783-13-1|4-(Trifluoromethoxy)cinnamic Acid| Ambeed

Structure of 783-13-1

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Quality Control of [ 783-13-1 ] Purity: 97% SDS Specification

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Product Details of [ 783-13-1 ]

CAS No. :	783-13-1
Formula :	C₁₀H₇F₃O₃
M.W :	232.16
SMILES Code :	O=C(O)/C=C/C1=CC=C(OC(F)(F)F)C=C1
MDL No. :	MFCD00066338
InChI Key :	RNYVTJANWYBGPW-ZZXKWVIFSA-N
Pubchem ID :	735857

Safety of [ 783-13-1 ]

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

Computational Chemistry of [ 783-13-1 ] Show Less

Physicochemical Properties

Num. heavy atoms	16
Num. arom. heavy atoms	6
Fraction Csp3	0.1
Num. rotatable bonds	4
Num. H-bond acceptors	6.0
Num. H-bond donors	1.0
Molar Refractivity	49.79
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.	1.95
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	3.89
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	3.83
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.	2.02
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	2.34
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.81

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-3.74
Solubility	0.0419 mg/ml ; 0.00018 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.	-4.56
Solubility	0.00632 mg/ml ; 0.0000272 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	-2.5
Solubility	0.743 mg/ml ; 0.0032 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	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	No
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	Yes
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.	-4.95 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<2.0
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)	1.84

Application In Synthesis of [ 783-13-1 ]

* 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.

Downstream synthetic route of [ 783-13-1 ]

[ 783-13-1 ] Synthesis Path-Downstream 1~31

2
[ 783-13-1 ]
[ 306936-02-7 ]

Yield	Reaction Conditions	Operation in experiment
	With oxalyl dichloride; N,N-dimethyl-formamide; In dichloromethane; at 20℃; for 2h;	A solution of Compound 4a (1.2 g, 5.2 mmol) in methylene chloride (20 mL) was treated with oxalyl chloride (7.8 mL, 3.6 mmol). To the solution was added DMF (0.02 mL). The reaction solution was stirred at room temperature for 2 h. The reaction solution was concentrated. The residue was dried in vacuo to provide Compound 4b, which was used without further purification in the next step.
	With thionyl chloride; for 2h;Reflux;	General procedure: Compound 10 was prepared by a procedure similar to that of Lu and co-workers, and Nagao and co-workers. A solution of octanoic acid (4.43g, 30.74mmol) and thionyl chloride (20mL) was heated under reflux for 3h. The excess thionyl chloride was removed in vacuo and the crude octanoyl chloride taken through to the next step without further purification. A solution of 2 (12.0g, 21.55mmol), triethylamine (4.6mL, 33.3mmol), dimethylaminopyridine (0.26g, 2.16mmol) and crude octanoyl chloride in dimethylformamide (150mL) was then stirred at room temperature for 3h. The mixture was then diluted with ethyl acetate (200mL) and washed with water (200mL). The separated aqueous phase was further extracted with ethyl acetate (2×100mL) and the combined organic phases washed with brine (4×100mL), dried over anhydrous magnesium sulfate, filtered and the solvent removed in vacuo. Purification by flash chromatography (hexane/ethyl acetate 2:1) afforded 10 as an off-white solid (9.92g, 14.66mmol, 68%).

References: [1]Patent: US2007/259936,2007,A1 .Location in patent: Page/Page column 162.
[2]Bioorganic and Medicinal Chemistry,2013,vol. 21,p. 5886 - 5899.

3
[3aS-(3aα,6α,7aβ)]-hexahydro-8,8-dimethyl-3H-3a,6-methano-2,1-benzisothiazole-2,2-dioxide [ No CAS ]
[ 783-13-1 ]
[3aS-[1(E),3aα,6α,7aβ]]-hexahydro-8,8-dimethyl-1-[1-oxo-2-propenyl-3-(4-trifluoromethoxyphenyl)]-3H-3a,6-methano-2,1-benzisothiazole-2,2-dioxide [ No CAS ]

References: [1]Patent: US6369064,2002,B1 .Location in patent: Example 69.

4
[ 141-82-2 ]
[ 659-28-9 ]
[ 783-13-1 ]

Yield	Reaction Conditions	Operation in experiment
85%	With piperidine; pyridine; for 3h;Heating / reflux;	A mixture of 5.00 g (3.80 ml, 26.3 mmol) 4-Trifluoromethoxy-benzaldehyde, 3.10 g (30.0 mmol) malonic acid, 0.26 g (3.0 mmol) piperidine and 15.0 ml pyridine was kept at reflux temperature until carbon dioxide development ceased (3 h). After cooling to room temperature the reaction mixture was poured onto 50 g ice and 15 ml 6N HCI. The precipitate was isolated, washed with water and dried. Yield: 5.20 g (85%) 3- (4-TRIFLUOROMETHOXY-PHENYL)-ACRYLIC acid. LH-NMR (400MHZ, D6-DMSO) : 8= 6. 57 (d, 1H, 2-H), 7.40 (d, 2H, 3'-/5'-H), 7.62 (d, 1H, 3-H), 7.84 (d, 2H, 2'-/6'-H), 12.5 (br, 1H, COOH).
85%	With piperidine; In pyridine; for 3h;Heating / reflux;	A mixture of 5.00 g (3.80 ml, 26.3 mmol) 4-trifluoromethoxy-benzaldehyde, 3.10 g (30.0 mmol) malonic acid, 0.26 g (3.0 mmol) piperidine and 15.0 ml pyridine was kept at reflux temperature until carbon dioxide development ceased (3 h). After cooling to room temperature the reaction mixture was poured onto 50 g ice and 15 ml 6N HCl. The precipitate was isolated, washed with water and dried. Yield: 5.20 g (85%) 3-(4-Trifluoromethoxy-phenyl)-acrylic acid. 1H-NMR(400 MHz, D6-DMSO): delta=6.57(d, 1H, 2-H), 7.40(d, 2H, 3'-/5'-H), 7.62(d, 1H, 3-H), 7.84(d, 2H, 2'-/6'-H), 12.5(br, 1H, COOH).
85%	With piperidine; In pyridine; for 3h;Heating / reflux;	A mixture of 5.00 g (3.80 ml, 26.3 mmol) 4-trifluoromethoxy-benzaldehyde, 3.10 g (30.0 mmol) malonic acid, 0.26 g (3.0 mmol) piperidine and 15.0 ml pyridine was kept at reflux temperature until carbon dioxide development ceased (3 h). After cooling to room temperature the reaction mixture was poured onto 50 g ice and 15 ml 6N HCl. The precipitate was isolated, washed with water and dried. Yield: 5.20 g (85%) 3-(4-Trifluoromethoxy-phenyl)-acrylic acid. 1H-NMR(400 MHz, D6-DMSO): delta=6.57(d, 1H, 2-H), 7.40(d, 2H, 3'-/5'-H), 7.62(d, 1H, 3-H), 7.84(d, 2H, 2'-/6'-H), 12.5(br, 1H, COOH).

A solution of 4-trifluoromethoxybenzaldehyde (26.3 mmol), malonic acid (5.6 g, 53.8 mmol) and piperidine (0.265 mL, 2.7 mmol) in pyridine (15 mL) was heated to 70 C. for 18 h. Water (200 mL) was added to the reaction solution. The mixture was acidified to pH 4 using concentrated hydrochloric acid. The solution was filtered. The solid was washed with water. The solid was dried in vacuo to give the title Compound 4a (1.2 g). 1H-NMR (d6-DMSO) delta (ppm): 6.80 (d, J=16.02 Hz, 1H), 6.72 (m, 2H), 6.38 (m, 2H), 5.55 (d, J=16.00 Hz, 1H).

References: [1]Patent: WO2004/85434,2004,A1 .Location in patent: Page 15.
[2]Patent: US2005/209290,2005,A1 .Location in patent: Page/Page column 11.
[3]Patent: US2005/267179,2005,A1 .Location in patent: Page/Page column 12.
[4]Patent: US2007/259936,2007,A1 .Location in patent: Page/Page column 162.

5
[ 783-13-1 ]
[ 259269-56-2 ]

Yield	Reaction Conditions	Operation in experiment
92%		To a suspension of 4.90 g (21.1 mmol) 3- (4-TRIFLUOROMETHOXY-PHENYL)-ACRYLIC acid in 30.0 ml tetrahydrofuran and 0.3 ml N, N-dimethyl formamide a solution of 2.70 ml (32.0 mmol) oxalyl chloride in 5.0 ml tetrahydrofuran was added dropwise at 0C within 10 min. Stirring was continued at 0-5C for 30 min. and 2 h at room temperature thereafter. The resulting solution was cooled to 0-5C again and then added within 15 min. to 75 ml of a 25% aqueous ammonia solution. After stirring for 30 min. the precipitated amide was collected, washed with water and dried at 40C in vacuo. 4.48 g (92%) 3- (4-TRIFLUOROMETHOXY-PHENYL)-ACRYLAMIDE.
92%		To a suspension of 4.90 g (21.1 mmol) 3-(4-Trifluoromethoxy-phenyl)-acrylic acid in 30.0 ml tetrahydrofuran and 0.3 ml N,N-dimethyl formamide a solution of 2.70 ml (32.0 mmol) oxalyl chloride in 5.0 ml tetrahydrofuran was added dropwise at 0 C. within 10 min. Stirring was continued at 0-5 C. for 30 min. and 2 h at room temperature thereafter. The resulting solution was cooled to 0-5 C. again and then added within 15 min. to 75 ml of a 25% aqueous ammonia solution. After stirring for 30 min. the precipitated amide was collected, washed with water and dried at 40 C. in vacuo. 4.48 g (92%) 3-(4-Trifluoromethoxy-phenyl)-acrylamide. MS: M=232.2(API+) 1H-NMR(400 MHz, D6-DMSO): delta=6.63(d, 1H, 2-H), 7.16(br, 1H, NH), 7.42(d, 2H, 3'-/5'-H), 7.45(d, 1H, 3-H), 7.58(br, 1H, NH), 7.70(d, 2H, 2'-/6'-H).
92%		To a suspension of 4.90 g (21.1 mmol) <strong>[783-13-1]3-(4-trifluoromethoxy-phenyl)-acrylic acid</strong> in 30.0 ml tetrahydrofuran and 0.3 ml N,N-dimethylformamide a solution of 2.70 ml (32.0 mmol) oxalyl chloride in 5.0 ml tetrahydrofuran was added dropwise at 0 C. within 10 min. Stirring was continued at 0-5 C. for 30 min. and 2 h at room temperature thereafter. The resulting solution was cooled to 0-5 C. again and then added within 15 min. to 75 ml of a 25% aqueous ammonia solution. After stirring for 30 min. the precipitated amide was collected, washed with water and dried at 40 C. in vacuo. Yield: 4.48 g (92%) 3-(4-Trifluoromethoxy-phenyl)-acrylamide. MS: M=232.2(API+) 1H-NMR(400 MHz, D6-DMSO): delta=6.63(d, 1H, 2-H), 7.16(br, 1H, NH), 7.42(d, 2H, 3'-/5'-H), 7.45(d, 1H, 3-H), 7.58(br, 1H, NH), 7.70(d, 2H, 2'-/6'-H).

6
[ 1380344-31-9 ]
[ 783-13-1 ]
[ 1352428-62-6 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 7496 - 7501.

7
[ 1374567-80-2 ]
[ 783-13-1 ]
C₂₈H₃₀F₃N₅O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In dichloromethane; at 0 - 20℃; for 6h;	General procedure: To a mixture of substituted cinnamic acid (1 mmol), EDC*HCl (1.2 mmol) and HOBt (1.2 mmol) in dry dichloromethane (10 mL) was added a mixture of amine (1 mmol) and triethyl amine (1.5 mmol) in dichloromethane (5 mL) at 0 C. The mixture was stirred at room temperature till the completion of reaction (judged by TLC). The reaction mixture was diluted with additional DCM (20 mL). The organic layer was washed with water, brine and dried (Na2SO4). Concentration and purification over silica gel (100-200 mesh) afforded the desired compound.