仙客来醛
仙客来醛（英語：Cyclamen aldehyde）是一种有机化合物，化学式为C13H18O。仙客来醛具有山谷百合味香气，其气味及强度与间位异丙基的异构体相似[3]，可用于香水制造[4]。
| 仙客来醛 | |
|---|---|
propionaldehyde.png)
| |
| IUPAC名 3-(4-Isopropylphenyl)-2-methylpropanal | |
| 别名 | 兔耳草醛 对异丙基-α-甲基苯丙醛 对异丙基-α-甲基氢化肉桂醛 3-枯基异丁醛[1] 3-(4-异丙基苯基)-2-甲基丙醛 |
| 识别 | |
| CAS号 | 103-95-7 
|
| PubChem | 517827 |
| ChemSpider | 451801 |
| SMILES |
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| 性质 | |
| 化学式 | C13H18O |
| 摩尔质量 | 190.28 g·mol−1 |
| 外观 | 无色至浅黄色液体 |
| 氣味 | 强烈的花香 |
| 密度 | 0.947 g·cm−3[2] |
| 沸点 | 104—105 °C（377—378 K）（3 mmHg）[2] |
| 溶解性（水） | 难溶 |
| 溶解性（其它溶剂） | 可溶于大部分混合油、乙醇；难溶于丙二醇、丙三醇 |
| 若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。 | |
合成
仙客来醛可由对异丙基-α-甲基肉桂醛在铑负载氧化铝（或镍负载二氧化硅）的催化氢化得到。[5]β-甲基-4-异丙基苯丙醇被马丁试剂氧化，也能制得仙客来醛。[6]
反应
仙客来醛和盐酸羟胺在四氯化钛-吡啶体系中反应，可以得到α-甲基-4-异丙基苯丙腈，[7]羟胺-O-磺酸在乙酸水溶液中也能完成这一转化。[8]
它和4-硝基苯甲醛在吡咯烷-乙酸催化下于二甲基亚砜中反应，经烯胺中间体，可以得到β-羟基-α-甲基-α-(4-异丙基苄基)-4-硝基苯丙醛。[9]
-2-methylpropanal.png)
它和氟试剂在乙酰丙酮亚铁催化下于乙腈中反应，得到β-氟-α-甲基-4-异丙基苯丙醛（syn:anti=2:1）。[11]
参考文献
- ^ 安家驹. 实用精细化工辞典. 中国轻工业出版社. 2000. ISBN 9787501927708.
- ^ 2.0 2.1 ABE, Shozou; YASUKAWA, Tadashi. Preparation of Cyclamen-type Perfume Compounds. I. Journal of Synthetic Organic Chemistry, Japan. 1964, 22 (2): 144–147 [2022-09-01]. ISSN 0037-9980. doi:10.5059/yukigoseikyokaishi.22.144. eISSN 1883-6526. （原始内容存档于2022-09-01）.
- ^ Sell, C. S. On the Unpredictability of Odor. Angewandte Chemie International Edition. 25 September 2006, 45 (38): 6254–6261. ISSN 1433-7851. PMID 16983730. doi:10.1002/anie.200600782. eISSN 1521-3773.
- ^ Danute Pajaujis Anonis. Lily of the Valley (Muguet) in Perfumery (PDF). Perfumer & flavorist. 1986, 11 (6): 31–36 [2022-09-03]. ISSN 0272-2666. （原始内容存档 (PDF)于2022-09-03）.CODEN PEFLDI
- ^ Pak, A. M.; Konuspaev, S. R.; Sagindykov, S. M.; Sokol'skii, D. V.; Zapletal, Vladimir; Prchlik, Jaroslav. Hydrogenation of forcyclamen- and forlilialaldehydes on supported metallic catalysts. Zhurnal Prikladnoi Khimii (Sankt-Peterburg, Russian Federation). 1986, 59 (5): 1135–1138. ISSN 0044-4618.CODEN ZPKHAB.
- ^ Limnios, Dimitris; Kokotos, Christoforos G. Microwave-assisted organocatalytic cross-aldol condensation of aldehydes. RSC Advances. 2013, 3 (14): 4496. doi:10.1039/c3ra00114h. eISSN 2046-2069.
- ^ Leggio, Antonella; Belsito, Emilia Lucia; Gallo, Sonia; Liguori, Angelo. One-pot conversion of aldehydes to nitriles mediated by TiCl4. Tetrahedron Letters. April 2017, 58 (15): 1512–1514. ISSN 0040-4039. doi:10.1016/j.tetlet.2017.03.007.
- ^ Quinn, Dylan J.; Haun, Graham J.; Moura-Letts, Gustavo. Direct synthesis of nitriles from aldehydes with hydroxylamine-O-sulfonic acid in acidic water. Tetrahedron Letters. August 2016, 57 (34): 3844–3847. ISSN 0040-4039. doi:10.1016/j.tetlet.2016.07.047.
- ^ Mase, Nobuyuki; Tanaka, Fujie; Barbas, Carlos F. Rapid Fluorescent Screening for Bifunctional Amine−Acid Catalysts: Efficient Syntheses of Quaternary Carbon-Containing Aldols under Organocatalysis. Organic Letters. 24 October 2003, 5 (23): 4369–4372. ISSN 1523-7060. PMID 14602002. doi:10.1021/ol035651p. eISSN 1523-7052.
- ^ Zou, Jianzhong; Yi, Fengping; Zhang, Lirong; Wang, Zhen. Facile Aldolization Catalyzed by Ionic Liquid [4-Sulfbmpyrazine][BF4]. Asian Journal of Chemistry. 2013, 25 (12): 6643–6646. ISSN 0970-7077. doi:10.14233/ajchem.2013.14396. eISSN 0975-427X.
- ^ Bloom, Steven; Sharber, Seth Andrew; Holl, Maxwell Gargiulo; Knippel, James Levi; Lectka, Thomas. Metal-Catalyzed Benzylic Fluorination as a Synthetic Equivalent to 1,4-Conjugate Addition of Fluoride. The Journal of Organic Chemistry. 17 October 2013, 78 (21): 11082–11086. ISSN 0022-3263. PMID 24073747. doi:10.1021/jo401796g. eISSN 1520-6904.