3-(Boc-aminomethyl)cyclobutanone
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3-(Boc-aminomethyl)cyclobutanone

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Category
BOC-Amino Acids
Catalog number
BAT-004792
CAS number
130369-09-4
Molecular Formula
C10H17NO3
Molecular Weight
199.3
3-(Boc-aminomethyl)cyclobutanone
IUPAC Name
tert-butyl N-[(3-oxocyclobutyl)methyl]carbamate
Synonyms
tert-Butyl ((3-oxocyclobutyl)methyl)carbamate
Purity
97.0%
Storage
Store at 2-8°C
InChI
InChI=1S/C10H17NO3/c1-10(2,3)14-9(13)11-6-7-4-8(12)5-7/h7H,4-6H2,1-3H3,(H,11,13)
InChI Key
GEPHRYHDJCQNAB-UHFFFAOYSA-N
Canonical SMILES
CC(C)(C)OC(=O)NCC1CC(=O)C1
1. Palladium-catalyzed radical cascade cyanoalkylsulfonylation/cyclization of 3-arylethynyl-[1,1'-biphenyl]-2-carbonitriles with cyclobutanone oxime esters and DABSO
Nengneng Zhou, Qiankun Xu, Ziqin Xia, Kaimo Kuang, Sixin Wu, Wenping Li, Man Zhang Chem Commun (Camb). 2022 Feb 15;58(14):2335-2338. doi: 10.1039/d1cc06825c.
A palladium-catalyzed radical cascade cyanoalkylsulfonylation/cyclization of 3-arylethynyl-[1,1'-biphenyl]-2-carbonitriles with DABCO·(SO2)2 and cyclobutanone oxime esters via cleavage of a C-C single bond and insertion of SO2 was described. A series of cyanoalkylsulfone-containing cyclopenta[gh]phenanthridines were obtained in moderate-to-good yields, thus featuring mild reaction conditions, a broad substrate scope, and a high functional group tolerance.
2. Modular approach to substituted Boc-protected 4-(aminomethyl)pyrroles
Songzhe Han, Samir Z Zard Org Lett. 2014 Apr 4;16(7):1992-5. doi: 10.1021/ol500544u. Epub 2014 Mar 19.
The radical addition of various α-xanthyl ketones to Boc-protected azetine gives adducts which, when treated with ammonia or primary amines, furnish 2,4-disubstituted, 2,3,4-trisubstituted, and polycyclic pyrroles having a protected aminomethyl group at position 4. An unusual ring-opening was observed in the case of a cyclobutanone precursor.
3. Copper-catalysed Csp3-Csp cross-couplings between cyclobutanone oxime esters and terminal alkynes induced by visible light
Binlin Zhao, Yixiao Wu, Yu Yuan, Zhuangzhi Shi Chem Commun (Camb). 2020 Apr 30;56(34):4676-4679. doi: 10.1039/d0cc00988a. Epub 2020 Mar 25.
A novel transformation for the construction of Csp3-Csp bonds was achieved via a photo-induced copper-catalysed C-C bond cleavage. This approach was applied to prepare a series of highly functionalized alkynyl nitriles using readily available cyclobutanones and terminal alkynes. Mechanistic exploration showed that the in situ generated copper acetylide complex is an effective photosensitive catalyst to promote the C-C bond cleavage of cycloketoxime esters through a radical process.
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