Dysidenine

Base Information

• Chemical Name: Dysidenine
• CAS No.: 65647-65-6
• Molecular Formula: C₁₇H₂₃Cl₆N₃O₂S
• Molecular Weight: 546.173
• DSSTox Substance ID: DTXSID50984205
• Wikipedia: Dysidenin
• Wikidata: Q104934920
• Mol file: 65647-65-6.mol

Synonyms:dysidenin;dysidenine

Chemical Property of Dysidenine

Chemical Property:

• Vapor Pressure: 1.15E-15mmHg at 25°C
• Boiling Point: 627.6°Cat760mmHg
• Flash Point: 333.4°C
• PSA: 94.03000
• Density: 1.423g/cm³
• LogP: 6.78040
• XLogP3: 5.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 8
• Exact Mass: 544.961264
• Heavy Atom Count: 29
• Complexity: 572

Purity/Quality:

85.0-99.8% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(CC(C(=O)NC(C)C1=NC=CS1)N(C)C(=O)CC(C)C(Cl)(Cl)Cl)C(Cl)(Cl)Cl

Technology Process of Dysidenine

There total 11 articles about Dysidenine 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: 83.0%

(1S)-1-(1,3-thiazol-2-yl)ethanamine (623143-42-0) + 5,5,5-trichloro-4(S)-methyl-2(S)-[methyl(4,4,4-trichloro-3(S)-methyl-1-oxobutyl)amino]pentanoic acid → dysidenin (65647-65-6,67528-34-1,72258-37-8)

Guidance literature:

With 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; at 20 - 25 ℃; for 12h; Inert atmosphere;

DOI:10.1002/asia.201100338

Reference yield:

(S)-4,4,4-trichloro-3-methylbutanenitrile (1207363-08-3) → dysidenin (65647-65-6,67528-34-1,72258-37-8)

Guidance literature:

Multi-step reaction with 6 steps

1.1: diisobutylaluminium hydride / dichloromethane / 2 h / -78 °C / Inert atmosphere

1.2: 2 h / -78 - 25 °C / Inert atmosphere

2.1: sodium dihydrogenphosphate; sodium chlorite / 2-methyl-but-2-ene; water; tert-butyl alcohol / 3.33 h / 0 - 25 °C / Inert atmosphere

3.1: dicyclohexyl-carbodiimide / dichloromethane / 48.5 h / 0 - 25 °C / Inert atmosphere

4.1: sodium hydrogencarbonate / tetrahydrofuran; water / 14 h / 20 - 25 °C / Inert atmosphere

5.1: sodium hydride / tetrahydrofuran; mineral oil / 24 h / 0 - 25 °C / Inert atmosphere

6.1: 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / tetrahydrofuran / 12 h / 20 - 25 °C / Inert atmosphere

With sodium chlorite; sodium dihydrogenphosphate; 1-hydroxy-7-aza-benzotriazole; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dicyclohexyl-carbodiimide; In tetrahydrofuran; 2-methyl-but-2-ene; dichloromethane; water; mineral oil; tert-butyl alcohol;

DOI:10.1002/asia.201100338

Reference yield:

C5H7Cl3O (1207363-11-8) → dysidenin (65647-65-6,67528-34-1,72258-37-8)

Guidance literature:

Multi-step reaction with 5 steps

1: sodium dihydrogenphosphate; sodium chlorite / 2-methyl-but-2-ene; water; tert-butyl alcohol / 3.33 h / 0 - 25 °C / Inert atmosphere

2: dicyclohexyl-carbodiimide / dichloromethane / 48.5 h / 0 - 25 °C / Inert atmosphere

3: sodium hydrogencarbonate / tetrahydrofuran; water / 14 h / 20 - 25 °C / Inert atmosphere

4: sodium hydride / tetrahydrofuran; mineral oil / 24 h / 0 - 25 °C / Inert atmosphere

5: 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / tetrahydrofuran / 12 h / 20 - 25 °C / Inert atmosphere

With sodium chlorite; sodium dihydrogenphosphate; 1-hydroxy-7-aza-benzotriazole; sodium hydride; sodium hydrogencarbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dicyclohexyl-carbodiimide; In tetrahydrofuran; 2-methyl-but-2-ene; dichloromethane; water; mineral oil; tert-butyl alcohol;

DOI:10.1002/asia.201100338

upstream raw materials:

(S)-2,5-dioxopyrrolidin-1-yl 4,4,4-trichloro-3-methylbutanoate

(2S,4S)-5,5,5-trichloro-4-methyl-2-((3S)-4,4,4-trichloro-3-methylbutanamido)pentanoic acid

(S)-4,4,4-trichloro-3-methylbutanenitrile

C₅H₇Cl₃O

Downstream raw materials:

(S)-5,5,5-Trichloro-2-[(2,4-dinitro-phenyl)-methyl-amino]-4-methyl-pentanoic acid methyl ester

(R)-5,5,5-Trichloro-2-[(2,4-dinitro-phenyl)-methyl-amino]-4-methyl-pentanoic acid methyl ester

(R)-(+)-ethyl 2-(4-bromophenyl)-2-oxo-3-methyl-4,4,4-trichlorobutanoate

(+)-3-methyl-4,4,4-trichlorobutanoic acid