n-Isobutyl-2,4-decadienamide

Base Information

• Chemical Name: n-Isobutyl-2,4-decadienamide
• CAS No.: 109-26-2
• Molecular Formula: C₁₄H₂₅NO
• Molecular Weight: 223.359
• DSSTox Substance ID: DTXSID90864855
• Wikidata: Q103815861,Q104392710,Q105160324
• Mol file: 109-26-2.mol

Synonyms:n-isobutyl-2,4-decadienamide;2,4-Decadienamide, N-(2-methylpropyl)-;109-26-2;N-(2-Methylpropyl)-2,4-Decadienamide;trans-Pellitorin;trans-Pellitorine;N-(2-methylpropyl)deca-2,4-dienamide;N-Isobutyldecadienamid;DTXSID90864855

Chemical Property of n-Isobutyl-2,4-decadienamide

Chemical Property:

• Boiling Point: 368.7°Cat760mmHg
• PKA: 15.49±0.46(Predicted)
• Flash Point: 224.6°C
• PSA: 0.00000
• Density: 0.882g/cm³
• LogP: 0.00000
• XLogP3: 4.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 8
• Exact Mass: 223.193614421
• Heavy Atom Count: 16
• Complexity: 229

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCCCCC=CC=CC(=O)NCC(C)C

Technology Process of n-Isobutyl-2,4-decadienamide

There total 91 articles about n-Isobutyl-2,4-decadienamide 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%

deca-2E,4Z-dienoic acid isobutylamide (639086-18-3,109-26-2,53608-76-7) → (2E,4E)-N-isobutyldecadienamide (18836-52-7,109-26-2,53608-76-7)

Guidance literature:

With iodine; In toluene; at 20 ℃; for 1h;

Reference yield: 85.0%

(E)-1-iodohept-1-ene (60595-37-1) + N-(2-methylpropyl)prop-2-enamide (35143-37-4) → (2E,4E)-N-isobutyldecadienamide (18836-52-7,109-26-2,53608-76-7)

Guidance literature:

With tetrabutyl-ammonium chloride; palladium diacetate; potassium carbonate; In water; N,N-dimethyl-formamide; at 70 ℃; stereoselective reaction; Inert atmosphere;

DOI:10.1134/S1070428012070032

Reference yield: 82.0%

(2E,4E)-deca-2,4-dienoic acid (30361-33-2) + isobutylamine (78-81-9) → (2E,4E)-N-isobutyldecadienamide (18836-52-7,109-26-2,53608-76-7)

Guidance literature:

With 1,1'-carbonyldiimidazole; In dichloromethane; 1.) 0 deg C, 45 min; 2.) 0 deg C to RT, 14 h;

DOI:10.1139/v96-046

upstream raw materials:

deca-2c,4c-dienoic acid

methyl (2Z,4Z)-2,4-decadienoate

deca-2,4-diynoic acid

deca-2,4-diynoic acid methyl ester

Downstream raw materials:

deca-2E,4E-dienoic acid 4-hydroxy-2-phenylethylamide

Refernces

• 1、 Tamura,Maeda,Choi,Ishibashi. "Ene reaction with pummerer reaction intermediates of a-(methylsulfinyl)-acetamides: A novel synthesis of pellitorine". . p. 56 - 57. Retrieved 1982.
• 2、 Jacobson. "-". . p. 2584 Anm. 11. Retrieved 1953.
• 3、 Banerji, Avijit,Pal, Sudhir C.. "TOTAL SYNTHESIS OF SYLVAMIDE, A PIPER ALKAMIDE". . p. 1028 - 1030. Retrieved 1983.
• 4、 Sato, Toshio,Kawashima, Masatoshi,Fujisawa, Tamotsu. "A NOVEL FIVE-CARBON HOMOLOGATION LEADING TO 3,4-ALKADIENOIC ACIDS BY SN2' REACTION OF β-ETHYNYL-β-PROPIOLACTONE WITH GRIGNARD REAGENTS IN THE PRESENCE OF COPPER(I) CATALYST". . p. 2375 - 2378. Retrieved 1981.
• 5、 Zakharkin, L. I.,Petrushkina, E. A.. "SYNTHESIS OF N-ISOBUTYLAMIDE OF 2E,4E-DECADIENOIC ACID (PELLITORINE) FROM BUTADIENE - ACETIC ACID TELOMER". . p. 2285 - 2286. Retrieved 1982.
• 6、 -. "Conjugated dienamides, methods of production thereof, compositions containing same and uses thereof". Page/Page column 14-15. . Retrieved 2010/02/11.