Category: 17190-29-3

Heterocyclic compounds can be divided into two categories: alicyclic heterocycles and aromatic heterocycles. Compounds whose heterocycles in the molecular skeleton cannot reflect aromaticity are called alicyclic heterocyclic compounds. Compound: 17190-29-3, is researched, Molecular C9H9NO, about Methods for the stereoselective cis-cyanohydroxylation and -carboxyhydroxylation of olefins, the main research direction is stereoselectivity cyanohydroxylation carboxyhydroxylation olefin; hydroxylation cyano carboxy olefin; isoxazoline derivative preparation cleavage.Category: pyrazoles-derivatives.

EtO2CCNO (I) and THPOCH2CNO (THP = tetrahydropyranyl) (II) are valuable reagents for cis-stereospecific vicinal cyanohydroxylation and carboxyhydroxylation of olefins. The cyanohydroxylation process is based on the decarboxylative ring cleavage of 3-carboxyisoxazolines, prepared by the [3 + 2]-cycloaddition reaction of I with various alkenes. Fragmentation of the isoxazolines prepared from cis- and trans-2-butene occurs without crossover in stereochem. The carboxyhydroxylation process begins with the dipolar cycloaddition reaction of II with olefins. Deprotection, hydrogenation, and oxidative cleavage of the derived dihydroxy ketone yield the stereochemically pure β-hydroxycarboxylic acid.

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Reference:
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

In general, if the atoms that make up the ring contain heteroatoms, such rings become heterocycles, and organic compounds containing heterocycles are called heterocyclic compounds. An article called Aryl halides as precursors of electrogenerated bases. Utilization in coupling reactions of acetonitrile with various electrophilic compounds, published in 1993-06-04, which mentions a compound: 17190-29-3, Name is 3-Hydroxy-3-phenylpropanenitrile, Molecular C9H9NO, Category: pyrazoles-derivatives.

An electrochem. alternative to classical cyanomethylation is possible by using electrogenerated bases (EGBs), obtained by electroreduction of aryl halides in an undivided cell fitted with a Cd-coated cathode and a sacrificial Mg anode. MeCN is used both as solvent and as H-active compound A coupling reaction with various electrophilic compounds was carried out. When the electrophilic compound was present from the beginning of the electrolysis, the expected coupling product with the cyanomethyl anion was obtained. If the electrophilic compound was added only after complete electrolysis of the aryl halide, dimerization of the cyanomethyl anion and a coupling reaction between the dimer anion and the electrophilic compound were observed

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Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of C9H9NO. Aromatic heterocyclic compounds can also be classified according to the number of heteroatoms contained in the heterocycle: single heteroatom, two heteroatoms, three heteroatoms and four heteroatoms. Compound: 3-Hydroxy-3-phenylpropanenitrile, is researched, Molecular C9H9NO, CAS is 17190-29-3, about Sulfonylisoxazolines: reliable intermediates for the preparation of β-hydroxy nitriles. Author is Wade, Peter A.; Bereznak, James F..

A series of six sulfonylisoxazolines, which were readily prepared via cycloaddition of PhSO2CNO to alkenes, were cleaved in 86-94% yield to β-hydroxy nitriles by the action of excess 2% Na-Hg. The stereochem. present at the isoxazoline C-4 and C-5 positions was retained during cleavage; since nitrile oxide cycloaddition to alkenes is a stereospecific process, the overall sequence permitted high diastereoselection. Under standard conditions, I gave a mixture of benzyl alc. and phenylacetonitrile rather than β-hydroxy nitriles; when the reactions were buffered, however, the β-hydroxy nitriles could be obtained in 88-91% yield. The β-hydroxy nitriles obtained from I rapidly underwent a retro-aldol reaction in the presence of aqueous base at room temperature The β-hydroxy nitrile obtained from 1-methylcyclopentene was epimerized by base and, at or above 80°, was cleaved to 6-oxoheptanenitrile.

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Reference:
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

COA of Formula: C9H9NO. The mechanism of aromatic electrophilic substitution of aromatic heterocycles is consistent with that of benzene. Compound: 3-Hydroxy-3-phenylpropanenitrile, is researched, Molecular C9H9NO, CAS is 17190-29-3, about LiOH-Catalyzed Simple Ring Opening of Epoxides under Solvent-Free Conditions. Author is Azizi, Najmedin; Khajeh-Amiri, Alireza; Ghafuri, Hossein; Bolourtchian, Mohammad.

LiOH has been found to be a very simple and selective catalyst for the rapid and mild synthesis of β-hydroxy sulfides and β-hydroxyl nitriles by ring opening of epoxides with aromatic, aliphatic, and heterocyclic thiols and trimethylsilyl cyanide at room temperature under solvent free conditions. All the reactions proceeded satisfactorily in short times and afforded the corresponding products in good to excellent yields with high regioselectivity and chemoselectivity under mild reaction conditions.

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Pyrazole – Wikipedia,
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HPLC of Formula: 17190-29-3. 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. Compound: 3-Hydroxy-3-phenylpropanenitrile, is researched, Molecular C9H9NO, CAS is 17190-29-3, about 1,3-Dipolar cycloadditions. 72. Reactions of fulminic acid with unsaturated compounds.

The slow generation of fulminic acid (I), the parent substance of nitrile oxides, from ICH:NOH and NEt3 in organic media makes in situ cycloadditions to alkenes and alkynes of sufficient dipolarophilic activity possible. The NMR spectra allow the structural elucidation of the produced 2-isoxazolines and isoxazoles. The observed directions of cycloaddition correspond largely to those of benzonitrile oxide. On using dipolarophiles of lower activity, the oligomerization of formonitrile oxide competes with its cycloadditions; in some cases cycloadducts of the dimeric I HON:CHC:N+O- were isolated. The so far nearly unknown 2-isoxazolines unsubstituted in 3-position suffer a base-catalyzed ring opening which leads to the formal adducts of OH and CN to the double bond of the olefinic dipolarophile. Free I is not an intermediate in the formation of PhNHCOCN+O- from MeNO2 and PhNCO in the presence of NEt3 as shown by competition experiments

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Pyrazole – Wikipedia,
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Epoxy compounds usually have stronger nucleophilic ability, because the alkyl group on the oxygen atom makes the bond angle smaller, which makes the lone pair of electrons react more dissimilarly with the electron-deficient system. Compound: 3-Hydroxy-3-phenylpropanenitrile, is researched, Molecular C9H9NO, CAS is 17190-29-3, about Rational design of pincer-nickel complexes for catalytic cyanomethylation of benzaldehyde: A systematic DFT study.Application In Synthesis of 3-Hydroxy-3-phenylpropanenitrile.

The current study dwells upon the efforts to computationally probe a phosphine-free pincer-nickel complex that would demonstrate an efficiency better than the reported phosphine-based pincer-nickel complex (iPr2POCNEt2)Ni(CH2CN) for cyanomethylation reaction. For this purpose, the mechanism of cyanomethylation of benzaldehyde was studied quantum mech. for a series of 11 pincer-nickel complexes. The energetics of various intermediates and transition states involved in the catalytic cycle for each catalyst was compared with the corresponding energetics of the Miller′s catalyst (iPr2POCNEt2)Ni(CH2CN) that is reported to accomplish the cyanomethylation at room temperature While pincer complexes (iPr4NNN)Ni(CH2CN) and (iPr4NCN)Ni(CH2CN) containing strong σ-donating amines were found to fare poorly, pincer-nickel complexes (iPr2NCN)Ni(CH2CN) and (dmPheboxNCN)Ni(CH2CN) based on weaker σ-donating imines had energetics more favorable than the reported efficient catalyst (iPr2POCNEt2)Ni(CH2CN). While strong trans-influencing C as the pincer central atom was found to be pivotal for lowering the cyanomethylation kinetics, presence of a poor trans-influencing N proved to be detrimental on the overall energetics.

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Reference:
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 17190-29-3. Aromatic heterocyclic compounds can also be classified according to the number of heteroatoms contained in the heterocycle: single heteroatom, two heteroatoms, three heteroatoms and four heteroatoms. Compound: 3-Hydroxy-3-phenylpropanenitrile, is researched, Molecular C9H9NO, CAS is 17190-29-3, about Novel multiaction of Zr catalyst: one-pot synthesis of β-cyanohydrins from olefins. Author is Yamasaki, Shingo; Kanai, Motomu; Shibasaki, Masakatsu.

A general one-pot synthesis of β-cyanohydrins, e.g., I (n = 1-4), from olefins, e.g., II, promoted by Zr diolate catalysts, is presented. E.g., Zr(OCMe3)4 was added to a mixture of triphenylphosphine oxide and Ph2C(OH)CH2CH2C(OH)Ph2 in 1,2-dichloroethane at 0° and stirred for 10 min. to yield a solution with 5 mol% catalyst; 2 equivalent of bis(trimethylsilyl)peroxide, 2 equivalent trimethylsilyl cyanide, and cyclohexene were added and the mixture stirred for 12 h to give I (n = 2) in 95% yield. The mechanism involves epoxidation and ring opening with the zirconium acting as a catalyst for both processes; a mechanism for the action of the zirconium diolate catalyst is proposed. The kinetics of both processes are examined Using a nonracemic TADDOL analog, cyanohydrin III was prepared enantioselectively in 85% yield and 62% ee under similar conditions.

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Reference:
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

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 RhI-catalyzed aldol-type reaction of organonitriles under mild conditions, published in 2008-05-21, which mentions a compound: 17190-29-3, mainly applied to nitrile aromatic heteroaromatic unsaturated aliphatic aldehyde rhodium tricyclohexylphosphine; chemoselective aldol hydroxynitrile preparation; aldol chemoselective catalyst rhodium tricyclohexylphosphine, Recommanded Product: 3-Hydroxy-3-phenylpropanenitrile.

An aldol-type reaction of organonitriles with aldehydes was catalyzed by a RhI(OR) species under ambient conditions, and the reaction displayed a broad substrate scope with respect to both organonitrile and aldehyde components.

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Reference:
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Name: 3-Hydroxy-3-phenylpropanenitrile. Aromatic heterocyclic compounds can also be classified according to the number of heteroatoms contained in the heterocycle: single heteroatom, two heteroatoms, three heteroatoms and four heteroatoms. Compound: 3-Hydroxy-3-phenylpropanenitrile, is researched, Molecular C9H9NO, CAS is 17190-29-3, about Tin-mediated organic reactions: a practical method for the synthesis of β-hydroxynitriles and β-hydroxyketones. Author is Sun, Peipei; Shi, Baochuan.

In the presence of chlorotrimethylsilane, the Sn mediated addition of bromoacetonitrile or α-bromoacetophenone to aldehydes in THF gives β-hydroxynitriles or β-hydroxyketones in moderate to good yields.

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Reference:
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Epoxy compounds usually have stronger nucleophilic ability, because the alkyl group on the oxygen atom makes the bond angle smaller, which makes the lone pair of electrons react more dissimilarly with the electron-deficient system. Compound: 3-Hydroxy-3-phenylpropanenitrile, is researched, Molecular C9H9NO, CAS is 17190-29-3, about Easy direct stereo- and regioselective formation of β-hydroxy nitriles by reaction of 1,2-epoxides with potassium cyanide in the presence of metal salts.Recommanded Product: 3-Hydroxy-3-phenylpropanenitrile.

The metal salt-catalyzed ring opening of epoxides with KCN in MeCN gave regioselectively and stereoselectively β-hydroxy nitriles. The ring opening reaction is regioselective with attack of the nucleophile only on the sterically less hindered carbon. Treatment of (±)-1-hexyloxirane with KCN/LiCLO4 in MeCN gave 95% C5H11CH(OH)CH2CH2CN (97.0% attack at the β-carbon and 1.8% attack at the α-carbon). The ring opening reaction is anti-stereoselective, whereby only the trans isomer of the β-hydroxy nitriles were formed. Ring opening of (+)-1,2-epoxycyclohexane gave 96% trans-3-hydroxy-1-cyclohexanecarbonitrile. With styrene oxide attack of the nucleophile occurred also on the more substituted benzylic carbon.

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Reference:
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics