(+)-(R)-p-tolyl vinyl sulphoxide

Base Information

• Chemical Name: (+)-(R)-p-tolyl vinyl sulphoxide
• CAS No.: 54828-68-1
• Molecular Formula: C9H10OS
• Molecular Weight: 166.244
• DSSTox Substance ID: DTXSID80455337
• Wikidata: Q82277293
• Mol file: 54828-68-1.mol

Synonyms:(+)-(R)-p-tolyl vinyl sulphoxide;54828-68-1;(r)-vinyl p-tolyl sulfoxide;DTXSID80455337;ODAVDFDCUDDZPI-LLVKDONJSA-N

Chemical Property of (+)-(R)-p-tolyl vinyl sulphoxide

Chemical Property:

• XLogP3: 2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 166.04523611
• Heavy Atom Count: 11
• Complexity: 157

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC=C(C=C1)S(=O)C=C
• Isomeric SMILES: CC1=CC=C(C=C1)[S@](=O)C=C

Technology Process of (+)-(R)-p-tolyl vinyl sulphoxide

There total 15 articles about (+)-(R)-p-tolyl vinyl sulphoxide 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: 95.0%

vinylmagnesium chloride (3536-96-7) + (1S,5R,7R)-10,10-Dimethyl-4-((R)-toluene-4-sulfinyl)-3-thia-4-aza-tricyclo[5.2.1.01,5]decane 3,3-dioxide (190448-84-1) → (R)-p-tolyl vinyl sulfoxide (54828-68-1)

Guidance literature:

In tetrahydrofuran; at -78 ℃; for 1h;

DOI:10.1016/S0040-4039(97)00472-3

Reference yield: 75.0%

vinylmagnesium chloride (3536-96-7) + (-)-menthyl p-toluenesulfinate (1517-82-4) → (R)-p-tolyl vinyl sulfoxide (54828-68-1)

Guidance literature:

In tetrahydrofuran; diethyl ether; for 0.166667h; Ambient temperature;

DOI:10.1016/S0957-4166(00)82318-6

Reference yield: 70.0%

1-[(R)-2-((1R,2S,5R)-2-Isopropyl-5-methyl-cyclohexyloxy)-ethanesulfinyl]-4-methyl-benzene → (R)-p-tolyl vinyl sulfoxide (54828-68-1)

Guidance literature:

With potassium hydride; methyl iodide; In tetrahydrofuran; for 3h; Ambient temperature;

DOI:10.1016/S0040-4039(98)01204-0

upstream raw materials:

vinylmagnesium chloride

(-)-menthyl p-toluenesulfinate

vinyl magnesium bromide

(1R,2S,5R,SS)-(-)-menthyl p-toluenesulfinate

Downstream raw materials:

(S)-3-phenyl-4-(p-tolylsulfinyl)isoxazolidine

(+)-1-<(S)-p-tolylsulfinyl>-p-tolylthioethene

(-)-(R)-2-(3-formylindol-4-yl)vinyl-p-tolylsulfoxide

N-methyl-(1R,5R,6S,R_S)-6-(p-tolylsulphinyl)-8-azabicyclo<3.2.1>oct-3-en-2-one

Refernces

High Asymmetric Induction in the 1,3-Dipolar Cycloaddition of (R)-(+)-p-Tolyl Vinyl Sulfoxide with Acyclic Nitrones

10.1021/jo00141a046

The research focuses on the exploration of asymmetric 1,3-dipolar cycloadditions, a field that has been less studied compared to asymmetric Diels-Alder reactions. The purpose of the study was to investigate the high chiral induction potential of a chiral vinyl sulfoxide, (R)-(+)-p-tolyl vinyl sulfoxide, in its reaction with typical acyclic nitrones. The researchers observed high chiral induction in these reactions, which suggests the potential use of this sulfoxide as a chiral inducing agent in cycloadditions. The study concluded with the successful synthesis and characterization of various isoxazolidines and their subsequent transformations, demonstrating the effectiveness of the chiral sulfoxide in inducing asymmetry. Key chemicals used in the process included (R)-(+)-p-tolyl vinyl sulfoxide, C,N-diphenylnitrone, and various reagents for the transformations and analyses, such as LiAlH4 for reduction, CH3-O and NaB3H3CN for N-methylation, and Eu(hfcI3) as a chiral NMR shift reagent for determining enantiomeric excess.