Category: 17190-29-3

Quality Control of 3-Hydroxy-3-phenylpropanenitrile. The fused heterocycle is formed by combining a benzene ring with a single heterocycle, or two or more single heterocycles. Compound: 3-Hydroxy-3-phenylpropanenitrile, is researched, Molecular C9H9NO, CAS is 17190-29-3, about Theoretical Investigation into the Mechanism of Cyanomethylation of Aldehydes Catalyzed by a Nickel Pincer Complex in the Absence of Base Additives. Author is Ariafard, Alireza; Ghari, Hossein; Khaledi, Yousef; Hossein Bagi, Amin; Wierenga, Tanita S.; Gardiner, Michael G.; Canty, Allan J..

D. functional theory was used to study the reaction mechanism of cyanomethylation of aldehydes catalyzed by nickel pincer complexes under base-free conditions. The C-bound cyanomethyl complex, which was initially thought to be the active catalyst, is actually a precatalyst, and in order for the catalytic reaction to commence, it has to convert to the less-stable N-bound isomer. The carbon-carbon bond formation then proceeds via direct coupling of the N-bound isomer and the aldehyde to give a zwitterionic intermediate with a pendant alkoxide function, which is further stabilized by hydrogen-bonding interaction with water mols. (or alc. product). The N-bound alkoxide group of the zwitterionic intermediate is subsequently substituted by MeCN via an associative mechanism, followed by deprotonation of the coordinated MeCN to afford the final product. It was found that the transition structure for the exchange reaction (substitution of MeCN for the alkoxide group) is the highest energy point on the catalytic cycle, and its energy crucially influences the catalyst efficiency. The Ni complexes ligated by bulky and weak trans-influencing pincer ligands are not appropriate catalysts for the cyanomethylation reaction due to the involvement of very-high-energy transition structures for the exchange reaction. In contrast, benzaldehydes with electron-withdrawing substituents are capable of stabilizing the exchange reaction transition structure due to the increased stability of the zwitterionic intermediate, leading to acceleration of the catalytic reaction.

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Takahashi, Kazumasa; Sasaki, Kazushige; Tanabe, Hiroaki; Yamada, Kazutoshi; Iida, Hirotada published an article about the compound: 3-Hydroxy-3-phenylpropanenitrile( cas:17190-29-3,SMILESS:N#CCC(O)C1=CC=CC=C1 ).Recommanded Product: 3-Hydroxy-3-phenylpropanenitrile. 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:17190-29-3) through the article.

The reaction of MeCN with p-anisaldehyde was studied in detail. In EtOH no reaction occurred, but in DMF, (Me2N)3PO or THF the reaction rapidly proceeded to give 2-cyano-1-(4-methoxyphenyl)-1-hydroxyethane (I) and 4-methoxycinnamonitrile (II) with total yield of 87 ∼ 95%. The yields of I and II were influenced by the reaction temperature and solvent. Prolonged treatment of MeCN with RC6H4CHO(R = H, p-MeO, p-Me2N), 2,4-(MeO)2-C6H3CHO or 3,4-(methylenedioxy)benzaldehyde under similar conditions gave β-hydroxy-β-phenylpropionitrile derivatives or cinnamonitrile derivatives Their yields were influenced by the substituents.

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Itoh, Toshiyuki; Takagi, Yumiko; Nishiyama, Shigenori published the article 《Enhanced enantioselectivity of an enzymatic reaction by the sulfur functional group. A simple preparation of optically active β-hydroxy nitriles using a lipase》. Keywords: methylthioacetoxybutyronitrile kinetic resolution lipase; nitrile beta hydroxy optically active.They researched the compound: 3-Hydroxy-3-phenylpropanenitrile( cas:17190-29-3 ).Computed Properties of C9H9NO. Aromatic heterocyclic compounds can be divided into two categories: single heterocyclic and fused heterocyclic. In addition, there is a lot of other information about this compound (cas:17190-29-3) here.

The enantioselectivity of a lipase-catalyzed hydrolysis was improved by varying the acyl residue into the sulfur functional one, i.e. the β-(phenylthio)- or β-(methylthio)acetoxy group, from acetate or valerate to realize satisfactory resolution of β-hydroxy nitriles using lipase P (Pseudomons sp.).

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Electric Literature of C9H9NO. The fused heterocycle is formed by combining a benzene ring with a single heterocycle, or two or more single heterocycles. Compound: 3-Hydroxy-3-phenylpropanenitrile, is researched, Molecular C9H9NO, CAS is 17190-29-3, about Study of the enantioselectivity of the CAL-B-catalyzed transesterification of α-substituted α-propylmethanols and α-substituted benzyl alcohols. Author is Garcia-Urdiales, Eduardo; Rebolledo, Francisca; Gotor, Vicente.

A study of the enantioselectivity exhibited by the lipase B from Candida antarctica in the transesterification of different α-substituted α-propylmethanols with vinyl acetate is shown. The best results are obtained when the large-sized (L) substituent of the alc. is either a Ph group or more especially a cyclohexyl group, although the reaction rates are lower than when linear or slightly branched groups are present. It is also found that ramification at the β-position of the L substituent has a deleterious effect on both lipase activity and enantioselectivity. Moreover, some α-substituted benzyl alcs. bearing medium-sized (M) substituents larger than an Et and smaller than a Pr group are resolved by means of this methodol. with moderate-good enantioselectivities (E = 46-57) and similar reaction rates.

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The preparation of ester heterocycles mostly uses heteroatoms as nucleophilic sites, which are achieved by intramolecular substitution or addition reactions. Compound: 3-Hydroxy-3-phenylpropanenitrile( cas:17190-29-3 ) is researched.COA of Formula: C9H9NO.Yang, Zhiheng; Cheng, Weiyan; Li, Zeyun published the article 《Iridium catalysed highly efficient transfer hydrogenation reduction of aldehydes and ketones in water》 about this compound( cas:17190-29-3 ) in Catalysis Communications. Keywords: alc preparation; aldehyde iridium catalyst transfer hydrogenation; ketone iridium catalyst transfer hydrogenation. Let’s learn more about this compound (cas:17190-29-3).

A new transfer hydrogenation of structurally diverse aldehydes and ketones in water using formic acid as hydride donor was developed, to get the corresponding alcs. The iridium complex of 4,4′,5,5′-tetrahydro-1H,1’H-2,2′-biimidazole, was used as an efficient catalyst. The S/C ratios in aldehyde and ketone reductions were as low as 20,000 and 10,000 resp. The TOF value in aldehyde reduction was as high as 60,000 h-1. A number of functional groups such as (hetero)aryl, alkenyl, halogen, phenolic and alc. hydroxyls, trifluromethyl, cyano, nitro, ester, carboxylic acid and acidic methylenes were well tolerated.

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HPLC of Formula: 17190-29-3. 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 Glucosinolate turnover in Brassicales species to an oxazolidin-2-one, formed via the 2-thione and without formation of thioamide. Author is Agerbirk, Niels; Matthes, Annemarie; Erthmann, Pernille Oe.; Ugolini, Luisa; Cinti, Susanna; Lazaridi, Eleni; Nuzillard, Jean-Marc; Muller, Caroline; Bak, Soeren; Rollin, Patrick; Lazzeri, Luca.

Glucosinolates are found in plants of the order Brassicales and hydrolyzed to different breakdown products, particularly after tissue damage. In Barbarea vulgaris R.Br. (Brassicaceae), the dominant glucosinolate in the investigated “”G-type”” is glucobarbarin [(S)-2-hydroxy-2-phenylethylglucosinolate]. The formation of the nitrile from glucobarbarin was observed in vitro, while a previously suggested thioamide (synonym thionamide) was not confirmed. Resedine (5-phenyl-1,3-oxazolidin-2-one) was detected after glucobarbarin hydrolysis in crushed B. vulgaris leaves and siliques, but not in intact parts. The abundance increased for several hours after completion of hydrolysis. The corresponding 1,3-oxazolidine-2-thione (OAT), with the common name barbarin, was also formed, and appeared to be the precursor of resedine. The addition of each of 2 non-endogenous OATs, (S)-5-ethyl-5-methylOAT and (R)-5-vinylOAT (R-goitrin), to a leaf homogenate resulted in formation of the corresponding 1,3-oxazolidin-2-ones (OAOs), confirming the metabolic connection of OAT to OAO. The formation of OAOs was inhibited by prior brief heating of the homogenate, suggesting enzymic involvement. We suggest the conversion of OATs to OAOs to be catalyzed by an enzyme (“”oxazolidinethionase””) responsible for turnover of OAT formed in intact plants. Resedine had been reported as an alkaloid from another species, Reseda luteola L. (Resedaceae), which naturally contains glucobarbarin. However, resedine was not detected in intact R. luteola plants, but formed after tissue damage. The formation of resedine in 2 families suggests a broad distribution of putative OATases in the Brassicales; potentially involved in glucosinolate turnover that needs myrosinase activity as the committed step. In agreement with the proposed function of OATase, several candidate genes for myrosinases in glucosinolate turnover in intact plants were discovered in the B. vulgaris genome. We also suggest that biotechnol. conversion of OATs to OAOs might improve the nutritional value of Brassicales protein. HPLC-MS/MS methods for detection of these glucobarbarin products are described.

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Computed Properties 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 The Stevens rearrangement of sulfur ylide generated by electrochemical reduction of sulfonium salt. Author is Okazaki, Yuichi; Asai, Tatsuro; Ando, Fumio; Koketsu, Jugo.

The cathodic reduction or a base treatment of a 1-cyanomethyltetrahydrothiophenonium salt gave the stabilized ylides which were conformed by the reaction with benzaldehyde. In the absence of benzaldehyde, the ring expanded product was obtained through the Stevens rearrangement in good yield by both methods. The reaction mechanism was investigated by using B3LYP d. functional calculations

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The preparation of ester heterocycles mostly uses heteroatoms as nucleophilic sites, which are achieved by intramolecular substitution or addition reactions. Compound: 3-Hydroxy-3-phenylpropanenitrile( cas:17190-29-3 ) is researched.Safety of 3-Hydroxy-3-phenylpropanenitrile.Kamal, Ahmed; Khanna, G. B. Ramesh; Ramu, R. published the article 《Chemoenzymatic synthesis of both enantiomers of fluoxetine, tomoxetine and nisoxetine: lipase-catalyzed resolution of 3-aryl-3-hydroxypropanenitriles》 about this compound( cas:17190-29-3 ) in Tetrahedron: Asymmetry. Keywords: aryl hydroxyphenylpropanenitrile preparation ring opening styrene oxide sodium cyanide; kinetic resolution aryl hydroxyphenylpropanenitrile transesterification lipase catalyst; chemoenzymic preparation enantiomer fluoxetine tomoxetine nisoxetine. Let’s learn more about this compound (cas:17190-29-3).

A facile preparation of (±)-3-hydroxy-3-phenylpropanenitrile has been carried out by ring-opening of styrene oxide with NaCN in aqueous ethanol. Subsequent kinetic resolution of this material via lipase-mediated transesterification gave the S-alc. and R-acetate in excellent yields and high enantioselectivities, particularly with lipase PS-C Amano’ II. The effect of solvents and immobilization of the lipase has also been investigated. It is interesting to note that the use of immobilized lipase for this transesterification process in hydrophobic solvents (diisopropyl ether, toluene and hexane) enhanced the reaction rate drastically and gave optimal yields with high enantioselectivity (>99%). Moreover, enantiopure 3-hydroxy-3-phenylpropanenitrile products have been converted via enantioconvergent routes into the (R)- and (S)-enantiomers of the important anti-depressants fluoxetine, tomoxetine, nisoxetine and norfluoxetine.

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Most of the compounds have physiologically active properties, and their biological properties are often attributed to the heteroatoms contained in their molecules, and most of these heteroatoms also appear in cyclic structures. A Journal, European Journal of Organic Chemistry called Exploring the synthetic applicability of a cyanobacterium nitrilase as catalyst for nitrile hydrolysis, Author is Mukherjee, Chandrani; Zhu, Dunming; Biehl, Edward R.; Hua, Ling, which mentions a compound: 17190-29-3, SMILESS is N#CCC(O)C1=CC=CC=C1, Molecular C9H9NO, Related Products of 17190-29-3.

The substrate specificity and synthetic applicability of the nitrilase from cyanobacterium Synechocystis sp. strain PCC 6803 have been examined This nitrilase catalyzed the hydrolysis of both aromatic and aliphatic nitriles to the corresponding acids in high yields. Furthermore, the stereoselective hydrolysis of phenyl-substituted β-hydroxy nitriles to (S)-enriched β-hydroxy carboxylic acids and selective hydrolysis of α,ω-dinitriles with five or less methylene groups to ω-cyano carboxylic acids have been achieved. This suggested that nitrilase from Synechocystis sp. PCC 6803 could be a useful enzyme catalyst for the “”green”” nitrile hydrolysis.

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Latouche, Regine; Texier-Boullet, Francoise; Hamelin, Jack published an article about the compound: 3-Hydroxy-3-phenylpropanenitrile( cas:17190-29-3,SMILESS:N#CCC(O)C1=CC=CC=C1 ).Application of 17190-29-3. 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:17190-29-3) through the article.

Condensation of Me3SiCH2R (R = CN, CO2Et) with BzH in the presence of dried alkali metal fluorides in heterogeneous media under microwaves leads readily to PhCH(OSiMe3)CH2R according to a Reformatskii-type reaction. The products could be hydrolyzed and dehydrated on the wet inorganic salt to give alkenes.

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