545872
(R)-(+)-Aminoglutethimide
97%
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About This Item
Empirical Formula (Hill Notation):
C13H16N2O2
CAS Number:
Molecular Weight:
232.28
MDL number:
UNSPSC Code:
12352005
PubChem Substance ID:
NACRES:
NA.22
Quality Level
Assay
97%
optical activity
[α]20/D +160°, c = 1 in methanol
mp
115.5-119.5 °C (lit.)
SMILES string
CC[C@@]1(CCC(=O)NC1=O)c2ccc(N)cc2
InChI
1S/C13H16N2O2/c1-2-13(8-7-11(16)15-12(13)17)9-3-5-10(14)6-4-9/h3-6H,2,7-8,14H2,1H3,(H,15,16,17)/t13-/m1/s1
InChI key
ROBVIMPUHSLWNV-CYBMUJFWSA-N
Gene Information
human ... CYP17A1(1586), CYP19A1(1588)
Related Categories
Application
(R)-(+)-Aminoglutethimide can be used:
- As a building block for the development of cephalosporin based prodrug for antibody-directed enzyme prodrug therapy (ADEPT).
- To prepare (R)-3-ethyl-3-(4-(3,4,5-trimethoxybenzylamino)phenyl)piperidine-2,6-dione by reacting with 3,4,5-trimethoxybenzylamine via deaminative coupling reaction.
- To synthesize (R)-2-fluoro-2-(4-methoxyphenyl)-N-(R)-(+)-aminoglutethimide by enantioselective α-fluorination.
Signal Word
Warning
Hazard Statements
Precautionary Statements
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
Target Organs
Respiratory system
Storage Class Code
11 - Combustible Solids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
Regulatory Information
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Synthesis of symmetric and unsymmetric secondary amines from the ligand-promoted ruthenium-catalyzed deaminative coupling reaction of primary amines
Arachchige PT K, et al.
The Journal of Organic Chemistry, 83(9), 4932-4947 (2018)
Toward the development of a cephalosporin-based dual-release prodrug for use in ADEPT
Grant JW and Smyth TP
The Journal of Organic Chemistry, 69(23), 7965-7970 (2004)
Combining asymmetric catalysis with natural product functionalization through enantioselective α-fluorination
E Jeremy, et al.
The Journal of Organic Chemistry, 75(3), 969-971 (2010)
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