159517-27-8

Basic information

• Product Name: (2R)-2-AMINO-3-PHENYLPROPANENITRILE
• Synonyms: D-ALPHA-AMINOHYDROCINNAMONITRILE;(2R)-2-AMINO-3-PHENYLPROPANENITRILE
• CAS NO: 159517-27-8
• Molecular Formula: C₉H₁₀N₂
• Molecular Weight: 146.19
• Mol File: 159517-27-8.mol

Chemical Properties

• Boiling Point: 285.2±28.0 °C(Predicted)
• Appearance: /
• Density: 1.073±0.06 g/cm3(Predicted)
• PKA: 5.16±0.33(Predicted)
• CAS DataBase Reference: (2R)-2-AMINO-3-PHENYLPROPANENITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: (2R)-2-AMINO-3-PHENYLPROPANENITRILE(159517-27-8)
• EPA Substance Registry System: (2R)-2-AMINO-3-PHENYLPROPANENITRILE(159517-27-8)

Safety Data

• Hazardous Substances Data: 159517-27-8(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
(2R)-2-AMINO-3-PHENYLPROPANENITRILE is used as a key intermediate in organic synthesis for the creation of various complex organic molecules. Its unique structure allows for multiple points of chemical modification, facilitating the development of new compounds with diverse properties.
Used in Pharmaceutical Research:
In the pharmaceutical industry, (2R)-2-AMINO-3-PHENYLPROPANENITRILE is utilized as a starting material for the synthesis of pharmacologically relevant compounds. Its potential biological activity and the ability to be modified into different molecular forms make it a promising candidate for drug discovery and development.
Used in Stereoselective Reactions:
Due to its chiral nature, (2R)-2-AMINO-3-PHENYLPROPANENITRILE is employed in stereoselective reactions, which are crucial for producing enantiomerically pure compounds. This is particularly important in pharmaceuticals, where the desired biological activity is often associated with a specific enantiomer.
Used in the Synthesis of Chiral Auxiliaries:
(2R)-2-AMINO-3-PHENYLPROPANENITRILE can be used to prepare chiral auxiliaries, which are essential in asymmetric synthesis to control the stereochemistry of the products. These auxiliaries help in obtaining the desired enantiomer with high selectivity, which is vital for the efficacy and safety of pharmaceutical compounds.
Used in the Development of Chiral Catalysts:
(2R)-2-AMINO-3-PHENYLPROPANENITRILE can also be employed in the development of chiral catalysts, which are used to accelerate chemical reactions with high enantioselectivity. Chiral catalysts are crucial in the synthesis of enantiomerically pure compounds, ensuring that the desired biological activity is achieved without unwanted side effects.

Upstream product

• 70591-26-3 2-(Benzhydrylidene-amino)-3-phenyl-propionitrile 
• 400652-45-1 (R)-2-(tert-butoxycarbonylamino)-3-phenylpropionitrile 
• 129095-62-1 (R)-tert-butyl (1-amino-1-oxo-3-phenylpropan-2-yl)carbamate 
• 19901-50-9 methyl (2R)-2-(t-butoxycarbonylamino)-3-phenylpropionate 
• 18942-49-9 Boc-D-Phe-OH 
• 13033-84-6 D-phenylalanine methyl ester hydrochloride 
• 177018-15-4 (2R,3S)-2-cyano-3-phenylaziridine 
• 155385-83-4 (-)-1-<(1-cyano-2-phenylethyl)amino>-2R-methyl-5R-(1-methylethenyl)cyclohexane-1R,3R-dicarbonitrile 
• 176847-60-2 2-[(S)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3-((2S,3S)-2-phenyl-3-trimethylsilanyl-aziridin-1-yl)-3H-quinazolin-4-one 
• 19372-00-0 1-(trimethylsilyl)-2-phenylethene 

Downstream Products

• 55379-75-4 2-amino-3-phenylpropanenitrile 
• 181376-74-9 (+)-(R)-N-(1-cyano-2-phenyl-ethyl)-acetamide 

Relevant 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

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.

Optimization strategy of single-digit nanomolar cross-class inhibitors of mammalian and protozoa cysteine proteases

Cysteine proteases (CPs) are involved in a myriad of actions that include not only protein degradation, but also play an essential biological role in infectious and systemic diseases such as cancer. CPs also act as biomarkers and can be reached by active-

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

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.

Identification of potent and reversible cruzipain inhibitors for the treatment of Chagas disease

Identification of potent and reversible cruzipain inhibitors for the treatment of Chagas disease is described. The identified inhibitors bearing an amino nitrile warhead in P1 exhibit low nanomolar in vitro potency against cruzipain. Further SAR in P2 por

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

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.

PROCESS FOR THE RACEMISATION OF ENANTIOMERICALLY ENRICHED ALPHA-AMINO NITRILES

Process for the racemisation of an enantiomerically enriched α-amino nitrile characterized in that the enantiomerically enriched α-amino nitrile is contacted with a lewis acid catalyst. Preferably an aprotic solvent is used. The lewis acid catalyst preferably comprises a metal chosen from main group elements IA-IVA of the Periodic Table (CAS version), the transition metals and the lanthanides, in particular Al, Ti, Zr, or lanthanides. The catalsyt for example has the general structure MnXpSqLr, and preferably is chosen from the group of aluminum alkoxides, aluminum alkyls, lanthanide alkoxydes and lanthanocenes. The racemisation may be performed in combination with a resolution process, for instance in combination with an enzymatic or a crystallization induced resolution process, preferably in situ, for instance in situ in a crystallization induced asymmetric transformation process.