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

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

Product Name:
(1H-indol-3-yl)(2,2,3,3-tetramethylcyclopropyl)methanone
Synonyms:
  • (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
CAS:
895152-66-6
MF:
C16H19NO
MW:
241.33
EINECS:
606-227-7
Product Categories:
  • 895152-66-6
Mol File:
895152-66-6.mol
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(1H-indol-3-yl)(2,2,3,3-tetramethylcyclopropyl)methanone Chemical Properties

Boiling point:
375.0±15.0 °C(Predicted)
Density 
1.099±0.06 g/cm3(Predicted)
storage temp. 
2-8°C
solubility 
DMF: 50 mg/ml; DMF:PBS (pH 7.2); (1:7): 0.13 mg/ml; DMSO: 33 mg/ml; Ethanol: 17 mg/ml
form 
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
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(1H-indol-3-yl)(2,2,3,3-tetramethylcyclopropyl)methanone Usage And Synthesis

Description

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.

Uses

(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

Definition

ChEBI: (1H-Indol-3-yl)(2,2,3,3-tetramethylcyclopropyl)methanone is a member of indoles.

Synthesis

 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) + .

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