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

Base Information

• Chemical Name: (1H-indol-3-yl)(2,2,3,3-tetramethylcyclopropyl)methanone
• CAS No.: 895152-66-6
• Molecular Formula: C16H19NO
• Molecular Weight: 241.333
• Hs Code.: 2933990090
• Mol file: 895152-66-6.mol

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

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

Chemical Property:

• Boiling Point: 375.009 °C at 760 mmHg
• PKA: 15.50±0.30(Predicted)
• Flash Point: 188.03 °C
• PSA: 32.86000
• Density: 1.099 g/cm³
• LogP: 4.03280
• Storage Temp.: 2-8°C

Purity/Quality:

99% ^*data from raw suppliers

(1H-Indol-3-yl)(2,2,3,3-tetramethylcyclopropyl)methanone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• 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

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

There total 4 articles about (1H-indol-3-yl)(2,2,3,3-tetramethylcyclopropyl)methanone which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 85.0%

indole (120-72-9) + 2,2,3,3-tetramethylcyclopropanecarbonyl chloride (24303-61-5) → (1H-indol-3-yl)(2,2,3,3-tetramethylcyclopropyl)methanone (895152-66-6)

Guidance literature:

indole; With zirconium(IV) chloride; In dichloromethane; at 0 ℃; for 0.0833333h; Inert atmosphere;

2,2,3,3-tetramethylcyclopropanecarbonyl chloride; In dichloromethane; at 0 ℃; for 4h; Inert atmosphere;

DOI:10.1055/s-0039-1691571

Reference yield: 42.0%

2,2,3,3-tetramethylcyclopropanecarbonyl chloride (24303-61-5) → 1-[(2,2,3,3-tetramethylcyclopropyl)carbonyl]-1H-indole (895157-31-0) + (1H-indol-3-yl)(2,2,3,3-tetramethylcyclopropyl)methanone (895152-66-6)

Guidance literature:

indole; With ethylmagnesium bromide; In tetrahydrofuran; dichloromethane; at 20 ℃; for 0.25h;

With zinc(II) chloride; In tetrahydrofuran; dichloromethane; at 20 ℃; for 0.5h;

2,2,3,3-tetramethylcyclopropanecarbonyl chloride; In tetrahydrofuran; dichloromethane; at 20 ℃; for 6h;

Reference yield:

indole (120-72-9) + 2,2,3,3-tetramethylcyclopropanecarbonyl chloride (24303-61-5) → 1-[(2,2,3,3-tetramethylcyclopropyl)carbonyl]-1H-indole (895157-31-0) + (1H-indol-3-yl)(2,2,3,3-tetramethylcyclopropyl)methanone (895152-66-6)

Guidance literature:

With ethylmagnesium bromide; zinc(II) chloride;

DOI:10.1038/sj.bjp.0707568

upstream raw materials:

2,2,3,3-tetramethylcyclopropanecarbonyl chloride

indole

2,2,3,3-tetramethylcyclopropane-1-carboxylic acid

Downstream raw materials:

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

(2,2,3,3-tetramethylcyclopropyl)[1-(4,4,4-trifluorobutyl)-1H-indol-3-yl]methanone

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

(1-propyl-1H-indole-3-yl)(2,2,3,3-tetramethylcyclopropyl)methanone

Refernces

• 1、 Frost, Jennifer M.,Dart, Michael J.,Tietje, Karin R.,Garrison, Tiffany R.,Grayson, George K.,Daza, Anthony V.,El-Kouhen, Odile F.,Yao, Betty B.,Hsieh, Gin C.,Pai, Madhavi,Zhu, Chang Z.,Chandran, Prasant,Meyer, Michael D.. "Indol-3-ylcycloalkyl ketones: Effects of N1 substituted indole side chain variations on CB2 cannabinoid receptor activity". scheme or table. p. 295 - 315. Retrieved 2010/06/11.
• 2、 Frost, Jennifer M.,Dart, Michael J.,Tietje, Karin R.,Garrison, Tiffany R.,Grayson, George K.,Daza, Anthony V.,El-Kouhen, Odile F.,Miller, Loan N.,Li, Lanlan,Yao, Betty B.,Hsieh, Gin C.,Pai, Madhavi,Zhu, Chang Z.,Chandran, Prasant,Meyer, Michael D.. "Indol-3-yl-tetramethylcyclopropyl ketones: Effects of indole ring substitution on CB2 cannabinoid receptor activity". . p. 1904 - 1912. Retrieved 2008/09/21.