118133-90-7

Basic information

• Product Name: p-methoxybenzaldehyde 9-fluorenyl imine
• Synonyms: p-methoxybenzaldehyde 9-fluorenyl imine
• CAS NO: 118133-90-7
• Molecular Weight: 299.372
• Mol File: 118133-90-7.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: p-methoxybenzaldehyde 9-fluorenyl imine(CAS DataBase Reference)
• NIST Chemistry Reference: p-methoxybenzaldehyde 9-fluorenyl imine(118133-90-7)
• EPA Substance Registry System: p-methoxybenzaldehyde 9-fluorenyl imine(118133-90-7)

Safety Data

• Hazardous Substances Data: 118133-90-7(Hazardous Substances Data)

Upstream product

• 525-03-1 9-aminofluorene 
• 123-11-5 4-methoxy-benzaldehyde 
• 5978-75-6 9H-fluoren-9-amine hydrochloride 

Downstream Products

• 486-25-9 9-fluorenone 
• 3424-93-9 4-methoxyphenylacetamide 
• 7465-87-4 N-benzyl-4-methoxybenzamide 
• 118133-84-9 2,2-spiro(9',9'-fluorenyl)-4-(4'-methoxyphenyl)-7-phenyl-6,8-dioxo-3,7-diazabicyclo<3.3.0>octane 

Relevant articles and documents

Aminofluorene-Mediated Biomimetic Domino Amination-Oxygenation of Aldehydes to Amides

A conceptually novel biomimetic strategy based on a domino amination-oxygenation reaction was developed for direct amidation of aldehydes under metal-free conditions employing molecular oxygen as the oxidant. 9-Aminofluorene derivatives acted as pyridoxamine-5′-phosphate equivalents for efficient, chemoselective, and operationally simple amine-transfer oxygenation reaction. Unprecedented RNH transfer involving secondary amine to produce secondary amides was achieved. In the presence of 18O2, 18O-amide was formed with excellent (95%) isotopic purity.

A catalytic asymmetric Strecker-type reaction promoted by Lewis acid-Lewis base bifunctional catalyst

A general asymmetric Strecker-type reaction is reported, catalyzed by the Lewis acid-Lewis base bifunctional catalyst 1. The reaction of trimethylsilyl cyanide (TMSCN) with various fluorenyl imines, including n-aldimines and α,β-unsaturated imines, proceeds with good to excellent enantioselectivities in the presence of a catalytic amount of phenol as additive (20 mol%) (catalytic system 1). The products were successfully converted to the corresponding amino acid derivatives in high yields without loss of enantiomeric purity. Furthermore, hydrogenation or dihydroxylation of the products from α,β-unsaturated imines afforded saturated or functionalized aminonitriles also without loss of enantiomeric purity. The absolute configuration of the products and a control experiment using catalyst 2 supported the proposed dual activation of the imine and TMSCN by the Lewis acid (Al) and the Lewis base moiety (phosphine oxide) of 1. From the mechanistic studies including kinetic and NMR experiments of the catalytic species, the role of PhOH seems to be a proton source to protonate the anionic nitrogen of the intermediate. Specifically, we have found that TMSCN is more reactive than HCN in this catalytic system, probably due to the activation ability of the phosphine oxide moiety of 1 toward TMSCN. This fact prompted us to develop the novel catalytic system 2, consisting of 1 (9 mol%), TMSCN (20 mol%) and HCN (1.2 mol eq). This new system afforded comparable results with obtained by system 1 (1 (9 mol%)-TMSCN (2 mol eq)-PhOH (20 mol%)).

X=Y-ZH SYSTEMS AS POTENTIAL 1,3-DIPOLES. PART 14. BRONSTED AND LEWIS ACID CATALYSIS OF CYCLOADDITIONS OF ARYLIDENE IMINES OF α-AMINO ACID ESTERS

Cycloadditions of arylidene imines of α-amino acid esters to a range of dipolarophiles show substantial rate enhancements in the presence of Bronsted and Lewis acids.For Bronsted acids the rate is related to the pKa of the acid and cycloadditio