942416-33-3

Basic information

• Product Name: (R)-(+)-3-methyl-5-phenylpentanaldehyde
• Synonyms: (R)-(+)-3-methyl-5-phenylpentanaldehyde
• CAS NO: 942416-33-3
• Molecular Weight: 176.258
• Mol File: 942416-33-3.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: (R)-(+)-3-methyl-5-phenylpentanaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-(+)-3-methyl-5-phenylpentanaldehyde(942416-33-3)
• EPA Substance Registry System: (R)-(+)-3-methyl-5-phenylpentanaldehyde(942416-33-3)

Safety Data

• Hazardous Substances Data: 942416-33-3(Hazardous Substances Data)

Upstream product

• 26429-97-0 methyl (2E)-5-phenyl-2-pentenoate 
• 37868-70-5 5-phenyl-pent-2-enal 
• 75-16-1 methylmagnesium bromide 
• 544-97-8 dimethyl zinc(II) 
• 103766-22-9 2-(3-phenylpropylidene)malonic acid diethyl ester 
• 55053-55-9 (+)-(R)-ethyl 3-methyl-5-phenylpentanoate 
• 33046-84-3 (2E)-5-phenyl-2-pentenal 
• 3277-89-2 phenethylmagnesium bromide 
• 123-73-9 crotonaldehyde 
• 72681-08-4 (E)-3-methyl-5-phenyl-pent-2-en-1-ol 
• 72681-02-8 (Z)-3-Methyl-5-phenyl-2-penten-1-ol 
• 36805-43-3 ethyl (E)-3-methyl-5-phenylpent-2-enoate 

Relevant articles and documents

Iron-Catalyzed Tunable and Site-Selective Olefin Transposition

The catalytic isomerization of C-C double bonds is an indispensable chemical transformation used to deliver higher-value analogues and has important utility in the chemical industry. Notwithstanding the advances reported in this field, there is compelling demand for a general catalytic solution that enables precise control of the C═C bond migration position, in both cyclic and acyclic systems, to furnish disubstituted and trisubstituted alkenes. Here, we show that catalytic amounts of an appropriate earth-abundant iron-based complex, a base and a boryl compound, promote efficient and controllable alkene transposition. Mechanistic investigations reveal that these processes likely involve in situ formation of an iron-hydride species which promotes olefin isomerization through sequential olefin insertion/β-hydride elimination. Through this strategy, regiodivergent access to different products from one substrate can be facilitated, isomeric olefin mixtures commonly found in petroleum-derived feedstock can be transformed to a single alkene product, and unsaturated moieties embedded within linear and heterocyclic biologically active entities can be obtained.

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.

Copper-catalyzed enantioselective 1,4-addition to α,β- unsaturated aldehydes

Figure presented The first asymmetric Cu-catalyzed conjugate addition of dialkylzinc zinc reagents to a large scope of enals in presence of phosphoramidite, SimplePhos, or (R)-BINAP ligands with enantiomeric excesses up to 90% is reported. Moreover, ACA of Grignard reagents afforded moderate to good 1,4-regioselectivities with enantioselectivities up to 90%.