5,6,7,8-Tetrahydro-1,6-naphthyridine

Base Information

• Chemical Name: 5,6,7,8-Tetrahydro-1,6-naphthyridine
• CAS No.: 80957-68-2
• Molecular Formula: C8H10N2
• Molecular Weight: 134.181
• Hs Code.: 2933990090
• DSSTox Substance ID: DTXSID40526259
• Wikidata: Q72506302
• Mol file: 80957-68-2.mol

Synonyms:5,6,7,8-tetrahydro-1,6-naphthyridine;tetrahydro-1,6-naphthyridine

Chemical Property of 5,6,7,8-Tetrahydro-1,6-naphthyridine

Chemical Property:

• Boiling Point: 47.62 °C at 760 mmHg
• PKA: 7.95±0.20(Predicted)
• Flash Point: 103.557 °C
• PSA: 24.92000
• Density: 1.069 g/cm³
• LogP: 1.05610
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• XLogP3: 0.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 134.084398327
• Heavy Atom Count: 10
• Complexity: 114

Purity/Quality:

97% ^*data from raw suppliers

5,6,7,8-Tetrahydro-1,6-naphthyridine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CNCC2=C1N=CC=C2
• Uses: 5,6,7,8-Tetrahydro-1,6-naphthyridine is used in the synthetic preparation of quinolizidinone carboxylic acid selective M1 allosteric modulators.

Technology Process of 5,6,7,8-Tetrahydro-1,6-naphthyridine

There total 11 articles about 5,6,7,8-Tetrahydro-1,6-naphthyridine 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: 100.0%

3-bromo-5,6,7,8-tetrahydro-1,6-naphthyridine (625100-00-7) → 5,6,7,8-tetrahydro-1,6-naphthyridine (80957-68-2)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In ethanol; for 3.5h; under 2844.39 Torr;

DOI:10.1021/acs.jmedchem.7b01171

Reference yield: 94.0%

6-benzyl-5,6,7,8-tetrahydro-1,6-naphthyridine (75510-02-0) → 5,6,7,8-tetrahydro-1,6-naphthyridine (80957-68-2)

Guidance literature:

With hydrogen; palladium on activated charcoal; In acetic acid; at 50 - 60 ℃;

DOI:10.1248/cpb.32.2522

Reference yield: 94.0%

→ 5,6,7,8-tetrahydro-1,6-naphthyridine (80957-68-2)

Guidance literature:

upstream raw materials:

6-benzyl-5,6,7,8-tetrahydro-1,6-naphthyridine

1-phenylmethyl-4-piperidone

3-bromo-5,6,7,8-tetrahydro-1,6-naphthyridine

methyl 2-methylnicotinate

Downstream raw materials:

6-<2-<4-(2-methoxyphenyl)-1-piperazinyl>-1-methyl-2-oxoethyl>-5,6,7,8-tetrahydro-1,6-naphthyridine

7,8-dihydro-5H-[1,6]naphthyridine-6-carboxylic acid tert-butyl ester

tert‐butyl 2‐oxo‐1,5,7,8‐tetrahydro‐1,6‐naphthyridine‐6(2H)‐carboxylate

N-(2-fluoro-4-chlorophenyl)-4-[(7,8-dihydro-1,6-naphthyridin-6(5H)-yl)carbonyl]-( 5-methyl)1,3-thiazol-2-amine

Refernces

Domino Aza-Michael-ih-Diels-Alder Reaction to Various 3-Vinyl-1,2,4-triazines: Access to Polysubstituted Tetrahydro-1,6-naphthyridines

10.1021/acs.orglett.7b02132

The research focuses on the development of a novel three-step domino transformation involving the aza-Michael-inverse electron-demand-hetero-Diels?Alder/retro-Diels?Alder (ihDA/rDA) reaction between primary and secondary propargylamine derivatives and 3-vinyl-1,2,4-triazines. The purpose of this study is to access polysubstituted tetrahydro-1,6-naphthyridine scaffolds, which are of significant interest in pharmaceutical industries due to their potential biological activities. The researchers successfully developed a straightforward method to synthesize these complex molecular structures, highlighting the versatility of 3-vinyl-1,2,4-triazines as both Michael acceptors and 4π components in the ihDA/rDA sequence. The study concluded that this approach offers a unique and efficient pathway to synthesize diversely substituted tetrahydro-1,6-naphthyridines, which could be valuable in drug discovery programs.

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