795280-56-7

Basic information

• Product Name: Oxiraneethanamine,3-ethyl-N-(phenylmethyl)-,(2R,3S)-rel-(9CI)
• Synonyms: Oxiraneethanamine,3-ethyl-N-(phenylmethyl)-,(2R,3S)-rel-(9CI)
• CAS NO: 795280-56-7
• Molecular Formula: C13H19NO
• Molecular Weight: 205.29606
• Product Categories: ETHYL
• Mol File: 795280-56-7.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Oxiraneethanamine,3-ethyl-N-(phenylmethyl)-,(2R,3S)-rel-(9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Oxiraneethanamine,3-ethyl-N-(phenylmethyl)-,(2R,3S)-rel-(9CI)(795280-56-7)
• EPA Substance Registry System: Oxiraneethanamine,3-ethyl-N-(phenylmethyl)-,(2R,3S)-rel-(9CI)(795280-56-7)

Safety Data

• Hazardous Substances Data: 795280-56-7(Hazardous Substances Data)

Upstream product

• 67393-83-3 2-((2SR,3RS)-3-ethyloxiran-2-yl)ethan-1-ol 
• 100-46-9 benzylamine 
• 67393-83-3 2-((2RS,3RS)-3-ethyloxiran-2-yl)ethan-1-ol 

Relevant articles and documents

Highly Regioselective 5-endo-tet Cyclization of 3,4-Epoxy Amines into 3-Hydroxypyrrolidines Catalyzed by La(OTf)3

Highly regioselective intramolecular aminolysis of 3,4-epoxy amines has been achieved. Key features of this reaction are (1) chemoselective activation of epoxides in the presence of unprotected aliphatic amines in the same molecules by a La(OTf)3 catalyst and (2) excellent regioselectivity for anti-Baldwin 5-endo-tet cyclization. This reaction affords 3-hydroxy-2-alkylpyrrolidines stereospecifically in high yields. DFT calculations revealed that the regioselectivity might be attributed to distortion energies of epoxy amine substrates. The use of this reaction was demonstrated by the first enantioselective synthesis of an antispasmodic agent prifinium bromide.

Epoxidation of Primary and Secondary Alkenylammonium Salts with Dimethyldioxirane, Methyl(trifluoromethyl)dioxirane, and m-Chloroperbenzoic Acid. A General Synthetic Route to Epoxyalkylamines

Selective syn-epoxidation of C=C double bonds in primary and secondary alkenylammonium arenesulfonate salts 3H(+), to give the corresponding epoxyalkylammonium salts 4H(+), has been achieved by reaction with electrophilic O-transfer reagents such as m-CPBA, methyl(trifluoromethyl)dioxirane (TFDO), and dimethyldioxirane (DMDO).Epoxyalkylamines 4 are easily obtained in high yields from the corresponding epoxyalkylammonium salts 4H(+) by simple deprotonation with sodium carbonate.The ammonium group deactivates the C=C double bond, and hence the epoxidation rate is slower than in the case of simple olefins.H-Bonding interaction between the ammonium group and the O-transfer reagent (m-CPBA and DMDO) in the transition state is claimed to account for the rate enhancement and diastereoselectivity observed when the necessary conformational requirements are established.The allylic ammonium group is shown to be very efficient in directing the epoxidation with m-CPBA and DMDO on the syn-diastereoface.