1,3-Diethyl 2-[cyano[(4-methylphenyl)sulfinyl]methylene]propanedioate

Base Information

• Chemical Name: 1,3-Diethyl 2-[cyano[(4-methylphenyl)sulfinyl]methylene]propanedioate
• CAS No.: 380630-88-6
• Molecular Formula: C₁₆H₁₇NO₅S
• Molecular Weight: 335.381
• DSSTox Substance ID: DTXSID301156546
• Nikkaji Number: J1.647.861J
• Mol file: 380630-88-6.mol

Synonyms:DTXSID301156546;380630-88-6;1,3-Diethyl 2-[cyano[(4-methylphenyl)sulfinyl]methylene]propanedioate

Chemical Property of 1,3-Diethyl 2-[cyano[(4-methylphenyl)sulfinyl]methylene]propanedioate

Chemical Property:

• XLogP3: 2.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 8
• Exact Mass: 335.08274382
• Heavy Atom Count: 23
• Complexity: 532

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCOC(=O)C(=C(C#N)S(=O)C1=CC=C(C=C1)C)C(=O)OCC

Technology Process of 1,3-Diethyl 2-[cyano[(4-methylphenyl)sulfinyl]methylene]propanedioate

There total 5 articles about 1,3-Diethyl 2-[cyano[(4-methylphenyl)sulfinyl]methylene]propanedioate 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: 66.0%

(Rs)-(+)-3,3-diethoxycarbonyl-3-hydroxy-2-p-tolylsulfinylpropionitrile (441718-04-3) → diethyl 2-[cyano(toluene-4-sulfinyl)methylene]propanedioate (380630-88-6)

Guidance literature:

With methanesulfonyl chloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at -78 ℃; for 2h;

DOI:10.1016/S0040-4020(02)00149-7

Reference yield: 66.0%

3,3-diethoxycarbonyl-3-hydroxy-2-p-tolylsulfinylpropionitrile → diethyl 2-[cyano(toluene-4-sulfinyl)methylene]propanedioate (380630-88-6)

Guidance literature:

With methanesulfonyl chloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at -78.15 ℃; for 2h;

DOI:10.1107/S0108270101012951

Reference yield:

Diethyl ketomalonate (609-09-6) → diethyl 2-[cyano(toluene-4-sulfinyl)methylene]propanedioate (380630-88-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: lithium hexamethyldisilazide / tetrahydrofuran / 0.5 h / -78 °C

1.2: 78 percent / tetrahydrofuran / 2 h / -78 °C

2.1: 66 percent / mesyl chloride; diisopropylethylamine / CH₂Cl₂ / 2 h / -78 °C

With methanesulfonyl chloride; N-ethyl-N,N-diisopropylamine; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane;

DOI:10.1016/S0040-4020(02)00149-7

upstream raw materials:

(R_s)-(+)-3,3-diethoxycarbonyl-3-hydroxy-2-p-tolylsulfinylpropionitrile

(R)-(+)-cyanomethyl p-tolyl sulfoxide

Diethyl ketomalonate

α-cyanomethyl p-tolyl sulphoxide