Isobutyl amide

Amide derivatives of unsaturated aliphatic fatty acids (Cio-Cie) are especially common in members of the Asteraceae, Piper-aceae, and Rutaceae. Among these, the isobutyl amides have pronounced insecticidal activity (119). Most of these compounds have not proven useful as commercial insecticides because of their irritating properties to mammals and their instability. 

The fruit of this plant contains the isobutyl amide of eicosa-2,4,8-trienoic acid. ... 

N-/ oZ dyZ CyHigOgNg. MW, 158. Needles from CgHg. M.p. 83°. N -p-roZyZ isobutyl-amide-P toluidide. Needles from EtOH. M.p. 177°. 

Jakupovic J, Schuster A, Bohlmann F, King R M, Robinson H 1986 New lignans and isobutyl-amides from Heliopsis buphthalmoides. Planta Med 18-20... 

On the other hand, the insecticidal activity of the polyacetylenic isobutyl-amide anacycHn (XXVII) is very weak compared to that of the corresponding ethylenic amide prepared from it by controlled hydrogenation (Crombie, 1955). 

This is a very general and mild method for the preparation of amides, applicable to large structural variations in both the acid and the amine. A variety of chloro-formates can be employed, but isobutyl chloroformate is used most often. The solvent is not critical, but generally, THE is used. 

If 2-n-propyl-3-methyl-3-isobutyloxaziranc is allowed to boil under nitrogen, the boiling point is lowered to 128°C from the initial 168°C within 2 hr. Methyl isobutyl ketone (0.92 mole), ammonia (0.32 mole), and a little amide (0.04 mole) are formed [Eq. (29)]. ... 

Like the carbodiimide method, the mixed anhydride method results in an amide complex (Table 5, Figure 17). The acid-containing hapten is dissolved in a dry, inert, dipolar, aprotic solvent such as p-dioxane, and isobutyl chloroformate is added with an amine catalyst. The activated mixed anhydride is chemically stable and can be isolated and characterized. The aqueous protein solution is added to the activated acid and the pH is maintained at around 8.5. A low temperature (around 10 °C) is necessary during the reaction to minimize side reactions. 

Scheme 1-1. Enantiomers of 2-isobutyl malonic acid mono amide have opposite optical rotations.

The cis-fagaramide (J) was synthesized as outlined below. The required acetylenic acid (c) was prepared from piperonal (a) by the Corey s procedure.Treatment of piperonal with carbon tetrabromide, triphenylphosphine and zinc gave the bromo olefin (b) as an oil in 71% yield. The bromo olefin (b) was treated with 2 equivalents of n-butyl lithium followed by quenching with dry ice to give acetylenic acid (c) in 54% yield. Treatment of (c) with excess thionyl chloride without solvent at 50 followed by addition of isobutyl amine in benzene gave the acetylenic amide (d) as a viscous oil in 96% yield. Partial reduction of (d) gave cis-fagarmide (7 ) in 89% yield. 

Cyclization of 2-aminonicotinic acid with butyric anhydride gave the 2-propyM//-pyrido[2,3-4 [l,3]oxazin-4-one 698 <2004W02004039774>, while the 2-isobutyl analogue 699 was prepared via the cyclization of amide 697, obtained from acylation of 2-aminonicotinic acid with isovaleryl chloride, in AC2O at 120°C <2003W02003103575>. 

Acrylic Acid, 2-Ethylhexyl Ester Acrylic Acid, Isobutyl Ester Acrylic Acid, Methyl Ester Acrylic Aldehyde Acrylic Amide, 50 %... 

The two sulfur-containing amides entadamides A (93) and B (94) have been isolated from the seeds and entadimides A and C (95) from the leaves of Entada phaseoloides Merr. (valid name Entada rheedii Spreng.) (Legu-minosae) (99-101). The known isobutylamide alkaloid pellitorine (N-isobutyl-2 ,4 -decadienamide) is found in the aerial parts of Piper ri-besoides Wall. (102). Pellitorine has also been isolated from the fruits of P. 

These branched alcohol products are also useful in solvents, plasticizers, and monomers. For example, isobutyl alcohol is converted into the acetate ester, which is used extensively as a lacquer solvent. Isobutyl alcohol is also used in lubricating oils and in the production of amide resins. Propyl alcohol (59 million kg/yr) is used heavily in herbicide syntheses and in solvents for coatings and inks. 

Figure 22-5. (A) The structure of A -acetyl-L-leucylmethyl amide derived from IR spectra. (B) The structure of A-acetyl-D,L-leucylmethylamide derived from X-ray diffraction (R = isobutyl). (Reprinted from reference 35, with permission.)...

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