4-N-Cbz-cyclohexanone Chemical Properties

Melting point:

86-87°C

Boiling point:

427.3±44.0 °C(Predicted)

Density 

1.17±0.1 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Room Temperature

form 

solid

pka

11.98±0.20(Predicted)

Appearance

White to off-white Solid

InChI

InChI=1S/C14H17NO3/c16-13-8-6-12(7-9-13)15-14(17)18-10-11-4-2-1-3-5-11/h1-5,12H,6-10H2,(H,15,17)

InChIKey

VHXBIBFCJISKFA-UHFFFAOYSA-N

SMILES

C(OCC1=CC=CC=C1)(=O)NC1CCC(=O)CC1

CAS DataBase Reference

16801-63-1(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36

Safety Statements 

26

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29242990

4-N-Cbz-cyclohexanone Usage And Synthesis

Application

4-N-Benzyloxycarbonylaminocyclohexanone can be used as an organic synthesis intermediate and a pharmaceutical intermediate in laboratory research and development as well as in chemical production synthesis.

Synthesis

General procedure for the synthesis of 4-N-benzyloxycarbonylaminocyclohexanone from benzyl (trans-4-hydroxycyclohexyl)carbamate: synthesis of compound 120.3. Jones reagent (~10 mL) was added slowly and dropwise to a solution of compound 120.2 (7.0 g, 28.08 mmol, 1.00 eq.) in acetone (100 mL) at 0 °C. The reaction process was monitored by thin layer chromatography (TLC). After stirring the reaction mixture for 30 minutes, the reaction was quenched with saturated aqueous sodium bisulfite (NaHSO3) solution. Subsequently, extraction was performed with ethyl acetate (EtOAc, 3 x 100 mL). The organic layers were combined, washed with saturated aqueous sodium chloride (NaCl), dried over anhydrous sodium sulfate (Na2SO4), and finally concentrated under reduced pressure to give 5.0 g (72% yield) of compound 120.3 as a white solid.

References

[1] Journal of Organic Chemistry, 2012, vol. 77, # 6, p. 3005 - 3009
[2] Bioorganic and Medicinal Chemistry, 2010, vol. 18, # 10, p. 3387 - 3402
[3] Synthetic Communications, 1990, vol. 20, # 7, p. 1073 - 1082
[4] Patent: WO2014/194242, 2014, A2. Location in patent: Paragraph 00693; 00695
[5] Patent: WO2015/164374, 2015, A1. Location in patent: Paragraph 00288; 00290

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