151918-10-4

Basic information

• Product Name: Benzenamine, 4-methoxy-N-(3-phenylpropylidene)-
• Synonyms: N-3-phenylpropylene-4-methoxybenzenamine;Benzenamine,4-methoxy-N-(3-phenylpropylidene);3-phenylpropanal N-(4-methoxyphenyl)imine
• CAS NO: 151918-10-4
• Molecular Formula: C16H17NO
• Molecular Weight: 239.317
• Mol File: 151918-10-4.mol
• Article Data: 9

Chemical Properties

• CAS DataBase Reference: Benzenamine, 4-methoxy-N-(3-phenylpropylidene)-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzenamine, 4-methoxy-N-(3-phenylpropylidene)-(151918-10-4)
• EPA Substance Registry System: Benzenamine, 4-methoxy-N-(3-phenylpropylidene)-(151918-10-4)

Safety Data

• Hazardous Substances Data: 151918-10-4(Hazardous Substances Data)

Upstream product

• 104-53-0 3-phenyl-propionaldehyde 
• 104-94-9 4-methoxy-aniline 

Downstream Products

• 1419351-69-1 benzyl ((E)-2-((2R,4R)-6-methoxy-2-phenethyl-1,2,3,4-tetrahydroquinolin-4-yl)vinyl)carbamate 
• 1244035-05-9 3,4-dibenzyl-1-(4-methoxyphenyl)-1H-pyrrole 
• 1170700-33-0 (S)-N-(4-methoxyphenyl)-α-phenylbenzenepropanamine 
• 562870-93-3 N-(4-methoxyphenyl)-N-[1-(2-phenylethyl)prop-2-en-1-yl]amine 
• 894777-35-6 N-(4-methoxyphenyl)-N-[1-(2-phenylethyl)prop-2-en-1-yl]amine 
• 160191-71-9 (R)-N-(4-methoxyphenyl)-α-methylbenzenepropanamine 

Relevant articles and documents

Asymmetric Petasis Borono-Mannich Allylation Reactions Catalyzed by Chiral Biphenols

Chiral biphenols catalyze the asymmetric Petasis borono-Mannich allylation of aldehydes and amines through the use of a bench-stable allyldioxaborolane. The reaction proceeds via a two-step, one-pot process and requires 2–8 mole % of 3,3′-Ph2-BINOL as the optimal catalyst. Under microwave heating the reaction affords chiral homoallylic amines in excellent yields (up to 99 %) and high enantioselectivies (er up to 99:1). The catalytic reaction is a true multicomponent condensation reaction whereas both the aldehyde and the amine can possess a wide range of structural and electronic properties. Use of crotyldioxaborolane in the reaction results in stereodivergent products with anti- and syn-diastereomers both in good diastereoselectivities and enantioselectivities from the corresponding E- and Z-borolane stereoisomers.

An efficient three-component synthesis of homoallylic amines catalysed by MgI2 etherate

A three-component reaction of aldehydes, amines and allyltributylstannane was efficiently carried out to afford the corresponding homoallylic amine derivatives in the presence of 20 mol% of MgI2 etherate [(MgI 2?(OEt2)n] under mild and neutral reaction conditions in good to excellent yields.

Studies on the bisoxazoline- and (-)-sparteine-mediated enantioselective addition of organolithium reagents to imines

The enantioselective addition of organolithium reagents to N-anisylaldimines promoted by chiral bisoxazolines and (-)-sparteine as external ligands is described. This reaction proceeds readily with a wide range of aldimine substrates (aliphatic, aromatic, olefinic) and organolithium nucleophiles (Me, n-Bu, Ph, vinyl) in excellent yields (81-99%) and with high enantioselectivities (up to 97:3.0 er). The external ligands can be used in substoichiometric amounts albeit with slightly attenuated enantioselectivities. A systematic evaluation of the structural features of the bisoxazolines revealed a primary contribution from the substituent at C(4) and a secondary influence from the bridging substituents. A computational analysis (PM3) provided a clear rationalization for the origin of enantioselectivity.