| Identification | Back Directory | [Name]
4-HYDROXY-CYCLOHEXANECARBOXYLIC ACID ETHYL ESTER | [CAS]
3618-04-0 | [Synonyms]
3618-04-0, 17159-80-7, 75877-66-6
3618-04-0, 75877-66-6, 17159-80-7
Ethyl trans-4-Hydroxycyclohexanecarboxylate
trans-Ethyl 4-hydroxycyclohexanecarboxylate
Ethyltrans-4-Hydroxycyclohexanecarboxylate>
Ethyl trans-4-hydroxycyclohexane-1-carboxylate
4-HYDROXY-CYCLOHEXANECARBOXYLIC ACID ETHYL ESTER
ethyl (1r,4r)-4-hydroxycyclohexane-1-carboxylate
trans-4-Hydroxycyclohexanecarboxylic Acid Ethyl Ester
trans-Ethyl (1r,4r)-4-hydroxycyclohexane-1-carboxylate
Cyclohexanecarboxylic acid, 4-hydroxy-, ethyl ester, trans- | [Molecular Formula]
C9H16O3 | [MDL Number]
MFCD16295187 | [MOL File]
3618-04-0.mol | [Molecular Weight]
172.22 |
| Chemical Properties | Back Directory | [Boiling point ]
144°C/12mmHg(lit.) | [density ]
1.093±0.06 g/cm3(Predicted) | [refractive index ]
1.4630 to 1.4670 | [storage temp. ]
Sealed in dry,Room Temperature | [form ]
clear liquid | [pka]
14.98±0.40(Predicted) | [color ]
Colorless to Almost colorless | [InChI]
InChI=1S/C9H16O3/c1-2-12-9(11)7-3-5-8(10)6-4-7/h7-8,10H,2-6H2,1H3/t7-,8- | [InChIKey]
BZKQJSLASWRDNE-ZKCHVHJHSA-N | [SMILES]
[C@@H]1(C(OCC)=O)CC[C@@H](O)CC1 |
| Hazard Information | Back Directory | [Uses]
trans-Ethyl 4-hydroxycyclohexanecarboxylate acts as a reagent in the discovery of Mer kinase inhibitors for the treatment of pediatric acute lymphoblastic leukemia, in the structural activity relationship study of piperidine-based derivatives as novel influenza virus inhibitors. | [Synthesis]
To a solution of ethyl 4-oxocyclohexanecarboxylate (13.5 g, 79 mmol) in methanol (150 mL) at 0 °C was slowly added sodium borohydride (5.3 g, 140 mmol). The reaction mixture was stirred continuously for 3 hours at room temperature. Upon completion of the reaction, the reaction was quenched by the addition of water (50 mL) followed by extraction with ethyl acetate (150 mL x 1, 50 mL x 2). The organic phases were combined, washed with water (50 mL), dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent ratio: hexane-ethyl acetate 1.5:1 to 1:1) to afford ethyl trans-4-hydroxycyclohexanecarboxylate (12 g, 88% yield, cis-trans ratio = 3:7) as a colorless transparent oil.1H NMR (300 MHz, CDCl3, cis-trans mixture) δ: 4.17-4.08 (m, 2H), 3.90 ( bs, 0.3H), 3.68-3.57 (m, 0.7H), 2.42-1.28 (m, 9H), 1.27-1.22 (m, 3H) ppm.(Hydroxyl signal was not observed.) | [References]
[1] Journal of Medicinal Chemistry, 2016, vol. 59, # 19, p. 8967 - 9004
[2] Organic Process Research and Development, 2010, vol. 14, # 4, p. 883 - 889
[3] Patent: WO2005/80317, 2005, A2. Location in patent: Page/Page column 150
[4] Tetrahedron Letters, 2000, vol. 41, # 39, p. 7567 - 7570
[5] Patent: US5175290, 1992, A |
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