(1R)-(-)-(10-Camphorsulfonyl)oxaziridine Struktur

(1R)-(-)-(10-Camphorsulfonyl)oxaziridine

Bezeichnung:(1R)-(-)-(10-Camphorsulfonyl)oxaziridine

CAS-Nr104372-31-8

Englisch Name:(1R)-(-)-(10-Camphorsulfonyl)oxaziridine

CBNumberCB9768000

SummenformelC10H15NO3S

Molgewicht229.3

MOL-Datei104372-31-8.mol

(1R)-(-)-(10-Camphorsulfonyl)oxaziridine physikalisch-chemischer Eigenschaften

Schmelzpunkt	170-174 °C
Siedepunkt	317.6±25.0 °C(Predicted)
alpha	-46.6 º (c=2, CHCl3 25 ºC)
Dichte	1.2486 (rough estimate)
Brechungsindex	1.5060 (estimate)
Flammpunkt	170℃
storage temp.	2-8°C
Löslichkeit	Chloroform (Slightly), Methanol (Slightly)
pka	-11.75±0.40(Predicted)
Aggregatzustand	Powder
Farbe	White
Optische Aktivität	[α]20/D 44°, c = 2.2 in chloroform
BRN	6274369
CAS Datenbank	104372-31-8(CAS DataBase Reference)

Sicherheit

Kennzeichnung gefährlicher	Xi
R-Sätze:	36/37/38
S-Sätze:	26-36-24/25
WGK Germany	3
F	10
HS Code	29349990

Gefahreninformationscode (GHS)

(1R)-(-)-(10-Camphorsulfonyl)oxaziridine 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.
S24/25:Berührung mit den Augen und der Haut vermeiden.
Chemische Eigenschaften
White crystalline powder
Verwenden
Reactant involved in:
- Asymmetric synthesis of proton pump inhibitors
- Asymmetric synthesis of polyhydroxylated pyrrolidines
- Diastereoselective hydroxylation of chlorophylls a and b enolate anions
Used in impregnated silica nanoparticles for removal of sulfur mustard from wastewater

Used to modify blebbistatin for investigations of myosin inhibitor design
Verwenden
(1R)-(-)-(10-Camphorsulfonyl)oxaziridine is a useful synthetic intermediate. Used for asymmetric hydroxylation.
Synthese
The enantiopure (1S)-(+)-(Camphorylsulfonyl)oxaziridine and (1R)-(-)-(10-Camphorsulfonyl)oxaziridine and [(8,8- dichlorocamphor)sulfonyl]oxaziridines (2) are commercially available. They can also be prepared on a large scale via the oxidation of corresponding camphorsulfonimines with buffered Potassium Monoperoxysulfate (Oxone) or buffered peracetic acid. Since oxidation takes place from the endo face of the C=N double bond, only a single oxaziridine isomer is obtained. The precursor camphorsulfonimines can be prepared in 3 steps (>80% yield) from inexpensive (+)- and (-)-10-Camphorsulfonic Acids. A variety of (camphorylsulfonyl)oxaziridine derivatives such as (2)-(4) are also readily available via the functionalization of the camphorsulfonimines followed by oxidation.
Synthese
(1R)-(-)-(10-Camphorsulfonyl)oxaziridine is a neutral, aprotic, electrophilic, and asymmetric oxidizing agents for the chemoselective oxidation of many nucleophilic substrates such as sulfides, enamines, enol esters, carbanions, and enolates.
Einzelnachweise
1. Mergelsberg, I.; Gala, D.; Scherer, D.; DiBenedetto, D.; Tanner TL 1992, 33, 161.
2. Davis, F. A.; Kumar, A.; Chen, B.-C. JOC 1991, 56, 1143.
3. Chen, B.-C.; Weismiller, M. C.; Davis, F. A.; Boschelli, D.; Empfield, J. R.; Smith, III, A. B. T 1991, 47, 173.

(1R)-(-)-(10-Camphorsulfonyl)oxaziridine Upstream-Materialien And Downstream Produkte

(1R)-(-)-(10-Camphorsulfonyl)oxaziridine Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

104372-31-8, (1R)-(-)-(10-Camphorsulfonyl)oxaziridine Verwandte Suche:

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