N-(p-toluenesulfonyl)-3-amino-3-(2-naphthyl)-1-trimethylsilylprop-1-yne

Base Information

• Chemical Name: N-(p-toluenesulfonyl)-3-amino-3-(2-naphthyl)-1-trimethylsilylprop-1-yne
• CAS No.: 947315-10-8
• Molecular Formula: C₂₃H₂₅NO₂SSi
• Molecular Weight: 407.609
• Mol file: 947315-10-8.mol

Synonyms:N-(p-toluenesulfonyl)-3-amino-3-(2-naphthyl)-1-trimethylsilylprop-1-yne

Chemical Property of N-(p-toluenesulfonyl)-3-amino-3-(2-naphthyl)-1-trimethylsilylprop-1-yne

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-(p-toluenesulfonyl)-3-amino-3-(2-naphthyl)-1-trimethylsilylprop-1-yne

There total 1 articles about N-(p-toluenesulfonyl)-3-amino-3-(2-naphthyl)-1-trimethylsilylprop-1-yne 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: 70.0%

2-naphthyl N-tosyl imine (17692-84-1) + trimethylsilylacetylene (1066-54-2) → N-(p-toluenesulfonyl)-3-amino-3-(2-naphthyl)-1-trimethylsilylprop-1-yne (947315-10-8)

Guidance literature:

With dimethyl zinc(II); In toluene; at 70 ℃; for 24h;

DOI:10.1021/jo070745o

Reference yield: 41.0%

N-(p-toluenesulfonyl)-3-amino-3-(2-naphthyl)-1-trimethylsilylprop-1-yne (947315-10-8) → N-(p-toluenesulfonyl)-1-amino-1-(2-naphthyl)prop-2-yne (947315-16-4)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 ℃; for 0.5h;

DOI:10.1021/jo070745o

Reference yield:

N-(p-toluenesulfonyl)-3-amino-3-(2-naphthyl)-1-trimethylsilylprop-1-yne (947315-10-8) → N-(p-toluenesulfonyl)-3-amino-3-(2-naphthyl)propanal

Guidance literature:

Multi-step reaction with 2 steps

1: 41 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.5 h / 0 °C

2: 85 percent / 6-(2,4,6-triphenylphenyl)-2-(diphenylphosphino)pyridine; water / [CpRu(η⁶-naphthalene)]PF6 / acetone / 19 h / 55 - 60 °C

With tetrabutyl ammonium fluoride; water; (η⁵-cyclopentadienyl) (η⁶-naphthalene)ruthenium hexafluorophosphate; In tetrahydrofuran; acetone; 2: anti-Markovnikov reaction;

DOI:10.1021/jo070745o

upstream raw materials:

2-naphthyl N-tosyl imine

trimethylsilylacetylene

Downstream raw materials:

N-(p-toluenesulfonyl)-1-amino-1-(2-naphthyl)prop-2-yne