Production Method 1

145485-43-4

885268-02-0

Reaction Conditions

1.1 90 °C

Reference

Highly enantioselective [3+2] coupling of cyclic enamides with quinone monoimines promoted by a chiral phosphoric acid

Zhang, Minmin; et al, Chemical Communications (Cambridge, 2016, 52(56), 8757-8760

Production Method 2

1899045-13-6

885268-02-0

Reaction Conditions

1.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Methanol ;  rt
2.1 90 °C

Reference

Highly enantioselective [3+2] coupling of cyclic enamides with quinone monoimines promoted by a chiral phosphoric acid

Zhang, Minmin; et al, Chemical Communications (Cambridge, 2016, 52(56), 8757-8760

Production Method 3

454-89-7

51114-94-4

885268-02-0

Reaction Conditions

1.1 Reagents: Lithium bis(trimethylsilyl)amide Solvents: Tetrahydrofuran ;  rt → 0 °C; 0 °C; 15 min, 0 °C; overnight, rt
1.2 Reagents: Hydrochloric acid Solvents: Water ;  1 h, 0 °C
2.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Methanol ;  rt
3.1 90 °C

Reference

Highly enantioselective [3+2] coupling of cyclic enamides with quinone monoimines promoted by a chiral phosphoric acid

Zhang, Minmin; et al, Chemical Communications (Cambridge, 2016, 52(56), 8757-8760

5-(Trifluoromethyl)-3,4-dihydronaphthalen-1(2H)-one Raw materials

• 3-(Trifluoromethyl)benzaldehyde
• (2-Carboxyethyl)-triphenylphosphonium Bromide
• 3-(Trifluoromethyl)-benzenebutanoic acid
• 3-Butenoic acid, 4-[3-(trifluoromethyl)phenyl]-

5-(Trifluoromethyl)-3,4-dihydronaphthalen-1(2H)-one Preparation Products

• 5-(Trifluoromethyl)-3,4-dihydronaphthalen-1(2H)-one (885268-02-0)

• 1. An anti-leakage liquid metal thermal interface material
  Kaiyuan Huang,Wangkang Qiu,Meilian Ou,Xiaorui Liu,Zenan Liao,Sheng Chu RSC Adv., 2020,10, 18824-18829
• 2. An anti-ultrasonic-stripping effect in confined micro/nanoscale cavities and its applications for efficient multiscale metallic patterning?
  Quan Xiang,Yiqin Chen,Zhiqin Li,Kaixi Bi,Guanhua Zhang,Huigao Duan Nanoscale, 2016,8, 19541-19550
• 3. An intensified π-hole in beryllium-doped boron nitride meshes: its determinant role in CO2 conversion into hydrocarbon fuels?
  Luis Miguel Azofra,Douglas R. MacFarlane,Chenghua Sun Chem. Commun., 2016,52, 3548-3551
• 4. An apparatus for testing water by measurement of its electrical conductivity
  Analyst, 1912,37, 538-543
• 5. An astrophysically-relevant mechanism for amino acid enantiomer enrichment
  Stephen P. Fletcher,Richard B. C. Jagt,Ben L. Feringa Chem. Commun., 2007, 2578-2580

5-(Trifluoromethyl)-3,4-dihydronaphthalen-1(2H)-one (CAS No. 885268-02-0): A Versatile Fluorinated Building Block for Pharmaceutical and Material Science

5-(Trifluoromethyl)-3,4-dihydronaphthalen-1(2H)-one (CAS No. 885268-02-0) is a fluorinated organic compound that has gained significant attention in recent years due to its unique structural features and broad applications in medicinal chemistry and material science. The presence of the trifluoromethyl group (-CF₃) in its molecular structure makes this compound particularly valuable for drug discovery and development, as fluorinated compounds often exhibit enhanced metabolic stability, bioavailability, and binding affinity to biological targets.

The compound belongs to the class of partially hydrogenated naphthalenones, characterized by a fused bicyclic system with a ketone functionality at the 1-position. Its molecular formula is C₁₁H₉F₃O, with a molecular weight of 214.18 g/mol. The 3,4-dihydronaphthalen-1(2H)-one scaffold serves as an important pharmacophore in many biologically active molecules, while the trifluoromethyl substitution at the 5-position introduces valuable electronic and steric properties that can significantly influence the compound's reactivity and interactions.

In pharmaceutical research, 5-(Trifluoromethyl)-3,4-dihydronaphthalen-1(2H)-one has emerged as a key intermediate for the synthesis of various drug candidates. Recent studies have explored its use in developing potential therapeutics for central nervous system disorders, inflammation, and metabolic diseases. The compound's ability to serve as a versatile synthetic building block stems from the reactivity of its ketone group, which can undergo various transformations including reduction, nucleophilic addition, and condensation reactions.

Material scientists have also shown growing interest in fluorinated dihydronaphthalenones like CAS No. 885268-02-0 for their potential applications in organic electronics and advanced materials. The electron-withdrawing nature of the trifluoromethyl group can significantly alter the electronic properties of conjugated systems, making these compounds attractive for developing novel organic semiconductors and liquid crystal materials.

Synthetic approaches to 5-(Trifluoromethyl)-3,4-dihydronaphthalen-1(2H)-one typically involve Friedel-Crafts acylation or related methodologies to construct the naphthalenone core, followed by selective introduction of the trifluoromethyl group. Recent advances in fluorination chemistry have provided more efficient routes to such compounds, addressing one of the key challenges in working with fluorinated building blocks.

The growing demand for fluorinated pharmaceutical intermediates has positioned 5-(Trifluoromethyl)-3,4-dihydronaphthalen-1(2H)-one as an important compound in the fine chemicals market. Its applications extend beyond drug discovery to areas such as agrochemicals and specialty materials, where the unique properties of fluorine-containing compounds are increasingly valued.

From a drug design perspective, the 3,4-dihydronaphthalen-1(2H)-one scaffold offers several advantages, including conformational rigidity and the potential for diverse functionalization. When combined with the trifluoromethyl group, these features create opportunities for optimizing drug-like properties such as lipophilicity, metabolic stability, and target binding affinity.

Recent publications have highlighted innovative applications of CAS No. 885268-02-0 in asymmetric synthesis and catalysis. The compound's structure makes it suitable for developing chiral auxiliaries and ligands, particularly in reactions where the trifluoromethyl group can influence stereoselectivity through steric or electronic effects.

Quality control and characterization of 5-(Trifluoromethyl)-3,4-dihydronaphthalen-1(2H)-one typically involve advanced analytical techniques such as HPLC, GC-MS, and NMR spectroscopy. The 19F NMR spectrum is particularly valuable for confirming the presence and environment of the trifluoromethyl group, providing important structural information.

As research into fluorinated organic compounds continues to expand, 5-(Trifluoromethyl)-3,4-dihydronaphthalen-1(2H)-one is likely to maintain its importance as a versatile building block. Future developments may focus on greener synthetic routes, expanded applications in materials science, and novel derivatives with enhanced biological activity.

The stability and handling characteristics of CAS No. 885268-02-0 make it suitable for various laboratory and industrial applications. Proper storage conditions typically involve protection from moisture and extreme temperatures to maintain the compound's integrity over extended periods.

In conclusion, 5-(Trifluoromethyl)-3,4-dihydronaphthalen-1(2H)-one represents an important class of fluorinated synthetic intermediates with wide-ranging applications across multiple scientific disciplines. Its unique combination of structural features and functional groups continues to inspire innovation in drug discovery, materials development, and synthetic methodology.

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