[ CAS No. 34246-54-3 ] {[proInfo.proName]}

Name: 34246-54-3|3-Ethylbenzaldehyde|95%
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Quality Control of [ 34246-54-3 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 34246-54-3 ]

Product Details of [ 34246-54-3 ]

CAS No. :	34246-54-3	MDL No. :	MFCD09263482
Formula :	C₉H₁₀O	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	LLYXUFQXCNIGDG-UHFFFAOYSA-N
M.W :	134.18	Pubchem ID :	118623
Synonyms :

Calculated chemistry of [ 34246-54-3 ]

Physicochemical Properties

Num. heavy atoms :	10
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.22
Num. rotatable bonds :	2
Num. H-bond acceptors :	1.0
Num. H-bond donors :	0.0
Molar Refractivity :	41.6
TPSA :	17.07 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.54 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.84
Log Po/w (XLOGP3) :	2.22
Log Po/w (WLOGP) :	2.06
Log Po/w (MLOGP) :	2.1
Log Po/w (SILICOS-IT) :	2.79
Consensus Log Po/w :	2.2

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	2.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-2.38
Solubility :	0.556 mg/ml ; 0.00414 mol/l
Class :	Soluble
Log S (Ali) :	-2.21
Solubility :	0.821 mg/ml ; 0.00612 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.1
Solubility :	0.106 mg/ml ; 0.000787 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.0

Safety of [ 34246-54-3 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 34246-54-3 ]

* 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.

Upstream synthesis route of [ 34246-54-3 ]
Downstream synthetic route of [ 34246-54-3 ]

[ 34246-54-3 ] Synthesis Path-Upstream 1~5

1
[ 3132-99-8 ]
[ 97-94-9 ]
[ 34246-54-3 ]

Yield	Reaction Conditions	Operation in experiment
46%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; cesium acetate In tetrahydrofuran for 6 h; Reflux; Inert atmosphere	Triethylborane (1.00 M in THF, 2.00 mL, 2.00 mmol) was addedto a suspension of 3-bromobenzaldehyde (84) (0.370 g,2.00 mmol), Pd(dppf)Cl2 (14.6 mg, 20.0 lmol), and CsOAc(0.384 g, 2.00 mmol) in THF (3.0 mL) under Ar., and the mixturewas heated until reflux began this being maintained for 6 h. Aftercooling to room temperature, the mixture was diluted with Et2O,washed with saturated aqueous NaHCO3 and brine, dried (Na2SO4),filtered and concentrated in vacuo. The residue was purified by silicagel flash CC to afford 3-ethylbenzaldehyde (63) (0.123 g,0.920 mmol, 46percent) as a colorless oil; 1H-NMR (CDCl3, 400 MHz) d:1.28 (t, J = 7.2 Hz, 3H, –CH3), 2.74 (q, J = 7.2 Hz, 2H, –CH2–), 7.42–7.48, 7.69–7.72 (m, each 2H, Ar–H), 10.0 (s, 1H, –CHO); spectraldata were in agreement with those in the literature (Wang et al.,2009).

Reference： [1] Phytochemistry, 2013, vol. 96, p. 132 - 147
[2] Patent: WO2005/95326, 2005, A2, . Location in patent: Page/Page column 114-115

2
[ 585-71-7 ]
[ 68-12-2 ]
[ 34246-54-3 ]

Reference： [1] Patent: US6218376, 2001, B1,

3
[ 97-94-9 ]
[ 17763-68-7 ]
[ 34246-54-3 ]

Reference： [1] European Journal of Organic Chemistry, 2009, # 22, p. 3688 - 3692

4
[ 19955-99-8 ]
[ 34246-54-3 ]

Reference： [1] ChemCatChem, 2013, vol. 5, # 1, p. 322 - 330

5
[ 82657-69-0 ]
[ 34246-54-3 ]

Reference： [1] Justus Liebigs Annalen der Chemie, 1918, vol. 417, p. 87

[ 34246-54-3 ] Synthesis Path-Downstream 1~51

1
[ 16433-88-8 ]
[ 34246-54-3 ]
9-(3-ethyl-benzylidene)-2,7-dibromo-fluorene [ No CAS ]

Reference： [1]Chemische Berichte,1920,vol. 53,p. 1236

2
[ 82657-69-0 ]
[ 34246-54-3 ]

Reference： [1]Justus Liebigs Annalen der Chemie,1918,vol. 417,p. 87

3
[ 87-41-2 ]
[ 34246-54-3 ]
[ 13935-93-8 ]

Reference： [1]Recueil des Travaux Chimiques des Pays-Bas,1966,vol. 85,p. 1259 - 1262

4
[ 34246-54-3 ]
[ 2181-44-4 ]
[ 30018-37-2 ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1995,vol. 43,p. 1488 - 1491

6
[ 98-03-3 ]
[ 34246-54-3 ]
[ 55241-49-1 ]
5-[5-(3-ethyl-phenyl)-2-thiophen-2-yl-3<i>H</i>-imidazol-4-yl]-1,3-dimethyl-1,3-dihydro-benzoimidazol-2-one [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 919 - 923

7
[ 418762-88-6 ]
[ 34246-54-3 ]
(2-Chloro-6-pyrrol-1-yl-benzyl)-[1-(3-ethyl-phenyl)-meth-(E)-ylidene]-amine [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 3453 - 3458

8
[ 34246-54-3 ]
2-(2-Dimethylamino-ethoxy)-1-(3-ethyl-phenyl)-ethanol [ No CAS ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1995,vol. 43,p. 1488 - 1491

9
[ 3132-99-8 ]
[ 97-94-9 ]
[ 34246-54-3 ]

Yield	Reaction Conditions	Operation in experiment
46%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; cesium acetate; In tetrahydrofuran; for 6h;Reflux; Inert atmosphere;	Triethylborane (1.00 M in THF, 2.00 mL, 2.00 mmol) was addedto a suspension of 3-bromobenzaldehyde (84) (0.370 g,2.00 mmol), Pd(dppf)Cl2 (14.6 mg, 20.0 lmol), and CsOAc(0.384 g, 2.00 mmol) in THF (3.0 mL) under Ar., and the mixturewas heated until reflux began this being maintained for 6 h. Aftercooling to room temperature, the mixture was diluted with Et2O,washed with saturated aqueous NaHCO3 and brine, dried (Na2SO4),filtered and concentrated in vacuo. The residue was purified by silicagel flash CC to afford 3-ethylbenzaldehyde (63) (0.123 g,0.920 mmol, 46%) as a colorless oil; 1H-NMR (CDCl3, 400 MHz) d:1.28 (t, J = 7.2 Hz, 3H, -CH3), 2.74 (q, J = 7.2 Hz, 2H, -CH2-), 7.42-7.48, 7.69-7.72 (m, each 2H, Ar-H), 10.0 (s, 1H, -CHO); spectraldata were in agreement with those in the literature (Wang et al.,2009).
	With potassium phosphate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In tetrahydrofuran; hexane; water; for 4h;Heating / reflux;	Example 7; Preparation of 3-Ethylbenzaldehyde from 3- bromobenzaldehyde; 3-Bromobenzaldehyde (Aldrich, 1.17 mL, 10.0 mmol) was dissolved in THF (20 mL) at rt. To it was added PdCl2 (dppf) *CH2Cl2 complex (Aldrich, 82 mg, 0.10 mmol), 2 M potassium phosphate (aq, 10 mL, 20 mmol), and triethylborane (Aldrich, 1.0 M solution in hexanes, 10 mL, 10 mmol). This was heated to reflux for 4 h, whereupon the mixture was allowed to cool to rt. The reaction mixture was partitioned between EtOAc and water. The organic layer was separated, dried (MgS04), and concentrated under reduced pressure. The residue was purified by flash chromatography (20% EtOAc/hexanes elution) to give a clear, colorless oil which was used without further purification

Reference： [1]Phytochemistry,2013,vol. 96,p. 132 - 147
[2]Patent: WO2005/95326,2005,A2 .Location in patent: Page/Page column 114-115

10
[ 34246-54-3 ]
[ 2234-82-4 ]
[ 676133-25-8 ]

Yield	Reaction Conditions	Operation in experiment
94%		Example 8; Preparation of 3-Ethyl-a-propylbenzyl alcohol from 3- ethylbenzaldehyde; To a solution of <strong>[34246-54-3]3-ethylbenzaldehyde</strong> (641 mg, 4.78 mmol) in THF (15 mL) cooled to 0 C was added a solution of propylmagnesium chloride (Aldrich, 2.0 M in diethyl ether, 7.0 mL, 14.0 mmol) dropwise with stirring. Upon completion of addition, the reaction mixture was allowed to warm to rt for 2 h. Reaction was then quenched by addition of water (1 mL), then concentrated under reduced pressure. The residue was purified by flash chromatography (Rf = 0.71 in 30% EtOAc/hexanes) to give a colorless oil as product (804 mg, 94%)

Reference： [1]Patent: WO2005/95326,2005,A2 .Location in patent: Page/Page column 115

11
[ 34246-54-3 ]
[ 868750-73-6 ]

Yield	Reaction Conditions	Operation in experiment
		49.1 2-(3-ethyl-phenyl)-4-chloromethyl-5-methyl-oxazole was prepared from <strong>[34246-54-3]3-ethyl-benzaldehyde</strong> in analogy to the procedure by Binggeli et al. (WO200292084).

Reference： [1]Patent: US2005/245515,2005,A1 .Location in patent: Page/Page column 23

12
[ 585-71-7 ]
[ 68-12-2 ]
[ 34246-54-3 ]

Yield	Reaction Conditions	Operation in experiment
	With n-butyllithium; In tetrahydrofuran;	i 3-Ethylbenzaldehyde A solution of 3-bromo-ethylbenzene (25 g) in dry tetrahydrofuran (350 ml) at -70 C. was treated dropwise with n-butyllithium (59 ml of a 2.5M solution in hexanes) and stirred for 1 hour. N,N-Dimethylformamide (30 ml) was added and the solution was stirred at -70 C. for 1 hour and allowed to warm to room temperature. The reaction mixture was partitioned between saturated ammonium chloride solution and ethyl acetate. The organic phase was washed with 1N hydrochloric acid, dried (MgSO4) and evaporated. Yield 18.55 g. 1H NMR: delta (DMSO) 10.00 (s, 1H), 7.71 (m, 2H), 7.47 (m, 2H), 2.74 (q, 2H), 1.28 (t, 3H)

Reference： [1]Patent: US6218376,2001,B1

13
C₆H₆NO₂PolS [ No CAS ]
[ 34246-54-3 ]
[ 74-88-4 ]
C₁₆H₁₈NO₃PolS [ No CAS ]

Reference： [1]Patent: US6353112,2002,B1 .Location in patent: Page column 13-15

14
[ 97-94-9 ]
[ 17763-68-7 ]
[ 34246-54-3 ]

Reference： [1]European Journal of Organic Chemistry,2009,p. 3688 - 3692

15
[ 1232224-90-6 ]
[ 34246-54-3 ]
[ 1232222-40-0 ]

Yield	Reaction Conditions	Operation in experiment
58%	acetic acid; In ethanol; at 1 - 30℃; for 3h;	To a solution of (7-morpholin-4-yl-2-pyrazin-2-yl-pyrazolo[1,5-a]pyrimidin-5-yl)-hydrazine (26 mg, 0.083 mM) in ethanol (3.0 mL), there were added <strong>[34246-54-3]3-ethyl-benz-aldehyde</strong> (17 mg, 0.12 mM) and acetic acid (5.0 muL) and the mixture was stirred at room temperature for 3 hours. The precipitated solid was filtered and washed with ethanol to thus give the title compound (21 mg, yield: 58%). 1H-NMR (300 MHz, DMSO): delta 1.20 (3H, J=7.8 Hz, t), 2.64 (2H, J=7.8 Hz, q), 3.73 (4H, s), 3.87-3.88 (4H, m), 6.37 (1H, s), 6.65 (1H, s), 7.21 (1H, J=7.8 Hz, d), 7.33 (1H, J=7.8 Hz, t), 7.49 (1H, s), 7.55 (1H, J=7.8 Hz, d), 8.04 (1H, s), 8.63 (1H, J=2.7 Hz, d), 8.70 (1H, m), 9.31 (1H, J=1.2 Hz, d), 11.29 (1H, s) MS (ESI) m/z (M+H)+ 429

Reference： [1]Patent: US2011/294781,2011,A1 .Location in patent: Page/Page column 58

16
[ 1232225-18-1 ]
[ 34246-54-3 ]
C₂₄H₂₅N₇O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
55%	acetic acid; In ethanol; at 1 - 30℃; for 3h;	There was suspended, in ethanol (3.0 mL), (7-morpholin-4-yl-2-pyridin-3-yl-pyrazolo[1,5-a]pyrimidin-5-yl)-hydrazine (24 mg, 0.077 mM), then <strong>[34246-54-3]3-ethyl-benz-aldehyde</strong> (16 mg, 0.12 mM) and acetic acid (5.0 muL) were added to the suspension and the mixture was stirred at room temperature for 3 hours. The precipitated solid was filtered and washed with ethanol to thus give the title compound (18 mg, yield: 55%). 1H-NMR (300 MHz, DMSO): delta 1.20 (3H, J=7.8 Hz, t), 2.64 (2H, J=7.8 Hz, q), 3.72 (4H, s), 3.86-3.87 (4H, m), 6.33 (1H, s), 6.67 (1H, s), 7.21 (1H, J=7.8 Hz, d), 7.33 (1H, J=7.8 Hz, t), 7.46-7.50 (2H, m), 7.55 (1H, J=7.8 Hz, d), 8.05 (1H, s), 8.28 (1H, J=1.8, 7.8 Hz, dt), 8.56 (1H, J=1.2, 4.5 Hz, dd), 9.14 (1H, J=1.2 Hz, d), 11.23 (1H, s) MS (ESI) m/z (M+H)+ 428

Reference： [1]Patent: US2011/294781,2011,A1 .Location in patent: Page/Page column 57; 58

17
[ 1313014-23-1 ]
[ 34246-54-3 ]
[ 1313013-89-6 ]

Yield	Reaction Conditions	Operation in experiment
82%	In ethanol; at 20℃; for 2h;	Example 10 Synthesis of N-(3-ethyl-benzylidene)-N'-(8-morpholin-4-yl-2-pyridin-4-yl-imidazo[1,2-b]pyridazin-6-yl)-hydrazine (Compound 10) (8-Morpholin-4-yl-2-pyridin-4-yl-imidazo[1,2-b]pyridazin-6-yl)-hydrazine (21.6mg, 0.0694mmol) was dissolved in ethanol (2mL). 3-Ethylbenzaldehyde (10.2mg, 0.0763mmol) was added thereto and stirred at room temperature for 2 hours. Then, the reaction liquid was filtered, and the obtained solid material was washed with diethyl ether to obtain a title compound (24.4mg, 82%). The characteristic value of the compound is shown below. 1H-NMR (300 MHz, DMSO): delta 1.20 (t, 3H, J=7.6 Hz), 2.62 (q, 2H, J=7.6 Hz), 3.83-3.85 (m, 4H), 3.95-3.97 (m, 4H), 6.44 (s, 1H), 7.18 (d, 1H, J=7.6 Hz), 7.32 (t, 1H, J=7.6 Hz), 7.46 (s, 1H), 7.52 (d, 1H, J=7.6 Hz), 7.87 (d, 2H, J=5.9 Hz), 8.00 (s, 1H), 8.56-8.57 (m, 3H), 10.95 (s, 1H); MS (ESI) m/z 428 (M+H)+.

Reference： [1]Patent: EP2518072,2012,A1 .Location in patent: Page/Page column 21-22

18
[ 34246-54-3 ]
[ 74-89-5 ]
C₁₀H₁₃N [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In methanol; water; at 20℃; for 0.333333h;	General procedure: m-Tolualdehyde (1.66 g, 14.0 mmol) was treated with methylamine (40% aqueous, 1.39 ml, 18.0 mmol) in methanol (20 ml) at room temperature. The reaction was stirred for 20 min and treated with sodium borohydride (0.26 g, 7.0 mmol) portionwise. The reaction was stirred for 1 h and treated with 3?-fluoro-2-bromoacetophenone (3.0 g, 14.0 mmol) followed by stirring for 45 min at room temperature. The reaction was finally treated with sodium borohydride (0.52 g, 14.0 mmol) portionwise, and stirring continued overnight. The reaction was diluted with water (100 ml) and extracted with methylene chloride (3 × 100 ml). The combined organic extracts were washed with brine and dried over anhydrous sodium sulfate, followed by filtration and concentration in vacuo. Purification by column chromatography on silica gel eluting with hexanes/ethyl acetate (3/1) provided the amino alcohol (4.3 g) as a yellow oil

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 7219 - 7222

19
[ 34246-54-3 ]
[ 1415240-20-8 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 7219 - 7222

20
[ 34246-54-3 ]
[ 1415240-40-2 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 7219 - 7222

21
[ 34246-54-3 ]
7-ethyl-2-methyl-4-phenyl-1,2,3,4-tetrahydroisoquinoline [ No CAS ]
[ 1415240-58-2 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 7219 - 7222

22
[ 34246-54-3 ]
C₁₀H₁₅N [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 7219 - 7222

23
[ 19955-99-8 ]
[ 34246-54-3 ]

Reference： [1]ChemCatChem,2013,vol. 5,p. 322 - 330

24
[ 34246-54-3 ]
[ 188945-44-0 ]
[ 1499179-27-9 ]

Yield	Reaction Conditions	Operation in experiment
72%		General procedure: Triton B (40% in MeOH, 7.30 mL, 17.5 mmol) was added dropwise to a solution of ethyl 2-[bis(2-isopropylphenoxy) phosphoryl]acetate (5.30 g, 13.1 mmol) in THF (150 mL) at -78 C under Ar. After 15 min of stirring, a solution of 2-methylbenzaldehyde (59) (1.50 g, 12.5 mmol) in THF (50 mL) was added dropwise to the solution. After 10 h of stirring, the mixture was quenched with satd. aq. NH4Cl (30 mL) and extracted with EtOAc (3 x 30 mL). The organic layer was washed successively with H2O, satd. aq. (20 mL) NaHCO3 (20 mL) and brine (20 mL), then dried (MgSO4), filtered and concentratedin vacuo.; The Z-selective olefination of 63 was performed using the proceduredescribed above to provide (Z)-ethyl 3-(2-ethylphenyl)acrylate (cis-119) (72%, Z:E = 98:2, determined by 1H-NMRspectrum) (silica gel CC, EtOAc/hexane, 3:97) as a colorless oil:1H-NMR (CDCl3, 400 MHz) d: 1.24 (t, J = 7.2 Hz, 6H, -CH3), 2.65(q, J = 7.2 Hz, 2H, Ar-CH2-), 4.17 (q, J = 7.2 Hz, 2H, -CO2-CH2-),5.93 (d, J = 12.6 Hz, 1H, CH-CO2-), 6.92 (d, J = 12.6 Hz, 1H, Ar-CH), 7.16 (d, J = 7.6 Hz, 1H, Ar-H), 7.26 (t, J = 7.6 Hz, 1H, Ar-H),7.39-7.42 (m, 2H, Ar-H).

Reference： [1]Phytochemistry,2013,vol. 96,p. 132 - 147

25
[ 34246-54-3 ]
[ 1499179-07-5 ]

Reference： [1]Phytochemistry,2013,vol. 96,p. 132 - 147

26
[ 5977-14-0 ]
[ 3922-47-2 ]
[ 34246-54-3 ]
2-(benzylthio)-7-(3-ethylphenyl)-5-methyl-4,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxamide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2015,vol. 58,p. 4194 - 4203

27
[ 34246-54-3 ]
[ 173443-43-1 ]
4-iodo-3’-ethyl-stilbene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	With sodium hydroxide; at 50℃; for 3h;	A batch of stilbene type compound was prepared by using the following reaction conditions in substantially the same manner as in Example 2, and the reaction conditions and the results are shown in Table 1.

Reference： [1]Patent: CN104591959,2016,B .Location in patent: Paragraph 0074-0080

28
[ 672-89-9 ]
[ 34246-54-3 ]
6-[(E)-2-(3-ethylphenyl)vinyl]-4-methoxy-2H-pyran-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
32%	With magnesium methanolate; In methanol; at 60℃;	General procedure: The synthesis of 5,6-dehydrokawain analogues were performed based on the method reported by McCracken, S. T. et al.2 Magnesium methoxide was prepared by gently heating Mg (156 mg) in anhydrous MeOH. 4-Methoxy-6-methyl-2-pyrone (3)3 (0.30 g, 2.1 mmol) or other 2-pyrones and each aldehyde (2.2 mmol) were added to the solution. The reaction mixture was heated at reflux for 3-6 hours, cooled, and dried in vacuo. The residual material was then suspended in acetic acid (3.3 M, 30 mL) and extracted with ethyl acetate for three times. The combined organic layer was washed with water and dried in vacuo. Purification of the compounds was conducted by preparative HPLC. NMR spectra were recorded on a JEOL JNM-ECZ400S in CDCl3. HRMS was recorded on a Thermo scientific Q Exactive instrument. Mp were recorded on a Yanagimoto micro melting point apparatus. The 1H and 13C NMR data observed for 11,4, 33, 73, 83, 105, 222, 256, 266 were agreed with those previously reported in the literature. The 1H NMR data of 247 and 278 were in agreement with literature values.
32%	With magnesium; In methanol; at 60℃; for 6h;	Metal Mg was heated in methanol (60 C.) and suspended. 4-methoxy-6-methyl-2-pyrone (0.20 g) and <strong>[34246-54-3]3-ethylbenzaldehyde</strong> (0.21 ml, 1.6 mmol) were added thereto, and the mixture was heated at 60 C. for 6 hours. After cooling, it was acidified with acetic acid and extracted with ethyl acetate. The extract was concentrated under reduced pressure and then purified by reverse phase preparative HPLC (mobile phase: water-acetonitrile = 3: 7).Yield: 32%.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2017,vol. 27,p. 2401 - 2406
[2]Patent: JP2018/123111,2018,A .Location in patent: Paragraph 0045

29
[ 34246-54-3 ]
[ 13297-17-1 ]
2-(3-(3-ethylphenyl)acryloyl)-3-methylquinoxaline-1,4-dioxide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; In methanol; at 0℃;	Take sodium hydroxide (0.6 g, 15 mmol, 1 eq)And 100 mL of methanol were added to a 250 mL eggplant vial,Ice bath to 0 C. 2-acetyl-3-methylquinoxaline 1,4-dioxide (3.27 g, 15 mmol, 1 eq)Join them,While maintaining the temperature of the solution at 0 C,The mixture was stirred for 10 to 15 minutes with <strong>[34246-54-3]3-ethylbenzaldehyde</strong> (2.4 g, 18 mmol, 1.2 eq) in an ice bath and the TLC showed the starting material2-acetyl-3-methylquinoxaline 1,4-dioxide is completely reacted.filter,The filter cake was washed with methanol (100 mL * 3)Get a yellow solid,TLC shows two points,Separating silica gel column chromatography to give 2-(3-(3-ethylphenyl)acryloyl)-3-methylquinoxaline-1,4-dioxide.

Reference： [1]Patent: CN104447587,2017,B .Location in patent: Paragraph 0115; 0116; 0117

30
[ 34246-54-3 ]
[ 108-45-2 ]
C₂₄H₂₄N₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In ethanol; at 50℃; for 3.66667h;	<strong>[34246-54-3]m-ethylbenzaldehyde</strong> and m-phenylenediamine,The molar ratio of ethylbenzaldehyde to the above m-phenylenediamine is 2: 1,With anhydrous ethanol as the reaction solvent;Add the above in a single jarM-ethylbenzaldehyde,And then filled with the above-mentioned ethyl benzaldehyde single-necked flask was added anhydrous ethanol,The above-mentioned anhydrous ethanol is added in an amount of 50% of the mass of the <strong>[34246-54-3]m-ethylbenzaldehyde</strong>,To obtain the first product, at room temperature and then to the first product contained in a single-neck flask dropwise m-phenylenediamine, after the dropwise addition reaction 40min to obtain a second product,After the second reactant was warmed to 50 C and reacted for 3h to obtain a third product,The third product was cooled to room temperature, and then reduced to room temperature, the third product was warmed to 35 C and distilled under reduced pressure 1.5h, and finally distilled under reduced pressure has been the third product literAfter the temperature was raised to 95 C and flash-off for 40 min, the fourth product was obtained after removing the reaction solvent,The fourth product is a novel imine compound Z2-1, having a molecular weight of 340,Chemical reaction formula as shown in formula 2.

Reference： [1]Patent: CN107118179,2017,A .Location in patent: Paragraph 0055; 0056; 0057; 0058; 0059; 0060

31
[ 3360-54-1 ]
[ 34246-54-3 ]
C₁₈H₂₀O [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2018,vol. 57,p. 7668 - 7672
Angew. Chem.,2018,vol. 130,p. 7794 - 7798,5

32
[ 34246-54-3 ]
(S)-3-(3-ethylphenyl)-5-phenyl-5-(2,2,2-trifluoroethyl)-4,5-dihydroisoxazole [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2018,vol. 57,p. 7668 - 7672
Angew. Chem.,2018,vol. 130,p. 7794 - 7798,5

33
[ 34246-54-3 ]
3-(3-ethylphenyl)-5-phenyl-5-(2,2,2-trifluoroethyl)-4,5-dihydroisoxazole [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2018,vol. 57,p. 7668 - 7672
Angew. Chem.,2018,vol. 130,p. 7794 - 7798,5

34
[ 34246-54-3 ]
C₁₈H₁₈O [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2018,vol. 57,p. 7668 - 7672
Angew. Chem.,2018,vol. 130,p. 7794 - 7798,5

35
[ 34246-54-3 ]
(E)-1-(3-ethylphenyl)-3-phenylbut-3-en-1-one oxime [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2018,vol. 57,p. 7668 - 7672
Angew. Chem.,2018,vol. 130,p. 7794 - 7798,5

36
[ 3699-66-9 ]
[ 34246-54-3 ]
ethyl (E)-3-(3-ethylphenyl)-2-methylacrylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		To a stirred suspension of NaH (60% dispersion in mineral oil) (101 mg, 4.20 mmol) in THF (3 mL) was added ethyl 2-(diethoxyphosphoryl)propanoate (0.47 mL, 2.23 mmol) at 0 C under nitrogen atmosphere. The reaction mixture was stirred at room temperature for 1 h. Again the reaction mixture was cooled 0 C and <strong>[34246-54-3]3-ethylbenzaldehyde</strong> (0.19 mL, 1 .49 mmol) in THF (2 mL) was added and the stirring was continued at room temperature for 16h. The reaction was monitored by TLC; after completion of the reaction, the reaction mixture was quenched with water (10 mL) and extracted with EtOAc (2x20 mL). Separated organic layer was washed with saturated NaHC03, dried over sodium sulfate, filtered and concentrated under reduced pressure. Obtained crude material was purified through silica gel column chromatography using 3% EtOAc/ hexanes to afford ethyl (E)-3-(3-ethylphenyl)-2-methylacrylate (250 mg, 77%) as white colour syrup.Ethyl (E)-3-(3-ethylphenyl)-2-methylacrylate:1H NMR (500MHz, CDCI3): delta 7.69 (s, 1 H), 7.35- 7.30 (m, 1 H), 7.26-7.23 (m, 2H), 7.18 (d, J = 7.5 Hz, 1 H), 4.29 (q, J = 7.0 Hz, 2H), 2.69 (q, J = 7.7 Hz, 2H), 2.14 (d, J=1 .2 Hz, 3H), 1.37 (t, J = 7.1 Hz, 3H), 1.27 (t, J = 7.7 Hz, 3H); LC-MS (ESI): 82.65%; m/z 218.9 [M+H]+at RT 3.15 min; (column; Ascentis Express C-18 (50 x 3.0mm, 2.7muGammaeta); 0.025% Aq TFA + 5% ACN: ACN + 5% 0.025% Aq TFA; 1 .2 mL/min).

Reference： [1]Patent: WO2018/138369,2018,A1 .Location in patent: Page/Page column 67

37
[ 34246-54-3 ]
(1-(2-methoxybenzyl)piperidin-4-yl)methanamine [ No CAS ]
C₂₃H₃₀N₂O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium sulfate; In dichloromethane; at 20℃; for 96h;Inert atmosphere;	General procedure: To a mixture of (1-benzylpiperidin-4-yl)methanamine 2 or 7d,g-l (typically 1.0 eq) and anhydrous Na2SO4 (typically 6.0 eq) in DCM (for compounds 7h and 7g, TEA (2.0 eq) was added), the corresponding benzaldehyde (typically 1.0 eq) was added. The mixture was stirred at rt until imine conversion was finished as judged by NMR analysis of a sample after mini-workup. The reaction mixture was filtered and the filtrate was evaporated in vacuo to afford the crude imine product.

Reference： [1]European Journal of Medicinal Chemistry,2019,vol. 162,p. 631 - 649

38
[ 34246-54-3 ]
C₁₂H₁₆O₂ [ No CAS ]

Reference： [1]Patent: CN108863991,2018,A

39
[ 34246-54-3 ]
C₁₉H₂₄O₃ [ No CAS ]

Reference： [1]Patent: CN108863991,2018,A

40
[ 34246-54-3 ]
C₁₉H₂₂O₂ [ No CAS ]

Reference： [1]Patent: CN108863991,2018,A

41
[ 34246-54-3 ]
C₁₂H₁₆O₂ [ No CAS ]

Reference： [1]Patent: CN108863991,2018,A

42
[ 34246-54-3 ]
[ 106-95-6 ]
C₁₂H₁₆O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65%	With copper; In water; at 20℃; for 3h;	Compound II-1 (100 g, 0.82 mol, 1.0 eq), compound III-1 (167.01 g, 1.24 mol, 1.5 eq) was dissolved in a 1.0 L aqueous solution, and Cu powder was added in portions (104.2 g, 1.64 mol, 2.0 eq). After the addition is completed, the reaction is stirred at room temperature for 3 hours, filtered, and the filter cake is washed with MTBE, extracted with aqueous phase MTBE, and the organic phases are combined, washed with 1 L of saturated brine, dried and concentrated to give compound IV-7. The pale yellow liquid was 93.94 g, and the yield was 65%

Reference： [1]Patent: CN108863991,2018,A .Location in patent: Paragraph 0107-0110

43
[ 74-85-1 ]
[ 696-41-3 ]
[ 34246-54-3 ]

Yield	Reaction Conditions	Operation in experiment
60%	With (1,2-dimethoxyethane)dichloronickel(II); N,N,N,N,-tetramethylethylenediamine; (4,4'-di-tert-butyl-2,2'-dipyridyl)-bis-(2-phenylpyridine(-1H))-iridium(III) hexafluorophosphate; water; N-ethyl-N,N-diisopropylamine; In dimethyl sulfoxide; at 80℃; under 760.051 Torr; for 24h;Schlenk technique; Sealed tube; Irradiation;	General procedure: Aryl-halide (0.2 mmol, 1 equiv.), Ir(dtbbpy)(ppy)2PF6 (1.8 mg, 0.002 mmol, 1 mol %), NiCl2.glyme (4.4mg, 0.02 mmol, 10 mol %), DMSO (2.0 mL) was added to a 10 mL schlenk flask equipped with a magnetic stirrer bar. This resulting mixture was sealed and degassed via vacuum evacuation and subsequent backfill with ethylene for three times. Then, N,N,N?,N?-tetramethylethylenediamine, TMEDA(60 muL, 2 equiv.), N,N-diisopropylethylamine, DIPEA (70 muL, 2 equiv.) and H2O (7.2 muL, 2 equiv.) were subsequently added in this order. The mixture was then irradiated with blue LED (2 meter strip, 18 W)with ethylene balloon for 24 hours at 80oC (Figure S1). The reaction was added water (30 mL) and extracted with ethyl acetate (10 mL) three times. Combined organic layer was successively washed with brine three times and dried over Na2SO4 and concentrated under reduced pressure. The residue was then subjected to flash column chromatography (hexane or hexane/ethyl acetate) to yield theproduct

Reference： [1]Chem,2019,vol. 5,p. 192 - 203

44
[ 3132-99-8 ]
[ 74-85-1 ]
[ 34246-54-3 ]

Yield	Reaction Conditions	Operation in experiment
49%	With (1,2-dimethoxyethane)dichloronickel(II); N,N,N,N,-tetramethylethylenediamine; (4,4'-di-tert-butyl-2,2'-dipyridyl)-bis-(2-phenylpyridine(-1H))-iridium(III) hexafluorophosphate; water; N-ethyl-N,N-diisopropylamine; In dimethyl sulfoxide; at 80℃; under 760.051 Torr; for 24h;Schlenk technique; Sealed tube; Irradiation;	General procedure: Aryl-halide (0.2 mmol, 1 equiv.), Ir(dtbbpy)(ppy)2PF6 (1.8 mg, 0.002 mmol, 1 mol %), NiCl2.glyme (4.4mg, 0.02 mmol, 10 mol %), DMSO (2.0 mL) was added to a 10 mL schlenk flask equipped with a magnetic stirrer bar. This resulting mixture was sealed and degassed via vacuum evacuation and subsequent backfill with ethylene for three times. Then, N,N,N?,N?-tetramethylethylenediamine, TMEDA(60 muL, 2 equiv.), N,N-diisopropylethylamine, DIPEA (70 muL, 2 equiv.) and H2O (7.2 muL, 2 equiv.) were subsequently added in this order. The mixture was then irradiated with blue LED (2 meter strip, 18 W)with ethylene balloon for 24 hours at 80oC (Figure S1). The reaction was added water (30 mL) and extracted with ethyl acetate (10 mL) three times. Combined organic layer was successively washed with brine three times and dried over Na2SO4 and concentrated under reduced pressure. The residue was then subjected to flash column chromatography (hexane or hexane/ethyl acetate) to yield theproduct

Reference： [1]Chem,2019,vol. 5,p. 192 - 203

45
[ 34246-54-3 ]
[ 82657-69-0 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium tetrahydroborate; In methanol; at 20℃; for 1h;Cooling with ice;	A solution of <strong>[34246-54-3]3-ethylbenzaldehyde</strong> (5 g, 37.3 mmol) in methanol (50 mL) was cooled with ice and sodium borohydride (2.1 g, 56 mmol) was added portion-wise. The reaction mixture was stirred at rt for 1 h. The mixture was concentrated and the residue was partitioned between saturated ammonium chloride and DCM. The organic layer was separated, dried over sodium sulfate and concentrated. The crude (3-ethylphenyl)methanol (4.5 g, 90%) was taken as such for next step without further purification.

Reference： [1]Patent: WO2019/99582,2019,A1 .Location in patent: Paragraph 0313; 0314; 0315

46
[ 34246-54-3 ]
[ 216658-62-7 ]