(1H-indol-3-yl)(2,2,3,3-tetramethylcyclopropyl)methanone

(1H-indol-3-yl)(2,2,3,3-tetramethylcyclopropyl)methanone Struktur
895152-66-6
CAS-Nr.
895152-66-6
Englisch Name:
(1H-indol-3-yl)(2,2,3,3-tetramethylcyclopropyl)methanone
Synonyma:
UR-144 Impurity 3;tert-butyl 4-acetoxy-octahydroindole-1-carboxylate;(1H-indol-3-yl)(2,2,3,3-tetramethylcyclopropyl)methanone;Methanone, 1H-indol-3-yl(2,2,3,3-tetramethylcyclopropyl)-
CBNumber:
CB72490299
Summenformel:
C16H19NO
Molgewicht:
241.33
MOL-Datei:
895152-66-6.mol

(1H-indol-3-yl)(2,2,3,3-tetramethylcyclopropyl)methanone Eigenschaften

Siedepunkt:
375.0±15.0 °C(Predicted)
Dichte
1.099±0.06 g/cm3(Predicted)
storage temp. 
2-8°C
Löslichkeit
DMF: 50 mg/ml; DMF:PBS (pH 7.2); (1:7): 0.13 mg/ml; DMSO: 33 mg/ml; Ethanol: 17 mg/ml
Aggregatzustand
A crystalline solid
pka
15.50±0.30(Predicted)
InChI
InChI=1S/C16H19NO/c1-15(2)14(16(15,3)4)13(18)11-9-17-12-8-6-5-7-10(11)12/h5-9,14,17H,1-4H3
InChIKey
WYZQBEQQQKCTHM-UHFFFAOYSA-N
SMILES
C(C1C2=C(NC=1)C=CC=C2)(C1C(C)(C)C1(C)C)=O
Sicherheit
  • Risiko- und Sicherheitserklärung
  • Gefahreninformationscode (GHS)
Bildanzeige (GHS) GHS hazard pictograms
Alarmwort Warnung
Gefahrenhinweise
Code Gefahrenhinweise Gefahrenklasse Abteilung Alarmwort Symbol P-Code
H302 Gesundheitsschädlich bei Verschlucken. Akute Toxizität oral Kategorie 4 Warnung GHS hazard pictogramssrc="/GHS07.jpg" width="20" height="20" /> P264, P270, P301+P312, P330, P501
H413 Kann für Wasserorganismen schädlich sein, mit langfristiger Wirkung. Langfristig (chronisch) gewässergefährdend Kategorie 4
Sicherheit
P264 Nach Gebrauch gründlich waschen.
P264 Nach Gebrauch gründlich waschen.
P270 Bei Gebrauch nicht essen, trinken oder rauchen.
P301+P312 BEI VERSCHLUCKEN: Bei Unwohlsein GIFTINFORMATIONSZENTRUM/Arzt/... (geeignete Stelle für medizinische Notfallversorgung vom Hersteller/Lieferanten anzugeben) anrufen.
P330 Mund ausspülen.
P501 Inhalt/Behälter ... (Entsorgungsvorschriften vom Hersteller anzugeben) zuführen.

(1H-indol-3-yl)(2,2,3,3-tetramethylcyclopropyl)methanone Chemische Eigenschaften,Einsatz,Produktion Methoden

Beschreibung

UR-144 and XLR11 are potent synthetic cannabinoids (CBs) that have been identified as adulterants of herbal products. (1H-Indol-3-yl)(2,2,3,3-tetramethylcyclopropyl)methanone is the scaffold for UR-144, XLR11, and a number of additional synthetic CBs. The tetramethylcyclopropyl group typically confers selectivity for the peripheral CB2 receptor. However, the addition of substituents at the N1-amine of the aminoalkylindole group is necessary for high affinity at either CB1 or CB2. This product is intended for forensic and research applications.

Verwenden

(1H-Indol-3-yl)(2,2,3,3-tetramethylcyclopropyl)methanone is the scaffold for UR-144, XLR11, and a number of additional synthetic CBs. The tetramethylcyclopropyl group typically confers selectivity for the peripheral CB2 receptor

Synthese

 To a solution of indole (11 g, 95 mmol) in 30 mL of dichloromethane at ambient temperature was added 105 mL of a 1 M solution of ethyl magnesium bromide in tetrahydrofuran (THF) (105 mmol) δropwise via syringe pump. After the addition was complete, the solution was stirred for 15 min at which time 105 mL of a 1 M solution of ZnCl2 in Et2O (105 mmol) was added. The mixture was stirred for an additional 30 min, and then 2,2,3,3-tetramethylcyclopropane carbonyl chloride (95 mmol) in 50 mL of dichloromethane was added via cannula. The mixture was stirred for 6 h at ambient temperature and then was quenched with 50 mL of saturated, aqueous NH4Cl and diluted with 50 mL of dichloromethane. The layers were separated, and the aqueous layer was extracted with dichloromethane (3 × 30 mL). The combined organics were washed with 20 mL of H2O and then were dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The crude material was purified via column chromatography (SiO2, 50% ethyl acetate/ hexanes) to give 9.7 g of the major regioisomer (1H-indol-3-yl)(2,2,3,3-tetramethylcyclopropyl)methanone (40 mmol, 42% yield) and 6.1 g of the minor regioisomer of 1-[(2,2,3,3-tetramethylcyclopropyl) carbonyl]-1H-indole (25 mmol, 27% yield). 1H NMR (major product) (300 MHz, CD3OD) δ ppm 1.32 (s, 6 H), 1.33 (s, 6 H), 2.14 (s, 1 H), 7.12-7.24 (m, 2 H), 7.38-7.46 (m, 1 H), 8.02 (s, 1 H), 8.19-8.25 (m, 1 H); 1H NMR (minor product) (300 MHz, CD3OD) δ ppm 1.29 (s, 6 H), 1.34 (s, 6 H), 1.94 (s, 1 H), 6.66 (dd,J =3.7, 0.7 Hz, 1 H), 7.16-7.32 (m, 2 H), 7.51-7.58 (m, 1 H), 7.67 (d, J = 3.7 Hz, 1 H), 8.32-8.39 (m, 1 H); MS (major and minor regioisomers) (DCI/NH3) m/z 242 (M + H) + .
(1H-indol-3-yl)(2,2,3,3-tetramethylcyclopropyl)methanone synthesis

(1H-indol-3-yl)(2,2,3,3-tetramethylcyclopropyl)methanone Upstream-Materialien And Downstream Produkte

Upstream-Materialien

Downstream Produkte


(1H-indol-3-yl)(2,2,3,3-tetramethylcyclopropyl)methanone Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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  • (1H-indol-3-yl)(2,2,3,3-tetramethylcyclopropyl)methanone
  • tert-butyl 4-acetoxy-octahydroindole-1-carboxylate
  • Methanone, 1H-indol-3-yl(2,2,3,3-tetramethylcyclopropyl)-
  • UR-144 Impurity 3
  • 895152-66-6
  • 895152-66-6
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