4-N-Boc-aminocyclohexanone Chemical Properties

Melting point:

114-118℃

Boiling point:

335.9±31.0 °C(Predicted)

Density 

1.06±0.1 g/cm3(Predicted)

storage temp. 

2-8°C

solubility 

soluble in Methanol

form 

powder to crystal

pka

12.19±0.20(Predicted)

color 

White to Almost white

InChI

InChI=1S/C11H19NO3/c1-11(2,3)15-10(14)12-8-4-6-9(13)7-5-8/h8H,4-7H2,1-3H3,(H,12,14)

InChIKey

WYVFPGFWUKBXPZ-UHFFFAOYSA-N

SMILES

C(OC(C)(C)C)(=O)NC1CCC(=O)CC1

CAS DataBase Reference

179321-49-4(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,N

Risk Statements 

36/37/38-50

Safety Statements 

26-36/37/39-61

RIDADR 

UN 3077 9 / PGIII

WGK Germany 

3

Hazard Note 

Irritant

HS Code 

29242990

4-N-Boc-aminocyclohexanone Usage And Synthesis

Uses

4-N-Boc-aminocyclohexanone is a chemical that inhibits the proliferation of cancer cells in vitro. It also has an antiproliferative effect on fibroblast cells, which may be due to its ability to inhibit protein synthesis and induce cell death by apoptosis.It can also be used for the preparation of photoresponsive polymers that are used in drug delivery systems. 

Synthesis

The general procedure for the synthesis of 4-N-Boc-aminocyclohexanone from 4-(Boc-amino)cyclohexanol was as follows: a dichloromethane solution of dimethyl sulfoxide (6 mL, containing 2.0 mL of dimethyl sulfoxide, 28.2 mmol) was added dropwise to a dichloromethane solution (30 mL) of oxalyl chloride (1.7 mL, 19.5 mmol) over a 10-minute period at -60°C. The dichloromethane solution was stirred for 10 minutes. After dropwise addition, stirring was continued at -60 °C for 10 min. Subsequently, tert-butyl 4-hydroxycyclohexylcarbamate (2.56 g, 11.9 mmol) was added dropwise to a dichloromethane solution (140 mL) over a period of 35 min and the reaction mixture was stirred at -60 °C for 40 min. Next, triethylamine (8.4 mL, 60.3 mmol) was added at -60 °C, after which the reaction mixture was allowed to warm up naturally to room temperature. After completion of the reaction, water was added to the mixture and extracted with chloroform. The organic layer was washed sequentially with saturated aqueous ammonium chloride solution and saturated aqueous sodium chloride solution, and then dried with magnesium sulfate. The solvent was removed by distillation under reduced pressure and the resulting residue was purified by silica gel column chromatography (eluent: chloroform/ethyl acetate) to give tert-butyl 4-oxocyclohexylcarbamate (2.23 g, 87% yield).1H-NMR (DMSO-d6) data were as follows: 1.06-1.20 (4H, m), 1.35 (9H, s), 1.69-1.76 (4H, m). 3.12-3.31 (2H, m), 4.48 (1H, s), 6.64 (1H, d, J = 7.5 Hz).

References

[1] Patent: EP1403255, 2004, A1. Location in patent: Page 71
[2] Medicinal Chemistry Research, 2013, vol. 22, # 6, p. 2633 - 2644
[3] Patent: WO2015/22664, 2015, A1. Location in patent: Paragraph 00219;00220
[4] Patent: TW2017/36341, 2017, A. Location in patent: Paragraph 0489-0491
[5] Patent: WO2005/21515, 2005, A2. Location in patent: Page/Page column 72-73

4-N-Boc-aminocyclohexanone(179321-49-4)Related Product Information

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