4-N-Boc-aminocyclohexanone CAS 179321-49-4
4-N-Boc-aminocyclohexanone Basic information
| Product Name: | 4-N-Boc-aminocyclohexanone |
| Synonyms: | BOC-4-AMINOCYCLOHEXANONE;(4-OXO-CYCLOHEXYL)-CARBAMIC ACID TERT-BUTYL ESTER;4-N-BOC-AMINOCYCLOHEXANONE;4-N-BOC-4-AMINOCYCLOHEXANONE;4-AMINOCYCLOHEXANONE N-BOC PROTECTED;N-4-BOC-AMINOCYCLOHEXANONE;N-T-BOC-4-AMINOCYCLOHEXANONE;TERT-BUTYL 4-OXOCYCLOHEXYLCARBAMATE |
| CAS: | 179321-49-4 |
| MF: | C11H19NO3 |
| MW: | 213.27 |
| EINECS: | 672-405-6 |
| Product Categories: | Acids and Derivatives;Carbonyl Compounds;pharmacetical;CHIRAL CHEMICALS;Building Blocks;C10 to C11;N-BOC;C11 to C12;Chemical Synthesis;Ethers;New Products for Chemical Synthesis;Nitrogen Compounds;Organic Building Blocks;Oxygen Compounds;Amines;blocks |
| Mol File: | 179321-49-4.mol |
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 |
| Storage Class | 11 - Combustible Solids |
| Hazard Classifications | Aquatic Acute 1 |
| 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 | 224309-64-2 179321-49-4 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 Preparation Products And Raw materials
| Raw materials | 4-N-BOC-AMINO-CYCLOHEXANOL-->BOC-TRANS-4-AMINOCYCLOHEXANOL-->Dimethyl sulfoxide-->Dichloromethane-->Oxalyl chloride-->Triethylamine |
| Preparation Products | 4,4-DIFLUOROCYCLOHEXYLAMINE HYDROCHLORIDE-->(2-AMino-5,6,7,8-tetrahydro-quinazolin-6-yl)-carbaMic acid tert-butyl ester-->4-(4-tert-ButoxycarbonylaMino-cyclohexyl)-piperazine-1-carboxylic acid benzyl ester-->4-Amino-1-methylcyclohexanol hydrochloride-->Trifluoro-methanesulfonic acid 4-tert-butoxycarbonylamino-cyclohex-1-enyl ester-->2-BroMo-4,5,6,7-tetrahydrobenzo[d]thiazol-6-aMine |
