(S)-(-)-1-(4-Pyridyl)ethanol

Bezeichnung:(S)-(-)-1-(4-Pyridyl)ethanol

CAS-Nr54656-96-1

Englisch Name:(S)-(-)-1-(4-Pyridyl)ethanol

CBNumberCB8219787

SummenformelC7H9NO

Molgewicht123.15

MOL-Datei54656-96-1.mol

(S)-(-)-1-(4-Pyridyl)ethanol physikalisch-chemischer Eigenschaften

Schmelzpunkt	67-69 °C(lit.)
Siedepunkt	239.7±15.0 °C(Predicted)
Dichte	1.082±0.06 g/cm3(Predicted)
storage temp.	Sealed in dry,2-8°C
Löslichkeit	soluble in Methanol
pka	13.52±0.20(Predicted)
Aggregatzustand	Needles
Farbe	White
Optische Rotation	[α]20/D 58°, c = 1 in chloroform
BRN	1524527
InChI	1S/C7H9NO/c1-6(9)7-2-4-8-5-3-7/h2-6,9H,1H3/t6-/m0/s1
InChIKey	HVOAMIOKNARIMR-LURJTMIESA-N
SMILES	C[C@H](O)c1ccncc1

Sicherheit

Kennzeichnung gefährlicher	Xi
R-Sätze:	36/37/38
S-Sätze:	26-36
WGK Germany	3
F	3-10
HS Code	29333990
Speicherklasse	11 - Combustible Solids
Hazard Classifications	Eye Irrit. 2 Skin Irrit. 2 STOT SE 3

Gefahreninformationscode (GHS)

(S)-(-)-1-(4-Pyridyl)ethanol Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
S-Sätze Betriebsanweisung:
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.
Chemische Eigenschaften
White needles
Verwenden
(S)-(-)-1-(4-Pyridyl)ethanol is a building block used in the synthesis of macrocycles which act as hydrogenation catalysts as well as other pharmaceutical agents
Synthese

1122-54-9

54656-96-1

The general procedure for the synthesis of (S)-4-pyridine-1-ethanol from 4-acetylpyridine was as follows: first, the relative activities of the 26 substrates were assessed by a previously described assay protocol and the enzyme-to-substrate concentration ratio was adjusted. In this procedure, the activity of α-chloroacetophenone was used as a benchmark (set at 100%). Subsequently, the reduction reaction of aromatic ketones was determined enantioselectively using a NADH regeneration system consisting of KcDH purified from Bacillus subtilis CGMCC 1.1398 and glucose dehydrogenase (GDH). The specific reaction conditions were as follows: 0.5 mM NAD+, 10 mM ketone substrate, 1 U KcDH, 50 mg glucose, and 2 U GDH were added to 1 mL of 50 mM potassium phosphate buffer (pH 7.0). the reaction was carried out for 16 h. After the reaction was carried out, the reaction mixture was homogenized into two parts. One portion was terminated by adding an equal volume of methanol and subsequently analyzed by HPLC to determine the conversion; the other portion was extracted with ethyl acetate and further analyzed for enantiomeric excess (ee). The chiral products were analyzed by HPLC or GC methods, and the specific operating conditions are detailed in Supplementary Table S1.
läuterung methode
Purify it by recrystallisation from pet ether. The m recorded after sublimation was 59.9-60.2o, and 55o after crystallisation from *C6H6/pet ether or pet ether/*C6H6. The (-)-di-O-benzoyl tartrate salt has m 146-148o (from EtOH). [UV, ORD: Harelli & Samori J Chem Soc Perkin Trans 2 1462 1974.] The racemate recrystallises from Et2O with m 74-76o,b 90-94o/1mm. The picrate has m 125-126o (from *C6H6). [Ferles & Attia Collect Czech Chem Commun 38 611 1973, UV, NMR: Nielson et al. J Org Chem 29 2898 1964, Beilstein 21 III/IV 522, 21/2 V 217.]
Einzelnachweise
[1] Organic Letters, 2000, vol. 2, # 12, p. 1749 - 1751
[2] Synthesis, 2009, # 14, p. 2413 - 2417
[3] Advanced Synthesis and Catalysis, 2014, vol. 356, # 10, p. 2293 - 2302
[4] Tetrahedron Asymmetry, 2002, vol. 13, # 20, p. 2201 - 2204
[5] Advanced Synthesis and Catalysis, 2016, vol. 358, # 24, p. 4006 - 4018

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