N-[1-(R)-(1-Naphthyl)ethyl]-3-[3-trifluoromethylphenyl]propanamide
[CAS 1005450-55-4]

Identification

• Classification: Organic raw materials >> Amino compound >> Amide compound
• Name: N-[1-(R)-(1-Naphthyl)ethyl]-3-[3-trifluoromethylphenyl]propanamide
• Molecular Formula: C₂₂H₂₀F₃NO
• Molecular Weight: 371.40
• CAS Registry Number: 1005450-55-4
• SMILES: C[C@H](C1=CC=CC2=CC=CC=C21)NC(=O)CCC3=CC(=CC=C3)C(F)(F)F

Properties

• Solubility: Insoluble (3.3E^-4 g/L) (25 $degree$C), Calc.^*
• Density: 1.210$+/-$0.06 g/cm³ (20 $degree$C 760 Torr), Calc.^*
• Melting point: 90-92 $degree$C (cyclohexane )^**
• Boiling point: 530.5$+/-$50.0 $degree$C 760 mmHg (Calc.)^*
• Flash point: 274.6$+/-$30.1 $degree$C (Calc.)^*
• Index of refraction: 1.57 (Calc.)^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 ($copyright$1994-2014 ACD/Labs)

^** Geoghegan, Kimberly$semicolon$ Journal of Organic Chemistry 2011, V76(7), P2187-2194.

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319-H335
• Safety Statements: P261-P305+P351+P338

Discovery and Applications

N-[1-(R)-(1-naphthyl)ethyl]-3-[3-trifluoromethylphenyl]propanamide is a chiral aromatic amide that has been investigated primarily in the context of asymmetric synthesis and stereochemical control in organic reactions. The compound contains several structural elements that are frequently employed in the design of chiral auxiliaries and related reagents, including a naphthyl-substituted chiral center and an amide linkage connecting aromatic systems. Such structural features have been widely used by chemists seeking to control the formation of enantiomerically enriched products during chemical transformations.

The development of asymmetric synthesis became a major focus of organic chemistry during the twentieth century as researchers recognized the importance of molecular chirality in biological systems and pharmaceutical compounds. Many biologically active molecules exist in two mirror-image forms that can exhibit different biological properties. This recognition led to extensive efforts to develop methods that allow chemists to prepare molecules with defined stereochemistry. One approach involved the use of chiral auxiliaries or chiral reagents capable of inducing stereoselectivity in chemical reactions.

Compounds derived from 1-(1-naphthyl)ethylamine became particularly useful in this area because the rigid aromatic framework of the naphthalene ring and the presence of a stereogenic center provide an effective environment for controlling molecular orientation during reactions. When this chiral fragment is incorporated into an amide or related derivative, it can influence the stereochemical course of reactions occurring at nearby functional groups. N-[1-(R)-(1-naphthyl)ethyl]-3-[3-trifluoromethylphenyl]propanamide represents an example of such a derivative in which the chiral amine component is linked through an amide bond to a substituted aromatic propanamide framework.

The introduction of a trifluoromethyl group into aromatic compounds has also been an important strategy in modern organic chemistry. The trifluoromethyl substituent is strongly electron-withdrawing and can significantly influence the physical and chemical properties of a molecule. Its presence can alter acidity, lipophilicity, and reactivity, making it a valuable functional group in both synthetic chemistry and medicinal chemistry research. In compounds like N-[1-(R)-(1-naphthyl)ethyl]-3-[3-trifluoromethylphenyl]propanamide, the combination of aromatic substituents and a trifluoromethyl group contributes to a rigid and well-defined molecular structure that can be useful for stereochemical studies.

Amide derivatives containing chiral aromatic substituents have frequently been employed as intermediates in the preparation of more complex molecules. The amide functional group is relatively stable under many reaction conditions while still allowing transformation of other parts of the molecule. As a result, such compounds can serve as temporary structural frameworks that guide the formation of stereochemically defined products. After the desired transformation has been achieved, the auxiliary portion can often be removed or modified to yield the target compound.

In laboratory practice, compounds of this type are typically prepared by acylation of a chiral amine with an appropriate carboxylic acid derivative. The amide bond formation reaction links the chiral 1-(1-naphthyl)ethylamine component to the substituted propanamide fragment containing the trifluoromethylphenyl group. The resulting molecule retains the stereochemical configuration of the original amine, allowing it to function as a chiral element within subsequent reactions.

The use of chiral amide derivatives has contributed significantly to the development of stereoselective synthetic methods. By examining how different substituents and structural features affect stereochemical outcomes, chemists have been able to design improved reagents and strategies for producing enantiomerically pure compounds. Within this broader context, N-[1-(R)-(1-naphthyl)ethyl]-3-[3-trifluoromethylphenyl]propanamide represents a functionalized chiral amide whose structural characteristics illustrate the principles underlying chiral auxiliary design and the use of aromatic substituents to influence molecular behavior in asymmetric synthesis.

References

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DOI: 10.1055/s-0036-1591772

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DOI: 10.1055/s-0035-1561506

2008. Cinacalcet hydrochloride. Pharmaceutical Substances.