仙客来醛

仙客来醛
	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; 3-(4-异丙基苯基)-2-甲基丙醛
识别
CAS号	103-95-7
PubChem	517827
ChemSpider	451801
SMILES	CC(C)c1ccc(cc1)CC(C)C=O;
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
沸点	104—105 °C（377—378 K）（3 mmHg）
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。

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]。

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]

在催化下，它可以和乙二醇形成缩醛：^[10]

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.

[1] 安家驹. 实用精细化工辞典. 中国轻工业出版社. 2000. ISBN 9787501927708.

[Abe-2] 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）.

[3] 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.

[4] 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

[5] 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.

[6] 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.

[7] 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.

[8] 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.

[9] 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.

[10] 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.

[11] 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.

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