40847-05-0

Basic information

• Product Name: Benzenepropanamide, a-amino-N-(1,1-dimethylethyl)-, (S)-
• CAS NO: 40847-05-0
• Molecular Formula: C13H20N2O
• Molecular Weight: 220.315
• Mol File: 40847-05-0.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: Benzenepropanamide, a-amino-N-(1,1-dimethylethyl)-, (S)-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzenepropanamide, a-amino-N-(1,1-dimethylethyl)-, (S)-(40847-05-0)
• EPA Substance Registry System: Benzenepropanamide, a-amino-N-(1,1-dimethylethyl)-, (S)-(40847-05-0)

Safety Data

• Hazardous Substances Data: 40847-05-0(Hazardous Substances Data)

Upstream product

• 13734-34-4 N-tert-butoxycarbonyl-L-phenylalanine 
• 17186-44-6 (S)-benzyl (1-(tert-butylamino)-1-oxo-3-phenylpropan-2-yl)carbamate 
• 1161-13-3 N-Cbz-L-Phe 
• 63-91-2 L-phenylalanine 

Downstream Products

• 908253-03-2 (S)-N-tert-butyl-3-phenylpropane-1,2-diamine 
• 714970-51-1 [2-[2-(1-tert-butylcarbamoyl-2-phenyl-ethylcarbamoyl)-pyrrolidin-1-yl]-1-(4-hydroxy-benzyl)-2-oxo-ethyl]-carbamic acid tert-butyl ester 

Relevant articles and documents

Direct synthesis of anthracenes from o-tolualdehydes and aryl iodides through Pd(II)-Catalyzed sp3 C–H arylation and electrophilic aromatic cyclization

The first direct synthesis of substituted anthracenes from o-tolualdehydes and aryl iodides via a Pd(II)-catalyzed C–H arylation using an alcohol-bearing transient directing group and subsequent AgOTf-assisted electrophilic aromatic cyclization is described. New transient directing groups consisting of amino acids and amino alcohols enhanced the reactivity, and the C–H arylation was complete in 12 h at 90 °C. By simply changing the silver salt to silver triflate, the one-pot synthesis of anthracene derivatives was carried out using the present reaction conditions.

Highly enantioselective epoxidation of α,β-unsaturated ketones catalyzed by primary-secondary diamines

The asymmetric epoxidation of α,β-unsaturated ketones has been achieved by using functional and readily accessible primary-secondary diamines as the catalysts, giving the useful alkyl epoxy products with good yields and high enantioselectivities (up to 99% ee). Copyright

Development of potent bifunctional endomorphin-2 analogues with mixed μ-/δ-opioid agonist and δ-opioid antagonist properties

The C terminus of endomorphin-2 (EM-2) analogues (Tyr-Pro-Phe-NH-X) was modified with aromatic, heteroaromatic, or aliphatic groups (X = phenethyl,benzyl, phenyl, naphthyl, pyridyl, quinolyl, isoquinolyl, tert-butyl, cyclohexyl, or adamantyl; 3-18) to study their effect on opioid activity. Only 9 (1-naphthyl), 11 (5-quinolyl), 16 (cyclohexyl), and 18 (2-adamantyl) exhibited μ-opioid receptor affinity in the nanomolar range (Ki = 2.41-6.59 nM), which, however, was 3-to 10-fold less than the parent peptide. Replacement of Tyr1 by Dmt (2′,6′-dimethyl-L-tyrosine) (19-32) exerted profound effects: (i) acquisition of high μ-opioid receptor affinity (Ki = 0.11-0.52 nM) except 23 (Ph); (ii) presence of potent functional μ-opioid receptor agonism (IC50 1]EM-2), 27 (1-naphthyl), 29 (5-quinolyl), and 32 (5-isolquinolyl); (iii) association of weak δ-opioid antagonist activity (pA2 = 5.41-7.18) except 19 ([Dmt1]EM-2), 20 (H), 27 (1-naphthyl), and in particular 29 (5-quinolyl) with its potent δ-agonism (IC50 = 0.62 nM, pA2 = 5.88); (iv) production of antinociception after ic administration of 32 (5-isoquinolyl) in mice, a bioactivity absent in the corresponding Tyr1 analogue (14); and (v) preferential cis orientation (cis/trans = 3:2 to 7:3) at the Dmt-Pro amide bond, in contrast to the Tyr-Pro amide trans orientation (cis/trans = 1:2 to 1:3). Thus, [Dmt1]EM-2 analogues with hydrophobic C-terminal extensions provide model compounds with potent μ-opioid receptor bioactivity and dual functional agonism.