1,2,3,4-テトラヒドロキノリン

外観

ごくうすい黄色～黄褐色, 澄明の液体

溶解性

エタノール及び塩酸に溶け、水にほとんど溶けない。

解説

C9H11N(133.19)．1,2,3,4-テトラヒドロキノリンは，キノリンをニッケル触媒を用いて水素添加すると得られる．"無色の液体．沸点248 ℃．n_D²⁴"1.5933．d_D²⁴"1.0546．5,6,7,8-テトラヒドロキノリンは，シクロヘキサノンオキシムのアリールエーテルをN-オキシドに異性化させ，ついで脱水環化させると得られる．無色の液体．沸点222 ℃．d₄²⁰"1.0546．n_D²⁴"1.5933．
森北出版「化学辞典（第2版）

使用上の注意

不活性ガス封入

化学的特性

clear pale yellow to yellow liquid

使用

1,2,3,4-Tetrahydroquinoline is a reagent used in the synthesis of N-substituted benzoyl-1,2,3,4-tetrahydroquinolyl-1-carboxamides displaying fungicidal activity.

定義

ChEBI: A member of the class of quinolines that is the 1,2,3,4-tetrahydro derivative of quinoline.

合成

1,2,3,4-Tetrahydroquinoline is synthesised using quinoline N-oxide as a raw material by chemical reaction. The specific synthesis steps are as follows:
General procedure: In a 1.5 mL reaction vial, B(C6F5)3 (0.025 mmol, 5.0 mol %) was dissolved in chloroform (0.60 mL), towhich diethylsilane (1.75 mmol, 3.5 equiv) was added. After shaking briefly, quinolines (1a-p, 0.50 mmol, 1.0equiv) was subsequently added to the above catalyst solution under argon atmosphere. The reaction mixturewas stirred at 25-65 oC for 6-24 h for the reaction of 1a-h, and at 25-100 oC for 2-24 h for the reaction of 1i-p,then allowed to cool down to room temperature and concentrated under reduced pressure to give the crudeproduct. This reaction mixture was then treated with 0.25 N HCl ethereal solution (7 mL) and stirred at roomtemperature for 1 h to give the solid residue, which was subsequently washed with ether. The solid residue wasthen dissolved or suspended in MeOH (1.0 mL) and neutralized with Na₂CO₃·H₂O (0.5 g) at 0 oC. After stirringfor 2 h, MeOH was removed under reduced pressure, and the neutralized reaction residue was dissolved inCH₂Cl₂ and washed with brine (5 mL) and water (5 mL). The crude product was then obtained from the organicphase of CH₂Cl₂ solution and finally purified by column chromatography on silica gel to give 2a-h(EtOAc/Hexane = 1/9) and 2i-p (EtOAc/Hexane = 3/7).