Heterocyclic Building Blocks-Benzisoxazole

Category: benzisoxazole. Aromatic compounds can be divided into two categories: single heterocycles and fused heterocycles. Compound: cis-Cyclohexane-1,2-dicarboxylic acid, is researched, Molecular C8H12O4, CAS is 610-09-3, about Stimulation of pollen tube growth in vitro by dicarboxylic acids. Author is Iwanami, Y..

At 50 ppm, capric acid [334-48-5] and 2-decenoic acid [3913-85-7] almost totally inhibited the germination of Camellia japonica pollen. Moderate inhibition was shown by traumatic acid [6402-36-4], caprylic acid [124-07-2], and IAA [87-51-4]. The above compounds also inhibited pollen tube elongation. At 10 ppm, oxalic acid [144-62-7], succinic acid [110-15-6], suberic acid [505-48-6], adipic acid [124-04-9], sebacic acid [111-20-6], cis-1,2-cyclohexanedicarboxylic acid [610-09-3], and 3,3-diethylglutaric acid [4160-95-6] stimulated pollen tube elongation.

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Benzisoxazole – Wikipedia,
Benzisoxazole – an overview | ScienceDirect Topics

Safety of cis-Cyclohexane-1,2-dicarboxylic acid. The reaction of aromatic heterocyclic molecules with protons is called protonation. Aromatic heterocycles are more basic than benzene due to the participation of heteroatoms. Compound: cis-Cyclohexane-1,2-dicarboxylic acid, is researched, Molecular C8H12O4, CAS is 610-09-3, about Probing Single-Chain Magnets in a Family of Linear Chain Compounds Constructed by Magnetically Anisotropic Metal-Ions and Cyclohexane-1,2-Dicarboxylate Analogues. Author is Zheng, Yan-Zhen; Xue, Wei; Tong, Ming-Liang; Chen, Xiao-Ming; Zheng, Shao-Liang.

Five new metal-carboxylate chain-based laminated compounds, namely, ∞2[FeII(e,e-trans-1,2-chdc)] (3) (1,2-chdc = cyclohexane-1,2-dicarboxylate), ∞2[NiII(μ-OH2)(e,a-cis-1,2-chdc)] (4), ∞2[CoII(μ-OH2)(1,2-chedc)] (5) (1,2-chedc = cyclohex-1-ene-1,2-dicarboxylate), ∞2[CoII5(μ3-OH)2(OH2)2(1,2-chedc)4] (6), and ∞2[CoII(4-Me-1,2-chdc)] (7) (4-Me-1,2-chdc = trans-4-methylcyclohexane-1,2-dicarboxylate) were hydrothermally synthesized. In these series of magnetic chain-based compounds, 3 and 7 have the same dimeric paddle-wheel M(II)-carboxylate chain as the previously reported compound, ∞2[CoII(trans-1,2-chdc)] (2). However, compound 3 does not behave as a single-chain magnet (SCM) but simply an alternating ferro-antiferro magnetic chain. Compound 4 has the cis conformation of 1,2-chdc ligand, which leads to a uniform aqua-carboxylate-bridged Ni(II) chain. Such a Ni-O chain exhibits strong antiferromagnetic interactions, leading to a diamagnetic ground state. Compound 5 features a corner-sharing triangular chain, or Δ-chain, which is part of a Kagome lattice. However, 5 does not exhibit a spin-frustrated effect but simply spin competition. Compound 6 has a unique pentanuclear CoII cluster, which is further connected by the syn-anti carboxylate into a chain structure. Compound 6 exhibits antiferromagnetic interactions among the Co(II) ions, and no SCM behavior is observed These results might indicate that the dimeric paddle-wheel Co(II)-carboxylate chain is essential in obtaining SCM behavior in this family of compounds Although 2 and 7 have very similar SCM behavior, a.c. magnetic studies show that 7 has a higher energy barrier than that of 2. Such behavior is probably caused by the larger anisotropic energy barrier in 7.

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The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Hydrogenation of aromatic compounds with the aid of platinum. III. Hydrogenation with platinum containing oxygen》. Authors are Willstatter, Richard; Jaquet, Daniel.The article about the compound:cis-Cyclohexane-1,2-dicarboxylic acidcas:610-09-3,SMILESS:O=C([C@H]1[C@@H](C(O)=O)CCCC1)O).SDS of cas: 610-09-3. Through the article, more information about this compound (cas:610-09-3) is conveyed.

cf. C. A. 7, 1508. Certain reductions, like that of phthalic anhydride (a), which cannot be effected catalytically with Pt free from O, can be initiated by loading the Pt with O and brought to completion by again treating the Pt with O as the catalyst gradually loses its O by the formation of H2O. Oxygen-free Pt and that containing O behave like 2 different contact substances in reduction processes. Thus, 20.3 g. (a) in 75 cc. glacial AcOH with 5 g. Pt absorbed only 400 cc. H; if, however, the H gasometer was shut off and the reaction bulb evacuated, then allowed to fill with air, shaken 1 min. (whereupon O was rapidly absorbed -about 5 cc. per g. Pt) and the air was driven out with H, about 500 cc. of H was again absorbed after each such activation until the 20th and 21st times, when the absorption of H was 1230 and 5600 cc., rasp. The total absorption was 17040 cc. (20°, 760 mm.) or, deducting about 1150 cc. used up by the O introduced in the activations, 15890 cc. or 4.8 mols. Of the 2 rings in (a) the 5-membered one is reduced before the C6H6 ring; the first product is phthalide (b) which is partially reduced to hexahydrophthalide (c) and partially to o-MeC6H4CO2H (d) which is then reduced to the hexahydrotoluic acid (e). If the process is interrupted when only a little H has been absorbed there is obtained, besides some C6H6(CO2H)2, a mixture of (b) and (c), and while (b) is easily reduced further to (d), (c) cannot be reduced to (e). If in the process of isolation alkali is employed the (c) is in part obtained as methylolhexahydrobenzoic acid. Among the reduction products is also cis-hexahydrophthalic acid (f). In the reduction described above were obtained 7 g. (c) (partially hydrolyzed), 7 g. (e) and 4 g. (f). In a similar reduction of (b) 3.4 mols. H were absorbed and there were obtained about equal parts of (e) and (c). Phthalimide behaves quite differently from (a) on reduction, the aromatic nucleus and not the CO groups taking up the O. The activation of the Pt with O is not necessary but the reduction is successful only with the best Pt sponge preparations; many which were active towards C6H6 were inactive towards the imide. Nor can MeOH, EtOH or cyclohexane be used as a solvent; in glacial AcOH the reduction proceeds smoothly. cis-Hexahydrophthalimide seps. from H2O, alc. and AcOH in monoclinic prisms, m. 132°. Naphthalic acid purified by crystallization from alc. cannot be reduced because it always contains some anhydride (g) but the acid freshly precipitated from alk. solution can be reduced; contrary to C10H8, it takes up only 4 atoms of H; the tetrahydronaphthalic acid (h) seps. in cube-like prisms, m. 196° with loss of H2O and conversion into the anhydride, m. 119°. (g), like (a), can be reduced only with Pt activated with O; after about 4 mols. H2 have been absorbed the reaction slows up. As far as the (g) itself is reduced, the anhydride ring is attacked, but as some of the (g) is hydrolyzed by the H2O formed, some (h) is obtained. Among the reduction products are tetrahydro-1-methylnaphthalene-8-carboxylic acid (i), tetra- and decahydronaphthalides and a small amount of decahydroacenaphthene. The 2 naphthalides could not be isolated pure. The (i) seps. from Et2O-petr. ether in needles, m. 150°. o-C6H4(CO2H)2 is easily reduced in AcOH when entirely free from the anhydride, yielding exclusively the cis-hexahydro acid, m. 191-2°. The p-acid in AcOH suspension is reduced much more rapidly on gentle warming, giving about equal parts of the cis- and cis-trans-hexahydro acids, m. 162-3° and about 300°, resp. The m-acid, if pure, is likewise easily reduced in AcOH suspension, forming chiefly the cis- and some cis-trans-hexahydro acid. p-Toluylic acid very quickly gives exclusively or almost exclusively the liquid hexahydro acid whose amide m. 175-6°. Indole in AcOH smoothly absorbs 8 atoms H with formation of perhydroindole, b720 182-3°, b12 65°, a basic oil of medium consistency and unpleasant, penetrating, onion-like odor, d420 0.9947; chloroplatinate, reddish yellow monoclinic tablets from alc., m. 172-3° (not sharply); picrate, fine needles from alc., m. 137-8° (not sharply). If the reduction is interrupted before it is complete (e. g., when 2 atoms of H have been absorbed), the product contains unchanged indole, dihydroindole and perhydroindole, the last being removed by shaking the Et2O solution with 0.1 N HCl until the alk. reaction just disappears, and the first two being separated by fractional precipitation from Et2O with picric acid.

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Benzisoxazole – Wikipedia,
Benzisoxazole – an overview | ScienceDirect Topics

So far, in addition to halogen atoms, other non-metallic atoms can become part of the aromatic heterocycle, and the target ring system is still aromatic.Chethan Prathap, K. N.; Shalini, P.; Lokanath, N. K. researched the compound: 2-Furoic hydrazide( cas:3326-71-4 ).Recommanded Product: 2-Furoic hydrazide.They published the article 《Synthesis, characterization, crystal structure, Hirshfeld surface analysis and DFT calculations of two novel pyrrole derivatives》 about this compound( cas:3326-71-4 ) in Journal of Molecular Structure. Keywords: pyrrolylethylidene benzenesulfonohydrazide diastereoselective preparation crystal structure Hirshfeld surface analysis; furancarbohydrazide ethylidenepyrrole diastereoselective preparation crystal structure Hirshfeld surface analysis. We’ll tell you more about this compound (cas:3326-71-4).

The novel pyrroles (E)-N’-(1-(1H-pyrrol-2-yl)ethylidene)benzenesulfonohydrazide and (E)-N’-(1-(1H-pyrrol-2-yl)ethylidene)furan-2-carbohydrazide were synthesized. The synthesized comps. were characterized by (1H and 13C) NMR, FT-IR, UV-visible, TG-DTA and XRD studies.

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In organic chemistry, atoms other than carbon and hydrogen are generally referred to as heteroatoms. The most common heteroatoms are nitrogen, oxygen and sulfur. Now I present to you an article called DMF as Methine Source: Copper-Catalyzed Direct Annulation of Hydrazides to 1,3,4-Oxadiazoles, published in 2019, which mentions a compound: 3326-71-4, mainly applied to DMF aryl hydrazide copper catalyst oxidative heterocyclization green chem; aryl oxadiazole preparation oxygen copper catalyst oxidation green chem; oxadiazolone aryl preparation, Product Details of 3326-71-4.

An unprecedented Cu-catalyzed direct annulation of hydrazides with N,N-dimethylformamide (DMF) was developed, providing an efficient synthesis of valuable 1,3,4-oxadiazoles. This process featured short reaction time and safely conducted on gram scale. The reaction also facilitated the convenient synthesis of 1,3,4-oxadiazole-2(3H)-ones. Moreover, the mechanistic studies suggested that the source of CH was from the N-Me group of DMF.

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So far, in addition to halogen atoms, other non-metallic atoms can become part of the aromatic heterocycle, and the target ring system is still aromatic.Nakagawa, Atsushi; Kato, Ko; Shinmyo, Atsuhiko; Suzuki, Toshio researched the compound: Methyl tetrahydrofuran-2-carboxylate( cas:37443-42-8 ).COA of Formula: C6H10O3.They published the article 《Asymmetric hydrolysis of 2-hydroxy-carboxylic esters using recombinant Escherichia coli》 about this compound( cas:37443-42-8 ) in Tetrahedron: Asymmetry. Keywords: whole cell kinetic resolution ester stereoselective. We’ll tell you more about this compound (cas:37443-42-8).

Optically active 2-hydroxy-carboxylates are important compounds for their use as intermediates in the synthesis of pharmaceuticals and stereoblock polymers. Enterobacter sp. DS-S-75 and the recombinant Escherichia coli harboring the 4-chloro-3-hydroxybutyrate (CHB) hydrolase gene from the strain DS-S-75 showed asym. hydrolytic activity towards 2-hydroxy-carboxylates, as well as towards CHB. It was discussed that the hydroxyl group in the substrate was particularly important for the asym. hydrolytic activity of the CHB hydrolase, and as such, it was re-designated to EnHCH (hydroxy-carboxylic ester hydrolase derived from Enterobacter sp.). Using the recombinant cell, both the reaction rate and the concentration of the substrates were significantly improved upon when compared to that of DS-S-75. Optically active 2-hydroxy-carboxylates could be synthesized on a practical basis for industrial production in this report.

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Most of the natural products isolated at present are heterocyclic compounds, so heterocyclic compounds occupy an important position in the research of organic chemistry. A compound: 37443-42-8, is researched, SMILESS is O=C(C1OCCC1)OC, Molecular C6H10O3Journal, Article, Research Support, U.S. Gov’t, Non-P.H.S., Journal of Physical Chemistry A called Low Temperature Chlorine-Initiated Oxidation of Small-Chain Methyl Esters: Quantification of Chain-Terminating HO2-Elimination Channels, Author is Muller, Giel; Scheer, Adam; Osborn, David L.; Taatjes, Craig A.; Meloni, Giovanni, the main research direction is small chain methyl ester low temperature chlorine initiated oxidation.Name: Methyl tetrahydrofuran-2-carboxylate.

Cl-initiated oxidation reactions of three small-chain Me esters, Me propanoate (CH3CH2COOCH3; MP), Me butanoate (CH3CH2CH2COOCH3; MB), and Me valerate (CH3CH2CH2CH2COOCH3; MV), are studied at 1 or 8 Torr and 550 and 650 K. Products are monitored as a function of mass, time, and photoionization energy using multiplexed photoionization mass spectrometry coupled to tunable synchrotron photoionization radiation. Pulsed photolysis of mol. chlorine is the source of Cl radicals, which remove an H atom from the ester, forming a free radical. In each case, after addition of O2 to the initial radicals, chain-terminating HO2-elimination reactions are observed to be important. Branching ratios among competing HO2-elimination channels are determined via absolute photoionization spectra of the unsaturated Me ester coproducts. At 550 K, HO2-elimination is observed to be selective, resulting in nearly exclusive production of the conjugated Me ester coproducts, Me propenoate, methyl-2-butenoate, and methyl-2-pentenoate, resp. However, in MV, upon raising the temperature to 650 K, other HO2-elimination pathways are observed that yield Me 3-pentenoate and Me 4-pentenoate. In each Me ester oxidation reaction, a peak is observed at a mass consistent with cyclic ether formation, indicating chain-propagating OH loss/ring formation pathways via QOOH intermediates. Evidence is observed for the participation of resonance-stabilized QOOH in the most prominent cyclic ether pathways. Stationary point energies for HO2-elimination pathways and select cyclic ether formation channels are calculated at the CBS-QB3 level of theory and assist in the assignment of reaction pathways and final products.

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Benzisoxazole – Wikipedia,
Benzisoxazole – an overview | ScienceDirect Topics

Qian, Hengyu; Yu, Shuyan; Song, Liping; Zhang, Tongyan; Yin, Zhigang; Zhao, Feng; Yang, Jiale; Wang, Caihong published an article about the compound: 2-Furoic hydrazide( cas:3326-71-4,SMILESS:O=C(C1=CC=CO1)NN ).Name: 2-Furoic hydrazide. Aromatic heterocyclic compounds can be classified according to the number of heteroatoms or the size of the ring. The authors also want to convey more information about this compound (cas:3326-71-4) through the article.

Four new palladium pincer complexes I (R = H, 3-OMe, 3-OEt, 5-Cl) incorporating ONO type furoylhydrazone ligands have been prepared in good yields. These palladium complexes were structurally characterized by elemental anal., IR, 1H- and 13C-NMR spectra. X-ray single crystal analyses of Pd1-Pd4 revealed that the metal center adopted a slightly distorted square planar geometry in which the hydrazone bound the metal ion via the phenolic-O, azomethine-N and imidolate-O atoms. Using these ONO pincer complexes as catalyst, excellent yields of biaryls could be obtained for coupling of arylboronic acids with aryl bromides at a low catalyst loading (0.01 mol%).

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Reference:
Benzisoxazole – Wikipedia,
Benzisoxazole – an overview | ScienceDirect Topics

The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Stereochemistry of catalytic hydrogenation. V. The assignment of cis and trans configurations》. Authors are Linstead, R. P.; Davis, Selby B.; Whetstone, Richard R..The article about the compound:cis-Cyclohexane-1,2-dicarboxylic acidcas:610-09-3,SMILESS:O=C([C@H]1[C@@H](C(O)=O)CCCC1)O).Synthetic Route of C8H12O4. Through the article, more information about this compound (cas:610-09-3) is conveyed.

cis-Hexahydrodiphenic acid (m. 240-1°) (I) with concentrated and fuming HNO3 gives only NO2 products and KMnO4 yields no useful products. I. (1g.) in 20 cc. warm AcOH, treated with O3 for 4 hrs. and then overnight with 50 cc. 3% H2O2 and the material separated by fractional acidification, gives about 0.5 g. unchanged I and 128 mg. (crude) cis-hexahydrophthalic acid (identified as the cis-dianilide, m. 238° and the phenylimide). This establishes the structure of I, of the acid m. 289° as cis-syn-cis-perhydrodiphenic acid and of the acid m. 223° as the trans-syn-trans isomer. trans-Δ10-9-Ketododecahydrophenanthrene (Rapson and Robinson, C. A. 29, 7996.1) with O3 in AcOH gives 2.45 g. of trans-2-keto-1, 1′-bicyclohexyl-2′-carboxylic acid (II), a pale yellow oil, isolated as the oxime (3.07g.), m. 162-3°. On acetylation and subsequent pyrolysis II is converted into an unsaturated lactone (not obtained pure) which is oxidized by KMnO4 to a poor yield of trans-hexahydrophthalic acid, m. 227-9° (after repeated crystallization from H2O; 215-20° given in the literature). This series of reactions is not as unequivocal as the oxidation of I. cis-9-Keto-as-octahydrophenanthrene (III) (cf. part VI) (0.4 g.), heated on the steam bath for 15 min. with 5 cc. concentrated HNO3 and 3 cc. fuming HNO3, gives 20 mg. cis-nitrohexahydrodiphenic acid (IV), m. 217-19°, and 0.1 g. of a tri-NO2 derivative of III, m. 151-2°. Heating 500 mg. of III with 1 cc. concentrated HNO3 and 1 cc. fuming HNO3 gives a di-NO2 derivative of III, m. 152°; this gives the tri-NO2 derivative with HNO3 on the steam bath. trans-III (350 mg.) with HNO3 gives about equal amounts (100 mg.) of trans-IV and the tri-NO2 derivative, needles from AcOH, m. 182-4°, or plates from hexane, m. 182.5-3.5°. The stereochem. implications of these results are discussed and it is shown that they are in agreement with other, less exact, evidence.

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Reference:
Benzisoxazole – Wikipedia,
Benzisoxazole – an overview | ScienceDirect Topics

Safety of Methyl tetrahydrofuran-2-carboxylate. The mechanism of aromatic electrophilic substitution of aromatic heterocycles is consistent with that of benzene. Compound: Methyl tetrahydrofuran-2-carboxylate, is researched, Molecular C6H10O3, CAS is 37443-42-8, about A Powerful Chiral Phosphoric Acid Catalyst for Enantioselective Mukaiyama-Mannich Reactions. Author is Zhou, Fengtao; Yamamoto, Hisashi.

A new BINOL-derived chiral phosphoric acid bearing 2,4,6-trimethyl-3,5-dinitrophenyl substituents at the 3,3′-positions was developed. The utility of this chiral phosphoric acid is demonstrated by a highly enantioselective (ee up to >99 %) and diastereoselective (syn/anti up to >99:1) asym. Mukaiyama-Mannich reaction of imines with a wide range of ketene silyl acetals. Moreover, this method was successfully applied to the construction of vicinal tertiary and quaternary stereogenic centers with excellent diastereo- and enantioselectivity. Significantly, BINOL-derived N-triflyl phosphoramide constitutes a complementary catalyst system that allows the title reaction to be applied to more challenging imines without an N-(2-hydroxyphenyl) moiety.

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Reference:
Benzisoxazole – Wikipedia,
Benzisoxazole – an overview | ScienceDirect Topics