135159-25-0|2,4,6-Trimethoxyphenylboronic acid| Ambeed

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Quality Control of [ 135159-25-0 ] Purity: 98% SDS Specification

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Product Details of [ 135159-25-0 ]

CAS No. :	135159-25-0
Formula :	C₉H₁₃BO₅
M.W :	212.01
SMILES Code :	COC1=CC(OC)=C(B(O)O)C(OC)=C1
MDL No. :	MFCD01114642
InChI Key :	PKLRXZVPEQJTTJ-UHFFFAOYSA-N
Pubchem ID :	4197996

Safety of [ 135159-25-0 ]

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

Computational Chemistry of [ 135159-25-0 ] Show Less

Physicochemical Properties

Num. heavy atoms	15
Num. arom. heavy atoms	6
Fraction Csp3	0.33
Num. rotatable bonds	4
Num. H-bond acceptors	5.0
Num. H-bond donors	2.0
Molar Refractivity	55.74
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	68.15 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	0.0
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	0.74
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	-0.61
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.	-0.5
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	-0.69
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	-0.21

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-1.65
Solubility	4.72 mg/ml ; 0.0223 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Very soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-1.75
Solubility	3.77 mg/ml ; 0.0178 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Very 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	-1.68
Solubility	4.44 mg/ml ; 0.0209 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	No
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	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.	-7.07 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.	0.55

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)	2.34

Application In Synthesis of [ 135159-25-0 ]

* 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 [ 135159-25-0 ]

[ 135159-25-0 ] Synthesis Path-Downstream 1~35

1
[ 3754-52-7 ]
[ 135159-25-0 ]
[ 135159-05-6 ]

References: [1]Tetrahedron Letters,1991,vol. 32,p. 2229 - 2232.

2
[ 621-23-8 ]
[ 135159-25-0 ]

Yield	Reaction Conditions	Operation in experiment
71%		The title compound was prepared using an adapted procedure for the same compound reported by Chaumeil et al.17 To a stirring solution of 1,3,5-trimethoxybenzene 7 (11.3 g, 67.2 mmol) in THF (200 mL) at 0 C, n-BuLi (45 mL, 1.60 M, 72.0 mmol) was added dropwise over 10 min. The resulting white suspension was stirred at this temperature for 2 h and then cooled to -78 C. B(OMe)3 (15.0 mL, 135 mmol) in THF (15 mL) was added dropwise over 1 h and the resulting mixture was stirred at -78 C for 1 h before being allowed to slowly warm in the cold bath to room temperature overnight. The resulting cloudy, white mixture was cooled to 0 C and water (100 mL) was added dropwise with stirring over 30 min. The mixture was poured into water (200 mL) and CH2Cl2 (300 mL) and stirred vigorously for 15 min. The phases were separated and the aqueous phase was extracted with CH2Cl2 (4×50 mL), and the combined organics were dried (Na2SO4), filtered and concentrated to provide a white powdery solid. The solid was dissolved in minimal boiling CHCl3 and a roughly equal portion of hot Et2O was added. The mixture was cooled to room temperature and placed in a -20 C freezer overnight to allow crystallization of the product. The resulting white crystals were isolated by suction, washed with cold Et2O (10 mL) and allowed to dry to provide 10.1 g (71%) of the desired boronic acid 9a. 1H NMR (400 MHz, CDCl3) delta 7.00 (s, 2H), 6.14 (s, 2H), 3.87 (s, 6H), 3.83 (s, 3H). NMR data for the synthesized compound corresponded to those reported for the title compound by Chaumeil et al.17

References: [1]Tetrahedron,2011,vol. 67,p. 2125 - 2131.
[2]Tetrahedron Letters,2006,vol. 47,p. 2451 - 2454.
[3]Tetrahedron,2000,vol. 56,p. 9655 - 9662.

3
[ 135159-25-0 ]
[ 126-30-7 ]
5,5-dimethyl-2-(2,4,6-trimethoxyphenyl)-1,3,2-dioxaborinane [ No CAS ]

References: [1]Tetrahedron,2000,vol. 56,p. 9655 - 9662.

4
[ 3934-20-1 ]
[ 135159-25-0 ]
2-chloro-4-(2,4,6-trimethoxy-phenyl)-pyrimidine [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 2083 - 2086.

5
[ 135159-25-0 ]
[ 724707-85-1 ]
[ 862885-68-5 ]

References: [1]Journal of Organic Chemistry,2006,vol. 71,p. 4956 - 4964.
[2]Synlett,2005,p. 1601 - 1605.

6
trifluoro-methanesulfonic acid 2-[2-(4-methoxy-phenyl)-ethyl]-6-oxo-3,6-dihydro-2<i>H</i>-pyran-4-yl ester [ No CAS ]
[ 135159-25-0 ]
6-[2-(4-methoxy-phenyl)-ethyl]-4-(2,4,6-trimethoxy-phenyl)-5,6-dihydro-pyran-2-one [ No CAS ]

References: [1]Tetrahedron Letters,2006,vol. 47,p. 2451 - 2454.

7
[ 135159-25-0 ]
cyclopentyl-propyl-[4-(2,4,6-trimethoxy-phenyl)-pyrimidin-2-yl]-amine [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 2083 - 2086.

8
[ 135159-25-0 ]
propyl-(1-thiophen-2-yl-cyclopropyl)-[4-(2,4,6-trimethoxy-phenyl)-pyrimidin-2-yl]-amine [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 2083 - 2086.

9
[ 135159-25-0 ]
(1-furan-3-yl-cyclopropyl)-propyl-[4-(2,4,6-trimethoxy-phenyl)-pyrimidin-2-yl]-amine [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 2083 - 2086.

10
[ 135159-25-0 ]
propyl-(1-thiophen-3-yl-cyclopropyl)-[4-(2,4,6-trimethoxy-phenyl)-pyrimidin-2-yl]-amine [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 2083 - 2086.

11
[ 135159-25-0 ]
(cyclopropyl-phenyl-methyl)-propyl-[4-(2,4,6-trimethoxy-phenyl)-pyrimidin-2-yl]-amine [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 2083 - 2086.

12
[ 135159-25-0 ]
allyl-dicyclopropylmethyl-[4-(2,4,6-trimethoxy-phenyl)-pyrimidin-2-yl]-amine [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 2083 - 2086.

13
[ 135159-25-0 ]
2-(N-dicyclopropylmethyl-N-propylamino)-4-(2',4',6'-trimethoxyphenyl)pyrimidine [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 2083 - 2086.

14
[ 135159-25-0 ]
naphthalen-1-yl-propyl-[4-(2,4,6-trimethoxy-phenyl)-pyrimidin-2-yl]-amine [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 2083 - 2086.

15
[ 135159-25-0 ]
[ 3778-26-5 ]

References: [1]Tetrahedron Letters,1991,vol. 32,p. 2229 - 2232.

16
[ 135159-25-0 ]
[ 135159-06-7 ]

References: [1]Tetrahedron Letters,1991,vol. 32,p. 2229 - 2232.

17
[ 135159-25-0 ]
[ 112776-83-7 ]
[ 856133-07-8 ]

Yield	Reaction Conditions	Operation in experiment
54%	With caesium carbonate;tetrakis(triphenylphosphine) palladium(0); In DMF (N,N-dimethyl-formamide); at 95℃; for 48h;	2,4, 6-trimethoxyphenylboronic acid (2.12 g, 10.0 mmol) and diethyl 4-bromopyridine-2, 6-dicarboxylate (3.33 g, 11.0 mmol) were dissolved in dry DMF (50 mL). Caesium carbonate (4.56 g, 14.0 mmol) and tetra- kis (triphenylphosphine)-palladium (0) (0.23 g, 0.20 mmol) were added, and the mixture was deaerated with argon. The mixture was heated at 95 C for 48 h. The mixture was allowed to cool to room temperature and filtered. The filtrate was concentrated in vacuo, the residue was dissolved in chloroform (60 mL) and washed with 10% aq. citric acid and water, dried over Na2SO4 and con- centrated. Purification was performed on silica gel (eluent petroleum ether bp 40-60 C ; ethyl acetate 5: 3 ~ 2: 5, v/v). Yield was 2.09 g (54%).'H NMR (CDCI3) : 5 1.45 (6H, t, J 7.1) ; 3.74 (6H, s); 3.90 (3H, s); 4,49 (4H, q, J 7.1) ; 6.22 (2H, s); 8.28 (2H, s). IR (film)/ cm-1 1743,1610 (C=O) ; 1339,1238, 1128 (C-O), ESI-MS : [M+H] + 390. 19 calc. for C2oH24N07+ 390.15.

References: [1]Patent: WO2005/58877,2005,A1 .Location in patent: Page/Page column 21; 31.

18
[ 856134-28-6 ]
[ 135159-25-0 ]
[ 856132-23-5 ]

Yield	Reaction Conditions	Operation in experiment
90%	With caesium carbonate;tetrakis(triphenylphosphine) palladium(0); In DMF (N,N-dimethyl-formamide); at 95℃;	Tetra (tert-butyl) 2,2', 2", 2"'-[6-N-(4- methoxytrityl) hexylimino] bis (methylene) bis- (4-bromopyridine-6,2- diyl) bis (methylenenitrilo)} tetrakis (acetate) (4.0 g, 2.4 mmol) and trimethoxy- phenylboronic acid (1.1 g, 5.3 mmol) were dissolved in dry DMF (50 mL) and Cs2CO3 (2.0 g, 6.0 mmol) and Pd (PPh3) 4 (0. 1 g, 96 mumol) were added. After stirring overnight at 95, trimethoxyphenylboronic acid (0.5 g, 2.4 mmol), Cs2CO3 (0.79 g, 2mmol) and Pd (PPh3) 4 (50 mg, 43 mmol) were added. After overnight reaction the mixture was cooled to room temperature, filtered and evaporated. The mixture was dissolved in CH2CI2 and washed with water (2 40 ml). The product was purified by flash chromatography (silica gel, petroleum ether (40-60)/AcOEt/TEA 5: 2: 1, v/v/v). Yield was 3.1 g (90 %). IR (film) : 1737 (C=O), 1128 (C-O).'H NMR (CDC13) : No. 1. 15-1.25 (4H, m); 1.40-1. 45 (40 H, m); 2.04 (2H, t, J 6); 2.55 (2H, t, J 7); 3.50 (1 H, s); 3.51 (3H, s). ESI-MS : [M+H] + 1417. 5 calc. for C82H109N6015+ 1417. 8.

References: [1]Patent: WO2005/58877,2005,A1 .Location in patent: Page/Page column 18; 29.

19
[ 100-39-0 ]
[ 135159-25-0 ]
[ 621-23-8 ]
[ 22807-99-4 ]

Yield	Reaction Conditions	Operation in experiment
Ca. 20%	With bis-triphenylphosphine-palladium(II) chloride; water; sodium hydroxide; In tetrahydrofuran; at 70℃; for 24h;Inert atmosphere;	General procedure: A 25 mL round bottom flask was charged with 9a (ca. 320 mg, 1.51 mmol), either anhydrous NaOH or K2CO3 (ca. 3 mmol) and Pd(PPh3)2Cl2 (1 mol %). THF (10 mL) was then added and the mixture was stirred until the boronic acid and catalyst dissolved. The resulting mixture was degassed with an Argon sparge for 30 min. Neat BnBr (120 muL, 1 mmol) was added via syringe, followed by water (2 mL) for the aqueous reactions. The resulting mixtures were stirred for 24 h at 70 C, then cooled to room temperature and quenched by the addition of satd aq NH4Cl (10 mL). The resulting mixture was extracted with CH2Cl2 (2×20 mL) and the combined organics were dried (Na2SO4), filtered and concentrated in vacuo. The title product 10 was obtained in 10% isolated yield using aqueous K2CO3 as the base and 20% using aqueous NaOH as the base. In both cases the product was isolated as a white, powdery solid following silica gel chromatography (CH2Cl2/hexanes, 1:1) of the crude mixtures. 1H NMR (400 MHz, CDCl3) delta 7.24-7.07 (m, 5H), 6.15 (s, 2H), 3.93 (s, 2H), 3.80 (s, 3H), 3.77 (s, 6H). 13C NMR (100 MHz, CDCl3) delta 159.5, 159.1, 142.5, 128.6, 128.1, 125.4, 110.6, 90.9, 55.9, 55.5, 28.5. Mp 93-94 C (lit. Mp 93-95 C). NMR and mp data for the synthesized compound corresponded to those reported by Katritzky et al.24 for the title compound.

References: [1]Tetrahedron,2011,vol. 67,p. 2125 - 2131.

20
[ 868374-72-5 ]
[ 135159-25-0 ]
2-(dipropylamino)-3,7-dimethyl-5-(2,4,6-trimethoxyphenyl)-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 2365 - 2371.

21
[ 858682-25-4 ]
[ 135159-25-0 ]
[ 1263303-70-3 ]

References: [1]Australian Journal of Chemistry,2010,vol. 63,p. 1638 - 1644.

22
[ 1352123-17-1 ]
[ 135159-25-0 ]
[ 1352123-18-2 ]
(2R,3S,4R)-3,5,7-Tris-benzyloxy-2-(3,4-bis-benzyloxy-phenyl)-4-(2,4,6-trimethoxy-phenyl)-chroman [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With trimethylsilyl trifluoromethanesulfonate; In tetrahydrofuran; at -78 - 20℃; for 4h;Inert atmosphere;	To a stirring solution of 6 (0.19 g, 0.21 mmol) and <strong>[135159-25-0]2,4,6-trimethoxyphenylboronic acid</strong> (12) (52 mg, 0.24 mmol) in THF (3 mL) at -78 C, neat TMSOTf (45.0 muL, 0.25 mmol) was added dropwise. Stirring was continued for 1 h at -78 C, and then the mixture was allowed to warm to room temperature in the cold bath over 3 h. The mixture was poured into satd aq NaHCO3 (10 mL)/EtOAc (20 mL) and stirred vigorously for 10 min. The phases were separated and the organic phase was sequentially washed with water (20 mL) and brine (20 mL), then dried (Na2SO4), filtered and concentrated. The residue was then purified by silica gel chromatography (EtOAc/hexanes 1:4) to provide title compound 13 (190 mg, 90%) as a white foamy solid after solvent removal. 1H NMR (600 MHz, CDCl3) 90:10 mixture of major and minor product. delta (major product only) 7.51-7.24 (m, 19H), 7.18-7.08 (m, 4H), 7.01 (d, 1H, J=8.3 Hz), 6.97 (m, 2H), 6.70 (d, 2H, J=7 Hz), 6.14 (s, 1H, C6-H), 6.04 (br s, 1H, TMB C-H), 5.98 (br s, 1H, TMB C-H), 5.25 (s, 2H, O-CH2-Ph), 5.17 (q, 2H, J=12 Hz, O-CH2-Ph), 5.06 (d, 1H, J=12 Hz, O-CH2-Ph), 5.04 (d, 1H, J=12 Hz, O-CH2-Ph) 4.85 (d, 1H, J=8.2 Hz, C4-H), 4.78 (d, 1H, J=11.5 Hz, O-CH2-Ph), 4.68 (d, 1H, J=9.72 Hz, C2-H), 4.55 (d, 1H, J=11.5 Hz, O-CH2-Ph), 3.95 (dd, 1H, J=9.7 and 8.2 Hz, C3-H), 3.82 (s, 3H, TMB-OMe), 3.72 (d, 1H, J=6 Hz, O-CH2-Ph), 3.59 (d, 1H, J=6 Hz, OCH2Ph), 3.47 (br s, 3H, TMB-OMe), 3.36 (br s, 3H, TMB-OMe). 13C NMR (125 MHz, CDCl3) delta (major product only) 159.3 (TMB-Cq-OMe), 159.2 (TMB-Cq-OMe), 158.3 (TMB-Cq-OMe), 156.0, 153.9, 153.7, 148.56, 148.51, 137.8, 137.33, 137.24, 136.8, 136.6, 132.4, 129-126 (Benzyl Ar-H), 120.6, 114.7, 114.2, 113.5, 111.3, 94.5 (C8), 92.7 (C6), 91.7 (TMB-C-H), 90.9 (TMB-C-H), 81.4 (O-CH2-Ph), 81.3 (C2), 73.9 (C3), 71.3 (O-CH2-Ph), 71.07 (O-CH2-Ph), 71.00 (O-CH2-Ph), 70.3 (O-CH2-Ph), 36.4 (C4). HRMS (ESI) calculated for C59H5379BrO9 [M+Na+], 1007.2765; found 1007.2767. FTIR (thin film): 3062, 3031, 2935, 2876, 2836, 1599, 1513, 1496, 1454, 1415, 1338, 1203, 1120, 1027, 811, 736, 698.

References: [1]Tetrahedron,2012,vol. 68,p. 340 - 348.

23
[ 624-31-7 ]
[ 135159-25-0 ]
[ 1040196-63-1 ]

References: [1]Journal of the Indian Chemical Society,2011,vol. 88,p. 1187 - 1194.

24
[ 685886-46-8 ]
[ 135159-25-0 ]
[ 1380434-47-8 ]

References: [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 5255 - 5269.

25
C₂₄H₂₀ClNO₂ [ No CAS ]
[ 135159-25-0 ]
C₃₃H₃₃NO₅ [ No CAS ]

References: [1]Advanced Synthesis and Catalysis,2012,vol. 354,p. 2101 - 2106.

26
[ 135159-25-0 ]
[ 99685-96-8 ]
[ 1402162-86-0 ]

References: [1]Journal of Organic Chemistry,2012,vol. 77,p. 9038 - 9043,6.

27
[ 106-38-7 ]
[ 135159-25-0 ]
[ 1040196-63-1 ]

References: [1]Advanced Synthesis and Catalysis,2013,vol. 355,p. 421 - 438.
[2]ARKIVOC,2012,vol. 2013,p. 228 - 248.

28
[ 1417896-41-3 ]
[ 135159-25-0 ]
[ 1417896-45-7 ]

Yield	Reaction Conditions	Operation in experiment
	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; at 70℃; for 15h;Inert atmosphere;	General procedure: To a suspension of Pd(PPh3)4 (0.271 g, 0.23 mmol), Aryl-B(OH)2 (11.7 mmol) and 12 (0.5 g, 1.17 mmol) in THF (50 ml) was added a saturated solution of K2CO3 (0.65 g, 4.7 mmol). Under the nitrogen atmosphere, the reaction mixture was heated to 70 C for 15 h. After cooling down, THF was removed under reduced pressure, and the residue was dissolved in CH2Cl2. Diluted HCl (10 ml) was added to neutralize the unreacted K2 CO3. The aqueous phase was extracted with CH2Cl2 (3×30 mL). The combined organic phases were subsequently washed with brine and dried. The solvent was removed under reduced pressure. The left residue was the crude product 2-aryl-3-O-methoxymethyl-17-deoxyestrone as yellow oil for next step unless more separations.

References: [1]Tetrahedron Letters,2013,vol. 54,p. 355 - 357.

29
[ 1466040-60-7 ]
[ 135159-25-0 ]
[ 1592413-76-7 ]

References: [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 3369 - 3381.

30
(Z)-(benzofuran-3(2H)-ylidenechloromethyl)tributylstannane [ No CAS ]
[ 135159-25-0 ]
(Z)-(benzofuran-3(2H)-ylidene(2,4,6-trimethoxyphenyl)methyl)tributylstannane [ No CAS ]

References: [1]Chemistry - A European Journal,2014,vol. 20,p. 10249 - 10254.

31
C₁₁H₁₁BrN₄ [ No CAS ]
[ 135159-25-0 ]
N-methyl-1-(2,4,6-trimethoxyphenyl)imidazo[1,2-a]quinoxalin-4-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
20%	With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,2-dimethoxyethane; water; at 140℃; for 0.333333h;Microwave irradiation;	General procedure: The Suzuki coupling of 4 (300 mg, 1.09 mmol) or5 with the corresponding aryl boronic acid in the presence ofpalladium catalyst Pd(PPh3)4 (60 mg), basic conditions Na2CO3(250 mg), DME (10 mL), H2O (5 mL) and under microwave assistance(140 C, 20 min) led to 6c-6j and 7a. These compounds werepurified by column chromatography on silica gel, leading to thepure desired products4.1.11 N-Methyl-1-(2,4,6-trimethoxyphenyl)imidazo[1,2-a]quinoxalin-4-amine (6j) 2,4,6-Trimethoxyphenyl boronic acid (365 mg, 2.17 mmol). Yellow solid (20%). 1H NMR (400 MHz, CDCl3) delta: 7.70 (d, J = 8 Hz, 1H), 7.30-7.21 (m, 3H), 6.88 (td, 1H), 6.41 (br s, 1H), 6.18 (s, 2H), 3.86 (s, 3H), 3.56 (s, 6H), 3.22 (br s, 3H). 13C NMR (400 MHz, CDCl3) delta: 163.06, 160.18, 148.20, 132.16, 132.06, 126.41, 125.90, 122.62115.04, 114.45, 100.45, 90.78, 55.79, 55.53, 27.77. HRMS: m/z calcd for C20H21N4O3 [M]+ 365.1614; found 365.1613.

References: [1]Bioorganic and Medicinal Chemistry,2016,vol. 24,p. 2433 - 2440.

32
[ 135159-25-0 ]
[ 585-71-7 ]
[ 1046126-93-5 ]

References: [1]Journal of the American Chemical Society,2016,vol. 138,p. 10774 - 10777.

33
[ 2374-05-2 ]
[ 135159-25-0 ]
[ 55977-85-0 ]

References: [1]Organic Letters,2016,vol. 18,p. 4324 - 4327.

34
[ 2374-05-2 ]
[ 135159-25-0 ]
C₄₁H₅₂O₁₀ [ No CAS ]

References: [1]Organic Letters,2016,vol. 18,p. 4324 - 4327.

35
[ 135159-25-0 ]
C₃₅H₄₀O₁₁ [ No CAS ]

References: [1]Organic Letters,2016,vol. 18,p. 4324 - 4327.

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• Nomenclature of Ethers • Preparation of Ethers • Reactions of Benzene and Substituted Benzenes • Reactions of Ethers

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CAS No.: 135159-25-0

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