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Usage

Uses

Used in Organic Synthesis:
(S)-1-(3-Nitrophenyl)propanol is used as a building block in organic synthesis for the production of pharmaceuticals and agrochemicals. Its unique structure and properties make it a versatile compound in the synthesis of various organic molecules.
Used in Pharmaceutical Production:
In the pharmaceutical industry, (S)-1-(3-Nitrophenyl)propanol is used as a key intermediate in the synthesis of drugs. Its chiral nature allows for the development of enantioselective processes, leading to more effective and targeted medications.
Used in Medicinal Chemistry:
(S)-1-(3-Nitrophenyl)propanol has potential applications in medicinal chemistry due to its unique structure and properties. It can be used as a starting material for the development of new drugs with improved therapeutic effects and reduced side effects.
Used in Material Science:
In the field of material science, (S)-1-(3-Nitrophenyl)propanol can be utilized in the design and synthesis of new materials with specific properties. Its chiral nature and functional groups offer opportunities for the development of novel materials with applications in various industries.

InChI:InChI=1/C9H11NO3/c1-2-9(11)7-4-3-5-8(6-7)10(12)13/h3-6,9,11H,2H2,1H3/t9-/m0/s1

Upstream product

• 557-20-0 diethylzinc 
• 99-61-6 3-nitro-benzaldehyde 
• 108-22-5 Isopropenyl acetate 
• 29067-53-6 α-ethyl-3-nitrobenzyl alcohol 
• 17408-16-1 3'-nitropropiophenone 

Downstream Products

• 215316-96-4 (S)-1-(3-nitrophenyl)propanol mesylate 
• 199439-34-4 (S)-3-(3-nitrophenyl)pentanoic Acid 

Relevant academic research and scientific papers

Supramolecular Interlocked Biphenyl Ligands for Enantioselective Ti-Catalyzed Alkylation of Aromatic Aldehydes

The substitution of tropos 2,2′-biphenols with (S)-amino-acid-derived interaction sites in the 5,5′-position results in a spontaneous desymmetrization. This process is driven by well-defined intermolecular hydrogen bonding, which leads to diastereoselecti

Synthesis of novel 1,4-bissulfonamide ligands for enantioselective addition of diethylzinc to aldehydes

Several novel chiral sulfonamide ligands based on (1R,2S,4R,5S)-1,4- diamino-2,5-dimethylcyclohexane skeleton have been synthesized and their application in the enantioselective addition of diethylzinc to aldehydes was investigated in the presence of Ti(O

Cobalt(II)-catalyzed asymmetric hydrosilylation of simple ketones using dipyridylphosphine ligands in air

In the presence of PhSiH3 as the hydride donor, catalytic amounts of non-racemic dipyridylphosphine and an easy-to-handle cobalt salt Co(OAc)2·4H2O formed in situ an effective catalyst system for the asymmetric reduction o

Enantioselective addition of diethylzinc to aldehydes catalyzed by d-glucosamine derivatives: Highly pronounced effect of trifluoromethylsulfonamide

We present the synthesis of β-hydroxy sulfonamides derived from d-glucosamine and their application as ligands in titanium tetraisopropoxide promoted enantioselective addition of diethylzinc to benzaldehyde and selected aromatic and aliphatic aldehydes. The N-trifluoromethylosulfonamido-d-glucosamine derivative is one of the most active ligands known and only 1 mol% of the ligand is sufficient for efficient catalysis of diethylzinc addition. The reaction is highly enantioselective for some aromatic aldehydes and enantiomeric excess up to 99% was obtained.

Synthesis of novel chiral tridentate aminophenol ligands for enantioselective addition of diethylzinc to aldehydes

Novel chiral tridentate aminophenol ligand (S)-3a was obtained by a Mannich-type reaction of cresol, paraformaldehyde, and (S)-1-(2-methoxyphenyl)-2-methylpropan-1-amine followed by a deprotection step. This tridentate aminophenol ligand shows high yield and enantioselectivity in the diethylzinc additions to a broad range of substrates, including alkyl, aryl, and α,β-unsaturated aldehydes.

Chiral linear polymers bonded alternatively with salen and 1,4-dialkoxy-2,6-diethynylbenzene: synthesis and application to diethylzinc addition to aldehydes

The synthesis of chiral polymers 1 bonded alternatively with salen and 1,4-dialkoxy-2,6-diethynylbenzene was accomplished. These polymers are recyclable and catalyze the Et2Zn addition to aldehydes with good enantioselectivity.

Preparation and application of polymer-grafted Ti-BINOL complexes as chiral catalysts in the enantioselective addition of diethylzinc to aldehydes

Enantiomeric BINOL has been anchored to aminomethylated polystyrene resin at the 3- and 3,3'-positions of BINOL respectively. The resulting functionalized polymers 4 and 7 have been used as chiral ligands in the Ti- catalytic enantioselective addition of

A convergent, scalable synthesis of HIV protease inhibitor PNU-140690

PNU-140690, an inhibitor of the HIV protease enzyme undergoing clinical evaluation as a chemotherapeutic agent for treatment of AIDS, was synthesized by a convergent approach amenable to large-scale preparation in a pilot plant environment. The key step is the aldol addition of nitroaromatic ester (+)-8 to aldehyde 19e. The two stereocenters present in the target molecule were each set independently by resolution of enantiomers. Intermediates along the synthetic routes were chosen to maximize opportunities for isolation and purification by crystallization.

Enantioselective addition of diethylzinc to aromatic aldehydes catalyzed by Ti(BINOL) complex

The enantioselective addition of diethylzine to aldehydes was conveniently achieved by using a catalyst prepared in situ by mixing titanium tetraisopropoxide with S-or R-binaphthol. Optical yields as high as 95.6% were obtained.

Enantioselective addition of diethylzinc to aromatic aldehydes catalyzed by titanium-5,5',6,6',7,7',8,8'-octahydro-1,1-bi-2-naphthol complex

The use of Ti(H8-BINOL=5,5',6,6',7,7',8,8'-octahydro-1,1'-bi-2- naphthol) as a catalyst for the diethylzinc addition to aldehydes has been studied, and high e.e.s (up to 98.5%) were obtained for the chiral alcohol products. The results were sig