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473049

Sigma-Aldrich

(1S,4S)-(−)-2-Boc-2,5-diazabicyclo[2.2.1]heptane

95%

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Synonym(s):
tert-Butyl (1S,4S)-(−)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate
Empirical Formula (Hill Notation):
C10H18N2O2
CAS Number:
Molecular Weight:
198.26
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

95%

optical activity

[α]22/D −44°, c = 1 in chloroform

mp

74-76 °C (lit.)

SMILES string

CC(C)(C)OC(=O)N1C[C@@H]2C[C@H]1CN2

InChI

1S/C10H18N2O2/c1-10(2,3)14-9(13)12-6-7-4-8(12)5-11-7/h7-8,11H,4-6H2,1-3H3/t7-,8-/m0/s1

InChI key

UXAWXZDXVOYLII-YUMQZZPRSA-N

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Show Differences

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This Item
C352226173477516
(1S)-(−)-Camphor 95%

C352

(1S)-(−)-Camphor

(1S)-(−)-Camphanic chloride 98%

226173

(1S)-(−)-Camphanic chloride

N-Boc-2,5-dihydro-1H-pyrrole 96%

477516

N-Boc-2,5-dihydro-1H-pyrrole

mp

74-76 °C (lit.)

mp

177-179 °C (lit.)

mp

71-73 °C (lit.)

mp

-

optical activity

[α]22/D −44°, c = 1 in chloroform

optical activity

-

optical activity

[α]23/D −18°, c = 2 in carbon tetrachloride

optical activity

-

Application

(1S,4S)-(-)-2-Boc-2,5-diazabicyclo[2.2.1]heptane may be used in the preparation of 2-boc-5-(4-nitrophenyl)-2,5-diaza-bicyclo[2.2.1]heptane by reacting with p-nitrobenzene.
It may also be used to develop:
  • indazolylpyrazolo[1,5-a]pyrimidine analogs based B-Raf inhibitors
  • CCR2 antagonists
  • α4β2 nicotinic acetylcholine receptor (nAChR) partial agonists
  • azabicyclic sulfonamide based 11β-hydroxysteroid dehydrogenase type 1 (11β-HSD1) inhibitors

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable


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Design and synthesis of novel CCR2 antagonists: Investigation of non-aryl/heteroaryl binding motifs.
Trujillo JI, et al.
Bioorganic & Medicinal Chemistry Letters, 21(6), 1827-1831 (2011)
4-(Phenylaminomethylene) isoquinoline-1, 3 (2H,4H)-diones as potent and selective inhibitors of the cyclin-dependent kinase 4 (CDK4).
Tsou HR, et al.
Journal of Medicinal Chemistry, 51(12), 3507-3525 (2008)
Synthesis and biological evaluation of novel hybrids of highly potent and selective a4?2-Nicotinic acetylcholine receptor (nAChR) partial agonists.
Zhang HK, et al.
European Journal of Medicinal Chemistry, 124, 689-697 (2016)
Indazolylpyrazolopyrimidine as highly potent B-Raf inhibitors with in vivo activity.
Wang Xi, et al.
Journal of Medicinal Chemistry, 53(21), 7874-7878 (2010)
Azabicyclic sulfonamides as potent 11?-HSD1 inhibitors.
Shah U, et al.
Bioorganic & Medicinal Chemistry Letters, 20(5), 1551-1554 (2010)

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