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159517-27-8

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159517-27-8 Usage

General Description

"(2R)-2-AMINO-3-PHENYLPROPANENITRILE" is a chemical compound with the molecular formula C9H10N2. It is a chiral molecule with a phenyl group attached to a propanenitrile moiety, and an amino group on the second carbon of the propanenitrile chain. (2R)-2-AMINO-3-PHENYLPROPANENITRILE is often used in organic synthesis and pharmaceutical research due to its potential as a building block for the construction of complex organic molecules. It may also have biological activity and could be used as a starting material for the synthesis of pharmacologically relevant compounds. However, the specific properties and applications of (2R)-2-AMINO-3-PHENYLPROPANENITRILE would depend on its stereochemistry and the other functional groups present in the molecule.

Check Digit Verification of cas no

The CAS Registry Mumber 159517-27-8 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,5,9,5,1 and 7 respectively; the second part has 2 digits, 2 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 159517-27:
(8*1)+(7*5)+(6*9)+(5*5)+(4*1)+(3*7)+(2*2)+(1*7)=158
158 % 10 = 8
So 159517-27-8 is a valid CAS Registry Number.

159517-27-8Relevant articles and documents

Reagent-controlled diastereoselectivity in aziridination of alkenes by chiral 3-acetoxyamino-3,4-dihydroquinazolin-4-ones: 1'-(t- butyldimethylsilyloxy)ethyl as the chiral 2-substituent on the quinazolinone

Atkinson, Robert S.,Coogan, Michael P.,Lochrie, Ian S. T.

, p. 5179 - 5182 (1996)

Conformational preferences within the (t)BuMe2SiOCH(Me)C=N unit in 3- acetoxyaminoquinazolinone 3 lead to well defined site preferences for H, Me and OSiMe21Bu in the transition state for, and hence high diastereoselectivity in, its reaction with β-trimethylsilylstyrene 4 to give aziridine 5.

Synthesis and structure-activity relationship of nitrile-based cruzain inhibitors incorporating a trifluoroethylamine-based P2 amide replacement

Gomes, Juliana C.,Cianni, Lorenzo,Ribeiro, Jean,dos Reis Rocho, Fernanda,da Costa Martins Silva, Samelyn,Batista, Pedro Henrique Jatai,Moraes, Carolina Borsoi,Franco, Caio Haddad,Freitas-Junior, Lucio H.G.,Kenny, Peter W.,Leit?o, Andrei,Burtoloso, Antonio C.B.,de Vita, Daniela,Montanari, Carlos A.

supporting information, (2019/09/30)

The structure-activity relationship for nitrile-based cruzain inhibitors incorporating a P2 amide replacement based on trifluoroethylamine was explored by deconstruction of a published series of inhibitors. It was demonstrated that the P3 biphenyl substituent present in the published inhibitor structures could be truncated to phenyl with only a small loss of affinity. The effects of inverting the configuration of the P2 amide replacement and linking a benzyl substituent at P1 were observed to be strongly nonadditive. We show that plotting affinity against molecular size provides a means to visualize both the molecular size efficiency of structural transformations and the nonadditivity in the structure-activity relationship. We also show how the relationship between affinity and lipophilicity, measured by high-performance liquid chromatography with an immobilized artificial membrane stationary phase, may be used to normalize affinity with respect to lipophilicity.

Regioselective hydration and deprotection of chiral, dissymmetric iminodinitriles in the scope of an asymmetric strecker strategy

Rossi, Jean-Christophe,Marull, Marc,Boiteau, Laurent,Taillades, Jacques

, p. 662 - 668 (2007/10/03)

The controlled, selective decomposition of dissymmetric iminodinitriles (DIDN) of formula RCH(CN)-NH-C(CN)R′R″ (considered as N-protected alpha-aminonitriles), is a critical issue for an original asymmetric Strecker strategy previously outlined by us for the enantioselective synthesis of amino acids. This strategy, derived from Harada's work, involves a double sequence of (i) stereoselective Strecker condensation of a chiral ketone R′R″CO with NH3 and HCN, followed by (ii) stereoselective Strecker condensation with an aldehyde RCHO and HCN, then (iii) regioselective retro-Strecker decomposition of the DIDN intermediate to release the target alpha-aminonitrile. In addition to the use of quite simple, cheap cyclic ketones (e.g. carvone derivatives) as chiral auxiliaries, another great advantage of this strategy is that step (iii) enables the recovery of the chiral ketone and hence its reuse. While our previous investigations on step (iii) under various conditions, either preceded or followed by the hydration of the secondary nitrile group RH(CN)- into an amide, had shown insufficient selectivity, we succeeded in the regioselective hydration of the secondary nitrile of DIDN without significant racemisation, by using a large excess of hydrogen peroxide in methanolic/aqueous ammonia (pH 12.5) at low temperature. The resulting imino nitrile/amide compound was then classically decomposed in acidic medium through a retro-Strecker reaction, affording the chiral alpha-amino amide. Alternately, the regioselective retro-Strecker decomposition of the tertiary moiety of the DIDN was achieved by reaction with silver cation in aqueous nitric acid, also without significant racemisation, thus establishing an original, enantioselective synthesis of alpha-aminonitriles. In both reactions, the chiral ketonic auxiliary resulting from DIDN decomposition was recovered in good yields. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.

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