3- -propanoic acid lactone

Hydroxypropionic acid lactone NSC-21626 Oxetanone Oxetan-2-one 2-Oxetanone Propanlllde Propanoic acid, 3-hydroxy-, p-lactone Propanolide 3-Propanolide P-Propanoic acid lactone p-Propiolactone p-propiolakton p-Propiono-lactone, p-Proprolactone 1,3-Propiolactone 3-Propio-lactone Propiolactona Propiolactone Propiolactone, p- Propiolactonum Propiolattone Propionic acid, 3-hydroxy-, p-lactone Propionolactone. Chemical inter-mediate used as a disinfectant. Liquid mp = -34.4" bp = 162° (dec) df = 1.1460 soluble in H2O (35 g/100 ml) LCso (rat ihl) = 25 ppm/6H. O Neal Jones Feldman Pharm. 

Substituted Cyclic Lactones by Condensation of ( + )-(/f)-3-(4-methylphenylsulfinyl)propanoic Acid with Carbonyl Compounds General Procedure46 ... 

Synonyms AI3-24257 AIDS-6024 Betaprone BPL BRN 0001360 Caswell No. 709 CCRIS 536 EINECS 200-340-1 EPA pesticide chemical code 010901 Hydracrylic acid p iactone 3-Hydroxypropionic acid lactone p Lactone NSC 21626 Oxetan-2-one 2-Oxetanone Propano-lide Propiolactone 1,3-Propiolactone 3-Propiolactone p Propionolactone 3-Propionolactone p Propro-lactone UN 2810. 

For example the 0-tetrahydropyran.yl derivative of 3g- hydroxy 17-oxo 5-androstene 8 reacted on the bianion and give after metha-nolysis of protective group the 3g, 178— dihydoxy 5-androstene 17a- propanoic acid y-lactone 9 (4). ... 

During the total synthesis of the pentacyclic sesquiterpene dilactone (+)-merrilactone A by S.J. Danishefsky et al., a two-carbon unit was introduced at C9 by a Johnson-Claisen rearrangement. This high yielding transformation was carried out in the presence of catalytic 2,2-dimethyl propanoic acid at 135 °C using mesitylene as the solvent. A mixture of diastereomeric esters were formed, which were later hydrolyzed and subjected to iodolactonization to form the second lactone ring present in merrilactone A. The natural product was synthesized in 20 steps with an overall yield of 10.7%. 

Treatment of 3-(l-benzyloxymethylcyclopropyl)propanoic acid with various mercury(II) salts such as nitrate, trifluoroacetate and perchlorate gave the lactones 25A and 25B in 35-86% yield after aqueous potassium bromide workup. A number of related cyclopropanecarboxylic esters were reacted in the same fashion to give bromomercurio-substituted lactones 26 and 27/28 from which the mercury was removed by reduction with sodium borohydride. ... 

To a solution of 430 mg (1.2 mmol) of(20R)-3/ -methoxychola-5.16-dieno-24,20-lactone in 40 mL of EtOH. 3 mL (50 mmol) of 80% hydrazine hydrate and 3.6 mL (50 mmol) of propanoic acid are added. The mixture is refluxed for 6 h with air stream bubbling. The product is extracted with CHC13 and purified by chromatography (silica gel. hexane/ EtOAc 95 5) yield 250 mg (58%) mp 150 152CC. 

Interestingly, as also shown in Scheme 9.111, diborane (B2H6) in oxacyclopentane (THF, i.e., HsB THF) preferentially reacts with the carboxylic acid portion of the same fran5 -P-(2-carbomethoxycyclohexane)propanoic acid. Presumably this is because the bond between oxygen and boron is more easily formed and a proton can be lost to, for example, solvent. Thus, it is predicted that reduction under these circumstances preferentially leads to rran5 -3-(2-carbomethoxycyclohexane)-1-propanol, which then leads to fran5 -3-oxa-2-oxobicyclo[5.4.0]undecane, a lactone isomeric with that in the first example of the scheme. 

Nomenclature of lactones is based on the nomenclature of hydroxycarboxyhc acids. The simplest P-lactone hypothetically derived from p-hydroxycarboxyhc acids is propano-3-lactone (formerly also known as 3-propanohde and P-propiolactone, 8-95), which can be considered an internal ester of 3-hydroxypropanoic acid. The simplest y-lactone is butano-4-lactone, also known as 4-butanolide or y-butyrolactone (8-96), which is derived from 4-hydroxybutanoic acid. The basic member of the homologous series of 5-lactones is pentano-5-lactone, also known as 5-pentanohde or 5-valerolactone (8-97), which is derived from... 

Hydroxyundecanoic acid lactone 5708 2-(4-Isobutylphenyl)propanoic acid 6207 Isopropyl ether 3805... 

Similarly, 2,3-dihydro-l,4-dioxin can be lithiated at a vinylic position with either n-BuLi at 0 °C or t-BuLi at -30 to -20 °C [43a], Related benzocondensed systems 54 were lithiated with LDA at -78 °C to give the dianionic intermediates 55, which were converted into lactones 56 upon successive reaction with acetaldehyde and propanoic acid [49] (Scheme 2.9). 

Apart from sotolon, the other compounds in Fig. 5 can be explained as the products of a Maillard reaction, and their carbon skeletons simply originate from the active Amadori intermediate in other words, they still preserve the straight carbon chain structure of monosaccharides. In spite of being a simple Cg lactone, sotolon has a branched carbon skeleton, which implies another formation process in the Maillard reaction. Sulser e al.(6) reported that ethyl sotolon (ll) was prepared from threonine with sulfuric acid, and that 2-oxobutyric acid, a degradation product of threonine, was a better starting material to obtain II. This final reaction is a Claisen type of condensation, which would proceed more smoothly under alkaline conditions. As we(lO) obtained II from 2-oxobutyric acid (see figure 6) with a high yield in the presence of potassium carbonate in ethanol, a mixed condensation of 2-oxobutyric and 2-oxo-propanoic (pyruvic) acids was attempted under the same conditions, and a mixture of sotolon (22% yield) and II were obtained however, the... 

An attractive route to (/ )- and (5)-2-amino-3-phosphonopropanoic acid (AP-3) involves the intermediacy of serine-deiived P-lactones. The nucleophilic addition of trimethyl phosphite to (/ )- and (5)-A-(ierZ-butoxycarboiiyl)-3-amino-2-oxetanone at 70°C for 42 h gives the (R)- and (5)-methyl A-(tert-butoxycarbonyl)-2-amino-3-(dimethoxyphosphinyl)propanoates in excellent yields. Exhaustive acid hydrolysis of the (S)- and (7 )-isomers, followed by treatment with propylene oxide, affords the corresponding (R)- and (S)-2-amino-3-phosphonopropanoic acids as their zwitterions (d- and l-AP-3) (Scheme 8.42). ... 

Esters constituted the largest family and included acetates (ethyl, propyl, isobutyl, butyl, isoamyl, and phenethyl), ethyl esters of fatty acids (propanoate, isobutanoate, butanoate, hexanoate, octanoate, 3-hydroxybutanoate, 3-hydroxyhexanoate and furcate), ethyl esters of organic acids (pyruvate, lactate, ethyl myristate, diethyl malate and, mono- and diethyl succinate) and various other esters, such as methyl butanoate, isobutyl lactate and phenylethyl octanoate. The acids quantified included isobutanoic, butanoic, hexanoic, octanoic, decanoic, lauiic and 3-methylbutanoic. The lactones included y-butyrolactone, pantolactone, y-decalactone and E- and Z-oak lactone and the terpenes included neral d-terpineol, P-dtronellol and Z-nerolidol. The aldehyde family comprised acetaldehyde, benzaldehyde, furfural, 5-methylfurfural and octanal, and the phenol family included eugenol, 4-ethylphenol and 4-ethylguaiacol. Finally, 1,1-diethoxyethane, acetoin, sotolon, 2, 3-butanedione, p-cymene and methionol were also determined. 

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