(αS)-α-Aminocyclohexaneacetic acid
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(αS)-α-Aminocyclohexaneacetic acid
structure -
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CAS No:
14328-51-9
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Formula:
C8H15NO2
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Chemical Name:
(αS)-α-Aminocyclohexaneacetic acid
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Synonyms:
Cyclohexaneacetic acid,α-amino-,(αS)-;Cyclohexaneacetic acid,α-amino-,L-;Cyclohexaneacetic acid,α-amino-,(S)-;(αS)-α-Aminocyclohexaneacetic acid;L-α-Cyclohexylglycine;(S)-2-Amino-2-cyclohexylacetic acid;(2S)-2-Amino-2-cyclohexylethanoic acid;L-Cyclohexylglycine;(2S)-2-Amino-2-cyclohexylacetic acid
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CAS No:
(αS)-α-Aminocyclohexaneacetic acid Basic Attributes
157.21
157.21
59Q5O5615E
DTXSID90353118
29224999
Characteristics
63.3
-1
1.120±0.06 g/cm3(Predicted)
255 °C (decomp)
292.8±23.0 °C(Predicted)
130.9±22.6 °C
1.510
Soluble
Store at RT.
34.5 º (c=1, 1N HCl 25 ºC)
Safety Information
36/37/38
26-37/39-24/25
Xi
P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
H315
|Warning|H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 3 companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
(αS)-α-Aminocyclohexaneacetic acid Use and Manufacturing
The selective hydrogenation of the optically active phenyl amino acid was carried out in a magnetically stirred stainless-steel autoclave (100 ml). Prior to the loading of the catalyst, the autoclavewas purged three times with hydrogen to expel the air. Typically, a freshly prepared suspension of nanoRu(at)hectorite (0.01592 mmol Ru, 10 ml H2O) and the appropriate amount of the substrate were carefully transferred into the autoclave under inert atmosphere, and then the autoclave was charged with H2 to the desired pressure. The autoclave was placed into the pre-heated heating mantle and the magnetic stirring was started for the indicated reaction time. After the reaction, the autoclave was cooled down and the pressure was released. The reactor was thoroughly rinsed with 2 N NaOH solution to wash out the entire product (in the case of acidic system, 2 N HCl was used). All the collected solutions were filtered (0.22 mm, PTFE) to remove the catalyst and then treated with diluted HCl (or NaOH) solution to adjust the pH to 5.5, which caused the partial precipitation of the product. The suspensionwas then reduced in vacuo to 10 ml in order to complete the precipitation. The precipitate was filtered off, washed with distilled water and dried in vacuo for 24 h.General procedure: Thestartingamino acid (1.0 eq)was dissolved in MeOH (2-4 mL/1 mmol), and catalytic 98%sulfuric acid (~0.1 eq) was then added. The mixture was heated to refluxovernight. The reaction solution was cooled to room temperature andconcentrated in vacuo. The resulting crude residue was dissolved in a sat.NaHCO3 (aq) solution, and extracted with EtOAc. The combined organiclayers were washed with sat. NaHCO3 (aq) and brine, dried over MgSO4and concentrated to afford the desired ester. 14-100%L10-b (1.36 g, 3.72 mmol) was dissolved in PhCl (30 mL).To this solution was added L-cyclohexylglycine (1.17 g, 11.2 mmol) andZnCl2 (1.12 g, 11.2 mmol). The mixture was refluxed for 24 hours.After cooling to room temperature, the mixture was quenched with EtOAc (EtOAc)EtOAc.The mixture was then stirred for 2 h and extracted with EtOAc (2×50 mL).The combined organics were washed with brine, dried over Na2~~The residue was obtained and purified by flash chromatography on silica gel.Elution with PE/EA gave L10 as a white solid (2.1 g, 92% yield).
Computed Properties
Molecular Weight:157.21
XLogP3:-1
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:2
Exact Mass:157.110278721
Monoisotopic Mass:157.110278721
Topological Polar Surface Area:63.3
Heavy Atom Count:11
Complexity:141
Defined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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(αS)-α-Aminocyclohexaneacetic acid
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