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Chemical Structure| 18031-40-8 Chemical Structure| 18031-40-8
Chemical Structure| 18031-40-8

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Perillaldehyde is a natural compound in the herb perilla and in the peel of citrus fruits. It is used in perfumery and has a mint-like cinnamon odor.

Synonyms: (S)-(-)-Perillaldehyde; (S)-Perillaldehyde; (–)-Perillaldehyde

4.5 *For Research Use Only! Not for Human Use. We Do Not Sell to Patients.

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Product Details of L-Perillaldehyde

CAS No. :18031-40-8
Formula : C10H14O
M.W : 150.22
SMILES Code : C=C([C@@H]1CC=C(C=O)CC1)C
Synonyms :
(S)-(-)-Perillaldehyde; (S)-Perillaldehyde; (–)-Perillaldehyde
English Name :(S)-4-(Prop-1-en-2-yl)cyclohex-1-ene-1-carbaldehyde
MDL No. :MFCD00001543
InChI Key :RUMOYJJNUMEFDD-SNVBAGLBSA-N
Pubchem ID :2724159

Safety of L-Perillaldehyde

Application In Synthesis of L-Perillaldehyde

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 18031-40-8 ]

[ 18031-40-8 ] Synthesis Path-Downstream   1~7

  • 1
  • [ 18031-40-8 ]
  • [ 18457-55-1 ]
YieldReaction ConditionsOperation in experiment
99% With triscarbonyl-(2,4-bis(trimethylsilyl)bicyclo[3.3.0]nona-1,4-dien-3-one)iron; hydrogen; potassium carbonate In water; isopropyl alcohol at 100℃; for 17h; Inert atmosphere;
99% With iron(II) fluoro{tris[2-(diphenylphosphino)phenyl]phospino}tetrafluoroborate; hydrogen; trifluoroacetic acid In isopropyl alcohol at 120℃; Inert atmosphere; Autoclave; chemoselective reaction;
97% With LiPyrrBH3 In tetrahydrofuran at 25℃; for 3h;
97% With sodium tetrahydroborate; cerium(III) chloride In methanol at 25℃; for 0.5h; General Procedure General procedure: A 50 mL round-bottom flask was charged with the substrate (1.0 mmol), CeCl3 (1.2equiv.), and MeOH (10 mL) was added. NaBH4 (1.2 mmol) is added in portions andthe mixture is stirring or standing for proper time monitored by TLC (0.5 to 2 hours).Then 10 mL water was added into the system. The mixture was concentrated underreduced pressure, extracted with DCM for three times (3 × 10.0 mL). The organiclayer was dried over Na2SO4 and concentrated under reduced pressure. The residuewas purified by chromatography on silica gel to afford the desired product.
87% With sodium tetrahydroborate In diethyl ether; ethanol for 1h; Ambient temperature;
86.8% With sodium tetrahydroborate In ethanol at 0 - 20℃; for 3h; 3.2. (S)-(4-(Prop-1-en-2-yl)cyclohex-1-enyl)methanol (I) To a solution of (S)-perillaldehyde (15.0 g, 0.1 mo1) in ethanol (100 mL) cooled to 0 °C, sodium borohydride (7.57 g, 0.2 mol) was added in portions. Then, the mixture was stirred at room temperature for 3 h. After the solvent was evaporated in vacuo, brine (30 mL) was added and the mixture was extracted with dichloromethane (3 × 30 mL). The combined organic extracts were washed with brine, dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated in vacuo.The residue was purified on a silica gel column with petroleum ether-ethyl acetate (3:1, Rf = 0.51) as eluent to afford compound I as a colorless liquid (13.2 g, yield 86.8%).
86.8% With sodium tetrahydroborate; ethanol at 20℃; for 3h; Cooling with ice; 1 Example 1 Synthesis of Perillyl Alcohol 0.1 mol of perilla aldehyde was dissolved in 100 mL of anhydrous ethanol, and 0.2 mol of NaBH4 was added in portions in an ice bath. After completion of the addition, the reaction was carried out at room temperature for 3 h. Ethanol was distilled off under reduced pressure, 30 mL of water and 30 mL of dichloromethane were added, the mixture was transferred to a separatory funnel, and the organic phase was separated. The aqueous phase was extracted with dichloromethane. The organic phases were combined, washed with water and saturated brine, and dried over anhydrous sodium sulfate. . After the concentration, it was obtained as a colorless and transparent liquid of perillol, with a yield of 86.8%.
86.8% With sodium tetrahydroborate; ethanol at 20℃; for 3h; Cooling with ice; 1 Synthesis of Perillyl Alcohol Dissolve 0.1 mol perillaldehydeIn 100 mL of anhydrous ethanol, 0.2 mol of NaBH4 was added in portions in an ice bath, and after completion of the addition, the reaction was carried out at room temperature for 3 h. Ethanol was distilled off under reduced pressure, 30 mL of water and 30 mL of dichloromethane were added, and the mixture was transferred to a separatory funnel.The organic phase is separated, the aqueous phase is extracted with dichloromethane, the organic phases are combined and washed with water and saturated brine.Dry over anhydrous sodium sulfate. After concentration, a colorless, transparent liquid was obtained with a yield of 86.8%.
85% With (2,4-bis(trimethylsilyl)bicyclo[3.3.0]nona-1,4-dien-3-one)iron acetonitriledicarbonyl; isopropyl alcohol at 80℃; for 18h; Inert atmosphere;
73% With C29H34BNOP2Ru In dichloromethane; isopropyl alcohol Schlenk technique; Inert atmosphere; Reflux;
With lithium aluminium tetrahydride In tetrahydrofuran regioselective reaction;
Stage #1: (-)-perillaldehyde With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; Inert atmosphere; Stage #2: With sodium hydroxide In tetrahydrofuran; water
With Ru(H)2(CO)(triphos); hydrogen In neat (no solvent) at 100℃; for 16h; chemoselective reaction;
3 g With lithium aluminium tetrahydride In tetrahydrofuran
With methanol; sodium tetrahydroborate

References: [1]Fleischer, Steffen; Zhou, Shaolin; Junge, Kathrin; Beller, Matthias [Angewandte Chemie - International Edition, 2013, vol. 52, # 19, p. 5120 - 5124][Angew. Chem., 2013, vol. 125, # 19, p. 5224 - 5228].
[2]Wienhöfer, Gerrit; Westerhaus, Felix A.; Junge, Kathrin; Ludwig, Ralf; Beller, Matthias [Chemistry - A European Journal, 2013, vol. 19, # 24, p. 7701 - 7707].
[3]Fisher, Gary B.; Fuller, Joseph C.; Harrison, John; Alvarez, Salvador G.; Burkhardt, Elizabeth R.; et al. [Journal of Organic Chemistry, 1994, vol. 59, # 21, p. 6378 - 6385].
[4]Huang, Xianting; Zhao, Jianyou; Wang, Qingxu; Fang, Pengkai; Xie, Wei; Chen, Meng; Han, Hongliang; Zhang, Lanlan; Zhang, Jiatai; Wang, Fan; Liu, Zhong-Quan [Synlett, 2024, vol. 36, # 6, p. 683 - 688].
[5]Buchecker; Marti; Eugster [Helvetica Chimica Acta, 1982, vol. 65, # 3, p. 896 - 912].
[6]Hui, Zi; Zhang, Meihui; Cong, Lin; Xia, Mingyu; Dong, Jinhua [Molecules, 2014, vol. 19, # 5, p. 6671 - 6682].
[7]Current Patent Assignee: SHENYANG PHARMACEUTICAL UNIVERSITY - CN104945334, 2018, B Location in patent: Paragraph 0025; 0026.
[8]Current Patent Assignee: SHENYANG PHARMACEUTICAL UNIVERSITY - CN104945335, 2018, B Location in patent: Paragraph 0028; 0029.
[9]Plank, Taylor N.; Drake, Jessica L.; Kim, Daniel K.; Funk, Timothy W. [Advanced Synthesis and Catalysis, 2012, vol. 354, # 4, p. 597 - 601].
[10]Farrar-Tobar, Ronald A.; Wei, Zhihong; Jiao, Haijun; Hinze, Sandra; de Vries, Johannes G. [Chemistry - A European Journal, 2018, vol. 24, # 11, p. 2725 - 2734].
[11]Location in patent: scheme or table Santos Pisoni, Diego dos; Sobieski da Costa, Jessé; Gamba, Douglas; Petzhold, Cesar Liberato; César de Amorim Borges, Antonio; Ceschi, Marco Antonio; Lunardi, Paula; Saraiva Gonçalves, Carlos Alberto [European Journal of Medicinal Chemistry, 2010, vol. 45, # 2, p. 526 - 535].
[12]Rigoli, Jared W.; Moyer, Sara A.; Pearce, Simon D.; Schomaker, Jennifer M. [Organic and Biomolecular Chemistry, 2012, vol. 10, # 9, p. 1746 - 1749].
[13]Christie, Francesca; Zanotti-Gerosa, Antonio; Grainger, Damian [ChemCatChem, 2018, vol. 10, # 5, p. 1012 - 1018].
[14]Wu, Xiang; Wang, Hai-Jun; Huang, Yong-Shuang; Li, Wei-Dong Z. [Organic Letters, 2018, vol. 20, # 7, p. 1871 - 1874].
[15]Dyrkheeva, Nadezhda S.; Filimonov, Aleksandr S.; Luzina, Olga A.; Zakharenko, Alexandra L.; Ilina, Ekaterina S.; Malakhova, Anastasia A.; Medvedev, Sergey P.; Reynisson, Jóhannes; Volcho, Konstantin P.; Zakian, Suren M.; Salakhutdinov, Nariman F.; Lavrik, Olga I. [Biomolecules, 2021, vol. 11, # 7].
  • 3
  • [ 18031-40-8 ]
  • [ 124755-24-4 ]
  • [ 639009-29-3 ]
  • 4
  • [ 18031-40-8 ]
  • [ 50329-23-2 ]
  • [ 2243574-44-7 ]
YieldReaction ConditionsOperation in experiment
76% With magnesium sulfate; 1,8-diazabicyclo[5.4.0]undec-7-ene In chlorobenzene at 100℃; for 12h; Inert atmosphere; Sealed tube; Green chemistry; 7 Example 7 Preparation of (S)-4-ethyl-6-(isopropenyl)-5,6,7,8-tetrahydroisoquinoline Add magnetic particles, a small amount of magnesium sulfate to the sealing tube, replace argon, and add 2mL of chlorobenzene in sequence under argon protection conditions.After the perillaldehyde (150mg, 1mmol), 2-butynylamine hydrochloride (117mg, 1 · lmmol) and DBU (320mg, 2. lmmol) will be sealedAt 100 ° C. After reacting for 12 h, the solvent was separated and purified by silica gel column chromatography to give a white solid.The yield was 76%.The specific reaction equation is:
76% With magnesium sulfate; 1,8-diazabicyclo[5.4.0]undec-7-ene In chlorobenzene at 100℃; for 12h; Inert atmosphere; Sealed tube;
  • 5
  • [ 36457-58-6 ]
  • [ 18031-40-8 ]
  • [ 3049696-95-6 ]
YieldReaction ConditionsOperation in experiment
74 % With Quinuclidine; chromium dichloride; [Ir(dF(CF3)ppy)2(dtbbpy)]PF6; (4S,4'S)-2,2'-(cyclopropane-1,1-diyl)bis(4-phenyl-4,5-dihydrooxazole) In 1,4-dioxane at 20℃; Inert atmosphere; Glovebox; Irradiation; stereoselective reaction;
  • 6
  • [ 36457-58-6 ]
  • [ 18031-40-8 ]
  • [ 3049696-96-7 ]
YieldReaction ConditionsOperation in experiment
77 % With Quinuclidine; chromium dichloride; [Ir(dF(CF3)ppy)2(dtbbpy)]PF6; (4R,4'R)-2,2'-(cyclopropane-1,1-diyl)bis(4-phenyl-4,5-dihydrooxazole) In 1,4-dioxane at 20℃; Inert atmosphere; Glovebox; Irradiation; stereoselective reaction;
  • 7
  • [ 18031-40-8 ]
  • [ CAS Unavailable ]
  • [ 79955-27-4 ]
  • [ 3061832-21-8 ]
  • [ 3061829-00-0 ]
YieldReaction ConditionsOperation in experiment
23.077 % ee With N,N-dimethylbutylamine; C76H96N4O16Rh2 In 1,2-dichloro-ethane at -10℃; Molecular sieve; Inert atmosphere; Overall yield = 14 percent; enantioselective reaction;
 

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