1256360-50-5

Basic information

• Product Name: 3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6,7,8-tetrahydroquinoline
• Synonyms: 3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6,7,8-tetrahydroquinoline;5,6,7,8-Tetrahydroquinoline-3-boronic acid, pinacol ester
• CAS NO: 1256360-50-5
• Molecular Formula: C₁₅H₂₂BNO₂
• Molecular Weight: 259.15168
• Mol File: 1256360-50-5.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6,7,8-tetrahydroquinoline(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6,7,8-tetrahydroquinoline(1256360-50-5)
• EPA Substance Registry System: 3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6,7,8-tetrahydroquinoline(1256360-50-5)

Safety Data

• Hazardous Substances Data: 1256360-50-5(Hazardous Substances Data)

Usage

General Description

3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6,7,8-tetrahydroquinoline is a chemical compound that contains a tetrahydroquinoline core with a boron-containing cyclic group attached. The boron atom in the compound is part of a boronate ester, and the tetramethyl substitution on the boron atom and tetrahydroquinoline ring make the compound highly stable and resistant to degradation. This chemical may have potential applications in medicinal chemistry, as boron-containing compounds are often used in drug development due to their unique reactivity and biological activity. Additionally, the tetrahydroquinoline structure is found in a variety of biologically active compounds, making this chemical an interesting candidate for further research and development. Overall, 3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6,7,8-tetrahydroquinoline has potential as a valuable building block for the synthesis of new compounds with potential pharmaceutical and biomedical applications.

Upstream product

• 10500-57-9 5,6,7,8-tetrahydroquinoline 
• 73183-34-3 bis(pinacol)diborane 

Downstream Products

• 82132-68-1 3-bromo-5,6,7,8-tetrahydroquinoline 
• 904929-24-4 3-bromo-6,7-dihydroguinolin-8(5H)-one 
• 1260536-88-6 2-((trans-4-hydroxycyclohexyl)amino)-4-(3-isopropyl-4-(5,6,7,8-tetrahydroquinolin-3-yl)-1H-pyrazolo[3,4-b]pyridin-1-yl)benzonitrile 

Relevant articles and documents

Competent Route to Unsymmetric Dimer Architectures: Total Syntheses of (?)-Lycodine and (?)-Complanadines A and B, and Evaluation of Their Neurite Outgrowth Activities

Valuable synthetic routes to the Lycopodium alkaloid lycodine (1) and its unsymmetric dimers, complanadines A (4) and B (5), have been developed. Regioselective construction of the bicyclo[3.3.1]nonane core structure of lycodine was achieved by a remote functionality-controlled Diels–Alder reaction and subsequent intramolecular Mizoroki–Heck reaction. A key coupling reaction of the lycodine units, pyridine N-oxide (66) and aryl bromide (65), through C?H arylation at the C1 position of 66 provided the unsymmetric dimer structure at a late stage of the synthesis. This strategy greatly simplified the construction of the dimeric architecture and functionalization. Complanadines A (4) and B (5) were synthesized by adjusting the oxidation level of the bipyridine mono-N-oxide (67). The diverse utility of this common intermediate (67) suggests a possible biosynthetic pathway of complanadines in Nature. Both enantiomers of lycodine (1) and complanadines A (4) and B (5) were prepared in sufficient quantities for biological evaluation. The effect on neuron differentiation of PC-12 cells upon treatment with culture medium, in which human astrocytoma cells had been cultured in the presence of 1, 4, or 5 was evaluated.

Total syntheses of complanadines A and B

Twice as nice: Total syntheses of dimeric alkaloids, (-)-complanadines A (1) and B (2), were achieved from (-)-lycodine. The unsymmetrical motif was assembled through direct arylation of the pyridine N-oxide. The absolute configuration and specific rotations of complanadines A and B were identified. Cbz=Benzyloxycarbonyl. Copyright