CN109776298B - A kind of synthetic method of cinnamaldehyde compound - Google Patents
A kind of synthetic method of cinnamaldehyde compound Download PDFInfo
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- CN109776298B CN109776298B CN201910200853.2A CN201910200853A CN109776298B CN 109776298 B CN109776298 B CN 109776298B CN 201910200853 A CN201910200853 A CN 201910200853A CN 109776298 B CN109776298 B CN 109776298B
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- -1 cinnamaldehyde compound Chemical class 0.000 title claims abstract description 14
- 229940117916 cinnamic aldehyde Drugs 0.000 title claims description 12
- KJPRLNWUNMBNBZ-UHFFFAOYSA-N cinnamic aldehyde Natural products O=CC=CC1=CC=CC=C1 KJPRLNWUNMBNBZ-UHFFFAOYSA-N 0.000 title claims description 12
- 238000010189 synthetic method Methods 0.000 title claims description 6
- 238000006243 chemical reaction Methods 0.000 claims abstract description 27
- KJPRLNWUNMBNBZ-QPJJXVBHSA-N (E)-cinnamaldehyde Chemical class O=C\C=C\C1=CC=CC=C1 KJPRLNWUNMBNBZ-QPJJXVBHSA-N 0.000 claims abstract description 12
- 150000001413 amino acids Chemical class 0.000 claims abstract description 7
- 150000002941 palladium compounds Chemical class 0.000 claims abstract description 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical group OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 12
- UCMIRNVEIXFBKS-UHFFFAOYSA-N beta-alanine Chemical compound NCCC(O)=O UCMIRNVEIXFBKS-UHFFFAOYSA-N 0.000 claims description 11
- 150000001875 compounds Chemical class 0.000 claims description 11
- 235000001014 amino acid Nutrition 0.000 claims description 6
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 claims description 6
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical group [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 claims description 6
- 239000000654 additive Substances 0.000 claims description 5
- 230000000996 additive effect Effects 0.000 claims description 5
- 229940000635 beta-alanine Drugs 0.000 claims description 5
- 239000007800 oxidant agent Substances 0.000 claims description 5
- 230000001590 oxidative effect Effects 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 claims description 3
- 239000002994 raw material Substances 0.000 claims description 3
- 229940126062 Compound A Drugs 0.000 claims description 2
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 150000001371 alpha-amino acids Chemical class 0.000 claims description 2
- 235000008206 alpha-amino acids Nutrition 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- PBDBXAQKXCXZCJ-UHFFFAOYSA-L palladium(2+);2,2,2-trifluoroacetate Chemical compound [Pd+2].[O-]C(=O)C(F)(F)F.[O-]C(=O)C(F)(F)F PBDBXAQKXCXZCJ-UHFFFAOYSA-L 0.000 claims description 2
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 claims description 2
- 150000001576 beta-amino acids Chemical class 0.000 claims 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 10
- 239000003054 catalyst Substances 0.000 abstract description 4
- 230000002194 synthesizing effect Effects 0.000 abstract description 4
- 239000007858 starting material Substances 0.000 abstract description 3
- 238000001308 synthesis method Methods 0.000 abstract description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 abstract description 2
- 239000003153 chemical reaction reagent Substances 0.000 abstract 1
- 238000005859 coupling reaction Methods 0.000 abstract 1
- 238000006356 dehydrogenation reaction Methods 0.000 abstract 1
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 16
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- AMIMRNSIRUDHCM-UHFFFAOYSA-N Isopropylaldehyde Chemical compound CC(C)C=O AMIMRNSIRUDHCM-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 238000004440 column chromatography Methods 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 3
- 238000006880 cross-coupling reaction Methods 0.000 description 3
- HBEDSQVIWPRPAY-UHFFFAOYSA-N 2,3-dihydrobenzofuran Chemical compound C1=CC=C2OCCC2=C1 HBEDSQVIWPRPAY-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- 150000001502 aryl halides Chemical class 0.000 description 2
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
- 238000007306 functionalization reaction Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 229910000640 Fe alloy Inorganic materials 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 238000005882 aldol condensation reaction Methods 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 230000000840 anti-viral effect Effects 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 239000003443 antiviral agent Substances 0.000 description 1
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzenecarboxaldehyde Natural products O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 1
- 235000013361 beverage Nutrition 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 235000015218 chewing gum Nutrition 0.000 description 1
- 235000009508 confectionery Nutrition 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 235000015243 ice cream Nutrition 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 238000005839 oxidative dehydrogenation reaction Methods 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
本发明公开了一种肉桂醛类化合物的合成方法，以脂肪醛和取代芳烃为起始原料，钯化物和氨基酸为催化剂，通过交叉脱氢偶联反应合成得到肉桂醛类化合物。本发明方法与传统肉桂醛类化合物的合成方法相比操作简单、反应条件温和、所用试剂价格低廉、效率高、原子利用率高。The invention discloses a method for synthesizing cinnamaldehyde compounds. The aliphatic aldehydes and substituted aromatic hydrocarbons are used as starting materials, palladium compounds and amino acids are used as catalysts, and cinnamaldehyde compounds are synthesized through a cross-dehydrogenation coupling reaction. Compared with the traditional synthesis method of cinnamaldehyde compounds, the method of the invention has the advantages of simple operation, mild reaction conditions, low price of used reagents, high efficiency and high atom utilization rate.
Description
Technical Field
The invention relates to a novel method for synthesizing cinnamaldehyde compounds, and belongs to the field of organic synthesis.
Background
Cinnamaldehyde is a very valuable organic compound which is widely used as a flavoring agent in chewing gums, ice creams, confections and beverages, as an antiviral and anticancer agent, or as an effective fungicide, agrochemical insecticide, and as a corrosion inhibitor for steel or other iron alloys in corrosive fluids such as hydrochloric acid. In addition, cinnamaldehyde is an important multifunctional intermediate in organic synthesis. The traditional synthesis methods of cinnamaldehyde compounds mainly comprise two methods, wherein one method is obtained by cross-coupling reaction of olefine aldehyde and aryl halide or aryl boric acid compounds; the other is prepared by a benzaldehyde compound and a catalyst containingα-hydrogen is produced by aldol condensation under basic conditions. The first method requires pre-functionalization of the raw materials to prepare the corresponding reaction precursor (such as aryl halide or aryl boronic acid compound), and the steps are complicated, and in addition, some aryl boronic acid compounds have high activity and harsh reaction conditions. The second method requires weakly basic conditions for preparing cinnamaldehyde, and is unstable in a strongly acidic or strongly basic medium, so that the reaction substrate is greatly limited. Thus, these conventional methods are advantageous in terms of step simplicity, operability, and atom economyThere is a large lifting space.
The formation of C-C bonds is the basic transformation subject of organic chemistry forever. Transition metal-catalyzed cross-coupling reactions have become a very valuable tool in organic chemistry for over 40 years to build C-C bonds. The transition metal catalyzed direct oxidative dehydrogenation cross-coupling reaction is an important branch of the reaction, and is to form a new C-C bond by breaking two C-H bonds. Such reactions avoid the need for pre-functionalization of the starting materials, making the synthetic schemes shorter and more efficient, while reducing costs and waste, and are considered to be the most desirable chemical reaction.
Disclosure of Invention
The invention aims to provide a method for synthesizing cinnamaldehyde compounds, which has the advantages of simple operation, low cost, high efficiency and high atom utilization rate and meets the requirement of green chemistry.
The invention is realized as follows:
a method for synthesizing cinnamaldehyde compounds comprises the following steps: taking the compound A and the compound B as initial raw materials, taking a palladite and amino acid as catalysts, preparing the cinnamaldehyde compound C,
in the formula, R1Is methyl or hydrogen;
R2and R3Independently selected from alkyl of H, C1-C6, alkoxy of C1-C6 or halogen group, wherein R is2And R3Not H at the same time or not;
or the compound B is
The amino acid is alpha-amino acid orβ-amino acids, preferablyβ-alanine.
The palladium compound is palladium acetate, palladium trifluoroacetate or palladium chloride.
An oxidant is added in the reaction process, and the oxidant is potassium peroxodisulfate or oxygen.
An additive is also added in the reaction process, and the additive is trifluoroacetic acid.
Compared with the traditional synthetic method of the cinnamaldehyde compound, the method has the advantages of simple operation, saving, high efficiency and high atom utilization rate.
Detailed description of the invention
The synthesis method comprises the following steps: a palladium catalyst (10 mol%), amino acid (50 mol%), oxidant, aromatic hydrocarbon and aliphatic aldehyde are sequentially added into a sealed tube, and then a solvent and an additive are added. The reaction tube was then sealed and stirred at room temperature for 10 minutes, followed by stirring in an oil bath at 60 ℃ for 24 hours. The reaction was checked by TLC plate until the starting material reaction was complete. After the reaction was complete the reaction tube was cooled to room temperature, the reaction mixture was filtered through celite (ethyl acetate wash) and the filtrate was concentrated in vacuo. Finally, the cinnamaldehyde compound is obtained by column chromatography separation and purification.
Example 1
Palladium acetate (4.5 mg, 10 mol%) was charged in this order in a 15mL sealed tube,βalanine (8.9 mg, 0.1 mmol, 50 mol%), potassium peroxodisulfate (108.1 mg, 0.4 mmol, 2 equiv), anisole (0.11 mL, 1.0 mmol, 5 equiv) and 2-methylpropanal (18.3)μL, 0.2mmol, 1 equiv), followed by 1mL acetonitrile, and finally trifluoroacetic acid (0.139 mL, 1.8 mmol, 9 equiv) with stirring. The reaction tube was then sealed, stirred at room temperature for 10 minutes and subsequently placed at a temperature of 60 deg.CoC stirring in oil bath for 24 hours. After the reaction was complete the reaction tube was cooled to room temperature, the reaction mixture was filtered through celite (ethyl acetate wash) and the filtrate was concentrated in vacuo. Finally, separation and purification by column chromatography gave compound C-1 (24.3 mg,69%）。
compound C-1: a yellow oil; IR (KBr) 2927, 2841, 1674, 1601, 1510, 1257, 1180, 1016, 827, 536 cm-1; 1H NMR (400 MHz, CDCl3) δ 9.54 (s, 1H), 7.53 (d, J= 8.8 Hz, 2H), 7.19 (s, 1H), 6.98 (d, J = 8.8 Hz, 2H), 3.86 (s, 3H), 2.08 (s, 3H); 13C NMR (100 MHz, CDCl3) δ 195.6, 160.9, 149.9, 136.4, 132.2, 128.2, 114.4, 55.5, 11.1; HRMS (ESI) m/z calculated for C11H13O2 [M+H]+: 177.0910; found: 177.0905。
Example 2
Palladium acetate (4.5 mg, 10 mol%) was charged in this order in a 15mL sealed tube,βalanine (8.9 mg, 0.1 mmol, 50 mol%), potassium peroxodisulfate (108.1 mg, 0.4 mmol, 2 equiv), cumene (1 mL) and 2-methylpropanal (18.3)μL, 0.2mmol, 1 equiv), and finally trifluoroacetic acid (0.139 mL, 1.8 mmol, 9 equiv) was added with stirring. The reaction tube was then sealed, stirred at room temperature for 10 minutes and subsequently placed at a temperature of 60 deg.CoC stirring in oil bath for 24 hours. After the reaction was complete the reaction tube was cooled to room temperature, the reaction mixture was filtered through celite (ethyl acetate wash) and the filtrate was concentrated in vacuo. Final purification by column chromatography gave Compound C-2 (21.4 mg, 57%).
Compound C-2: a yellow oil; IR (KBr) 2962, 2925, 2870, 2711, 1680, 1626, 1458, 1360, 1311, 1188, 1014, 892, 822, 555 cm-1; 1H NMR (400 MHz, CDCl3) δ 9.57 (s, 1H), 7.49 (d, J = 8.3 Hz, 2H), 7.32 (d, J = 8.2 Hz, 2H), 7.25 (s, 1H), 2.96 (hept, J = 7.0 Hz, 1H), 2.09 (s, 3H), 1.28 (d, J = 6.9 Hz, 6H); 13C NMR (100 MHz, CDCl3) δ 195.8, 151.1, 150.2, 137.7, 132.9, 130.5, 127.0, 34.2, 23.9, 11.1; HRMS (ESI) m/z calculated for C13H16NaO [M+Na]+: 211.1093; found: 211.1090。
Example 3
Palladium acetate (4.5 mg, 10 mol%) was charged in this order in a 15mL sealed tube,βalanine (8.9 mg, 0.1 mmol, 50 mol%), potassium peroxodisulfate (108.1 mg, 0.4 mmol, 2 equiv), 4-tert-butyl methyl ether (0.18 mL, 1.0 mmol, 5 equiv) and 2-methylpropanal (18.3)μL, 0.2mmol, 1 equiv), followed by 1mL acetonitrile, and finally trifluoroacetic acid (0.139 mL, 1.8 mmol, 9 equiv) with stirring. The reaction tube was then sealed, stirred at room temperature for 10 minutes and subsequently placed at a temperature of 60 deg.CoC stirring in oil bath for 24 hours. After the reaction was complete the reaction tube was cooled to room temperature, the reaction mixture was filtered through celite (ethyl acetate wash) and the filtrate was concentrated in vacuo. Final purification by column chromatography gave Compound C-3 (24.6 mg, 53%).
Compound C-3: a yellow oil; IR (KBr) 2958, 2867, 2709, 1684, 1622, 1496, 1444, 1257, 1194, 1022, 818 cm-1; 1H NMR (400 MHz, CDCl3) δ 9.63 (s, 1H), 7.62 (s, 1H), 7.48 (d, J = 2.5 Hz, 1H), 7.40 (dd, J = 8.7, 2.6 Hz, 1H), 6.89 (d, J= 8.6 Hz, 1H), 3.87 (s, 3H), 2.04 (s, 3H), 1.33 (s, 9H); 13C NMR (100 MHz, CDCl3) δ 196.1, 155.6, 145.8, 143.1, 138.2, 128.0, 127.4, 123.5, 110.5, 55.8, 34.3, 31.6, 11.2; HRMS (ESI) m/z calculated for C15H21O2 [M+H]+: 233.1536; found: 233.1537。
Example 4
Palladium acetate (4.5 mg, 10 mol%) was charged in this order in a 15mL sealed tube,β-alanine(8.9 mg, 0.1 mmol, 50 mol%), potassium peroxodisulfate (108.1 mg, 0.4 mmol, 2 equiv), 2, 3-dihydrobenzofuran (0.11 mL, 1.0 mmol, 5 equiv) and n-propionaldehyde (14.4μL, 0.2mmol, 1 equiv), followed by 1mL acetonitrile, and finally trifluoroacetic acid (0.139 mL, 1.8 mmol, 9 equiv) with stirring. The reaction tube was then sealed, stirred at room temperature for 10 minutes and subsequently placed at a temperature of 60 deg.CoC stirring in oil bath for 24 hours. After the reaction was complete the reaction tube was cooled to room temperature, the reaction mixture was filtered through celite (ethyl acetate wash) and the filtrate was concentrated in vacuo. Finally separating and purifying by column chromatography to obtain compound C4（18.5mg，53%）。
Compound C-4: white solid, melting point 65-66oC；IR (KBr): 2923, 2854, 2798, 1664, 1600, 1491, 1240, 1124, 976, 808, 613 cm-1; 1H NMR (400 MHz, CDCl3) δ 9.63 (d, J = 7.8 Hz, 1H), 7.45 (s, 1H), 7.40 (d, J = 15.8 Hz, 1H), 7.34 (dd, J = 8.2, 1.9 Hz, 1H), 6.82 (d, J = 8.3 Hz, 1H), 6.58 (dd, J = 15.8, 7.7 Hz, 1H), 4.65 (t, J = 8.7 Hz, 2H), 3.25 (t, J = 8.7 Hz, 2H); 13C NMR (100 MHz, CDCl3) δ 193.9, 163.4, 153.4, 130.6, 128.6, 127.1, 126.1, 125.0, 110.1, 72.2, 29.3; HRMS (ESI) m/z calculated for C11H11O2 [M+H]+: 175.0754; found: 175.0759。
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN103880790A (en) * | 2014-03-13 | 2014-06-25 | 西北大学 | Synthetic method for furan coupling compound |
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| CN103880790A (en) * | 2014-03-13 | 2014-06-25 | 西北大学 | Synthetic method for furan coupling compound |
Non-Patent Citations (5)
| Title |
|---|
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| Dehydrogenative β‑Arylation of Saturated Aldehydes Using Transient Directing Groups;Xing-Long Zhang,等;《Organic Letters》;20190327;第21卷;第2732页 entry 19、20 * |
| Design and synthesis of chitin synthase inhibitors as potent fungicides;Qi Chena,等;《Chinese Chemical Letters》;20171231;第28卷(第6期);全文 * |
| Potassium modified alumina as a catalyst for the aldol condensation of benzaldehyde with linear C3–C8 aldehydes;Eva Vrbkova，等;《Reac Kinet Mech Cat》;20170201;第121卷;全文 * |
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