Category: 31253-08-4

Kamiya, Naoshi published the artcileDehalogenation of α-halo carbonyl compounds by a new efficient reagent, triphenylphosphonium iodide, Recommanded Product: Ethyl 2-Iodopropionate, the publication is Chemistry Letters (1992), 293-6, database is CAplus.

Ph₃PHI is an efficient reagent for the dehalogenation of α-halo carbonyl compounds, e.g., MeCHClAc to EtAc. α-Halo esters, which were difficult to reduce with Me₃SiCl/NaI reagent, were smoothly debrominated by Ph₃PHI. Treatment of α-halo carbonyl compounds with Ph₃PDI produced the corresponding α-deuterated compounds

Chemistry Letters published new progress about 31253-08-4. 31253-08-4 belongs to iodides-buliding-blocks, auxiliary class Iodide,Ester, name is Ethyl 2-Iodopropionate, and the molecular formula is C5H9IO2, Recommanded Product: Ethyl 2-Iodopropionate.

Referemce:
https://en.wikipedia.org/wiki/Iodide,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Lei, Lin published the artcileSystematic Study on Alkyl Iodide Initiators in Living Radical Polymerization with Organic Catalysts, HPLC of Formula: 31253-08-4, the publication is Macromolecules (Washington, DC, United States) (2014), 47(19), 6610-6618, database is CAplus.

Several low-molar-mass alkyl iodides were studied as initiating dormant species in living radical polymerization with organic catalysts. Primary, secondary, and tertiary alkyl iodides with different stabilizing groups (ester, Ph, and cyano groups) were systematically studied for the rational design of initiating alkyl iodides. The activation rate constants of these alkyl iodides were exptl. determined for quant. comparison. These alkyl iodides were used in the polymerizations of Me methacrylate and Bu acrylate to examine their initiation ability in these polymerizations A telechelic polymer was prepared using an alkyl iodide with a functional group. Alkyl iodides with multi-initiating sites were also studied.

Macromolecules (Washington, DC, United States) published new progress about 31253-08-4. 31253-08-4 belongs to iodides-buliding-blocks, auxiliary class Iodide,Ester, name is Ethyl 2-Iodopropionate, and the molecular formula is C5H9IO2, HPLC of Formula: 31253-08-4.

Referemce:
https://en.wikipedia.org/wiki/Iodide,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Koike, Takeshi published the artcileTotal synthesis of racemic ligularone and isoligularone, Computed Properties of 31253-08-4, the publication is Chemical & Pharmaceutical Bulletin (1999), 47(6), 897-899, database is CAplus.

Racemic ligularone (I) and isoligularone (II) were synthesized from the cis-4aβ,5,6,7,8,8a-hexahydro-8β,8aβ-dimethylnaphthalene-1,3(2H,4H)-dione (III) by furannulation reaction with diethyl(prop-2-ynyl)sulfonium bromide, prepared from di-Et sulfide and propargyl bromide.

Chemical & Pharmaceutical Bulletin published new progress about 31253-08-4. 31253-08-4 belongs to iodides-buliding-blocks, auxiliary class Iodide,Ester, name is Ethyl 2-Iodopropionate, and the molecular formula is C5H9IO2, Computed Properties of 31253-08-4.

Referemce:
https://en.wikipedia.org/wiki/Iodide,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Mizota, Isao published the artcileTandem N,N-Dialkylation Reaction of N-Trimethylsilyl α-Iminoesters Utilizing an Umpolung Reaction and Characteristics of the Silyl Substituent: Synthesis of Pyrrolidine, Piperidine, and Iminodiacetate, Quality Control of 31253-08-4, the publication is Organic Letters (2019), 21(8), 2663-2667, database is CAplus and MEDLINE.

Umpolung reactions of N-trimethylsilyl α-iminoester with organometallics gave directly N-alkylaminoesters in high yields without the need for removing a protecting group at the nitrogen atom. Efficient syntheses of pyrrolidines, piperidines, and iminodiacetate derivatives were also developed via tandem N,N- or N,C-dialkylation reactions utilizing characteristics of the silyl substituent. Furthermore, under the influence of silica gel, the addition of an enolate to the imino nitrogen proceeded to give an iminodiacetate derivative

Organic Letters published new progress about 31253-08-4. 31253-08-4 belongs to iodides-buliding-blocks, auxiliary class Iodide,Ester, name is Ethyl 2-Iodopropionate, and the molecular formula is C5H9IO2, Quality Control of 31253-08-4.

Referemce:
https://en.wikipedia.org/wiki/Iodide,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Bodroux, F. published the artcileTransformation of Esters of Aliphatic α-Brom Acids into the Corresponding Iodo Compounds, Synthetic Route of 31253-08-4, the publication is Bulletin de la Societe Chimique de France (1908), 909-11, database is CAplus.

By means of magnesium iodide in ethereal solution, ethyl bromacetate is converted into ethyl iodoacetate, b₂₅ 85-6°, d₂₄=1.702. Ethyl a-iodopropionate, C₅H₉O₂I, liquid, slightly colored, irritating odor, b₃₈ 85°, b₇₆₅ 181-3° with partial decomposition, d₁₇=1.662. Ethyl a-iodobutyrate, C₆H₁₁O₂I, colorless liquid, odor like pippin apples, b. 195-8° with partial decomposition, d₁₇=1.570.

Bulletin de la Societe Chimique de France published new progress about 31253-08-4. 31253-08-4 belongs to iodides-buliding-blocks, auxiliary class Iodide,Ester, name is Ethyl 2-Iodopropionate, and the molecular formula is C5H9IO2, Synthetic Route of 31253-08-4.

Referemce:
https://en.wikipedia.org/wiki/Iodide,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Bodroux, F. published the artcileTransformation of Esters of α-Bromaliphatic Acids into the Corresponding α-Iodine Derivatives, Safety of Ethyl 2-Iodopropionate, the publication is Compt. rend. (1907), 1216-17, database is CAplus.

Ethyl α-chloracetate reacts with magnesium iodide giving ethyl iodacetate (Ibid, 140, 1597). The authors find that the α-brom substituted esters react in a smooth manner with magnesium iodide in ether giving the iodine derivatives. Experimental: Ethyl iodacetate, ICH₂.CO₂C₂H₄. b₂₄ 85-86°; d₂₄ 1.762. Ethyl α-iodpropionate, CH₂.CHI.CO₂C₂H₄, b₂₄ 85°, d₁₇ 1.662. Ethyl α-iodbutyrate, C₂H₅CHI.CO₂C₂H₄, b₂₁ 100-101°; d₁₇ 1.570. The iodine-substituted esters are unstable and decompose under influence of light and heat with liberation of iodine. They volatilize at ordinary temperature

Compt. rend. published new progress about 31253-08-4. 31253-08-4 belongs to iodides-buliding-blocks, auxiliary class Iodide,Ester, name is Ethyl 2-Iodopropionate, and the molecular formula is C5H9IO2, Safety of Ethyl 2-Iodopropionate.

Referemce:
https://en.wikipedia.org/wiki/Iodide,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Kusche, Brian R. published the artcileNonactin biosynthesis: Setting limits on what can be achieved with precursor-directed biosynthesis, Product Details of C5H9IO2, the publication is Bioorganic & Medicinal Chemistry Letters (2009), 19(4), 1233-1235, database is CAplus and MEDLINE.

Nonactin, produced by Streptomyces griseus ETH A7796, is a macrotetrolide assembled from nonactic acid. It is an effective inhibitor of drug efflux in multidrug resistant erythroleukemia K562 cells at sub-toxic concentrations and has been shown to possess both antibacterial and antitumor activity. As total synthesis is impractical for the generation of nonactin analogs the authors have studied precursor-directed biosynthesis as an alternative as it is known that nonactic acid can serve as a nonactin precursor in vivo. To determine the scope of the approach the authors prepared and evaluated a furan-based nonactic acid derivative, (I). Although no new nonactin analogs were detected when (I) was administered to S. griseus fermentative cultures, a significant inhibition of nonactin biosynthesis was noted (IC₅₀ âˆ?100 μM). Cell mass, nonactic acid production and the generation of other secondary metabolites in the culture were unaffected by (I) demonstrating that (I) selectively inhibited the assembly of nonactin from nonactic acid. While the authors were unable to generate new nonactin analogs the authors have discovered, however, a useful inhibitor that can be used to probe the mechanism of nonactin assembly with the ultimate goal of developing more successful precursor-directed biosynthesis transformations.

Bioorganic & Medicinal Chemistry Letters published new progress about 31253-08-4. 31253-08-4 belongs to iodides-buliding-blocks, auxiliary class Iodide,Ester, name is Ethyl 2-Iodopropionate, and the molecular formula is C5H9IO2, Product Details of C5H9IO2.

Referemce:
https://en.wikipedia.org/wiki/Iodide,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Locke, David M. published the artcileAtisine. The synthesis of 1-methyl-6-ethyl-3-azaphenanthrene, HPLC of Formula: 31253-08-4, the publication is Journal of the American Chemical Society (1959), 2246-50, database is CAplus.

cf. C.A. 52, 20143g. Pyrrolidine (33.4 ml.) in 400 ml. PhMe was refluxed 2 hrs. (Bidwell-Sterling moisture collector), 34.8 g. 7-ethyl derivative of tetralone with 100 mg. p-MeC₆H₄SO₃H added, refluxed 48 hrs. and the toluene distilled off. Ethyl α-iodopropionate (I) was prepared from 39.8 g. ethyl α-bromopropionate, 33 g. NaI, and 300 ml. dry Me₂CO. The mixture was filtered, and the Me₂CO removed by azeotropic distillation with 250 ml. C₆H₆. I was added to the pyrrolidine enamine mixture with 300 ml. dioxane, refluxed 8.5 hrs., concentrated in vacuo, saponified with methanolic KOH, concentrated, and extracted with C₆H₆. The C₆H₆ extract was concentrated in vacuo, taken up in a large volume of ether, filtered, and refrigerated to give 10.64 g. 7-ethyl-1-oxo-1,2,3,4-tetrahydro-α-methyl-2-naphthaleneacetic acid (II), m. 112-20° (Et₂O). II (7.31 g.) was reduced according to Martin (C.A. 30, 6726¹) and the precipitated crystals washed with ligroine to give 308 mg. 7-ethyl-1,2,3,4-tetrahydro-α-methyl-2-naphthaleneacetic acid (III), m. 195-99° (ligroine). 7-Ethyl-α-methyl-2-naphthaleneacetic acid (IV) was prepared as follows: the noncrystalline residue from the preparation of III treated with CH₂N₂ in Me₂CO, the solution evaporated to dryness with C₆H₆, the residue mixed with 10% Pd-C, heated 5 hrs. at 265-70°, cooled, dissolved in C₆H₆, filtered, evaporated to dryness in vacuo, saponified, concentrated in vacuo, diluted with H₂O, and extracted with C₆H₆ gave IV, m. 109-10°. IV (1.42 g.) heated with 1 ml. SOCl₂ for 1 hr., evaporated in vacuo, the residue taken up in benzene, anhydrous NH₃ bubbled through 1 hr., extracted with CHCl₃, and chromatographed over alumina gave crystals (precipitated from EtOAc) of 7-ethyl-α-methyl-2-naphthaleneacetamide (V), m. 105-7°. V (1.1 g.) in 100 ml. anhydrous Et₂O added to 1.8 g. LiAlH₄ was refluxed 4 hrs., cooled, and then EtOAc was added until reflux ceased. Salts which were precipitated by Et₂O and H₂O were filtered off, washed (Et₂O), dissolved in C₆H₆, extracted with HCl, basified and extracted with benzene. Anhydrous HCl was passed through the solution which was evaporated to dryness in vacuo. Recrystallization of the residue from C₆H₆ gave 780 mg. of the hydrochloride of 7-ethyl-α-methyl-2-naphthaleneëthylamine (VI), m. 208-9° (Et₂O-EtOH); picrate m. 215-18° (Me₂CO-Et₂O). VI (445 mg.) heated 2.5 hrs. (steam bath) with 100 ml. 2N HCl and 2 ml. 40% formalin, kept overnight at room temperature, evaporated to dryness in vacuo with C₆H₆, the residue dissolved in EtOH, and diluted with Et₂O gave 367 mg. of 1-methyl-6-ethyl-1,2,3,4-tetrahydro-3-azaphenanthrene (VII), m. 217-21° (from ethanol-ether). VII (262 mg.) was treated with 100 mg. 10% Pd-C at 225-35° for 45 min. The mixture was cooled, dissolved in hot ligroine, filtered, and concentrated to give 121 mg. of 1-methyl-6-ethyl-3-azaphenanthrene, m. 83.5-85.0°. Infrared and ultraviolet spectra were identical with an authentic sample; picrate m. 220-21°; trinitrobenzene adduct m. 122.5-123.5°.

Journal of the American Chemical Society published new progress about 31253-08-4. 31253-08-4 belongs to iodides-buliding-blocks, auxiliary class Iodide,Ester, name is Ethyl 2-Iodopropionate, and the molecular formula is C5H9IO2, HPLC of Formula: 31253-08-4.

Referemce:
https://en.wikipedia.org/wiki/Iodide,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Canonica, Luigi published the artcileReformatskiǐ reactions. V. Further data on the stereochemical aspects of the Reformatskiǐ reaction, COA of Formula: C5H9IO2, the publication is Gazzetta Chimica Italiana (1955), 130-6, database is CAplus.

cf. C.A. 50, 6377d. In 3 cases already studied, α,β-disubstituted hydracrylic acids, obtained by alk. saponification of esters prepared by the Reformatskiǐ condensation, were found to be mixtures of 2 racemic stereoisomers, as predicted by theory. The present work shows that the esters are sterically unitary and that the inversion of configuration takes place within the esters themselves and precedes saponification The racemic HO acids are stable to alkalies. By the action of CH₂N₂ on the 2-iso-BuCH(OH)CH(CHMe₂)CO₂H, the corresponding esters are obtained. Their sapon, verifies the configuration of an ester formed by the Reformatskiǐ condensation. The experiments show also the influence of the temperature on the relative velocities of the reactions and the relative yields of the saponification products. Condensation of Me₂CHCH₂CHO (I) with Me₂CHCHBrCO₂Me (II) was carried out as with the Et ester (III) in earlier work, but with (Me₂CH)₂O as solvent. I (20 g.) and 40 g. II gave 33 g. crude product, which, rectified, yielded Me₂CHCH₂CH(OH)CH(CHMe₂)CO₂Me(IV), b₃ 103-4°, n_D²⁵ 1.4421. III, IV, PhCH(OH)CH(CHMe₂)CO₂Et (V), and PhCH(OH)CHEtCO₂Et (VI) were saponified by 10% NaOH at different temperatures (IV in MeOH; III, V, and VI in EtOH, and 10 cc. NaOH/g. ester). The time and temperature of saponification, yields of acids, % demolition to aldehydes, and % esters recovered are tabulated. Each acid (200 mg.) was refluxed 5 hrs. with 8 cc. 10% NaOH in MeOH, the free NaOH neutralized, the solution evaporated, H₂SO₄ added, and the mixture extracted with Et₂O. After crystallization, almost 100% of the acid was recovered; no stereoisomeric acid was found. The form of Me₂CHCH₂CH(OH)CH(CHMe₂)CO₂H m. 88° (900 mg.) in 6 cc. Et₂O treated slowly with 360 mg. CH₂N₂ in 7 cc. Et₂O (kept ice-cold), evaporated in vacuo, and the ester and 10 cc. 10% NaOH in MeOH heated 5 hrs. at 65° and treated as usual give, from petr. ether, an acid fraction, m. 88°, and, from C₆H₆-petr. ether, a fraction, m. 126°. The mother liquor contains Me₂CHCH₂CO₂H.

Gazzetta Chimica Italiana published new progress about 31253-08-4. 31253-08-4 belongs to iodides-buliding-blocks, auxiliary class Iodide,Ester, name is Ethyl 2-Iodopropionate, and the molecular formula is C5H9IO2, COA of Formula: C5H9IO2.

Referemce:
https://en.wikipedia.org/wiki/Iodide,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Panchaud, Philippe published the artcileRadical Carboazidation: Expedient Assembly of the Core Structure of Various Alkaloid Families, HPLC of Formula: 31253-08-4, the publication is Journal of Organic Chemistry (2004), 69(8), 2755-2759, database is CAplus and MEDLINE.

A procedure for one-pot intermol. radical addition of 2-iodo esters to terminal alkenes followed by azidation of the radical adduct has been developed. This sequential reaction represents an alkene carboazidation process. Its efficacy is demonstrated by the two-step preparation of various lactams such as pyrrolidinones, pyrrolizidinones, and indolizidinones. An easy access to spirolactams bearing an amino-substituted quaternary carbon center is also described. These compounds are important building blocks for the synthesis of numerous alkaloids such as, for instance, FR901483.

Journal of Organic Chemistry published new progress about 31253-08-4. 31253-08-4 belongs to iodides-buliding-blocks, auxiliary class Iodide,Ester, name is Ethyl 2-Iodopropionate, and the molecular formula is C5H9IO2, HPLC of Formula: 31253-08-4.

Referemce:
https://en.wikipedia.org/wiki/Iodide,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com