562870-92-2

Basic information

• Product Name: Benzenamine, 4-methoxy-N-[(1S)-1-methyl-2-propenyl]- (9CI)
• Synonyms: Benzenamine, 4-methoxy-N-[(1S)-1-methyl-2-propenyl]- (9CI)
• CAS NO: 562870-92-2
• Molecular Formula: C11H15NO
• Molecular Weight: 177.2429
• Product Categories: METHOXY
• Mol File: 562870-92-2.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Benzenamine, 4-methoxy-N-[(1S)-1-methyl-2-propenyl]- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Benzenamine, 4-methoxy-N-[(1S)-1-methyl-2-propenyl]- (9CI)(562870-92-2)
• EPA Substance Registry System: Benzenamine, 4-methoxy-N-[(1S)-1-methyl-2-propenyl]- (9CI)(562870-92-2)

Safety Data

• Hazardous Substances Data: 562870-92-2(Hazardous Substances Data)

Upstream product

• 100-17-4 para-methoxynitrobenzene 
• 21969-32-4 (1-methylallyl)magnesium chloride 
• 75999-66-5 N-(4-methoxyphenyl)trifluoroacetimidoyl chloride 
• 104-94-9 4-methoxy-aniline 
• 562870-86-4 (R)-2,2,2-trifluoro-N-(4-methoxyphenyl)-N-(1-methylallyl)acetamide 
• 75999-66-5 (Z)-2,2,2-trifluoro-N-(4-methoxyphenyl)acetimidoyl chloride 
• 894777-26-5 2,2,2-trifluoro-N-(4-methoxyphenyl)acetimidic acid but-2-enyl ester 
• 95151-35-2 3-buten-2-yl methyl carbonate 
• 562870-85-3 (S)-2,2,2-trifluoro-N-(4-methoxyphenyl)-N-(1-propylallyl)acetamide 

Relevant articles and documents

Rh(I)/Bisoxazolinephosphine-Catalyzed Regio- And Enantioselective Allylic Substitutions

Rhodium(I)/bisoxazolinephosphine combination has been developed as a general catalyst to achieve the dynamic kinetic asymmetric allylation of a variety of nitrogen, carbon, oxygen, and sulfur pronucleophiles from branched racemic allylic carbonates. Exclusive branch-selectivity and up to 99% enantiomeric excess could be obtained under neutral conditions. Linear allylic substrates (both Z and E) could be converted to the same chiral branched products with excellent regio- and enantioselectivities as well. Chiral π-allyl-Rh(III)/NPN intermediate was isolated and characterized to understand the origin of the high selectivities.

Hydrogen-Borrowing Amination of Secondary Alcohols Promoted by a (Cyclopentadienone)iron Complex

Thanks to a highly active catalyst, the scope of the (cyclopentadienone)iron complex-promoted 'hydrogen-borrowing' (HB) amination has been expanded to secondary alcohols, which had previously been reported to react only in the presence of large amounts of co-catalysts. A range of cyclic and acyclic secondary alcohols were reacted with aromatic and aliphatic amines giving fair to excellent yields of the substitution products. The catalyst was also able to promote the cyclization of diols bearing a secondary alcohol group with primary amines to generate saturated N-heterocycles.

Cobalt-Catalyzed Regio- and Enantioselective Allylic Amination

The first earth-abundant cobalt-catalyzed highly branched- and enantioselective allylic amination of racemic branched allylic carbonates bearing alkyl groups with both aromatic and aliphatic amines has been developed. The process allows rapid access of allylic amines in high yields with exclusively branched selectivity and excellent enantioselectivities (normally 99% ee) under mild reaction conditions.

Paramagnetic palladacycles with PdIII centers are highly active catalysts for asymmetric aza-Claisen rearrangements

A combination of spectroscopic and electrochemical methods - XANES, EXAFS, X-ray, 1H NMR, EPR, Moessbauer, and cyclic voltammetry - demonstrate that the most efficient Pd catalysts for the asymmetric rearrangement of allylic trifluoroacetimidates unexpectedly possess in the activated oxidized form a PdIII center bound to a ferrocene core which remains unchanged (FeII) during the oxidative activation. These are the first recognized PdIII complexes acting as enantioselective catalysts.

The asymmetric aza-claisen rearrangement: development of widely applicable pentaphenylferrocenyl palladacycle catalysts

Systematic studies have been performed to develop highly efficient catalysts for the asymmetric aza-Claisen rearrangement of trihaloacetimidates. Herein, we describe the stepwise development of these catalyst systems involving four different catalyst generations finally resulting in the development of a planar chiral pentaphenylferrocenyl oxazoline palladacycle. This complex is more reactive and has a broader substrate tolerance than all previously known catalyst systems for asymmetric aza-Claisen rearrange-ments. Our investigations also reveal that subtle changes can have a big impact on the activity. With the enhanced catalyst activity, the asymmetric aza-Claisen rearrangement has a very broad scope: the methodology not only allows the formation of highly enantioenriched primary allylic amines, but also secondary and tertiary amines; al-lylic amines with N-substituted quaternary stereocenters are conveniently accessible as well. The reaction conditions tolerate many important functional groups, thus providing stereoselective access to valuable functionalized building blocks, for example, for the synthesis of unnatural amino acids. Our results suggest that face-selective olefin coordination is the enantioselectivitydetermining step, which is almost exclusively controlled by the element of planar chirality.

Macrocyclic ferrocenyl-bisimidazoline palladacycle dimers as highly active and enantioselective catalysts for the Aza-Claisen rearrangement of Z-configured N-para-methoxyphenyl trifluoroacetimidates

(Chemical Equation Presented) In just four steps from ferrocene, macrocyclic ferrocenyl bispalladacyles have been synthesized by using a diastereoselective biscyclopalladation reaction as the key step. The complexes not only possess a fascinating structur

Practical, highly active, and enantioselective ferrocenyl-imidazoline palladacycle catalysts (FIPs) for the aza-claisen rearrangement of N-para-methoxyphenyl trifluoroacetimidates

Just a pinch of catalyst: Just 0.05 mol % of a novel planar chiral ferrocenyl-imidazoline palladacycle catalyst (FIP) is sufficient to catalyze a highly efficient aza-Claisen rearrangement of N-para-methoxyphenyl trifluoroacetimidates and thereby provide access to chiral protected primary allylic amines with unprecedentedly high enantioselectivities (see scheme). (Chemical Equation Presented).

Catalytic asymmetric rearrangement of allylic N-aryl trifluoroacetimidates. A useful method for transforming prochiral allylic alcohols to chiral allylic amines.

[reaction: see text] A useful method for the conversion of prochiral allylic alcohols to chiral allylic amines of high enantiopurity is reported. N-(4-Methoxyphenyl)trifluoroacetimidates are excellent substrates for the palladium(II)-catalyzed allylic imi

N-Allylhydroxylamines from 1,2-Addition of Allyl Grignard Reagents to Nitro Compounds: Generality and Drawbacks of the Reaction

Allyl Grignard reagents react with both aromatic and aliphatic nitro derivatives via 1,2-addition to the nitro group.Conversely, nitroalkanes give either intractable mixtures or exclusively 1,4-conjugate addition.Nitroarenes with high steric hindrance at the ortho position and low aromatic stabilisation give competive or exclusive conjugate addition at the reactive para position.The 'in situ' treatment of the unstable 1,2-adducts with aluminium hydrides in the presence of catalytic amounts of palladium on charcoal provides a general method of synthesis ofN-allylhydroxylamines.LiAlH4 is a very efficient reducing agent, but, in some cases, it does not allow the reduction to be stopped at the hydroxylamino stage.Red-Al and DIBAL-H are less efficient but they ensure greater selectivity.Red-Al avoids the complete reduction to amines except when a strongly electron-donating substituent such as a methoxy group is present in the para position of the aromatic ring.Hydroxylamines can be obtained by reaction of nitrosoarenes followed by aqueous quenching.However, this alternative reaction does not offer any improvement, since relevant amounts of azo and azoxy derivatives are recovered as by-products.