4-((1S,3S,4S,5S,6R)-2-Chloromethyl-3-methyl-5-phenylsulfanyl-tricyclo[2.2.1.0^2,6]hept-3-yl)-butyronitrile

Base Information

• Chemical Name: 4-((1S,3S,4S,5S,6R)-2-Chloromethyl-3-methyl-5-phenylsulfanyl-tricyclo[2.2.1.0^2,6]hept-3-yl)-butyronitrile
• CAS No.: 77243-08-4
• Molecular Formula: C₁₉H₂₂ClNS
• Molecular Weight: 331.909
• Mol file: 77243-08-4.mol

Synonyms:4-((1S,3S,4S,5S,6R)-2-Chloromethyl-3-methyl-5-phenylsulfanyl-tricyclo[2.2.1.0^2,6]hept-3-yl)-butyronitrile

Chemical Property of 4-((1S,3S,4S,5S,6R)-2-Chloromethyl-3-methyl-5-phenylsulfanyl-tricyclo[2.2.1.0^2,6]hept-3-yl)-butyronitrile

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-((1S,3S,4S,5S,6R)-2-Chloromethyl-3-methyl-5-phenylsulfanyl-tricyclo[2.2.1.0^2,6]hept-3-yl)-butyronitrile

There total 6 articles about 4-((1S,3S,4S,5S,6R)-2-Chloromethyl-3-methyl-5-phenylsulfanyl-tricyclo[2.2.1.0^2,6]hept-3-yl)-butyronitrile 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: 100.0%

4-((1R,2S,4S)-2-Methyl-3-methylene-bicyclo[2.2.1]hept-5-en-2-yl)-butyronitrile (77228-93-4) + benzenesulfenyl chloride (931-59-9) → 4-((1S,3S,4S,5S,6R)-2-Chloromethyl-3-methyl-5-phenylsulfanyl-tricyclo[2.2.1.02,6]hept-3-yl)-butyronitrile (77243-08-4)

Guidance literature:

In dichloromethane; at 0 ℃;

DOI:10.1016/0040-4039(80)88100-7

Reference yield:

(1R,2S,4S)-2-Methyl-3-methylene-bicyclo[2.2.1]hept-5-ene-2-carbaldehyde (73565-76-1) → 4-((1S,3S,4S,5S,6R)-2-Chloromethyl-3-methyl-5-phenylsulfanyl-tricyclo[2.2.1.02,6]hept-3-yl)-butyronitrile (77243-08-4)

Guidance literature:

Multi-step reaction with 5 steps

1: dimethylsulfoxide / Ambient temperature

2: acidic silica gel / CH₂Cl₂ / 48 h

3: 92 percent / CH₃S(O)CH₂Na / dimethylsulfoxide / Horner-Emmons reaction

4: 96 percent / Mg / methanol

5: 100 percent / CH₂Cl₂ / 0 °C

With silica gel; sodium methylsulfinylmethanide; magnesium; In methanol; dichloromethane; dimethyl sulfoxide;

DOI:10.1016/0040-4039(80)88100-7

Reference yield:

((1R,2S,4S)-2-Methyl-3-methylene-bicyclo[2.2.1]hept-5-en-2-yl)-acetaldehyde (77228-96-7) → 4-((1S,3S,4S,5S,6R)-2-Chloromethyl-3-methyl-5-phenylsulfanyl-tricyclo[2.2.1.02,6]hept-3-yl)-butyronitrile (77243-08-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 92 percent / CH₃S(O)CH₂Na / dimethylsulfoxide / Horner-Emmons reaction

2: 96 percent / Mg / methanol

3: 100 percent / CH₂Cl₂ / 0 °C

With sodium methylsulfinylmethanide; magnesium; In methanol; dichloromethane; dimethyl sulfoxide;

DOI:10.1016/0040-4039(80)88100-7

upstream raw materials:

4-((1R,2S,4S)-2-Methyl-3-methylene-bicyclo[2.2.1]hept-5-en-2-yl)-butyronitrile

benzenesulfenyl chloride

(1R,2S,4S)-2-Methyl-3-methylene-bicyclo[2.2.1]hept-5-ene-2-carbaldehyde

((1R,2S,4S)-2-Methyl-3-methylene-bicyclo[2.2.1]hept-5-en-2-yl)-acetaldehyde

Downstream raw materials:

C₁₉H₂₁NS