Category: 2818-08-8

Application of 2818-08-8On September 14, 1990 ,《Caffeoylmalic and two pyrrole acids from Parietaria officinalis》 was published in Phytochemistry. The article was written by Budzianowski, Jaromir. The article contains the following contents:

A methanolic extract from leaves and flowers of P. officinalis afforded 3 acids, namely caffeoylmalic, 1H-pyrrole-2,3-dicarboxylic, and 1-[(caffeoyloxy)(carboxy)methoxy]-1H-pyrrole-2,3,5-tricarboxylic acids. In the experimental materials used by the author, we found Dimethyl 1H-pyrrole-2,3-dicarboxylate(cas: 2818-08-8Application of 2818-08-8)

Dimethyl 1H-pyrrole-2,3-dicarboxylate(cas: 2818-08-8) belongs to pyrroles. Pyrroles are components of more complex macrocycles, including the porphyrinogens and products derived therefrom, including porphyrins of heme, the chlorins, bacteriochlorins, and chlorophylls. Porphobilinogen, a trisubstituted pyrrole, is the biosynthetic precursor to many natural products such as heme.Application of 2818-08-8

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

The author of 《Synthesis of pyrrole-3-carboxylic acids》 were Rapoport, Henry; Willson, Clyde D.. And the article was published in Journal of Organic Chemistry in 1961. Application of 2818-08-8 The author mentioned the following in the article:

When 3-carbethoxy-4-methoxy-Δ3-pyrrolines were refluxed with alkali, elimination of the MeO group occurred and pyrrole-3-carboxylic acids were formed. 1,3-Dicarbethoxy-4-pyrrolidone (69 g.) left 3 hrs. at room temperature with excess CH2N2 in Et2O gave 60 g. 1,3-dicarbethoxy-4-methoxy-Δ3-pyrroline (I), m. 65-6°. Similar treatment of 9.7 g. 1,3-dicarbethoxy-2-methyl-4-pyrrolidone with CH2N2 gave 9.8 g. 1,3-dicarbethoxy-2-methyl-4-methoxy-Δ3-pyrrolidone (II), b1 123-5°. Likewise, 1,2,3-tricarbethoxy-4-pyrrolidone gave 1,2,3-tricarbethoxy-4-methoxy-Δ3-pyrroline (III). I (5 g.) in 60% aqueous MeOH treated at 60° with NaOH solution to pH 11 (after 9 hrs. 100 mole % of alkali had been used, and the pH remained constant after an addnl. 12 hrs.), the solution acidified, extracted with BuOH, and the residue treated with CH2N2 in Et2O 3 hrs. at room temperature gave 3.1 g. 1-carbethoxy-3-carbomethoxy-4-methoxy-Δ3-pyrroline, m. 90-3°. I (12.2 g.) and 50 g. Ba(OH)2.8H2O in 250 ml. H2O refluxed 4 hrs. gave 3 g. pyrrole-3-carboxylic acid (IV), m. 150-50.5°. IV with excess CH2N2 3 hrs. at room temperature gave 90% Me pyrrole-3-carboxylate, m. 86-7°. II (1 g.) and 5 g. Ba(OH)2.8H2O similarly treated gave 310 mg. 2-methylpyrrole-3-carboxylic acid, m. 178-9°; Me ester (95% yield) m. 67-8°. III (7 g.) and 30 g. Ba(OH)2.8H2O refluxed 4 hrs. in 100 ml. H2O and the product isolated as above gave 170 mg. pyrrole-2,3-dicarboxylic acid, m. 220° (decomposition); di-Me ester (36 mg. from 170 mg.) m. 69-71°. The ultraviolet and infrared absorption spectra were given for the above compounds After reading the article, we found that the author used Dimethyl 1H-pyrrole-2,3-dicarboxylate(cas: 2818-08-8Application of 2818-08-8)

Dimethyl 1H-pyrrole-2,3-dicarboxylate(cas: 2818-08-8) belongs to pyrroles. Pyrroles are components of more complex macrocycles, including the porphyrinogens and products derived therefrom, including porphyrins of heme, the chlorins, bacteriochlorins, and chlorophylls. Porphobilinogen, a trisubstituted pyrrole, is the biosynthetic precursor to many natural products such as heme.Application of 2818-08-8

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

The author of 《Pyrrolecarboxylic acids. XXI. Theoretical and experimental aspects of the reactivities of carboxypyrroles.》 were Del Re, Giuseppe; Scarpati, Rachele. And the article was published in Rend. Accad. Sci. Fis. Mat. in 1964. Electric Literature of C8H9NO4 The author mentioned the following in the article:

cf. CA 62, 5173e. The results of a theor. and exptl. study on the 9 pyrrolecarboxylic acids are presented. The theor. part presents complete data on charges, energies, and localization energies for nucleophilic, radicalic, and electrophilic reactions of pyrrole and its carboxy derivatives The exptl. part, designed to provide a systematic test of the reactivities of the compounds in question involves the electrophilic formylation, hydrolysis, and mild oxidation of the various pyrrolecarboxylic acid Me esters. Paper-chromatog. of the resulting acids gives accurate data concerning the position of substitution in the products and a rough estimation of the relative yields. The exptl. data are used to discuss the theor. charge distribution and localization energies. Localization energies appear to give the best predictions, although some discrepancies still exist which are discussed extensively. In the experimental materials used by the author, we found Dimethyl 1H-pyrrole-2,3-dicarboxylate(cas: 2818-08-8Electric Literature of C8H9NO4)

Dimethyl 1H-pyrrole-2,3-dicarboxylate(cas: 2818-08-8) belongs to pyrroles. Pyrroles are components of more complex macrocycles, including the porphyrinogens and products derived therefrom, including porphyrins of heme, the chlorins, bacteriochlorins, and chlorophylls. Porphobilinogen, a trisubstituted pyrrole, is the biosynthetic precursor to many natural products such as heme.Electric Literature of C8H9NO4

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

The author of 《Pyrrolecarboxylic acids. VI. 2,3- and 2,4-pyrroledicarboxylic acids》 were Nicolaus, Rodolfo A.; Mangoni, Lorenzo. And the article was published in Gazzetta Chimica Italiana in 1956. SDS of cas: 2818-08-8 The author mentioned the following in the article:

cf. C.A. 52, 351b. 2,4-Pyrroledicarboxylic acid (I) is synthesized by the action of SO2Cl2 on 5-methyl-3-bromo-2,4-dicarbethoxypyrrole (II) to give 5-formyl-3-chloro-2,4-dicarbethoxypyrrole (III), converted by KMnO4 to the 5-carboxy-3-chloro compound (IV), brominated to the 5-bromo intermediate (V). Catalytic reduction of V gave 2,4-dicarbethoxypyrrole (VI), saponified to I. 2,3-Pyrroledicarboxylic acid (VII) is prepared by saponification of 2-carboxy-3-carbethoxypyrrole (VIII) (cf. Rinkes, C.A. 32, 33891, 66481). VII crystallizes from H2O as VII.H2O; m. (anhydrous) 225° (decomposition). 2,5-Pyrroledicarboxylic acid (IX) is prepared by the action of SO2Cl2 on 2,5-dimethylpyrrole to give the 3,4-dichloro compound (X) which, on catalytic reduction, gives IX (cf. Colacicchi, C.A. 5, 1280). The following compounds were prepared (m.p. given): I, 290° (decomposition); III, 151-2°; III phenylhydrazone, 152-3°; III 2,4-dinitrophenylhydrazone, 200-1°; IV, 180-1°; V, 143-4°; VI, 74-5°, VIII, 76-8°; IX, 265° (decomposition); X, 300°; I Me ester, 126-7°; VII Me ester, 72-3°; IX di-Me ester, 129-30°; X Me ester, 147-9°. After reading the article, we found that the author used Dimethyl 1H-pyrrole-2,3-dicarboxylate(cas: 2818-08-8SDS of cas: 2818-08-8)

Dimethyl 1H-pyrrole-2,3-dicarboxylate(cas: 2818-08-8) belongs to pyrroles. Pyrroles are components of more complex macrocycles, including the porphyrinogens and products derived therefrom, including porphyrins of heme, the chlorins, bacteriochlorins, and chlorophylls. Porphobilinogen, a trisubstituted pyrrole, is the biosynthetic precursor to many natural products such as heme.SDS of cas: 2818-08-8

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

《Lithiations of 1-trialkylsilylpyrroles: nitrogen-to-carbon silyl-group rearrangement》 was written by Chadwick, Derek J.; Hodgson, Simon T.. Name: Dimethyl 1H-pyrrole-2,3-dicarboxylate And the article was included in Journal of the Chemical Society on August 31 ,1982. The article conveys some information:

The regiochem. of lithiation of 1-(trimethylsilyl)- (I) and 1-(triethylsilyl)pyrrole (II) with BuLi and Me3CLi was studied under a variety of conditions. With short reaction times, BuLi reacts with I in hexane predominantly at the 2-position, whereas with Me3CLi in pentane the unusual 3-metalated product is preferred. During prolonged reaction of I and II with Me3CLi the 2-monolithio and 2,4- and 2,5-dilithio intermediates were formed, in which the silyl groups migrated to C-2. Under conditions favoring enhanced ionicity, BuLi cleaved the N-SiMe3 bond in preference to ring metalation. In the part of experimental materials, we found many familiar compounds, such as Dimethyl 1H-pyrrole-2,3-dicarboxylate(cas: 2818-08-8Name: Dimethyl 1H-pyrrole-2,3-dicarboxylate)

Dimethyl 1H-pyrrole-2,3-dicarboxylate(cas: 2818-08-8) belongs to pyrroles. Pyrroles are components of more complex macrocycles, including the porphyrinogens and products derived therefrom, including porphyrins of heme, the chlorins, bacteriochlorins, and chlorophylls. Porphobilinogen, a trisubstituted pyrrole, is the biosynthetic precursor to many natural products such as heme.Name: Dimethyl 1H-pyrrole-2,3-dicarboxylate

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

In 1957,Journal of the American Chemical Society included an article by Henry, David W.; Leete, Edward. Formula: C8H9NO4. The article was titled 《Amine oxides. I. Gramine oxide》. The information in the text is summarized as follows:

Gramine (I) (17.4 g.) in 40 cc. EtOH treated with 28.2 cc. 30% aqueous H2O2 and cooled gave 18.5 g. N-oxide (II) of I containing 1 mole H2O2 of crystallization, m. 135-6° (decomposition) (rapid heating), 121-2° (decomposition) (slow heating); recrystallization of II.H2O2 from EtOH did not remove the H2O2. If the excess H2O2 in a similar oxidation run was decomposed with a small amount of 10% Pt-C no crystallization occurred, but the addition of H2O2 to the solution precipitated II.H2O2. Samples of II.H2O2 were pale brown after several months and contained a slightly lower percentage of H2O2. I.MeI (1.0 g.) added to 80 mg. Na in 3.3 g. Me2NOH at room temperature and evaporated after 19 hrs. in vacuo, and the semisolid residue extracted with 20 cc. H2O left 0.24 g. I; the aqueous filtrate was shown to contain II by paper chromatography. Rf values for II, I, and I.MeI: 0.78, 0.72, 0.56 (15% aqueous NH4OH); 0.79, 0.76, 0.61 (6:5 Me2CO-7.5% NH4OH); 0.89, 1.0, 1.0 (1.3:1 PrOH-H2O). All reactions with II in this investigation were performed with the product obtained by the decomposition of II.H2O with 10% Pt-C; all weights of II refer to the II.H2O2. II (0.1 g.) in 20 cc. H2O treated with 5 g. Zn dust and 10 cc. glacial AcOH, stirred 0.5 hr., and filtered, the filtrate added to aqueous KOH, and the precipitate isolated with Et2O yielded 0.72 g. I, m. 133°. II (1.0 g.) in 20 cc. MeOH evaporated at 10° in vacuo, the pale brown residual sirup heated 10 min. at 125°, the tarry residue extracted with Et2O, the extract concentrated to 10 cc., diluted with 20 cc. pentane, and chromatographed on Al2O3 yielded 0.15 g. O-skatyl-N,N-dimethylhydroxylamine (III), m. 93-4° (pentane). II refluxed with a variety of solvents 1 hr. and evaporated in vacuo, and the residue chromatographed on Al2O3 gave III (solvent and % yield given): PhMe 16, HCONMe2 25, dioxane 37, MeCN containing a trace pyridine 61. III (42 mg.) added to 42 mg. LiAlH4 in 20 cc. Et2O, refluxed 1 hr., treated with wet Et2O, filtered, and evaporated, and the residue dissolved in MeOH and treated with 1,3,5-C6H3(NO2)3 (IV) gave the IV-skatole adduct, orange needles, m. 184-5°. II (2.0 g.) refluxed 3 hrs. with 40 cc. piperidine and evaporated in vacuo gave 1.59 g. 3-piperidinomethylindole (V), m. 158-9° (EtOH). Aqueous II and piperidine warmed at 100° gave V. Aqueous I.MeI treated with piperidine at room temperature gave immediately a precipitate of the piperidino derivative II refluxed with Et2NH yielded 3-diethylaminomethylindole, m. 102.5-104°. II refluxed in Me2NH gave I. II and morpholine gave at 100° 3-morpholinomethylindole, m. 119-21°. PhNHMe and II gave at 100° 3-(N-methyl-N-phenylaminomethyl)indole, m. 85-6.5°, in 58% yield. II (1.6 g.) in 20 cc. MeOH added to 0.17 g. Na in 20 cc. MeOH, refluxed 1 min., cooled to room temperature, treated with 0.65 g. NaHCO3 and 0.2 cc. H2O, and evaporated in vacuo, the vapors condensed in a Dry Ice trap, and the condensate treated with picric acid gave the picrate of Me2NOH, yellow needles, m. 160-1° (EtOH); the residue extracted with Et2O, and the extract dried, and evaporated gave 0.72 g. 3-methoxymethylindole (VI), m. 97-8° (pentane). II and NaOEt yielded 59% 3-ethoxymethylindole (VII),. m. 62-3°. II (1.0 g.) refluxed 2 hrs. with 25 cc. iso-BuOH and evaporated and the residue chromatographed on Al2O3 with 1:3 Et2O-pentane to pure Et2O yielded 3-(isobutoxymethyl)indole, b0.0005 120°, n25D 1.5574, which was also obtained in 44% yield from I with EtI and iso-BuONa; later elution of the column and sublimation of the resulting semisolid at 80°/0.0002 mm. gave III, m. 92-3°. III, VII, and Et2O-insoluble, apparently polymeric material, was obtained by refluxing II and EtOH. II (1.0 g.) in 50 cc. H2O added dropwise with stirring to refluxing 50 cc. 10% aqueous NaOH and 50 cc. Et2O, and the Et2O layer worked up after 4 hrs. refluxing gave 0.11 g. 3-hydroxymethylindole, m. 99-100° (pentane). II (1.0 g.) in 20 cc. H2O heated 20 hrs. at 100° and extracted with Et2O and the extract chromatographed on Al2O3 yielded 0.10 g. 3,3′-diindolylmethane, m. 163-4°, and much Et2O-insoluble polymeric material. The aqueous solution of a duplicate run treated at the end of the reaction with dimedon gave the CH2O derivative, m. 190-1°. II (1.0 g.) in 25 cc. H2O stirred 1.5 hrs. at 100° with 25 cc. PhMe, 10 g. NaCN, and 25 cc. saturated aqueous NaCN and the PhMe layer dried with K2CO3 and worked up gave a liquid residue which with IV in MeOH gave 1.36 g. IV adduct of 3-cyanomethylindole (VIII), orange needles, m. 135.5-37°. II treated with NaCN in MeOH gave a mixture of VIII and VI. II (1.0 g.) in 15 cc. MeNO2 treated with 0.10 g. Na in 2 cc. EtOH, refluxed 1 hr. with stirring, treated with 0.2 H2O, and evaporated in vacuo, and the residue extracted with Et2O, diluted with pentane, and chromatographed on Al2O3 yielded 0.27 g. 3-(2-nitroethyl)indole, m. 53.5-54°. II (1.0 g.) in 15 cc. H2O heated 2 hrs. at 100° with 1 cc. 4N HCl gave a white amorphous polymer which was also obtained from 3-hydroxymethylindole and acids; the aqueous filtrate evaporated, and the residual sirup treated with picric acid gave the picrate of IV, m. 160-1°. II treated with alc. picric acid gave only resinous material. In addition to this study using Dimethyl 1H-pyrrole-2,3-dicarboxylate, there are many other studies that have used Dimethyl 1H-pyrrole-2,3-dicarboxylate(cas: 2818-08-8Formula: C8H9NO4) was used in this study.

Dimethyl 1H-pyrrole-2,3-dicarboxylate(cas: 2818-08-8) belongs to pyrroles. Pyrroles are components of more complex macrocycles, including the porphyrinogens and products derived therefrom, including porphyrins of heme, the chlorins, bacteriochlorins, and chlorophylls. Porphobilinogen, a trisubstituted pyrrole, is the biosynthetic precursor to many natural products such as heme.Formula: C8H9NO4

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

《A study on the ultraviolet spectroscopy of pyrrolecarboxylic acid esters》 was written by Rhee, Kyu Hyun; Han, In Sook. Category: esters-buliding-blocks And the article was included in Nonchong – Han’guk Saenghwal Kwahak Yonguwon in 1979. The article conveys some information:

The UV spectra of 32 pyrrolecarboxylic acid esters and 13 pyrrolecarboxylic acids were examined and their absorption wavelengths and absorption coefficients were classified according to π-π* or ET transition. The absorption maximum of N-arylpyrrole derivatives with electron-withdrawing substituents were linearly related according to the Hammett equation. The experimental part of the paper was very detailed, including the reaction process of Dimethyl 1H-pyrrole-2,3-dicarboxylate(cas: 2818-08-8Category: esters-buliding-blocks)

Dimethyl 1H-pyrrole-2,3-dicarboxylate(cas: 2818-08-8) belongs to pyrroles. Pyrroles are components of more complex macrocycles, including the porphyrinogens and products derived therefrom, including porphyrins of heme, the chlorins, bacteriochlorins, and chlorophylls. Porphobilinogen, a trisubstituted pyrrole, is the biosynthetic precursor to many natural products such as heme.Category: esters-buliding-blocks

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

In 1964,Ricerca Scientifica, Parte 2: Rendiconti, Sezione A: Abiologica included an article by Chierici, Luigi; Scapini, Giancarlo. Safety of Dimethyl 1H-pyrrole-2,3-dicarboxylate. The article was titled 《Chromatographic study of pyrrole acids. Gas chromatography of the C-pyrrolecarboxylic acids》. The information in the text is summarized as follows:

Mixtures of C-pyrrolecarboxylic acids are separated as Me esters on a 100-cm. column packed with 3% ethylene-glycol-succinate on Chromosorb W. The instrument is operated with a 300° injection port temperature, a flame ionization detector, a 15 ml./min. N flow, and the column is temperature-programmed from 150 to 210° at 25°/min. The temperature program starts after separation of the 2-pyrrolecarboxylic acid.Dimethyl 1H-pyrrole-2,3-dicarboxylate(cas: 2818-08-8Safety of Dimethyl 1H-pyrrole-2,3-dicarboxylate) was used in this study.

Dimethyl 1H-pyrrole-2,3-dicarboxylate(cas: 2818-08-8) belongs to pyrroles. Pyrroles are components of more complex macrocycles, including the porphyrinogens and products derived therefrom, including porphyrins of heme, the chlorins, bacteriochlorins, and chlorophylls. Porphobilinogen, a trisubstituted pyrrole, is the biosynthetic precursor to many natural products such as heme.Safety of Dimethyl 1H-pyrrole-2,3-dicarboxylate

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

The author of 《Infrared and ultraviolet spectra of pyrrolecarboxylic acid esters》 were Scrocco, Marisa; Nicolaus, Rodolfo. And the article was published in Atti accad. nazl. Lincei. Rend., Classe sci. fiz., mat. e nat. in 1957. Application of 2818-08-8 The author mentioned the following in the article:

Infrared and ultraviolet spectra of Me 2-pyrrolecarboxylate (I), Me 1-pyrrolecarboxylate (II), di-Et 2,3-pyrroledicarboxylate (III), di-Me 1,4-pyrroledicarboxylate (IV), di-Me 1,2-pyrroledicarboxylate (V), di-Me 1,3-pyrroledicarboxylate (VI), tri-Et 1,2,3-pyrroletricarboxylate (VII), and tri-Me 1,2,4-pyrroletricarboxylate (VIII) were examined to determine conjugation effects and relation to pKa for the NH group. Δν in the infrared for bound and free NH bands in cm.-1 was I 170, II 146, IV 170, V 140, VI 162, VII 170. Ultraviolet maximum were I 247, II 267, III 250, IV 277, V 246, 282, VI 267, VII 267, VIII 275 mμ. It was shown that substitution in α-position has greater conjugation effects than in β, that the spectra are affected by intramol. chelation with α-substituents, and that the spectra and the effects on the NH band can be explained on the basis of resonance contributions and relative inductive effects. In addition to this study using Dimethyl 1H-pyrrole-2,3-dicarboxylate, there are many other studies that have used Dimethyl 1H-pyrrole-2,3-dicarboxylate(cas: 2818-08-8Application of 2818-08-8) was used in this study.

Dimethyl 1H-pyrrole-2,3-dicarboxylate(cas: 2818-08-8) belongs to pyrroles. Pyrroles are components of more complex macrocycles, including the porphyrinogens and products derived therefrom, including porphyrins of heme, the chlorins, bacteriochlorins, and chlorophylls. Porphobilinogen, a trisubstituted pyrrole, is the biosynthetic precursor to many natural products such as heme.Application of 2818-08-8

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics