1-Phenyl-2-nitropropene

• CAS: 705-60-2
• Catalog Number: ACM705602
• Category: Alkenes
• Molecular Weight: 163.17
• Molecular Formula: C₉H₉NO₂
• Synonyms: (2-Nitro-1-propenyl)benzene;(2-Nitropropenyl)benzene;[(1E)-2-Nitro-1-propenyl]benzene;1-(2-nitropropenyl)-benzen;1-(2-Nitropropenyl)benzene;1-Phenyl-2-nitro-1-propene;1-Phenyl-2-nitro-propylen-(1,2);2-Nitro-1-phenyl-1-propene
• Melting Point: 63-65°C(lit.)
• Hazard Statements: Xi
• RIDADR: UN 1993C 3 / PGIII
• Safety Description: 26-36-37/39
• Supplemental Hazard Statements: H302-H315-H319-H335
• Symbol: GHS07

Case Study

Enantioselective Synthesis of Trans-β-Alkyl-β-Nitrostyrene by Addition of Malonate

Natalja Orlova, et al. Chemistry of Heterocyclic Compounds, 2020, 56, 997-1009.

Enantiopure 4,5-disubstituted pyrrolidin-2-one derivatives with potential biological activity were prepared using Michael adducts formed from the addition of malonates to trans-β-alkyl-β-nitrostyrenes. This reaction was carried out in the presence of a chiral Mg2+ bisoxazoline complex and Ni2+ and Co2+ bis((S,S)- or (R,R)-N,N'-dibenzylcyclohexane-1,2-diamine) complexes. The resulting Michael adducts contained two stereo-centers and served as key precursors for the synthesis of the target compounds.
Addition reaction of 1-Phenyl-2-nitropropene
· As shown in the figure, compound 9a is trans-β-alkyl-β-nitrostyrene whose R is methyl, that is, 1-Phenyl-2-nitropropene.
· The complexes Aa and Ab provided high ee values for all four stereoisomers of adducts 13a-c obtained by the conjugated addition of malonate 10a to β-methylβ-nitrostyrene 9a (1-Phenyl-2-nitropropene).

Custom Q&A

What is the molecular formula of 1-Phenyl-2-nitropropene?

The molecular formula of 1-Phenyl-2-nitropropene is C9H9NO2.

What is the molecular weight of 1-Phenyl-2-nitropropene?

The molecular weight of 1-Phenyl-2-nitropropene is 163.17 g/mol.

What is the IUPAC name of 1-Phenyl-2-nitropropene?

The IUPAC name of 1-Phenyl-2-nitropropene is [(E)-2-nitroprop-1-enyl]benzene.

What is the InChI of 1-Phenyl-2-nitropropene?

The InChI of 1-Phenyl-2-nitropropene is InChI=1S/C9H9NO2/c1-8(10(11)12)7-9-5-3-2-4-6-9/h2-7H,1H3/b8-7+.

What is the InChIKey of 1-Phenyl-2-nitropropene?

The InChIKey of 1-Phenyl-2-nitropropene is WGSVFWFSJDAYBM-BQYQJAHWSA-N.

What is the canonical SMILES of 1-Phenyl-2-nitropropene?

The canonical SMILES of 1-Phenyl-2-nitropropene is CC(=CC1=CC=CC=C1)[N+](=O)[O-].

How many hydrogen bond donor count does 1-Phenyl-2-nitropropene have?

1-Phenyl-2-nitropropene has 0 hydrogen bond donor count.

How many hydrogen bond acceptor count does 1-Phenyl-2-nitropropene have?

1-Phenyl-2-nitropropene has 2 hydrogen bond acceptor count.

How many rotatable bond count does 1-Phenyl-2-nitropropene have?

1-Phenyl-2-nitropropene has 1 rotatable bond count.

What is the topological polar surface area of 1-Phenyl-2-nitropropene?

The topological polar surface area of 1-Phenyl-2-nitropropene is 45.8Ų.