51114-72-8

Basic information

• Product Name: 2-(phenylsulfonyl)-3,4-dihydro-1(2H)-naphthalenone
• Synonyms: 2-(phenylsulfonyl)-3,4-dihydro-1(2H)-naphthalenone
• CAS NO: 51114-72-8
• Molecular Formula: C₁₆H₁₄O₃S
• Molecular Weight: 286.34556
• Mol File: 51114-72-8.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-(phenylsulfonyl)-3,4-dihydro-1(2H)-naphthalenone(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(phenylsulfonyl)-3,4-dihydro-1(2H)-naphthalenone(51114-72-8)
• EPA Substance Registry System: 2-(phenylsulfonyl)-3,4-dihydro-1(2H)-naphthalenone(51114-72-8)

Safety Data

• Hazardous Substances Data: 51114-72-8(Hazardous Substances Data)

Upstream product

• 117012-44-9 1-Benzenesulfonyl-1-diazo-4-phenyl-butan-2-one 
• 98-09-9 benzenesulfonyl chloride 
• 873-55-2 sodium benzenesulfonate 
• 1056246-70-8 2-bromo-1-tetralone 
• 69627-08-3 1-(phenylsulfonyl)-1-(trimethylsilyl)ethene 
• 62762-20-3 1-phenylthio-1-trimethylsilylethene 
• 117012-21-2 C₁₇H₁₈O₂S₂ 
• 117037-41-9 (2-Methylsulfanyl-prop-2-ene-1-sulfonyl)-benzene 
• 93434-80-1 1-phenyl-4-phenylsulphonylbutan-3-one 
• 2525-40-8 prop-2-ynylsulfonylbenzene 
• 128881-76-5 2-(3-Benzenesulfonyl-propyl)-N,N-diethyl-benzamide 

Downstream Products

• 1130816-79-3 (1R,2S)-2-(phenylsulfonyl)-1,2,3,4-tetrahydronaphthalen-1-ol 
• 529-34-0 3,4-dihydronaphthalene-1(2H)-one 
• 1191924-78-3 2-(3-oxobutyl)-2-(phenylsulfonyl)-3,4-dihydronaphthalen-1(2H)-one 

Relevant articles and documents

Controlled Synthesis of β-Keto Sulfones and Vinyl Sulfones under Electrochemical Oxidation

Selective sulfonylation and oxosulfonylation of alkenes with sulfinates have been developed via anodic oxidation in an undivided cell. The novel electrosynthetic method provided β-keto sulfones and vinyl sulfones with good to excellent yields in the absence of any transition metal catalyst and oxidants. Mechanism studies show that two different pathways involved in these two transformations.

Convincing Catalytic Performance of Oxo-Tethered Ruthenium Complexes for Asymmetric Transfer Hydrogenation of Cyclic α-Halogenated Ketones through Dynamic Kinetic Resolution

A highly efficient dynamic kinetic resolution of cyclic halohydrins was achieved by the asymmetric transfer hydrogenation of racemic α-haloketones. Bifunctional oxo-tethered Ru(II) catalysts could promote the reduction without deterioration of halogens. By structural tuning of the catalyst, chiral alcohols having halogen, ester, carboxamide, and sulfone functions were obtained variably with excellent diastereo- and enantioselectivities (up to >99:1 d.r. and >99.9 ee), which provided a concise synthetic approach to a dopamine D3 receptor ligand, (+)-PHNO.

Oxidative Sulfonylation of Hydrazones Enabled by Synergistic Copper/Silver Catalysis

A copper/silver-cocatalyzed protocol for oxidative sulfonylation of hydrazones is demonstrated. A wide range of β-ketosulfones and N-acylsulfonamides are directly synthesized in moderate to good yields. Our work provides a viable method for scalable preparation of β-ketosulfone derivatives that have found wide applications in the pharmaceutical industry.

An efficient access to β-ketosulfones: Via β-sulfonylvinylamines: Metal-organic framework catalysis for the direct C-S coupling of sodium sulfinates with oxime acetates

A copper-based framework Cu2(OBA)2(BPY) was synthesized and used as a recyclable heterogeneous catalyst for the synthesis of β-sulfonylvinylamines from sodium sulfinates and oxime acetates via direct C-S coupling reaction. The transformation was remarkably affected by the solvent, and chlorobenzene emerged as the best option. This Cu-MOF displayed higher activity than numerous conventional homogeneous and MOF-based catalysts. The catalyst was reutilized many times in the synthesis of β-sulfonylvinylamines without considerably deteriorating in catalytic efficiency. These β-sulfonylvinylamines were readily converted to the corresponding β-ketosulfones via a hydrolysis step with aqueous HCl solution. To the best of our knowledge, this direct C-S coupling reaction to achieve β-sulfonylvinylamines was not previously conducted with a heterogeneous catalyst.

Desulfonylative Methenylation of β-Keto Sulfones

A one-step strategy for the synthesis of α-methenyl ketones from β-keto sufones is reported. Success of the methodology is elaborated for the synthesis of chromanones and isoflavanones in one-step.

Metal-free desulfonylation reaction through visible-light photoredox catalysis

The desulfonylation of β-arylketosulfones has been achieved in good to excellent yields by using 3-W blue LEDs light, 1 mol-% organic dye eosin Y bis(tetrabutylammonium salt) as photocatalyst, and diisopropylethylamine as reducing agent. Mechanistic studies demonstrate that oxidative quenching of the excited eosin Y by β-arylketosulfones plays a crucial role in the present photoredox catalytic cycle. Reductive desulfonylation is essential to enable to use of a sulfone as an auxiliary group. For reductive removal of sulfones, highly aggressive metal-containing reducing agents and harsh reaction conditions are often employed. In this paper, metal-free desulfonylation of β-arylketosulfones can be achieved efficiently at room temperature under visible-light irradiation.

CYCLOPENTANATION WITH β-METHYLTHIO-ALLYL PHENYL SULFONE

The allylic thiosulfones 2 resulting from the addition of thiols to propargylic sulfone 1 have been used to convert enones into diketo-sulfones which then led to bicyclo alkanediones by either tris-anionization then cupric oxidation or treatment with rhodium acetate of the corresponding diazoketo-sulfone.