137469-85-3

Basic information

• Product Name: tert-butyl (quinolin-8-yl)carbamate
• Synonyms: tert-butyl (quinolin-8-yl)carbamate
• CAS NO: 137469-85-3
• Molecular Weight: 244.293
• Mol File: 137469-85-3.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: tert-butyl (quinolin-8-yl)carbamate(CAS DataBase Reference)
• NIST Chemistry Reference: tert-butyl (quinolin-8-yl)carbamate(137469-85-3)
• EPA Substance Registry System: tert-butyl (quinolin-8-yl)carbamate(137469-85-3)

Safety Data

• Hazardous Substances Data: 137469-85-3(Hazardous Substances Data)

Upstream product

• 1217336-01-0 C₃₅H₃₆N₆O₅S 
• 1228349-26-5 N-tert-butoxycarbonyl-N-(quinolin-8-yl) Nα-phthaloyl-1-leucinamide 
• 99-09-2 3-nitro-aniline 
• 1581308-72-6 tert-butyl (8-quinolinyl)(2-(trimethylsilyl)benzoyl)carbamate 

Downstream Products

• 578-66-5 8-amino quinoline 
• 137469-86-4 8-(N-tert-Butoxycarbonylamino)-1,2,3,4-tetrahydroquinoline 

Relevant articles and documents

Late-stage and strain-accelerated oxidation enabled synthesis of haouamine A

Herein we report a new synthetic entry to the strained cyclophane alkaloid natural product, haouamine A. The successful strategy featured a rhodium-catalyzed diazo-insertion reaction to install the all-carbon quaternary center and a rhodium-catalyzed intramolecular aziridination reaction to establish the nitrogen-bearing stereocenter, of the target molecule. Most notably, a late-stage, site-selective and strain-accelerated oxidation of a deoxygenated macrocyclic intermediate was successfully implemented, and in doing so provided a novel solution to the infamous biphenol cyclophane system of haouamine A.

Palladium-catalyzed direct C-H silylation and germanylation of benzamides and carboxamides

A palladium-catalyzed regioselective activation of C(sp2)-H and C(sp3)-H bonds of benzamides and carboxamides, followed by coupling with disilanes to afford organosilanes in moderate to high yields, with the aid of 8-aminoquinoline as a directing group, is reported. Catalytic C(sp 2)-H germanylation of benzamides also proceeds under the same palladium catalysis. The reaction tolerates a wide variety of functional groups and is scalable without yield reduction. The bidentate directing group is readily removed and recovered by the reaction with a hydrazine, with concominant generation of an acyl hydrazide.

Total synthesis of celogentin C by stereoselective C-H activation

(Figure Presented) A total gent: Inspired by the biosynthesis of celogentin C, a highly stereoselective and efficient palladium-catalyzed C-H functionalization strategy is employed to construct the key Leu-Trp linkage of this bicyclic compound. A streamlined synthesis is completed in 23 steps from simple amino acid building blocks.