128376-65-8|4-(5,5-Dimethyl-1,3,2-dioxaborinan-2-yl)benzaldehyde| Ambeed

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Quality Control of [ 128376-65-8 ] Purity: 98% SDS Specification

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Product Details of [ 128376-65-8 ]

CAS No. :	128376-65-8
Formula :	C₁₂H₁₅BO₃
M.W :	218.06
SMILES Code :	CC1(C)COB(OC1)C1=CC=C(C=O)C=C1
MDL No. :	MFCD06796332
InChI Key :	JUHDMCQVJGHKFW-UHFFFAOYSA-N
Pubchem ID :	4197234

Safety of [ 128376-65-8 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Computational Chemistry of [ 128376-65-8 ] Show Less

Physicochemical Properties

Num. heavy atoms	16
Num. arom. heavy atoms	6
Fraction Csp3	0.42
Num. rotatable bonds	2
Num. H-bond acceptors	3.0
Num. H-bond donors	0.0
Molar Refractivity	63.16
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	35.53 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	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	2.32
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.27
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.	0.77
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	1.73
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.22

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.8
Solubility	0.346 mg/ml ; 0.00159 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.	-2.7
Solubility	0.43 mg/ml ; 0.00197 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	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	-3.47
Solubility	0.0742 mg/ml ; 0.00034 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	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.	-5.98 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	2.0 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)	2.68

Application In Synthesis of [ 128376-65-8 ]

* 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 [ 128376-65-8 ]

[ 128376-65-8 ] Synthesis Path-Downstream 1~35

1
[ 100945-15-1 ]
[ 128376-65-8 ]
Methyl (E)-2-(benzyloxycarbonylamino)-3-[4-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)phenyl]acrylate [ No CAS ]
Methyl (Z)-2-(benzyloxycarbonylamino)-3-[4-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)phenyl]acrylate [ No CAS ]

References: [1]Synthesis,1999,p. 2041 - 2044.
[2]Synthesis,1999,p. 2041 - 2044.

2
[ 87199-17-5 ]
[ 126-30-7 ]
[ 128376-65-8 ]

Yield	Reaction Conditions	Operation in experiment
95%	In tetrahydrofuran; at 20℃; for 2h;Product distribution / selectivity;	To a solution of 4-formylphenylboronic acid (4.11 g) in anhydrous tetrahydrofuran (THF) (40 ml_) was added 2,2-dimethyl-1 ,3-propanediol (3.14 g) and the mixture was stirred at room temperature for 2 hours. The solvent was evaporated to dryness. The residue was dissolved in dichloromethane (120 ml_), washed with water (80 ml_ x 3), dried and evaporated under vacuum to obtain 4-(5,5-dimethyl-[1 ,3,2]dioxaborinan-2-yl)-benzaldehyde (5.66 g, 95% yield).
	In toluene; for 2h;Heating / reflux;Product distribution / selectivity;	To a mixture of 4-formylphenylboronic acid (50 g) in toluene (250 ml_) was added 2,2-dimethyl-1 ,3-propanediol (34.39 g) and the dispersion was heated at reflux for 2 h. The water while formed was azeotropically separated and the residue (330 ml_) was used directly in the next step. 1H-NMR (400 MHz,CDCI3): delta 1.04 (s, 6 H, 2 CH3), 3.79 (s, 4 H, 2 CH2), 7.84 (d, J = 6.4 Hz, 2 H, H-Ar), 7.96 (d, J = 8 Hz, 2 H, H-Ar), 10.04 (s, 1 H, CHO) ppm.
	In toluene; for 2h;Heating / reflux;	Example 1 : Preparation of 4-(5,5-dimethyl-H ,3,21dioxaborinan-2-yl)- benzaldehvde;To a mixture of 4-formylphenylboronic acid (50 g) in toluene (250 mL) was added 2,2-dimethyl-1 ,3-propanediol (34.39 g) and the dispersion was heated at reflux for 2 h. The water while formed was azeotropically separated and the residue (330 mL) was used directly in the next step.1H-NMR (400 MHz, CDCI3): delta 1.04 (s, 6 H, 2 CH3), 3.79 (s, 4 H, 2 CH2), 7.84 (d, J = 6.4 Hz, 2 H,H-Ar), 7.96 (d, J = 8 Hz, 2 H, H-Ar), 10.04 (s, 1 H, CHO) ppm.

References: [1]Inorganic Chemistry,2001,vol. 40,p. 5507 - 5517.
[2]Synthesis,1999,p. 2041 - 2044.
[3]Tetrahedron,2010,vol. 66,p. 583 - 590.
[4]Patent: WO2006/67216,2006,A2 .Location in patent: Page/Page column 13.
[5]Advanced Synthesis and Catalysis,2014,vol. 356,p. 1527 - 1532.
[6]Acta Crystallographica, Section C: Crystal Structure Communications,2008,vol. 64,p. o177-o179.
[7]Acta Crystallographica, Section C: Crystal Structure Communications,2008,vol. 64,p. o177-o179.
[8]Patent: WO2006/67216,2006,A2 .Location in patent: Page/Page column 13.
[9]Angewandte Chemie - International Edition,2008,vol. 47,p. 5792 - 5795.
[10]Patent: WO2007/71750,2007,A1 .Location in patent: Page/Page column 17.
[11]Angewandte Chemie - International Edition,2012,vol. 51,p. 3642 - 3645.

3
[ 68076-36-8 ]
[ 128376-65-8 ]
tert-butyl N-{4-{[4-(5,5-dimethyl[1,3,2]dioxaborinan-2-yl)phenyl]methylidene}amino}butyl}carbamate [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2001,vol. 44,p. 3653 - 3664.

4
[ 68076-39-1 ]
[ 128376-65-8 ]
tert-butyl N-{3-{[4-(5,5-dimethyl[1,3,2]dioxaborinan-2-yl)phenyl]methylidene}amino}propyl}-N-{4-[(tert-butyloxy)carbonyl]amino}butyl}carbamate [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2001,vol. 44,p. 3653 - 3664.

5
[ 625-82-1 ]
[ 121-44-8 ]
[ 128376-65-8 ]
C₂₄H₂₈B₂F₂N₂O₂ [ No CAS ]

References: [1]Tetrahedron Letters,2001,vol. 42,p. 9105 - 9108.

6
[ 50-00-0 ]
[ 128376-65-8 ]
[ 249764-06-5 ]
[ 429687-52-5 ]
C₃₈H₄₆BN₃O₈ [ No CAS ]

References: [1]Journal of the American Chemical Society,2002,vol. 124,p. 12969 - 12971.

7
[ 17610-00-3 ]
[ 126136-05-8 ]
[ 128376-65-8 ]
5-(3,5-di-tert-butylphenyl)-15-[4-(5,5-dimethyl-1,3-dioxa-2-borinyl)phenyl]-2,8,12,18-tetra-n-hexyl-3,7,13,17-tetramethylporphin [ No CAS ]

References: [1]Journal of Organic Chemistry,2000,vol. 65,p. 8747 - 8757.

8
[ 106456-88-6 ]
[ 126136-05-8 ]
[ 128376-65-8 ]
(5Z,10Z,14Z,19Z)-5-[4-(5,5-Dimethyl-[1,3,2]dioxaborinan-2-yl)-phenyl]-15-[4-(5,5-dimethyl-[1,3]dioxan-2-yl)-phenyl]-2,8,12,18-tetrahexyl-3,7,13,17-tetramethyl-porphyrin [ No CAS ]

References: [1]Journal of Organic Chemistry,2000,vol. 65,p. 8747 - 8757.

9
[ 126136-05-8 ]
[ 128376-65-8 ]
[ 321733-42-0 ]
2-(2,5-di-<i>tert</i>-butyl-phenyl)-6-[2-(4-{15-[4-(5,5-dimethyl-[1,3,2]dioxaborinan-2-yl)-phenyl]-2,8,12,18-tetrahexyl-3,7,13,17-tetramethyl-porphyrin-5-yl}-phenyl)-[1,3]dioxan-5-yl]-pyrrolo[3,4-<i>f</i>]isoindole-1,3,5,7-tetraone [ No CAS ]

References: [1]Journal of Organic Chemistry,2000,vol. 65,p. 8747 - 8757.

10
[ 586-78-7 ]
[ 128376-65-8 ]
[ 98648-23-8 ]

References: [1]Tetrahedron,2007,vol. 63,p. 10596 - 10602.

11
[ 104-92-7 ]
[ 128376-65-8 ]
[ 52988-34-8 ]

References: [1]Tetrahedron,2007,vol. 63,p. 10596 - 10602.

12
[ 1006598-62-4 ]
[ 128376-65-8 ]

References: [1]Tetrahedron,2008,vol. 64,p. 688 - 695.

13
[ 128376-65-8 ]
[ 378785-65-0 ]

References: [1]Journal of Medicinal Chemistry,2001,vol. 44,p. 3653 - 3664.

14
[ 128376-65-8 ]
N-(4-aminobutyl)[4-(dihydroxyboryl)phenyl]methyl}amine dihydrochloride [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2001,vol. 44,p. 3653 - 3664.

15
[ 128376-65-8 ]
N-(4-aminobutyl){{4-(5,5-dimethyl[1,3,2]dioxaborinan-2-yl)phenyl}methyl}amine dihydrochloride [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2001,vol. 44,p. 3653 - 3664.

16
[ 128376-65-8 ]
[ 378785-71-8 ]

References: [1]Journal of Medicinal Chemistry,2001,vol. 44,p. 3653 - 3664.

17
[ 128376-65-8 ]
N-{3-[(4-aminobutyl)amino]propyl}[4-(dihydroxyboryl)phenyl]methyl}amine trihydrochloride [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2001,vol. 44,p. 3653 - 3664.

18
[ 128376-65-8 ]
N-{3-[(4-aminobutyl)amino]propyl}{{4-(5,5-dimethyl[1,3,2]dioxaborinan-2-yl)phenyl}methyl}amine trihydrochloride [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2001,vol. 44,p. 3653 - 3664.

19
[ 1122-91-4 ]
decyl magnesium halide [ No CAS ]
[ 128376-65-8 ]

References: [1]Synthesis,1999,p. 2041 - 2044.

20
[ 61568-51-2 ]
[ 128376-65-8 ]

References: [1]Synthesis,1999,p. 2041 - 2044.

21
[ 6306-52-1 ]
[ 128376-65-8 ]
C₁₈H₂₆BNO₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In tetrahydrofuran; at 20℃; for 72h;Molecular sieve;Product distribution / selectivity;	A mixture of L-Valine methyl ester hydrochloride (548 mg), 4-(5,5-dimethyl- [1 ,3,2]dioxaborinan-2-yl)-benzaldehyde (476 mg) and molecular sieves in anhydrous THF (17 ml_) was stirred at room temperature for three days. Then, the mixture was cooled to O0C and a solution of NaBH3CN (155 mg) in dry MeOH (3 ml_) was added dropwise. The mixture was stirred at room temperature for 4 hours and the solids were removed by filtration. The filtrate was evaporated under vacuum to yield the desired product (632 mg) that was used in the next reaction without further purification.

References: [1]Patent: WO2006/67216,2006,A2 .Location in patent: Page/Page column 14.

22
[ 16652-76-9 ]
[ 128376-65-8 ]
C₂₄H₃₀BNO₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In toluene; for 1h;Heating / reflux;Product distribution / selectivity;	A mixture of L-Valine benzyl ester tosylate (132.7 g), 4-(5,5-dimethyl- [1 ,3,2]dioxaborinan-2-yl)-benzaldehyde (330 ml_), Et3N (48.4 ml_) and toluene (413 ml_) was heated at reflux temperature for 1 h. The water while formed was azeotropically separated. Then, the mixture was cooled to room temperature and the solution was washed with aqueous NaHCO3 (317 ml_ x 2) and water (317 ml_). The residual water was azeotropically removed. The toluene was partially distilled (134 ml_) and MeOH (134 ml_) was added. The solution was then cooled to 0-5 0C and NaBH4 (6.5 g) was slowly added. The reaction mixture was stirred at room temperature overnight. Then the solvent was partially distilled (half volume) and the residue was washed with aqueous NaHCO3 (270 ml_). The separated aqueous phase was extracted with toluene (135 ml_ x 2). The combined organic phases were then washed with water (135 ml_). The residual water in the organic layer was azeotropically removed and the residue (aprox. 730 ml_) was used directly in the next step. 1H-NMR (400 MHz, CDCI3): delta 0.91 and 1.02 (s and m, 12 H, CH3), 1.77 (bs, 1 H, NH), 1.93 (m, 1 H, CH(CH3)2), 1.82 (bs, 1 H, NH), 3.05 (d, 1 H, J = 6.4 Hz, CH-N), EPO <DP n="18"/>3.58 and 3.83 (2 d, J = 13.2 Hz, 1 H each, CH2-Ph), 5.16 (s, 2 H, CH2-Ph), 7.28 (d, 2 H, J = 8 Hz, H-Ar), 7.36 (bs, 5 H, H-Ar), 7.73 (d, 2 H, J = 8 Hz, H- Ar) ppm.

References: [1]Patent: WO2006/67216,2006,A2 .Location in patent: Page/Page column 16-17.

23
[ 128376-65-8 ]
C₁₈H₂₆BNO₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		A mixture of L-Valine methyl ester hydrochloride (6.77 g), anhydrous MgSO4 (5.51 g) and Et3N (5.68 ml_) in anhydrous THF (40 ml_) was stirred for 15 minutes. To this solution was added while stirring at 0-50C 4-(5,5-dimethyl- [1 ,3,2]dioxaborinan-2-yl)-benzaldehyde (5.87 g) and the mixture was stirred at room temperature for 24 hours. The precipitated salts were removed by filtration and the filtrate evaporated under vacuum. The residue was dissolved in anhydrous methanol (120 ml_) and to this solution was added NaBH4 (1.59g) in small portions, for 1 h The resulting mixture was stirred at room temperature for 3 hours. Then, was cooled to O0C and water (10 ml_) was added dropwise. The reaction mixture was concentrated under vacuum, and the residue was partitioned between dichloromethane (100 ml_) and water (500 ml_). Extraction was carried with dichloromethane (2 x 50 ml_) followed by drying and evaporating to dryness to obtain 8.86 g of the desired product that was used in the next reaction without further purification. 1H-NMR (400 MHz, CDCI3): delta 0.92-0.96 (m, 6 H, 2 CH3 (1Pr)), 1.02 (s, 6 H, C(CH3J2), 1 -77 EPO <DP n="16"/>(bs, 1 H, NH), 1.91 (m, 1 H, CH(CH3)2), 3.01 (d, 1 H, J = 6.0 Hz, CH-N), 3.59 and 3.85 (2 d, 1 H each, J = 13 Hz, CH2-Ph), 3.71 (s, 3 H, CH3O), 3.76 (s, 4 H, 2CH2O), 7.32 (d, 2 H, J = 8 Hz, H-Ar), 7.75 (d, 2 H, J = 8 Hz, H-Ar) ppm.

References: [1]Patent: WO2006/67216,2006,A2 .Location in patent: Page/Page column 14-15.

24
[ 128376-65-8 ]
C₂₄H₃₀BNO₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		A mixture of L-Valine benzyl ester tosylate (0.5 g), anhydrous MgSO4 (0.18 g) and Et3N (0.19 ml_) in anhydrous THF (6.6 ml_) was stirred for 15 minutes. To this solution was added while stirring at 0-50C 4-(5,5-dimethyl- [1 ,3,2]dioxaborinan-2-yl)-benzaldehyde (0.19 g) and the mixture was stirred at room temperature for 24 hours. The precipitated salts were removed by filtration and the filtrate evaporated under vacuum. The residue was dissolved in anhydrous methanol (6.6 ml_) and to this solution was added NaBH4 (52 mg) in small portions, for 1 h The resulting mixture was stirred at room temperature for 3 hours. Then, was cooled to O0C and water (2 ml_) was added dropwise. The reaction mixture was concentrated under vacuum, and the residue was partitioned between dichloromethane (15 ml_) and water (30 ml_). Extraction was carried with dichloromethane (2 x 5 ml_) followed by drying and evaporating to dryness to obtain 426 mg of the desired product that was used in the next reaction without further purification.

References: [1]Patent: WO2006/67216,2006,A2 .Location in patent: Page/Page column 16.

25
[ 128376-65-8 ]
C₂₁H₃₂BNO₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		A mixture of L-Valine tert-butyl ester hydrochloride (1 g), anhydrous MgSO4 (732 mg) and Et3N (0.67 ml_) in anhydrous THF (24 ml_) was stirred for 15 minutes. To this solution was added while stirring at 0-50C 4- formylphenylboronic acid (799 mg) and the mixture was stirred at room temperature overnight. The precipitated salts were removed by filtration and the filtrate evaporated under vacuum. The residue was dissolved in anhydrous methanol (24 ml_) and to this solution was added NaBH4 (208 mg) in small portions, for 1 h The resulting mixture was stirred at room temperature for 3.5 h. Then, was cooled to O0C and water (8 ml_) was added dropwise. The reaction mixture was concentrated under vacuum, and the residue was partitioned between dichloromethane (35 ml_) and water (100 ml_). Extraction was carried with dichloromethane (4 x 15 ml_) followed by drying and evaporating to dryness to obtain 1.44 g of the desired product that was used in the next reaction without further purification. 1H-NMR (400 MHz, CDCI3): delta 0.94 and 0.95 (2 d, 3 H each, J = 6.8 Hz, 2 CH3 (1Pr)), 1.02 (s, 6 H, C(CHa)2), 1 -48 (s, 9 H, 'Bu), 1.94 (m, 1 H, CH(CH3)2), 2.89 (d, 1 H, J = 6.0 Hz, EPO <DP n="21"/>CH-N), 3.65 and 3.89 (2 d, 1 H each, J = 13.4 Hz, CH2-Ph), 3.76 (s, 4 H, 2 CH2O), 7.35 (d, 2 H, J = 8 Hz, H-Ar), 7.75 (d, 2 H, J = 8 Hz, H-Ar) ppm.

References: [1]Patent: WO2006/67216,2006,A2 .Location in patent: Page/Page column 19-20.

26
[ 16652-76-9 ]
[ 128376-65-8 ]
benzyl N-[4-(5,5-dimethyl-[1,3,2]dioxaborinan-2-yl)phenyl-4-yl-methyl]-L-valinate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Example 3: Preparation of (benzyl N-r4-(5,5-dimethyl-H ,3,21dioxaborinan-2- yl)phenyl-4-yl-methyll-L-valinate); A mixture of L-Valine benzyl ester tosylate (132.7 g), 4-(5,5-dimethyl- <n="19"/>[1 ,3,2]dioxaborinan-2-yl)-benzaldehyde (330 ml_), Et3N (48.4 mL) and toluene (413 mL) was heated at reflux temperature for 1 h. The water while formed was azeotropically separated. Then, the mixture was cooled to room temperature and the solution was washed with aqueous NaHCO3 (317 mL x 2) and water (317 mL). The residual water was azeotropically removed. The toluene was partially distilled (134 mL) and MeOH (134 mL) was added. The solution was then cooled to 0-5 0C and NaBH4 (6.5 g) was slowly added. The reaction mixture was stirred at room temperature overnight. Then the solvent was partially distilled (half volume) and the residue was washed with aqueous NaHCO3 (270 mL). The separated aqueous phase was extracted with toluene (135 mL x 2). The combined organic phases were then washed with water (135 mL). The residual water in the organic layer was azeotropically removed and the residue (aprox. 730 mL) was used directly in the next step.

References: [1]Patent: WO2007/71750,2007,A1 .Location in patent: Page/Page column 17-18.

27
[ 109-97-7 ]
[ 98-95-3 ]
[ 128376-65-8 ]
5,10,15,20-tetrakis(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)porphyrin nitrobenzene disolvate [ No CAS ]

References: [1]Acta Crystallographica, Section C: Crystal Structure Communications,2008,vol. 64,p. o177-o179.

28
[ 109-97-7 ]
[ 128376-65-8 ]
5,10,15,20-tetrakis[4-(dihydroxyboryl)phenyl]-21H,23H-porphine [ No CAS ]

References: [1]Journal of the Chemical Society. Chemical communications,1994,p. 1557 - 1558.

29
[ 109-97-7 ]
[ 17610-00-3 ]
[ 128376-65-8 ]
H₂N₄(C₄H₂CC₆H₃(C₄H₉)2)3C₄H₂CC₆H₄B(OCH₂)2C(CH₃)2 [ No CAS ]
H₂N₄(C₄H₂CC₆H₃(C₄H₉)2)2(C₄H₂CC₆H₄B(OCH₂)2C(CH₃)2)2 [ No CAS ]

References: [1]Inorganic Chemistry,2001,vol. 40,p. 5507 - 5517.

30
[ 109-97-7 ]
[ 24083-13-4 ]
[ 128376-65-8 ]
C₇₃H₈₇BN₄O₅ [ No CAS ]

References: [1]Chemical Communications,1996,p. 1867 - 1868.

31
[ 109-97-7 ]
[ 98-95-3 ]
[ 128376-65-8 ]
5,10,15,20-tetrakis(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)porphyrin nitrobenzene disolvate [ No CAS ]

References: [1]Acta Crystallographica, Section C: Crystal Structure Communications,2008,vol. 64,p. o177-o179.

32
[ 124-38-9 ]
[ 128376-65-8 ]
[ 619-66-9 ]

References: [1]Angewandte Chemie - International Edition,2008,vol. 47,p. 5792 - 5795.
[2]Chemical Communications,2012,vol. 48,p. 6292 - 6294.

33
[ 668987-38-0 ]
[ 1122-91-4 ]
[ 128376-65-8 ]

Yield	Reaction Conditions	Operation in experiment
10%	1,3-bis[(diphenylphosphino)propane]dichloronickel(II); In toluene; at 100℃; for 18h;Product distribution / selectivity;	A round-bottom flask charged with the aryl halide (5.0 mmol, 1.0 equiv), Ni (For exact amount of catalyst and co-ligand see Table 8; 10% loading was used for Ni catalysts not specified in Table 8). (NiCl2(L)x , Ni(COD)2) or Pd (No co-ligand was used for Pd catalyst) catalysts (PdCl2(dppf)) (0.5 mmol, 0.1 to 0.02 equiv), ligand (L: dppp, dppe, dppf, PPh3, Et3N, bpy, PCy3) (0.5 mmol, 0.1 equiv), and a Teflon coated stir bar was evacuated three times for 10 min under high vacuum and backfilled with N2. Toluene (5 mL) and base (Et3N or (i-Pr)2EtN (15.0 mmol, 3.0 equiv) were added to the reaction mixture at rt. Freshly prepared neopentylglycolborane (10.0 mmol, 2.0 equiv in 5 ml toluene) was added to the red colored suspension via syringe at 23 0C. The reaction mixture was heated to 100 0C and the conversion was followed by GC. After 2 h-12 h (reaction time depends on the type of the aryl halide; iodo derivatives were found to react faster, in 2-4 h , while bromo derivatives in 8-12h), the reaction mixture was quenched via slow addition of saturated aqueous ammonium chloride (10 mL). The quenched reaction mixture was three times washed with saturated aqueous ammonium chloride and extracted with ethyl acetate (50 mL). The combined organic layers were dried over anhydrous MgSO4, filtered, and concentrated. The crude product was purified by silica gel chromatography or recrystallization.

References: [1]Patent: WO2009/137322,2009,A2 .Location in patent: Page/Page column 20; 30; 32; 33.
[2]Organic Letters,2008,vol. 10,p. 4879 - 4882.

34
[ 40310-32-5 ]
[ 128376-65-8 ]
[ 1216976-90-7 ]

References: [1]Synlett,2010,p. 67 - 72.

35
4-(4-(trifluoromethoxy)phenyl)piperidine [ No CAS ]
[ 128376-65-8 ]
[ 1236001-10-7 ]

Yield	Reaction Conditions	Operation in experiment
		Intermediate 71 1-[4-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)phenyl]methyl}-4-{4-[(trifluoromethyl)oxy]phenyl} piperidine Intermediate 71 was prepared according to a method similar to that described in WO 2006/067216 (page 41 ), as described below:A mixture of 4-{4-[(trifluoromethyl)oxy]phenyl}piperidine (4.91 g, 20.03 mmol) and N, N- diisopropylethylamine (5.95 ml, 33.4 mmol) in anhydrous THF (25ml) was stirred at room temp for 15 minutes. To this solution was added while stirring at 0-5C 4-(5,5-dimethyl- 1 ,3,2-dioxaborinan-2-yl)benzaldehyde (3.639 g, 16.69 mmol) and the mixture was stirred at 5O0C overnight. The residue was concentrated to dryness under vacuum and re- dissolved in anhydrous ethanol (25ml). To this solution previously cooled at O0C was added sodium borohydride (840 mg, 22.2 mmol) in small portions during 1 h. The resulting mixture was stirred at room temperature. After 3 hours the reaction was completed. Solvent was evaporated under vacuum and residue was cooled to O0C and partitioned between dichloromethane and water. Aqueous phase was extracted with dichloromethane (2x20ml). Combined organic phase was dried (Na2SO4), filtered and concentrated to dryness to give 5.25 g of a brown solid. Residue was triturated with few drops of methanol and acetonitrile. Solid was filtrated through a glass frited funnel and filtrate was concentrated under vacuum to dryness. 3.4 g of the title compound as an off-white solid were collected and dried under vacuum.1H-NMR(delta, ppm, CDCI3): 7.77(d, 2H); 7.35(d, 2H); 7.23(d, 2H); 7.12(d, 2H); 3.77(s, 4H); 3.59(d, 2H); 3.02(m, 2H); 2.50(s, 1H); 2.10(m,2H); 1.80(m, 2H); 1.66(m, 2H); 1.02(s, 3H).

References: [1]Patent: WO2010/81904,2010,A1 .Location in patent: Page/Page column 64.

Historical Records

Technical Information

• Barbier Coupling Reaction • Baylis-Hillman Reaction • Benzylic Oxidation • Birch Reduction • Blanc Chloromethylation • Bucherer-Bergs Reaction • Clemmensen Reduction • Complex Metal Hydride Reductions • Corey-Chaykovsky Reaction • Corey-Fuchs Reaction • Fischer Indole Synthesis • Friedel-Crafts Reaction • Grignard Reaction • Hantzsch Dihydropyridine Synthesis • Henry Nitroaldol Reaction • Horner-Wadsworth-Emmons Reaction • Hydride Reductions • Hydrogenolysis of Benzyl Ether • Julia-Kocienski Olefination • Knoevenagel Condensation • Leuckart-Wallach Reaction • McMurry Coupling • Meerwein-Ponndorf-Verley Reduction • Mukaiyama Aldol Reaction • Nozaki-Hiyama-Kishi Reaction • Passerini Reaction • Paternò-Büchi Reaction • Petasis Reaction • Pictet-Spengler Tetrahydroisoquinoline Synthesis • Preparation of Aldehydes and Ketones • Preparation of Alkylbenzene • Preparation of Amines • Prins Reaction • Reactions of Aldehydes and Ketones • Reactions of Amines • Reactions of Benzene and Substituted Benzenes • Reformatsky Reaction • Schlosser Modification of the Wittig Reaction • Schmidt Reaction • Stetter Reaction • Stobbe Condensation • Tebbe Olefination • Ugi Reaction • Vilsmeier-Haack Reaction • Wittig Reaction • Wolff-Kishner Reduction

Related Functional Groups of
[ 128376-65-8 ]

Organoborons

A173594 [380151-86-0]

3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde

Similarity: 0.85

A188411 [128376-64-7]

4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde

Similarity: 0.85

A117333 [380151-85-9]

2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde

Similarity: 0.84

A101923 [5123-13-7]

5,5-Dimethyl-2-phenyl-1,3,2-dioxaborinane

Similarity: 0.80

A266479 [847560-50-3]

4-Methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde

Similarity: 0.79

Aryls

A173594 [380151-86-0]

3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde

Similarity: 0.85

A188411 [128376-64-7]

4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde

Similarity: 0.85

A117333 [380151-85-9]

2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde

Similarity: 0.84

A101923 [5123-13-7]

5,5-Dimethyl-2-phenyl-1,3,2-dioxaborinane

Similarity: 0.80

A266479 [847560-50-3]

4-Methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde

Similarity: 0.79

Aldehydes

A173594 [380151-86-0]

3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde

Similarity: 0.85

A188411 [128376-64-7]

4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde

Similarity: 0.85

A117333 [380151-85-9]

2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde

Similarity: 0.84

A266479 [847560-50-3]

4-Methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde

Similarity: 0.79

A340775 [87199-17-5]

4-Formylphenylboronic acid

Similarity: 0.73

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CAS No.: 128376-65-8

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