1,2,3,4-Tetrahydroquinolin-2-one

Base Information

• Chemical Name: 1,2,3,4-Tetrahydroquinolin-2-one
• CAS No.: 553-03-7
• Molecular Formula: C9H9NO
• Molecular Weight: 147.177
• Hs Code.: 29337900
• Mol file: 553-03-7.mol

Synonyms:Carbostyril,3,4-dihydro- (7CI,8CI);Hydrocarbostyril (6CI);1,2,3,4-Tetrahydro-2(1H)-quinolinone;1,2,3,4-Tetrahydro-2-oxoquinoline;1,2,3,4-Tetrahydroquinolin-2-one;2-Oxo-1,2,3,4-tetrahydroquinoline;3,4-Dihydro-1H-quinolin-2-one;3,4-Dihydro-2(1H)-quinolone;3,4-Dihydro-2-quinolinol;3,4-Dihydro-2-quinolinone;3,4-Dihydro-2-quinolone;3,4-Dihydrocarbostyril;3,4-Dihydroquinolin-2(1H)-one;NSC 49170;o-Aminohydrocinnamic acid lactam;3,4-Dihydro-2(1H)-quinolinone;

Chemical Property of 1,2,3,4-Tetrahydroquinolin-2-one

Chemical Property:

• Appearance/Colour: Off-white crystalline powder
• Vapor Pressure: 0.000194mmHg at 25°C
• Melting Point: 165-167 °C
• Refractive Index: 1.564
• Boiling Point: 328.1 °C at 760 mmHg
• PKA: 14.76±0.20(Predicted)
• Flash Point: 189.4 °C
• PSA: 29.10000
• Density: 1.142 g/cm³
• LogP: 1.70930
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Sensitive.: Light Sensitive
• Water Solubility.: Slightly soluble in water.

Purity/Quality:

99% ^*data from raw suppliers

3,4-Dihydro-2-quinolone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn,Xi
• Statements: 22-36/37/38-43
• Safety Statements: 26-36/37

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 3,4-Dihydro-2-(1H)-quinolinone may be employed as medium supplement in the culture medium of Pseudomonas ayucida during enrichment culture experiments. It is used to prepare potent bicyclic peptide deformylase inhibitors with antibacterial effects. It is also used to synthesize substituted iminopiperidines as inhibitors of human nitric oxide synthase isoforms. 3,4-Dihydro-2(1H)-quinolinone may be employed as medium supplement in the culture medium of Pseudomonas ayucida during enrichment culture experiments.

Technology Process of 1,2,3,4-Tetrahydroquinolin-2-one

There total 47 articles about 1,2,3,4-Tetrahydroquinolin-2-one 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: 73.0%

6-bromo-3,4-dihydro-1H-quinolin-2-one (3279-90-1) → 1,2,3,4-tetrahydroisoquinoline (635-46-1) + 3,4-dihydro-2(1H)-quinolone (553-03-7) + 6-bromo-1,2,3,4-tetrahydroquinoline (22190-35-8)

Guidance literature:

With [RuCl₂(N-heterocyclic carbene)(bis[2-(diphenylphosphino)ethyl]amine)]; hydrogen; caesium carbonate; In toluene; butan-1-ol; at 120 ℃; for 6h; under 22502.3 Torr; Schlenk technique; Autoclave;

DOI:10.1021/acs.orglett.9b03878

Reference yield: 71.0%

2-quinolone (59-31-4,70254-42-1,493-62-9) → 1,2,3,4-tetrahydroisoquinoline (635-46-1) + 3,4-dihydro-2(1H)-quinolone (553-03-7)

Guidance literature:

With hydrogenchloride; samarium; for 0.166667h; Ambient temperature;

DOI:10.1248/cpb.43.1422

Reference yield: 68.0%

1,2,3,4-tetrahydroisoquinoline (635-46-1) → quinoline (91-22-5) + 3,4-dihydro-2(1H)-quinolone (553-03-7)

Guidance literature:

With glucose dehydrogenase; D-glucose; cytochrome P₄₅₀ enzyme CYP₁₀₂A₁ A₈₂M/F₈₇A/H₁₇₁L/E₂₆₇F/Q₃₀₇H/N₃₁₉Y mutant; C₂₁H₂₅N₇O₁₇P₃^(3-)*2H⁽¹⁺⁾*Na⁽¹⁺⁾; In aq. phosphate buffer; ethanol; at 20 ℃; for 4h; pH=8.4; Catalytic behavior; Enzymatic reaction;

DOI:10.1002/anie.201904157

upstream raw materials:

(2-nitro-benzyl)-malonic acid

1-phenylmethyl-4-piperidone

dihydrocinnamamide

N-hydroxy-3-phenylpropanamide

Downstream raw materials:

N-benzyl-1,2,3,4-tetrahydroisoquinoline-2-one

6-benzoyl-3,4-dihydro-2(1H)-quinolinone

6-acetyl-3,4-dihydro-2(1H)-quinolinone

6-chloroacetyl-1,2,3,4-tetrahydroquinolin-2-one

Refernces

• 1、 Cai, Hu,Tan, Wei,Xie, Yongfa,Yang, Ruchun,Yue, Shusheng. "DMSO/t-BuONa/O2-Mediated Aerobic Dehydrogenation of Saturated N-Heterocycles". . p. 7501 - 7509. Retrieved 2020/07/07.
• 2、 Ogata, Osamu,Nara, Hideki,Matsumura, Kazuhiko,Kayaki, Yoshihito. "Formal Deoxygenative Hydrogenation of Lactams Using PNHP-Pincer Ruthenium Complexes under Nonacidic Conditions". supporting information. p. 9954 - 9959. Retrieved 2019/12/24.