维基百科

环丙基甲醛

化合物

环丙基甲醛是一种有机化合物，化学式为C4H6O，是环丙烷的一个氢被甲酰基取代的产物。它是无色至黄色的液体，可溶于水及一些有机溶剂。

环丙基甲醛
IUPAC名
cyclopropanecarbaldehyde
英文名 Cyclopropanecarboxaldehyde
别名 环丙甲醛
甲酰基环丙烷
识别
CAS号 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
性质
化学式 C4H6O
摩尔质量 70.09 g·mol−1
外观 无色液体
密度 0.938 g·cm−3[1]
沸点 98—101 °C（371—374 K）[2]
溶解性（水） 可溶
危险性
GHS提示词 危险
H-术语 H225, H314
P-术语 P210, P233, P240, P241, P242, P243, P260, P264, P280, P301+330+331, P303+361+353, P304+340, P305+351+338, P310
相关物质
相关化学品 环丁基甲醛
环戊基甲醛
环己基甲醛
若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。

合成 编辑

环丙基甲醛可由9-硼杂双环[3.3.1]壬烷[3]、二(二乙氨基)氢化铝[4]、1,1,2-三甲基丙基溴代甲硼烷二甲基硫醚配合物[5]等还原剂还原环丙基甲酸制得。高碘酸[6]、重铬酸钠[7]、3-亚碘酰苯甲酸[8]、硝酸铈铵[9]、氧气[10]等氧化剂氧化环丙基甲醇也能得到环丙基甲醛。

丁二酸二乙酯的酮醇缩合反应可以得到2-羟基环丁酮[11]，它可以被氢化铝锂还原为1,2-环丁二醇，再在三氟化硼二丁醚缩环，可以得到环丙基甲醛：[12]

 

2,3-二氢呋喃在加热、加压下经氧化铝催化下发生重排反应，也能得到环丙基甲醛，副产物是反式（德语：Trans-Crotonaldehyd）巴豆醛：[13]

 

反应 编辑

环丙基甲醛可以发生醛的特征反应，如加氢还原为环丙基甲醇[14]或氧化为环丙基甲酸[15]；它和苄胺在对甲苯磺酸的催化下缩合，得到N-(环丙基亚甲基)苄胺[16]，在该体系中，加入二硼酸可以将亚胺加氢为胺[17]；和氰乙酸乙酯发生Knoevenagel缩合反应，生成2-氰基-3-环丙基-2-丙烯酸乙酯。[18]在三氟化硼乙醚的存在下，它和2-叠氮基乙醇于二氯甲烷中反应，可以得到2-环丙基-4,5-二氢噁唑。[19]

它和二环戊基锌反应，可以得到α-环丙基环戊基甲醇。[20]

应用 编辑

环丙基甲醛和正丙胺缩合后氢化，得到N-(环丙基甲基)丙胺，它再与4-氯-3,5-二硝基三氟甲苯反应，可以得到除草剂环丙氟灵（德语：Profluralin）：[21]

 

以环丙基甲醛为原料可以合成环丙基乙炔。它首先和三氯乙酸反应，得到α-三氯甲基环丙基甲醇，经对甲基苯基磺酰氯（TsCl）转化为对甲苯磺酸酯，所得的酯再与甲基锂反应，水解后生成环丙基乙炔。[22]

 

参考文献 编辑

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  9. ^ Young, Lewis Brewster; Trahanovsky, Walter S. Cerium(IV) oxidation of organic compounds. III. Preparation of cyclopropanecarboxaldehyde from cyclopropanemethanol. The Journal of Organic Chemistry (American Chemical Society (ACS)). 1967, 32 (7): 2349–2350. ISSN 0022-3263. doi:10.1021/jo01282a058 （英语）. 
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  12. ^ Cyclopropanecarboxaldehyde. Organic Syntheses (Organic Syntheses). 1981, 60: 25. ISSN 0078-6209. doi:10.15227/orgsyn.060.0025 （英语）. 
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