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545872

Sigma-Aldrich

(R)-(+)-Aminoglutethimide

97%

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Empirical Formula (Hill Notation):
C13H16N2O2
CAS Number:
55511-44-9
Molecular Weight:
232.28
UNSPSC Code:
12352005
PubChem Substance ID:
24878857
NACRES:
NA.22

Quality Level

100

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.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

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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