131574-01-1

Basic information

• Product Name: (-)-3-hydroxy-1-methyl-3-phenylazetidin-2-one
• CAS NO: 131574-01-1
• Molecular Weight: 177.203
• Mol File: 131574-01-1.mol

Chemical Properties

• CAS DataBase Reference: (-)-3-hydroxy-1-methyl-3-phenylazetidin-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-3-hydroxy-1-methyl-3-phenylazetidin-2-one(131574-01-1)
• EPA Substance Registry System: (-)-3-hydroxy-1-methyl-3-phenylazetidin-2-one(131574-01-1)

Safety Data

• Hazardous Substances Data: 131574-01-1(Hazardous Substances Data)

Upstream product

• 131574-00-0 (1R,6R)-1,6-Bis-(2-chloro-phenyl)-1,6-diphenyl-hexa-2,4-diyne-1,6-diol; compound with N,N-dimethyl-2-oxo-2-phenyl-acetamide 
• 51579-87-4 N,N-dimethyl-2-oxo-2-phenylacetamide 
• 143168-28-9 [(2S,3S)-3-(Hydroxy-diphenyl-methyl)-1,4-dioxa-spiro[4.5]dec-2-yl]-diphenyl-methanol; compound with N,N-dimethyl-2-oxo-2-phenyl-acetamide 
• 143168-27-8 [(2S,3S)-3-(Hydroxy-diphenyl-methyl)-1,4-dioxa-spiro[4.4]non-2-yl]-diphenyl-methanol; compound with N,N-dimethyl-2-oxo-2-phenyl-acetamide 

Relevant articles and documents

Enantioselective photocyclization of amides to β-lactam derivatives in inclusion crystals with an optically active host

Irradiation of inclusion crystals of 2-(N-acyl-N-alkylamino)cyclohex-2- enones and N,N-dimethylphenylglyoxylamide with chiral host molecules gave the optically active N-alkyl-1-azaspiro[3,5]-nonane-2,5-diones and 3-hydroxy-1- methyl-3-phenylazetidin-2-one

Chiral Arrangement of N-Ethyl-N-isopropylphenylglyoxylamide Molecule in Its Own Crystal and in an Inclusion Crystal with a Host Compound and Their Photoreactions in the Solid State That Give Optically Active β-Lactam Derivatives. X-ray Analytical and CD Spectral Studies

N-Ethyl-N-isopropylphenylglyoxylamide (3c) forms chiral crystal in which its achiral molecules are arranged in a chiral form, and the chirality in the crystal was identified by measurement of the CD spectrum in Nujol mull. Generation of the chirality occurs by twisting of the CO-CO bond of 3c in the crystal. Photoirradiation of the chiral crystal of 3c in the solid state gave optically active β-lactam derivative (4c) of 80% ee. By X-ray analysis, absolute configurations of the chiral crystal and 4c were elucidated. The achiral molecules of 3c are also arranged in chiral forms in inclusion complexes with chiral hosts such as (R,R)-(-)-trans-2,3-bis(hydroxydiphenylmethyl)-1,4-dioxaspiro[4,4]nonane (5a), (R,R)-(-)-trans-2,3-bis(hydroxydiphenylmethyl)-1,4-dioxaspiro[5.4]-decane (5b), and their (S,S)-(+)-enantiomers, 6a and 6b, respectively. The crystal structure of a 1:1 inclusion complex of 3c with 5b (7b) was analyzed. Photoirradiation of 7b in the solid state gave (R)-(+)-4c of 85% ee. Photochemical conversions of some other derivatives of 3c to the corresponding β-lactams were also studied. Interestingly, however, irradiation of the 1:1 inclusion complex of N,N-dimethylglyoxylamide (3a) with 5a, which had been prepared by mixing both components in the absence of solvent, gave (R)-(+)-β-lactam (9a) of 45% ee, although the 1:1 complex that had been prepared by recrystallization of the components from toluene gave (S)-(-)-9a of 100% ee. Mixing of powdered chiral (-)-3c crystal with a 2:1 inclusion complex of 5b and MeOH gave a new 1:1 complex of 5b and chiral (+)-3c. The inversion of the chirality of 3c in the solid state was studied by continuous measurements of CD spectra in Nujol mulls.

Enantioselective photoreaction in inclusion crystal

Mixing of powdered chiral hosts and achiral guest compounds gives inclusion complexes in which the latter molecules are arranged in a chiral form. Freezing of the chirality of the guest compounds by photoirradiation in the solid state gives optically active photoreaction products.

Designs of host/guest molecular and crystal structures

When an optically active host compound was mixed with an achiral guest compound in the solid state, host-guest inclusion crystals were formed by molecular movement and the achiral molecules became arranged in a chiral form in the inclusion crystals.

Achiral molecules move and order themselves in a chiral form in host-guest inclusion crystals

When optically active host compound was mixed with achiral guest compound in the solid state, host-guest inclusion crystals were formed by molecular movement and the achiral molecules became arranged in a chiral form in the inclusion crystals.Mixing of powdered (+)-host crystals with powdered (-)-guest crystals which are formed by a chiral arrangement of achiral guest molecules gave inclusion crystals of (+)-host and the (+)-guest molecules newly produced through an inversion of the (-)-guest molecules during the complexation in the solid state.

Formation by Mixing of Chiral Host-Achiral Guest Inclusion Complexes in which the Guest Molecules are Arranged in a Chiral Form. Production of Optically Active Photocyclisation Compounds by Irradiation of the Inclusion Complexes

Mixing of powdered chiral hosts and achiral N,N-dialkylphenylglyoxylamide guest compounds gives inclusion complexes in which the latter molecules are arranged in a chiral form, although such complexes are not obtained by recrystallisation: the chirality of the guest compounds are frozen by photoreaction which gives optically active β-lactams and oxazolidinones.

Photocyclisation of Phenylglyoxylamides as Inclusion Complexes with an Optically Active Host Derived from Tartaric Acid: Delicate Dependence on the Substituent of the Host and Glyoxylamide

Optically active β-lactams and/or oxazolidinones have been obtained selectively by photoirradiation of a 1:2 inclusion complex of phenylglyoxylamide with an optically active host derived from tartaric acid.Delicate selectivity which is dependent on substituents in the phenylglyoxylamide and the host is described.

SELECTIVE REACTIONS IN THE SOLID STATE AND ORGANIC SOLID-SOLID REACTIONS

Since guest molecules in a host-guest complex are arranged regularly and are packed closely, reaction of the guest in the complex is expected to proceed selectively and efficiently in the solid state.When the host compound is chiral, reaction of the guest would proceed enantioselectively.Some such reactions were studied.Furthermore, some usual organic reactions were found to proceed in the solid state.In some cases, organic solid state reactions proceeded more selectively and much faster than in solution.Such solid-solid reactions were also investigated.