472654
N-Boc-2-aminoacetaldehyde
95%
Synonyme(s) :
tert-Butyl N-(2-oxoethyl)carbamate
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About This Item
Formule linéaire :
HCOCH2NHCO2C(CH3)3
Numéro CAS:
Poids moléculaire :
159.18
Numéro MDL:
Code UNSPSC :
12352100
ID de substance PubChem :
Nomenclature NACRES :
NA.22
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Niveau de qualité
Essai
95%
Indice de réfraction
n20/D 1.455 (lit.)
Groupe fonctionnel
aldehyde
amine
Température de stockage
−20°C
Chaîne SMILES
CC(C)(C)OC(=O)NCC=O
InChI
1S/C7H13NO3/c1-7(2,3)11-6(10)8-4-5-9/h5H,4H2,1-3H3,(H,8,10)
Clé InChI
ACNRTYKOPZDRCO-UHFFFAOYSA-N
Informations sur le gène
human ... CTSK(1513)
Description générale
N-Boc-2-aminoacetaldehyde is an organic building block. It reacts with Horner-Wadsworth-Emmons (HWE) reagent to afford γ-aminobutyric acid (GABA)-derived α-keto amide/ester units.[1]
Application
α-Methylenation of this amino aldehyde proceeds in a quick and efficient manner using a recently reported protocol involving formaldehyde and catalysis by either pyrrolidine proprionic acid or the dipeptide L-Pro-β-Ala.[2]
Also used in a three-component synthesis of pyrrolidines involving 1,3-dipolar cycloaddition.[3]
Also used in a three-component synthesis of pyrrolidines involving 1,3-dipolar cycloaddition.[3]
N-Boc-2-aminoacetaldehyde may be employed in the following:
A building block in the synthesis of a protected pyrroloproline.[7]
Code de la classe de stockage
11 - Combustible Solids
Classe de danger pour l'eau (WGK)
WGK 3
Point d'éclair (°F)
235.4 °F - closed cup
Point d'éclair (°C)
113 °C - closed cup
Équipement de protection individuelle
Eyeshields, Gloves, type N95 (US)
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Anniina Erkkilä et al.
The Journal of organic chemistry, 71(6), 2538-2541 (2006-03-11)
A rapid and extremely convenient method for alpha-methylenation of aldehydes with aqueous formaldehyde is described. Two optimal catalytic systems are presented that allow short reaction times and afford the functionalized products in good to excellent yields (up to 99%) and
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Yoshio Hayashi et al.
Chemical communications (Cambridge, England), (20)(20), 2379-2381 (2008-05-14)
Herein, we describe an efficient strategy for the total synthesis of (+)-negamycin using commercially available achiral N-Boc-2-aminoacetaldehyde as starting material with 42% overall yield for a limited number of steps.
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