)-3-phenylthio-1,4-naphthoquinones (4a-d) in excellent yields. The thio-substituted group at the 2-position of the parent 1,4-naphthoquinone was crucial for determining the regiochemistry. Furthermore, the researchers successfully transformed one of the products, 2-(2-oxo-2-phenylethyl)-3-phenylthio-1,4-naphthoquinone (4c), into a naphthofuran-4,9-dione ring system through bromination and subsequent treatment with triethylamine. The study concludes that the regioselective 1,4-addition of lithium enolates to thio-substituted 1,4-naphthoquinones provides an efficient method for synthesizing naphthofuran-4,9-dione derivatives, and further research on synthesizing naturally-occurring cytotoxic naphthofuran-4,9-diones is ongoing.

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