192987-90-9

Basic information

• Product Name: 2-Pyrrolidinone, 4,5-dihydroxy-1-(phenylmethyl)-, (4S)-
• CAS NO: 192987-90-9
• Molecular Formula: C11H13NO3
• Molecular Weight: 207.229
• Mol File: 192987-90-9.mol

Chemical Properties

• CAS DataBase Reference: 2-Pyrrolidinone, 4,5-dihydroxy-1-(phenylmethyl)-, (4S)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Pyrrolidinone, 4,5-dihydroxy-1-(phenylmethyl)-, (4S)-(192987-90-9)
• EPA Substance Registry System: 2-Pyrrolidinone, 4,5-dihydroxy-1-(phenylmethyl)-, (4S)-(192987-90-9)

Safety Data

• Hazardous Substances Data: 192987-90-9(Hazardous Substances Data)

Upstream product

• 101469-91-4 (3S)-1-benzyl-3-hydroxypyrrolidine-2,5-dione 

Downstream Products

• 1017553-60-4 (3aR,6aS)-4-benzyl-2-(3,4-dimethoxyphenyl)-6,6a-dihydro-3aH-pyrrolo[2,3-d]oxazol-5(4H)-one 
• 1017553-59-1 (3aR,6aS)-4-benzyl-2-phenyl-6,6a-dihydro-3aH-pyrrolo[2,3-d]oxazol-5(4H)-one 
• 1017553-57-9 (3aR,6aS)-4-benzyl-2-methyl-6,6a-dihydro-3aH-pyrrolo[2,3-d]oxazol-5(4H)-one 
• 1011295-36-5 (1S,5S)-2-benzyl-6-oxa-2-aza-bicyclo[3.1.0]hexan-3-one 
• 1011295-39-8 (4S,5R)-5-(benzofuran-2-yl)-1-benzyl-4-hydroxypyrrolidin-2-one 
• 1011295-48-9 (4S,5R,E)-1-benzyl-4-hydroxy-5-styrylpyrrolidin-2-one 
• 1011295-37-6 (4S,5S,E)-1-benzyl-4-hydroxy-5-styrylpyrrolidin-2-one 
• 1011295-40-1 (4S,5R)-1-benzyl-5-(3,4-dimethoxyphenyl)-4-hydroxypyrrolidin-2-one 
• 1166275-27-9 (4S,5R)-1-benzyl-4-hydroxy-5-methoxypyrrolidin-2-one 

Relevant articles and documents

Autotandem Catalysis: Inexpensive and Green Access to Functionalized Ketones by Intermolecular Iron-Catalyzed Amidoalkynylation/Hydration Cascade Reaction via N-Acyliminium Ion Chemistry

Iron-based catalysts were applied in cascade-type reactions for the synthesis of different carbonyl compounds. The reactions proceeded by a new iron-catalyzed cascade of alkynylation/hydration by using both the σ- and π-Lewis acid properties of iron salts. The alkynylation reactions of several endo and exocyclic acetoxylactams were achieved with three different catalysts including FeCl3 ? 6H2O, FeCl3, and Fe(OTf)3 showing the efficiency of σ-Lewis acidity of iron (III) salts in catalyzing the alkynylation reaction. We also demonstrated that the reaction sequence could be shortened by the direct use of hydroxylactams, leading to an environmentally friendly protocol, avoiding the need to perform unnecessary lengthy steps. A combination of the hard/soft iron Lewis acid properties was then used to implement an unprecedented tandem intermolecular alkynylation/intramolecular hydration sequence allowing expedient access to a new carbonyl structures from trivial materials.

Reductive cyclization and petasis-like reaction for the synthesis of functionalized γ-lactams

An efficient reductive cyclization strategy was employed for the synthesis of N-substituted β,γ-dihydroxy-γ-lactams. A subsequent Petasis-like reaction (PLR) through nucleophilic additions of boronic acids to intermediate N-acyliminium ions produced substituted γ-lactams. Overall, the application of this protocol provides β,γ-dihydroxy-γ-lactams and functionalized γ-lactams with potential interest for synthetic and bioorganic chemistry.

Diastereoselective borono-Mannich reactions on cyclic N-acyliminium ions

The addition of boronic acids to five- and six-membered ring N-acyliminium ions has been employed to prepare 5- and 6-substituted 4-hydroxypyrrolidin-2-ones and 5-hydroxypiperidin-2-ones, respectively, in a diastereoselective fashion. Crown Copyright