72824-04-5|2-Allyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane| Ambeed

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Quality Control of [ 72824-04-5 ] Purity: 97% (stabilized with Phenothiazine) SDS Specification

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Product Details of [ 72824-04-5 ]

CAS No. :	72824-04-5
Formula :	C₉H₁₇BO₂
M.W :	168.04
SMILES Code :	C=CCB1OC(C)(C)C(C)(C)O1
MDL No. :	MFCD00013347
InChI Key :	YMHIEPNFCBNQQU-UHFFFAOYSA-N
Pubchem ID :	2763171

Safety of [ 72824-04-5 ]

GHS Pictogram:
Signal Word:	Danger
Hazard Statements:	H225-H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338
Class:	3
UN#:	1993
Packing Group:	Ⅲ

Computational Chemistry of [ 72824-04-5 ] Show Less

Physicochemical Properties

Num. heavy atoms	12
Num. arom. heavy atoms	0
Fraction Csp3	0.78
Num. rotatable bonds	2
Num. H-bond acceptors	2.0
Num. H-bond donors	0.0
Molar Refractivity	51.85
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	18.46 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	2.35
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	2.26
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.	1.07
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	1.27
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.39

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.23
Solubility	0.989 mg/ml ; 0.00588 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.	-2.38
Solubility	0.705 mg/ml ; 0.00419 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	-2.32
Solubility	0.799 mg/ml ; 0.00475 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.	-5.66 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	1.0
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)	2.86

Application In Synthesis of [ 72824-04-5 ]

* 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 [ 72824-04-5 ]

[ 72824-04-5 ] Synthesis Path-Downstream 1~35

1
[ 591-50-4 ]
[ 72824-04-5 ]
[ 873-66-5 ]
[ 98-83-9 ]

References: [1]Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry,1987,vol. 41,p. 569 - 576.

2
[ 2146-67-0 ]
[ 72824-04-5 ]
[ 114716-34-6 ]
[ 118574-32-6 ]

References: [1]Organometallics,1983,vol. 2,p. 1529 - 1535.

3
[ 63830-85-3 ]
[ 72824-04-5 ]
[ 72824-00-1 ]

References: [1]Journal of Organometallic Chemistry,1980,vol. 184,p. C41 - C43.

4
[ 72824-04-5 ]
[ 2344-80-1 ]
[ 72824-00-1 ]

References: [1]Organometallics,1983,vol. 2,p. 230 - 236.

5
[ 6524-17-0 ]
[ 83622-42-8 ]
[ 69611-01-4 ]
[ 72824-04-5 ]

References: [1]Journal of the American Chemical Society,1986,vol. 108,p. 3422.

6
[ 13154-14-8 ]
[ 83622-42-8 ]
[ 69611-01-4 ]
[ 72824-04-5 ]

References: [1]Journal of the American Chemical Society,1986,vol. 108,p. 3422.

7
[ 6386-72-7 ]
2-(1-bromo-1-methylethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane [ No CAS ]
[ 96041-10-0 ]
[ 72824-04-5 ]

References: [1]Journal of the American Chemical Society,1986,vol. 108,p. 3422.

8
[ 845724-59-6 ]
[ 72824-04-5 ]
[ 1038991-27-3 ]

References: [1]Journal of Organic Chemistry,2008,vol. 73,p. 4949 - 4955.

9
C₁₈H₂₄O [ No CAS ]
[ 72824-04-5 ]
C₂₄H₃₅BO₃ [ No CAS ]
C₂₄H₃₅BO₃ [ No CAS ]

References: [1]Journal of the American Chemical Society,2008,vol. 130,p. 13110 - 13119.

10
[ 1210836-07-9 ]
[ 72824-04-5 ]
[ 1210836-01-3 ]

Yield	Reaction Conditions	Operation in experiment
59%	tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In dichloromethane; at 50℃; for 8h;Inert atmosphere;	In a 50 ml Schlenck flask was placed 1.78 g (5.09 mmole) of (1), 0.216 g (0.25 mmole, 5%) of Grubb's catalyst (second generation), 1.71 g (10.2 mmole, 2 equivalent) of propenyl boronic acid pinacol ester, and 32 ml of dichloromethane. The mixture was evacuated and back filled with argon and refluxed at 50 C. for 8 hrs. The solvent was evaporated and the residue was purified by flash chromatography on silica gel eluting with 0 to 10% ethyl acetate/hexane. Obtained 1.44 g of (2), 59% yield as a light brown solid.

References: [1]Patent: US2010/56535,2010,A1 .Location in patent: Page/Page column 37-38.

11
[ 1262800-04-3 ]
[ 72824-04-5 ]
[ 1262800-05-4 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; at 90℃; for 16h;Inert atmosphere; sealed vessel;	A mixture of 25 mg of 9ca, 13 mg OfK2CO3 , 7 mg of 4,4,5, 5-tetramethyl-2-(2-methyl- vinyl)- 1, 3, 2-dioxaboro lane and 5 mg of tetrakis(triphenylphosphine) palladium in 3 ml of degassed 90% aq. dimethoxyethane was heated in a sealed vessel under N2 atmosphere for 16 hr at 9O0C as described for 7ca to give 9 mg of 9cb. MS-ESI:[M+H]+ 488.4. NMR(CDCl3) delta 1.05 and 1.07 (2x d, 6, oC3H7), 1.53 (s, 9, tertC4H9), 1.69 and 1.61 (2x d, 3, CH3), 2.90 (bd, 4, CH2CH2), 3.14 (s, 3, NCH3), 3.82 (s, 3, OCH3), 3.78 (m, 1, CH), 6.02 and 6.15 (2x m, 2, vinyl), 6.10 and 6.78 (2x s, 2, Ar-H), 7.32, 7.43, 7.65 (3x m, 4, phenyl-H).

References: [1]Patent: WO2011/12674,2011,A1 .Location in patent: Page/Page column 35; 36.

12
[ 1233335-28-8 ]
[ 72824-04-5 ]
(4R,6R,7S)-4,7-di(tert-butyldimethylsilyloxy)-2-(2-methyl)vinyl-4,5,6,7-tetrahydrobenzo[b]thiophene-4,6-carbolactone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
63%	With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; at 100℃; for 1.5h;Inert atmosphere;	Example 44 (4R, 6R, 7S)-4,7-di(tert-butyldimethylsilyloxy)-2-(2-methyl)vinyl-4,5,6,7-tetrahydrobenzo[b]thiophen-4,6-carbolactone (V-9) A Shlenck tube was charged with iodide VII (150 mg, 0.26 mmol), Pd(PPh3)4 (31 mg, 0.03 mmol) and dry dioxane (2.6 mL). Anhydrous K2CO3 (0.7 mL, 0.79 mmol, 1.1 M) and 4,4,5,5-tetramethyl-2-(2-methyl)vinyl-1,3,2-dioxaborolane (75 muL, 0.40 mmol) was then added and the resultant solution was deoxygenated and heated at 100 C. for 1.5 h. After cooling to room temperature, the reaction mixture was filtered through a plug of Celite and the precipitate was washed with hexane. The filtrate and the washings were concentrated and the obtained residue was purified by columm chromatography over silica gel, previously neutralized with triethylamine-hexanes (5:95), using diethyl ether-hexanes (10:90) as eluent. It was obtained 80 mg of tiophene V-9 (63%) as colourless oil. [alpha]D20 -53.7 (c1.5, in CHCl3). 1H NMR (300 MHz, CDCl3) delta 6.96 (s, 1H), 5.33 (s, 1H), 4.96 (s, 1H), 4.83 (d, 1H, J=3.3 Hz), 4.66 (dd, 1H, J=6.0 and 3.3 Hz), 2.59 (d, 1H, J=10.8 Hz), 2.51 (dd, 1H, J=10.8 and 6.0 Hz), 2.10 (s, 3H), 0.99 (s, 9H), 0.93 (s, 9H), 0.26 (s, 3H), 0.23 (s, 3H), 0.20 (s, 3H) and 0.15 (s, 3H) ppm. 13C NMR (75 MHz, CDCl3) delta 175.2 (C), 146.3 (C), 141.8 (C), 136.9 (C), 133.2 (C), 119.4 (CH2), 112.0 (CH), 77.3 (CH), 75.4 (C), 66.3 (CH), 37.8 (CH2), 25.7 (C(CH3)3), 25.6 (C(CH3)3), 21.5 (CH3), 18.2 (C(CH3)3), 18.0 (C(CH3)3), -3.0 (SiCH3), -3.2 (SiCH3), -4.6 (SiCH3) and -4.7 (SiCH3) ppm. IR (film): 1803 (C=O) cm-1. MS (ESI) m/z (%) 447 (MNa+-tBu).

References: [1]Patent: US2011/313032,2011,A1 .Location in patent: Page/Page column 19-20.

13
[ 1392284-94-4 ]
[ 72824-04-5 ]
(5S,7S,9S,10S)-9-methoxy-5-((4-((S,Z)-1-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)but-3-en-1-yl)oxazol-2-yl)methyl)-2,2,3,3,6,6,10,13,13,14,14-undecamethyl-4,12-dioxa-3,13-disilapentadecan-7-ol [ No CAS ]
[ 1392284-95-5 ]

References: [1]Angewandte Chemie - International Edition,2012,vol. 51,p. 5667 - 5670.

14
[ 1379527-09-9 ]
[ 72824-04-5 ]
[ 1379527-17-9 ]
[ 1379527-06-6 ]

References: [1]Organic Letters,2012,vol. 14,p. 3064 - 3067.

15
[ 1392284-89-7 ]
[ 72824-04-5 ]
[ 1414941-27-7 ]
[ 1414941-28-8 ]

References: [1]Journal of Organic Chemistry,2012,vol. 77,p. 10782 - 10788.
[2]Chemistry - A European Journal,2013,vol. 19,p. 15993 - 16018.

16
[ 1427549-01-6 ]
[ 72824-04-5 ]
[ 1427549-14-1 ]

References: [1]Journal of the American Chemical Society,2013,vol. 135,p. 4878 - 4883.

17
[ 1427549-05-0 ]
[ 72824-04-5 ]
[ 1427549-22-1 ]

References: [1]Journal of the American Chemical Society,2013,vol. 135,p. 4878 - 4883.

18
[ 1427549-07-2 ]
[ 72824-04-5 ]
[ 1427549-36-7 ]

References: [1]Journal of the American Chemical Society,2013,vol. 135,p. 4878 - 4883.

19
[ 1427549-09-4 ]
[ 72824-04-5 ]
[ 1427549-37-8 ]

References: [1]Journal of the American Chemical Society,2013,vol. 135,p. 4878 - 4883.

20
[ 1427549-13-0 ]
[ 72824-04-5 ]
[ 1427549-40-3 ]

References: [1]Journal of the American Chemical Society,2013,vol. 135,p. 4878 - 4883.

21
[ 1427549-03-8 ]
[ 72824-04-5 ]
[ 1427549-18-5 ]

References: [1]Journal of the American Chemical Society,2013,vol. 135,p. 4878 - 4883.

22
[ 24395-10-6 ]
[ 72824-04-5 ]
[ 1440508-23-5 ]

References: [1]Journal of the American Chemical Society,2013,vol. 135,p. 8460 - 8463.

23
[ 72824-04-5 ]
[ 1440508-08-6 ]

References: [1]Journal of the American Chemical Society,2013,vol. 135,p. 8460 - 8463.

24
[ 952609-40-4 ]
[ 72824-04-5 ]
C₁₃H₂₅BO₅ [ No CAS ]

References: [1]Organic Letters,2014,vol. 16,p. 1450 - 1453.

25
[ 1562431-30-4 ]
[ 72824-04-5 ]
C₂₆H₄₈BNO₆Si [ No CAS ]

References: [1]Organic Letters,2014,vol. 16,p. 1450 - 1453.

26
[ 1392284-94-4 ]
[ 72824-04-5 ]
[ 1392284-95-5 ]

References: [1]Chemistry - A European Journal,2013,vol. 19,p. 15993 - 16018.

27
[ 1616877-83-8 ]
[ 72824-04-5 ]
(2Z,4Z)-2,3-dimethyl-N-(quinolin-8-yl)hexa-2,4-dienamide [ No CAS ]
(2Z,4E)-2,3-dimethyl-N-(quinolin-8-yl)hexa-2,4-dienamide [ No CAS ]

References: [1]Journal of the American Chemical Society,2014,vol. 136,p. 14349 - 14352.

28
[ 443638-87-7 ]
[ 72824-04-5 ]
(Z)-5-methyl-2-(prop-1-en-1-yl)-N-(quinolin-8-yl)benzamide [ No CAS ]
(E)-5-methyl-2-(prop-1-en-1-yl)-N-(quinolin-8-yl)benzamide [ No CAS ]