27855-02-3

Basic information

• Product Name: (3S)-3-Phenylpentanal
• Synonyms: (3S)-3-Phenylpentanal
• CAS NO: 27855-02-3
• Molecular Weight: 162.232
• Mol File: 27855-02-3.mol
• Article Data: 20

Chemical Properties

• CAS DataBase Reference: (3S)-3-Phenylpentanal(CAS DataBase Reference)
• NIST Chemistry Reference: (3S)-3-Phenylpentanal(27855-02-3)
• EPA Substance Registry System: (3S)-3-Phenylpentanal(27855-02-3)

Safety Data

• Hazardous Substances Data: 27855-02-3(Hazardous Substances Data)

Upstream product

• 2386-64-3 ethylmagnesium chloride 
• 138234-70-5 (4R)-2-((E)-2-Phenylethenyl)-4-phenyl-1,3-oxazolidine 
• 14371-10-9 (E)-3-phenylpropenal 
• 557-20-0 diethylzinc 
• 29743-74-6 ethyl (E)-3-phenyl-2-pentenoate 
• 93-55-0 1-phenyl-propan-1-one 
• 201230-82-2 carbon monoxide 
• 2039-93-2 1-ethylstyrene 
• 1576-87-0 trans-2-pentenal 
• 100-58-3 phenylmagnesium bromide 
• 137845-37-5 4-methyl-N-((1E,2E)-3-phenylallylidene)benzenesulfonamide 
• 384333-59-9 (E)-3-phenyl-pent-2-en-1-ol 
• 104-55-2 3-phenyl-propenal 
• 925-90-6 ethylmagnesium bromide 

Downstream Products

• 2845-25-2 (+)-(S)-3-phenylpentan-1-ol 
• 85000-01-7 (3S)-3-Phenylpentyl-acetat 

Relevant articles and documents

NMR-spectroscopic and solid-state investigations of cometal-free asymmetric conjugate addition: A dinuclear paracyclophaneimine zinc methyl complex

We present herein the first indications for dimeric structures in cometal-free asymmetric conjugate addition reactions of dialkylzinc reagents with aldehydes. These are revealed by nonlinear effect (NLE) studies. A monomer-dimer equilibrium can be assumed which explains the increase of the ee value in the product over time. Also, DOSY NMR spectroscopic measurements indicate the existence of the catalyst as [LZnEt]n complexes in solution. Additionally, the first X-ray structure of a zinc complex with a [2.2]paracyclophane ligand was determined. The structures of the zinc complexes are supported by DFT calculations of monomeric and dimeric species.

Copper-Catalyzed Enantioselective Conjugate Addition to α,β-Unsaturated Aldehydes with Various Organometallic Reagents

β-Substituted aldehydes constitute a very important class of compounds found in nature. Synthesis of this motif can be envisioned by C-C bond formation on enals. For this purpose, we report herein the development of enantioselective copper-catalyzed conjugate addition of various organometallic reagents to α,β-unsaturated aldehydes with (R)-H8BINAP, (R)-TolBINAP, and (R)-SEGPHOS as chiral ligands. Three sets of conditions were successfully developed and several enals were used. Reactivity and regio- and enantioselectivities were strongly dependent on reaction conditions and substrates. Good to excellent regio- and enantioselectivities were obtained with zinc reagents R2Zn and aluminum reagents R3Al. However, the asymmetric conjugate addition of Grignard reagents afforded only moderate to good regio- and enantioselectivities.

Enantioselective isomerization of primary allylic alcohols into chiral aldehydes with the tol-binap/dbapen/ruthenium(II) catalyst

Efficient isomerization: The title reaction was catalyzed by the [RuCl 2{(S)-tol-binap}{(R)-dbapen}]/KOH system in ethanol at 25°C (see scheme). A series of E- and Z-configured aromatic and aliphatic allylic alcohols, including a simple primary alkyl-substituted compound (E)-3-methyl-2-hepten-1-ol, were transformed into the chiral aldehydes with at least 99 % ee. dbapen=2-dibutylamino-1-phenylethylamine, tol-binap=2,2′- bis(di-4-tolylphosphanyl)-1,1′-binaphthyl. Copyright