122024-75-3|3-(3-(Benzyloxy)phenyl)acrylic acid| Ambeed

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Quality Control of [ 122024-75-3 ] Purity: 97% SDS Specification

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Product Details of [ 122024-75-3 ]

CAS No. :	122024-75-3
Formula :	C₁₆H₁₄O₃
M.W :	254.28
SMILES Code :	O=C(O)/C=C/C1=CC=CC(OCC2=CC=CC=C2)=C1
MDL No. :	MFCD02331624
InChI Key :	OFMOWGZEBJKDCT-MDZDMXLPSA-N
Pubchem ID :	717814

Safety of [ 122024-75-3 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Computational Chemistry of [ 122024-75-3 ] Show Less

Physicochemical Properties

Num. heavy atoms	19
Num. arom. heavy atoms	12
Fraction Csp3	0.06
Num. rotatable bonds	5
Num. H-bond acceptors	3.0
Num. H-bond donors	1.0
Molar Refractivity	74.09
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	46.53 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.34
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	3.86
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	3.1
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	2.96
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	3.35
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	3.12

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-3.99
Solubility	0.0263 mg/ml ; 0.000103 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-4.53
Solubility	0.00744 mg/ml ; 0.0000293 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Moderately soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-4.53
Solubility	0.00756 mg/ml ; 0.0000297 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Moderately soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	High
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	Yes
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	No
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	Yes
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	No
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	No
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	No
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-5.11 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	0.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	0.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	0.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.56

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	0.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	1.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<1.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12'782'590 molecules and tested on 40 external molecules (r² = 0.94)	2.35

Application In Synthesis of [ 122024-75-3 ]

* 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.

Downstream synthetic route of [ 122024-75-3 ]

[ 122024-75-3 ] Synthesis Path-Downstream 1~35

1
[ 14755-02-3 ]
[ 100-39-0 ]
[ 122024-75-3 ]

Yield	Reaction Conditions	Operation in experiment
92%		(£)-3-(3-(Benzyloxy)phenyl)prop-2-enoic acid (4).3; To a stirred suspension of 3- hydroxycinnamic acid (5.00 g, 30.5 mmol) in EtOH (100 mL) was added 1 M aq. NaOH (65 mL) and the reaction mixture was stirred for 5 min, then treated with benzyl bromide (3.72 mL, 31.1 mmol) and stirred for 14 h at room temperature under N2. The mixture was concentrated under reduced pressure to yield a white solid, which was suspended in water (400 mL) and acidified with cone. aq. HC1. The mixture was filtered and the resulting solid was washed with water and Et20, then dried under high vacuum to give 4 (7.10 g, 92%>) as a white solid: IR (ATR, neat) 3400-2500 (br), 1691, 1629, 1577, 1260 cm"1; 1H NMR (DMSO- d6, 600 MHz) delta 7.49 (d, 1 H, J= 16.0 Hz), 7.46 (app d, 2 H, J= 7.4 Hz), 7.39 (t, 2 H, J= 7.6 Hz), 7.35-7.29 (m, 3 H), 7.22 (d, 1 H, J= 7.6 Hz), 7.03 (dd, 1 H, J= 8.2, 2.3 Hz), 6.56 (d, 1 H, J= 16.0 Hz), 5.14 (s, 2 H); 13C NMR (DMSO-d6, 150 MHz) delta 168.1, 158.7, 142.7, 137.0, 136.1, 130.0, 128.5, 128.0, 127.9, 121.2, 120.9, 116.8, 113.7, 69.3; HRMS (EI) m/z calcd for Ci6Hi403 254.0943, found 254.0950.

References: [1]Journal of Medicinal Chemistry,1992,vol. 35,p. 958 - 965.
[2]Patent: WO2012/78859,2012,A2 .Location in patent: Page/Page column 48-49.

2
[ 122024-75-3 ]
[ 122024-71-9 ]

Yield	Reaction Conditions	Operation in experiment
61%	With pyridine; thionyl chloride;N,N-dimethyl-formamide; In chlorobenzene; at 120℃; for 22h;Inert atmosphere;	Methyl 5-(benzyloxy)-3-chlorobenzo[6]thiophene-2-carboxylate (5).; To a mixture of 4 (8.80 g, 34.6 mmol) in chlorobenzene (50 mL), anhydrous pyridine (0.26 mL, 3.29 mmol) and anhydrous DMF (2.60 mL) was added dropwise SOCl2 (12.6 mL, 173 mmol) at room temperature. The reaction mixture was heated at 120 C for 22 h under N2. The solution was concentrated by rotary evaporation and traces of pyridine were removed by azeotropic distillation with toluene. The resulting brown oil was dried under high vacuum overnight to yield a brown solid, which was suspended in Et20, filtered and dried under high vacuum to yield 3-chloro-5-(benzyloxy)-benzo[£]thiophene-2-carbonyl chloride (5.87 g). Upon cooling the filtrate, a second crop of product (1.25 g) was collected by filtration (7.12 g, 61% combined yield). Representative experimental data are as follows: Mp 138-143 C (lit Mp 139-142 C);3 IR (ATR, neat) 1745, 1602, 1483, 1284, 1158 cm"1; 1H NMR (DMSO- d6, 600 MHz) delta 8.01 (d, 1 H, J= 8.8 Hz), 7.50 (d, 2 H, J= 7.3 Hz), 7.44 (d, 1 H, J= 2.3 Hz), 7.41 (t, 2 H, J= 7.3 Hz), 7.37-7.33 (m, 2 H), 5.25 (s, 2 H); MS (EI) m/z 338 (90), 336 (M+, 100), 303 (40), 301 ([M-C1]+, 88).

References: [1]Patent: WO2012/78859,2012,A2 .Location in patent: Page/Page column 49.
[2]Journal of Medicinal Chemistry,1992,vol. 35,p. 958 - 965.

3
[ 122024-75-3 ]
[ 183865-96-5 ]
(E)-N-[(S)-1-(2-Benzhydryloxy-ethyl)-pyrrolidin-2-ylmethyl]-3-(3-benzyloxy-phenyl)-acrylamide [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1996,vol. 39,p. 4704 - 4716.

4
[ 141-82-2 ]
[ 1700-37-4 ]
[ 122024-75-3 ]

Yield	Reaction Conditions	Operation in experiment
96%	With piperidine; pyridine; at 120℃; for 3h;	General procedure: To themixture of the corresponding aldehyde (2.52 g, 12.7 mmol) andmalonic acid (1.99 g, 19.1 mmol), dry pyridine (6.5 ml) and piperidine(0.2 ml) were successively added. The mixture was stirred at120 C for 3 h, cooled to 10 C and acidified with HCl (~14 ml) at 1:1ratio with cooling and stirring. After 30 min, the precipitate wasfiltered, washed 3 times with H2O (20 ml) and air dried. The yieldsof o-, m- and p-PhO-CA were 92, 91 and 96%, respectively.

References: [1]European Journal of Medicinal Chemistry,2019,vol. 183.
[2]Journal of labelled compounds and radiopharmaceuticals,2001,vol. 44,p. S433 - S435.

5
[ 122024-75-3 ]
m-benzyloxy cinnamoyl chloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With oxalyl dichloride; In dichloromethane; at 0 - 20℃; for 4h;Inert atmosphere; Large scale reaction;	To a stirred solution of 4 (2 kg, 8 mol) in CH2Cl2 (2 L) was added oxalyl chloride (1.4 L, 16 mol) dropwise at 0 C. The resulting solution was stirred at room temperature for another 4 h and concentrated in vacuo. To a stirred solution of (R)-4-phenyloxazolidin-2-one (1.3 kg, 8 mol) and TEA (1.7 L, 12 mol) in CH2Cl2 (4.8 L) at 0 C was added the substituted cinnamic chloride in CH2Cl2 (800 mL) dropwise. The mixture was stirred at 0 C for 1 h and then raised to room temperature for 3 h when a saturated solution of NH4Cl (600 mL) was added. The aqueous layer was separated, and the organic solution was washed with water (600 mL × 3), brine (800 mL), and dried over Na2SO4. The organic solution was evaporated and 2.9 kg of 5 was obtained after recrystallization in EtOH in 93% yield
	With thionyl chloride; for 1h;Reflux;	(R,E)-3- (3- (3-benzyloxy) phenyl) acryloyl)-4- phenyl oxazolidin-2-one <strong>[122024-75-3]m-benzyloxy cinnamic acid</strong> (9.0g, 35.4mmol) was dissolved in thionyl chloride (25ml) and refluxed for 1 hour, and the mixture was concentrated to remove thionyl chloride for further use. 4R-phenyl-2-oxazolidinone (5.6g, 34.4mmol) was placed in a three-necked flask, after it was purged with nitrogen, tetrahydrofuran (25ml) was added and when it was cooled to -78C, n-butyl lithium (1.6M, 22ml, 35.4mmol) was added dropwise, and the reaction was carried out for 30 minutes. Then the solution (35ml) of m-benzyloxy cinnamoyl chloride in tetrahydrofuran as prepared above was added dropwise and the reaction was continued for 30 minutes. After that, it was slowly raised to 0C, the reaction was continued for 2 hours, then it was quenched with saturated ammonium chloride solution. The resulted mixture was then concentrated to remove tetrahydrofuran and extracted with ethyl acetate for three times, then the organic phases were combined, washed with saturated brine, dried over anhydrous sodium sulfate, concentrated and recrystallized with petroleum ether and ethyl acetate to give a white solid 14g, yield: 93%. 1HNMR(300MHz, CDCl3): delta 7.9(1H, d, J=15.5), 7.7(1H, d, J=15.3), 7.3-7.5(11H, m), 7.2 (2H, m), 7.0(1H, dd, J=2.3, 8.6), 5.6(1H, dd, J=4.0,9.0), 5.1(2H, s), 4.8 (1H, t, J=8.9, 17.7), 4.3(1H, dd, J=3.9, 8.8). ESI-MS: 422.2 (M+Na).
	With thionyl chloride; for 1h;Reflux;	Example 1 (R,E)-3-(3-(3-benzyloxy)phenyl)acryloyl)-4-phenyl oxazolidin-2-one <strong>[122024-75-3]m-benzyloxy cinnamic acid</strong> (9.0 g, 35.4 mmol) was dissolved in thionyl chloride (25 ml) and refluxed for 1 hour, and the mixture was concentrated to remove thionyl chloride for further use. 4R-phenyl-2-oxazolidinone (5.6 g, 34.4 mmol) was placed in a three-necked flask, after it was purged with nitrogen, tetrahydrofuran (25 ml) was added and when it was cooled to -78 C., n-butyl lithium (1.6M, 22 ml, 35.4 mmol) was added dropwise, and the reaction was carried out for 30 minutes. Then the solution (35 ml) of m-benzyloxy cinnamoyl chloride in tetrahydrofuran as prepared above was added dropwise and the reaction was continued for 30 minutes. After that, it was slowly raised to 0 C., the reaction was continued for 2 hours, then it was quenched with saturated ammonium chloride solution. The resulted mixture was then concentrated to remove tetrahydrofuran and extracted with ethyl acetate for three times, then the organic phases were combined, washed with saturated brine, dried over anhydrous sodium sulfate, concentrated and recrystallized with petroleum ether and ethyl acetate to give a white solid 14 g, yield: 93%. 1HNMR (300 MHz, CDCl3): delta 7.9 (1H, d, J=15.5), 7.7 (1H, d, J=15.3), 7.3-7.5 (11H, m), 7.2 (2H, m), 7.0 (1H, dd, J=2.3, 8.6), 5.6 (1H, dd, J=4.0, 9.0), 5.1 (2H, s), 4.8 (1H, t, J=8.9, 17.7), 4.3 (1H, dd, J=3.9, 8.8). ESI-MS: 422.2 (M+Na).

References: [1]Journal of labelled compounds and radiopharmaceuticals,2001,vol. 44,p. S433 - S435.
[2]Journal of Medicinal Chemistry,2010,vol. 53,p. 3964 - 3972.
[3]Tetrahedron Asymmetry,2012,vol. 23,p. 577 - 582.
[4]Patent: EP2671878,2013,A1 .Location in patent: Paragraph 0064; 0065.
[5]Patent: US2014/46074,2014,A1 .Location in patent: Paragraph 0150-0151.

6
[ 35661-40-6 ]
[ 122024-75-3 ]
[ 109425-51-6 ]
[ 143674-78-6 ]
[ 76-05-1 ]
N^α-3-[3-(benzyloxy)phenyl]-E-acryloyl-L-histidyl-L-phenylalanyl-L-tyrosine hydrotrifluoroacetate [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry,2003,vol. 11,p. 2591 - 2615.

7
[ 35661-40-6 ]
[ 122024-75-3 ]
[ 143674-78-6 ]
N_α-fmoc-N_(im)-trityl-D-histidine [ No CAS ]
[ 76-05-1 ]
N^α-3-[3-(benzyloxy)phenyl]-Z-acryloyl-D-histidyl-L-phenylalanyl-L-tyrosine hydrotrifluoroacetate [ No CAS ]
N^α-3-[3-(benzyloxy)phenyl]-E-acryloyl-D-histidyl-L-phenylalanyl-L-tyrosine hydrotrifluoroacetate [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry,2003,vol. 11,p. 2591 - 2615.

8
[ 141-82-2 ]
[ 1700-37-4 ]
3-amino-3-(3-(benzyloxy)phenyl)propanoic acid [ No CAS ]
[ 122024-75-3 ]

References: [1]Russian Journal of General Chemistry,2005,vol. 75,p. 1113 - 1124.

9
[ 122024-75-3 ]
(+/-)-para-hydroxytranylcypromine [ No CAS ]

References: [1]Journal of labelled compounds and radiopharmaceuticals,2001,vol. 44,p. S433 - S435.

10
[ 122024-75-3 ]
(1R,2S)-2-(3-Benzyloxy-phenyl)-cyclopropylamine [ No CAS ]

References: [1]Journal of labelled compounds and radiopharmaceuticals,2001,vol. 44,p. S433 - S435.

11
[ 122024-75-3 ]
(1S,2S)-2-(3-Benzyloxy-phenyl)-cyclopropanecarboxylic acid [ No CAS ]

References: [1]Journal of labelled compounds and radiopharmaceuticals,2001,vol. 44,p. S433 - S435.

12
[ 122024-75-3 ]
[ 945589-02-6 ]

References: [1]Journal of labelled compounds and radiopharmaceuticals,2001,vol. 44,p. S433 - S435.

13
[ 122024-75-3 ]
(1S,2S)-2-(3-Benzyloxy-phenyl)-cyclopropanecarboxylic acid tert-butyl ester [ No CAS ]

References: [1]Journal of labelled compounds and radiopharmaceuticals,2001,vol. 44,p. S433 - S435.

14
[ 122024-75-3 ]
[(1S,2R)-2-(3-Benzyloxy-phenyl)-cyclopropyl]-carbamic acid tert-butyl ester [ No CAS ]

References: [1]Journal of labelled compounds and radiopharmaceuticals,2001,vol. 44,p. S433 - S435.

15
[ 122024-75-3 ]
[ 172832-10-9 ]