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環丙基甲醛

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環丙基甲醛
IUPAC名
cyclopropanecarbaldehyde
英文名 Cyclopropanecarboxaldehyde
別名 環丙甲醛
甲醯基環丙烷
識別
CAS編號 1489-69-6  checkY
PubChem 123114
SMILES
 
  • C1CC1C=O
InChI
 
  • 1S/C4H6O/c5-3-4-1-2-4/h3-4H,1-2H2
InChIKey JMYVMOUINOAAPA-UHFFFAOYSA-N
性質
化學式 C4H6O
莫耳質量 70.09 g·mol−1
外觀 無色液體
密度 0.938 g·cm−3[1]
沸點 98—101 °C(371—374 K)[2]
溶解性 可溶
危險性
GHS提示詞 危險
H-術語 H225, H314
P-術語 P210, P233, P240, P241, P242, P243, P260, P264, P280, P301+330+331, P303+361+353, P304+340, P305+351+338, P310
相關物質
相關化學品 環丁基甲醛
環戊基甲醛
環己基甲醛
若非註明,所有數據均出自標準狀態(25 ℃,100 kPa)下。

環丙基甲醛是一種有機化合物,化學式為C4H6O,是環丙烷的一個氫被甲醯基取代的產物。它是無色至黃色的液體,可溶於水及一些有機溶劑。

合成

環丙基甲醛可由9-硼雜雙環[3.3.1]壬烷[3]、二(二乙胺基)氫化鋁[4]、1,1,2-三甲基丙基溴代甲硼烷二甲基硫醚錯合物[5]等還原劑還原環丙基甲酸製得。過碘酸[6]重鉻酸鈉[7]、3-亞碘醯苯甲酸[8]硝酸鈰銨[9]氧氣[10]等氧化劑氧化環丙基甲醇也能得到環丙基甲醛。

丁二酸二乙酯酮醇縮合反應可以得到2-羥基環丁酮[11],它可以被氫化鋁鋰還原為1,2-環丁二醇,再在三氟化硼二丁醚縮環,可以得到環丙基甲醛:[12]

2,3-二氫呋喃在加熱、加壓下經氧化鋁催化下發生重排反應,也能得到環丙基甲醛,副產物是反式德語Trans-Crotonaldehyd巴豆醛[13]

反應

環丙基甲醛可以發生的特徵反應,如加氫還原為環丙基甲醇[14]或氧化為環丙基甲酸[15];它和苄胺對甲苯磺酸的催化下縮合,得到N-(環丙基亞甲基)苄胺[16],在該體系中,加入二硼酸可以將亞胺加氫為胺[17];和氰乙酸乙酯發生Knoevenagel縮合反應,生成2-氰基-3-環丙基-2-丙烯酸乙酯。[18]三氟化硼乙醚的存在下,它和2-疊氮基乙醇二氯甲烷中反應,可以得到2-環丙基-4,5-二氫㗁唑。[19]

它和二環戊基鋅反應,可以得到α-環丙基環戊基甲醇。[20]

應用

環丙基甲醛和正丙胺縮合後氫化,得到N-(環丙基甲基)丙胺,它再與4-氯-3,5-二硝基三氟甲苯反應,可以得到除草劑環丙氟靈德語Profluralin[21]

以環丙基甲醛為原料可以合成環丙基乙炔。它首先和三氯乙酸反應,得到α-三氯甲基環丙基甲醇,經對甲基苯基磺醯氯(TsCl)轉化為對甲苯磺酸酯,所得的酯再與甲基鋰反應,水解後生成環丙基乙炔。[22]

參考文獻

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