[ CAS No. 1504-74-1 ] {[proInfo.proName]}

Name: 1504-74-1|2-Methoxycinnamaldehyde|98%
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Quality Control of [ 1504-74-1 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 1504-74-1 ]

Product Details of [ 1504-74-1 ]

CAS No. :	1504-74-1	MDL No. :	MFCD00007001
Formula :	C₁₀H₁₀O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	KKVZAVRSVHUSPL-GQCTYLIASA-N
M.W :	162.19	Pubchem ID :	641298
Synonyms :	o-Methoxycinnamaldehyde

Calculated chemistry of [ 1504-74-1 ]

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.1
Num. rotatable bonds :	3
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	48.03
TPSA :	26.3 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) :	-5.73 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.01
Log Po/w (XLOGP3) :	2.2
Log Po/w (WLOGP) :	1.8
Log Po/w (MLOGP) :	1.66
Log Po/w (SILICOS-IT) :	2.48
Consensus Log Po/w :	2.03

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-2.4
Solubility :	0.64 mg/ml ; 0.00395 mol/l
Class :	Soluble
Log S (Ali) :	-2.39
Solubility :	0.666 mg/ml ; 0.00411 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.55
Solubility :	0.454 mg/ml ; 0.0028 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	2.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.87

Safety of [ 1504-74-1 ]

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 [ 1504-74-1 ]

* 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 [ 1504-74-1 ]
Downstream synthetic route of [ 1504-74-1 ]

[ 1504-74-1 ] Synthesis Path-Upstream 1~14

1
[ 1504-74-1 ]
[ 33538-83-9 ]

Yield	Reaction Conditions	Operation in experiment
54%	With 10% palladium on activated charcoal In methanol at 20℃; for 2 h;	The suspension of 2-methoxycinnamaldehyde (1.00 g, 6.17 mmol) and Pd/C (131 mg, 0.20 mmol) werestirred in MeOH (12 mL) at room temperature for 2 h. The reaction mixture was filtered on celite with dichloromethane. The mixture solvent was evaporated under reduced pressure, and the residue was purifiedby column chromatography with hexane/ethyl acetate (3/1, v/v) to obtain 3-(2-methoxyphenyl)propanal.

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 2, p. 237 - 241
[2] Bioorganic and Medicinal Chemistry Letters, 1997, vol. 7, # 19, p. 2473 - 2476
[3] Chemical Communications, 2014, vol. 50, # 94, p. 14752 - 14755

2
[ 1504-61-6 ]
[ 1504-74-1 ]

Yield	Reaction Conditions	Operation in experiment
94%	With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; copper diacetate In water; acetonitrile at 20℃; for 4 h; Green chemistry	General procedure: A mixture of alcohol (5.0 mmol), Cu(OAc)₂ (9.1 mg, 0.05 mmol), and TEMPO (7.8 mg, 0.05 mmol) in CH₃CN/H₂O (5/10 mL) was stirred at room temperature for specified time. After completion of the reaction (monitored by TLC, eluents: petroleum ether/ethyl acetate = 4/1), dichloromethane (10 mL) was added to the resulting mixture. The dichloromethane phase was separated, and the aqueous phase was further extracted with dichloromethane (10 mL × 2). The combined organic layers were dried over anhydrous sodium sulfate and concentrated to give a residue, which was purified by column chromatography (eluents: petroleum ether/ethyl acetate = 10/1) to provide the desired product.

Reference： [1] Tetrahedron Letters, 2014, vol. 55, # 10, p. 1677 - 1681
[2] European Journal of Organic Chemistry, 2016, vol. 2016, # 20, p. 3401 - 3407
[3] Bioorganic and Medicinal Chemistry Letters, 1997, vol. 7, # 19, p. 2473 - 2476

3
[ 33538-83-9 ]
[ 1504-74-1 ]

Reference： [1] ACS Catalysis, 2017, vol. 7, # 6, p. 4000 - 4003
[2] Chemistry - An Asian Journal, 2009, vol. 4, # 11, p. 1712 - 1716
[3] Advanced Synthesis and Catalysis, 2009, vol. 351, # 9, p. 1229 - 1232

4
[ 75-07-0 ]
[ 135-02-4 ]
[ 1504-74-1 ]

Reference： [1] Organic Letters, 2016, vol. 18, # 1, p. 4 - 7
[2] Bulletin de la Societe Chimique de France, 1963, p. 1171 - 1175
[3] Bulletin de la Societe Chimique de France, 1967, p. 865 - 870

5
[ 75-27-4 ]
[ 612-15-7 ]
[ 1504-74-1 ]

Reference： [1] Chemical Science, 2018, vol. 9, # 11, p. 2986 - 2990

6
[ 3698-28-0 ]
[ 1504-74-1 ]

Reference： [1] Synlett, 2013, vol. 24, # 4, p. 487 - 490

7
[ 75-07-0 ]
[ 135-02-4 ]
[ 1504-74-1 ]

Reference： [1] Organic Letters, 2016, vol. 18, # 1, p. 4 - 7

8
[ 86657-75-2 ]
[ 1504-74-1 ]

Reference： [1] Archiv der Pharmazie (Weinheim, Germany), 1983, vol. 316, # 6, p. 574 - 576

9
[ 6099-03-2 ]
[ 1504-74-1 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 1997, vol. 7, # 19, p. 2473 - 2476

10
[ 98288-15-4 ]
[ 1504-74-1 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 1997, vol. 7, # 19, p. 2473 - 2476

11
[ 86657-70-7 ]
[ 1504-74-1 ]

Reference： [1] Archiv der Pharmazie (Weinheim, Germany), 1983, vol. 316, # 6, p. 574 - 576

12
[ 2136-75-6 ]
[ 135-02-4 ]
[ 1504-74-1 ]

Reference： [1] Organic Letters, 2016, vol. 18, # 4, p. 752 - 755

13
[ 624-67-9 ]
[ 100-66-3 ]
[ 1963-36-6 ]
[ 1504-74-1 ]

Reference： [1] Catalysis Science and Technology, 2017, vol. 7, # 19, p. 4422 - 4430

14
[ 109-92-2 ]
[ 135-02-4 ]
[ 1504-74-1 ]

Reference： [1] Journal of pharmaceutical sciences, 1971, vol. 60, # 8, p. 1188 - 1192

[ 1504-74-1 ] Synthesis Path-Downstream 1~88

1
[ 1504-74-1 ]
[ 1504-61-6 ]

Yield	Reaction Conditions	Operation in experiment
94%	With Cp*Ir(6,6'-dionato-2,2'-bipyridine)(H2O); isopropyl alcohol; at 120℃; for 12h;Inert atmosphere; Green chemistry;	2-Methoxycinnamaldehyde (162 mg, 1.0 mmol), cat. [Ir] (1.1 mg, 0.002 mmol, 0.2 mol%) and isopropanol (5 mL) were sequentially added to a 25 mL Kelvin tube, N2 protected, The reaction was carried out at 120 C for 12 h. Cool to room temperature and remove the solvent by rotary evaporation.The pure target compound was obtained by column chromatography (developing solvent: petroleum ether / ethyl acetate), yield: 94%
99%Chromat.	With formic acid; iron(II) tetrafluoroborate hexahydrate; tris(2-diphenylphosphinoethyl)phosphine; In tetrahydrofuran; at 60℃; for 2h;Schlenk technique; Inert atmosphere;	General procedure: Fe(BF4)2·6H2O (0.7 mg; 0.002 mmol) and tris[2-(diphenyl-phosphino)-ethyl]phosphine [P(CH2CH2PPh2)3; tetraphos] (1.4 mg; 0.002 mmol) are placed in a Schlenk-tube under argon atmosphere. 1 mL dry tetrahydrofurane is added and the purple solution is stirred for 2 min. Cinnamaldehyde (63 muL; 0.5 mmol) and 100 muL n-hexadecane as an internal GC-standard are injected and a sample is taken for GC-analysis. The solution is heated to 60 C and the reaction starts by addition of 1.1 equiv formic acid (22 muL; 0.55 mmol). After 2 h, a second sample is taken for GC-analysis and conversion and yield are determined by comparison with authentic samples. For the isolation, the reaction is scaled up by a factor of 20. When the reaction is completed, the reaction solution is diluted with a mixture of n-hexane and ethyl acetate (3:1), filtered through a plug of silica and the solvent removed in vacuum.

Reference： [1]Chemistry - A European Journal,2013,vol. 19,p. 7701 - 7707
[2]Journal of Organic Chemistry,2018,vol. 83,p. 2274 - 2281
[3]Patent: CN110015947,2019,A .Location in patent: Paragraph 0034-0038
[4]Journal of Medicinal Chemistry,1965,vol. 8,p. 326 - 331
[5]Journal of Organometallic Chemistry,2013,vol. 744,p. 156 - 159
[6]Chemical Science,2015,vol. 6,p. 4978 - 4985
[7]Angewandte Chemie - International Edition,2015,vol. 54,p. 12645 - 12648
Angew. Chem.,2015
[8]Organic Letters,2018,vol. 20,p. 5040 - 5043

2
[ 75-07-0 ]
[ 135-02-4 ]
[ 1504-74-1 ]

Reference： [1]Organic Letters,2016,vol. 18,p. 4 - 7
[2]Bulletin de la Societe Chimique de France,1963,p. 1171 - 1175

3
[ 1504-61-6 ]
[ 1504-74-1 ]

Yield	Reaction Conditions	Operation in experiment
94%	With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; copper diacetate; In water; acetonitrile; at 20℃; for 4h;Green chemistry;	General procedure: A mixture of alcohol (5.0 mmol), Cu(OAc)2 (9.1 mg, 0.05 mmol), and TEMPO (7.8 mg, 0.05 mmol) in CH3CN/H2O (5/10 mL) was stirred at room temperature for specified time. After completion of the reaction (monitored by TLC, eluents: petroleum ether/ethyl acetate = 4/1), dichloromethane (10 mL) was added to the resulting mixture. The dichloromethane phase was separated, and the aqueous phase was further extracted with dichloromethane (10 mL × 2). The combined organic layers were dried over anhydrous sodium sulfate and concentrated to give a residue, which was purified by column chromatography (eluents: petroleum ether/ethyl acetate = 10/1) to provide the desired product.

Reference： [1]Tetrahedron Letters,2014,vol. 55,p. 1677 - 1681
[2]Organic Letters,2020,vol. 22,p. 3149 - 3154
[3]European Journal of Organic Chemistry,2016,vol. 2016,p. 3401 - 3407
[4]Bioorganic and Medicinal Chemistry Letters,1997,vol. 7,p. 2473 - 2476
[5]Journal of Organic Chemistry,2019,vol. 84,p. 5313 - 5327

4
[ 1504-74-1 ]
[ 10493-37-5 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,1997,vol. 7,p. 2473 - 2476

5
[ 2314-97-8 ]
[ 1504-74-1 ]
(E)-1,1,1-Trifluoro-4-(2-methoxy-phenyl)-but-3-en-2-ol [ No CAS ]

Reference： [1]Organic Letters,2001,vol. 3,p. 4271 - 4273

6
[ 6099-03-2 ]
[ 1504-74-1 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,1997,vol. 7,p. 2473 - 2476

7
[ 1504-74-1 ]
[ 33538-83-9 ]

Yield	Reaction Conditions	Operation in experiment
54%	With palladium on activated charcoal; In methanol; at 20℃; for 2h;	The suspension of 2-methoxycinnamaldehyde (1.00 g, 6.17 mmol) and Pd/C (131 mg, 0.20 mmol) werestirred in MeOH (12 mL) at room temperature for 2 h. The reaction mixture was filtered on celite with dichloromethane. The mixture solvent was evaporated under reduced pressure, and the residue was purifiedby column chromatography with hexane/ethyl acetate (3/1, v/v) to obtain 3-(2-methoxyphenyl)propanal.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2017,vol. 27,p. 237 - 241
[2]Bioorganic and Medicinal Chemistry Letters,1997,vol. 7,p. 2473 - 2476
[3]Chemical Communications,2014,vol. 50,p. 14752 - 14755
[4]Organic Letters,2019,vol. 21,p. 5962 - 5966

8
[ 1504-74-1 ]
[ 105-53-3 ]
[ 1126906-43-1 ]

Reference： [1]Chemistry Letters,2010,vol. 39,p. 379 - 381
[2]European Journal of Organic Chemistry,2013,p. 5917 - 5922
[3]Advanced Synthesis and Catalysis,2008,vol. 350,p. 1383 - 1389

9
[ 62147-49-3 ]
[ 1504-74-1 ]
[ 1186656-08-5 ]

Reference： [1]Angewandte Chemie - International Edition,2009,vol. 48,p. 5701 - 5704
Angewandte Chemie,2009,vol. 121,p. 5811 - 5814

10
[ 33538-83-9 ]
[ 1504-74-1 ]

Reference： [1]ACS Catalysis,2017,vol. 7,p. 4000 - 4003
[2]Chemistry - An Asian Journal,2009,vol. 4,p. 1712 - 1716
[3]Advanced Synthesis and Catalysis,2009,vol. 351,p. 1229 - 1232

11
[ 75-52-5 ]
[ 1504-74-1 ]
[ 1020270-19-2 ]

Reference： [1]Organic Letters,2010,vol. 12,p. 1480 - 1483

12
[ 392734-33-7 ]
[ 1504-74-1 ]
(2R,11bR,Z)-3-(1-hydroxyethylidene)-9,10-dimethoxy-2-(2-methoxyphenyl)-2,3,6,7-tetrahydro-1H-pyrido[2,1-a]isoquinolin-4(11bH)-one [ No CAS ]
[ 1306623-89-1 ]

Yield	Reaction Conditions	Operation in experiment
		General procedure: To a mixture of catalyst 9 (0.01 mmol, 0.1 equiv) and benzoic acid (0.01 mmol, 0.1 equiv) in DCM (0.2 mL) was added beta-ketoamide 8 (0.1 mmol, 1 equiv) under an atmosphere of N2. Followed by the addition of alpha,beta-unsaturated aldehyde 1 (0.15 mmol, 1.5 equiv). The reaction was stirred at 20 C and followed by TLC. After full consumption of beta-ketoamide 8, the reaction mixture was diluted with DCM (0.3 mL). Then TFA (0.1 mmol, 1 equiv) was added. The reaction mixture was stirred at 20 C for 0.5 h. The reaction mixture was diluted with DCM (5 mL) and washed with saturated NaHCO3 (3 mL). The aqueous phase was extracted with DCM (2×5 ml). The combined organic phases were dried over Na2SO4 and concentrated in vacuo. The residue was purified by flash chromatography on silica gel eluting with a petroleum ether and ethyl acetate mixture to give pure compounds 10.

Reference： [1]Tetrahedron,2011,vol. 67,p. 3034 - 3040

13
[ 1504-74-1 ]
[ 63664-38-0 ]
[ 1306623-68-6 ]
(2R,12bR,Z)-3-(1-hydroxyethylidene)-2-(4-methoxyphenyl)-1,2,3,6,7,12b-hexahydroindolo[2,3-a]quinolizin-4(12H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		General procedure: To a mixture of catalyst 9 (0.01 mmol, 0.1 equiv) and benzoic acid (0.01 mmol, 0.1 equiv) in DCM (0.2 mL) was added beta-ketoamide 8 (0.1 mmol, 1 equiv) under an atmosphere of N2. Followed by the addition of alpha,beta-unsaturated aldehyde 1 (0.15 mmol, 1.5 equiv). The reaction was stirred at 20 C and followed by TLC. After full consumption of beta-ketoamide 8, the reaction mixture was diluted with DCM (0.3 mL). Then TFA (0.1 mmol, 1 equiv) was added. The reaction mixture was stirred at 20 C for 0.5 h. The reaction mixture was diluted with DCM (5 mL) and washed with saturated NaHCO3 (3 mL). The aqueous phase was extracted with DCM (2×5 ml). The combined organic phases were dried over Na2SO4 and concentrated in vacuo. The residue was purified by flash chromatography on silica gel eluting with a petroleum ether and ethyl acetate mixture to give pure compounds 10.

Reference： [1]Tetrahedron,2011,vol. 67,p. 3034 - 3040

14
[ 1504-74-1 ]
[ 78-94-4 ]
[ 1342895-30-0 ]

Yield	Reaction Conditions	Operation in experiment
98%	With dmap; 1,3-bis(mesityl)imidazolium chloride; In tetrahydrofuran; at 20℃; for 12h;	General procedure: The alpha,beta-unsaturated aldehyde (1.5 equiv), IMesCl (0.15 equiv) and vinylketone (1 equiv) were taken in THF. After addition of DMAP (0.2 equiv) the reaction mixture was allowed to stir at room temperature for 12 h. The reaction mixture on column chromatography on silica gel (100-200 mesh) using 1:20 ethylacetate:hexane mixture yielded the corresponding [2H]-pyranone as a pale brown liquid.

Reference： [1]Tetrahedron Letters,2011,vol. 52,p. 5992 - 5994

15
[ 1504-74-1 ]
[ 768-03-6 ]
[ 1342895-36-6 ]

Yield	Reaction Conditions	Operation in experiment
30%	With dmap; 1,3-bis(mesityl)imidazolium chloride; In tetrahydrofuran; at 20℃; for 12h;	General procedure: The alpha,beta-unsaturated aldehyde (1.5 equiv), IMesCl (0.15 equiv) and vinylketone (1 equiv) were taken in THF. After addition of DMAP (0.2 equiv) the reaction mixture was allowed to stir at room temperature for 12 h. The reaction mixture on column chromatography on silica gel (100-200 mesh) using 1:20 ethylacetate:hexane mixture yielded the corresponding [2H]-pyranone as a pale brown liquid.

Reference： [1]Tetrahedron Letters,2011,vol. 52,p. 5992 - 5994

16
[ 3988-74-7 ]
[ 1504-74-1 ]
C₂₂H₂₀O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
84%	With 1,8-diazabicyclo[5.4.0]undec-7-ene; 1,3-bis(mesityl)imidazolium chloride; In dichloromethane; at 20℃; for 14h;Inert atmosphere;	General procedure: The alpha,beta-unsaturated aldehyde (1.5 equiv), IMesCl (0.15 equiv), and heterocycle substituted chalcone (1 equiv) were taken in DCM (6 ml/1 mmol of chalcone). After addition of DBU (0.2 equiv), the reaction mixture was allowed to stir at room temperature for the time mentioned in the table. The reaction mixture on column chromatography on silica (100-200 mesh) using 15:85 ethylacetate/hexane mixture yielded the corresponding cyclopentene as an yellow viscous liquid.