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Chemical Structure| 80041-89-0 Chemical Structure| 80041-89-0

Structure of 80041-89-0

Chemical Structure| 80041-89-0

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Product Details of [ 80041-89-0 ]

CAS No. :80041-89-0
Formula : C3H9BO2
M.W : 87.91
SMILES Code : CC(B(O)O)C
MDL No. :MFCD01319021
InChI Key :QIPHSSYCQCBJAX-UHFFFAOYSA-N
Pubchem ID :2734750

Safety of [ 80041-89-0 ]

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

Computational Chemistry of [ 80041-89-0 ] Show Less

Physicochemical Properties

Num. heavy atoms 6
Num. arom. heavy atoms 0
Fraction Csp3 1.0
Num. rotatable bonds 1
Num. H-bond acceptors 2.0
Num. H-bond donors 2.0
Molar Refractivity 25.67
TPSA ?

Topological Polar Surface Area: Calculated from
Ertl P. et al. 2000 J. Med. Chem.

40.46 Ų

Lipophilicity

Log Po/w (iLOGP)?

iLOGP: in-house physics-based method implemented from
Daina A et al. 2014 J. Chem. Inf. Model.

0.0
Log Po/w (XLOGP3)?

XLOGP3: Atomistic and knowledge-based method calculated by
XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry

0.5
Log Po/w (WLOGP)?

WLOGP: Atomistic method implemented from
Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.

-0.13
Log Po/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.

-0.63
Log Po/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

-1.84
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

-0.42

Water Solubility

Log S (ESOL):?

ESOL: Topological method implemented from
Delaney JS. 2004 J. Chem. Inf. Model.

-0.63
Solubility 20.4 mg/ml ; 0.232 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.

-0.92
Solubility 10.6 mg/ml ; 0.12 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

0.51
Solubility 283.0 mg/ml ; 3.22 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.

-6.48 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

2.0
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)

1.27

Application In Synthesis of [ 80041-89-0 ]

* 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 [ 80041-89-0 ]

[ 80041-89-0 ] Synthesis Path-Downstream   1~35

  • 1
  • [ 688-74-4 ]
  • [ 920-39-8 ]
  • [ 80041-89-0 ]
  • 2
  • [ 80041-89-0 ]
  • [ 66740-05-4 ]
  • 3
  • [ 80041-89-0 ]
  • [ 108-24-7 ]
  • 1,3-diacetoxy-1,3-diisopropyl-diboroxane [ No CAS ]
  • 4
  • [ 80041-89-0 ]
  • [ 111-42-2 ]
  • [ 119246-82-1 ]
  • 5
  • [ 80041-89-0 ]
  • [ 513-86-0 ]
  • [ 92304-40-0 ]
  • 6
  • [ 80041-89-0 ]
  • [ 119-53-9 ]
  • [ 60217-87-0 ]
  • 7
  • [ 80041-89-0 ]
  • 1,2:5,6-di-O-cyclohexylidene-D-mannitol [ No CAS ]
  • 1,2:5,6-di-O-cyclohexylidene-D-mannitol-isopropylboronate [ No CAS ]
  • 8
  • [ 80041-89-0 ]
  • [ 18680-27-8 ]
  • [ 90084-26-7 ]
YieldReaction ConditionsOperation in experiment
83% In diethyl ether; at 23℃; for 16h;Inert atmosphere; Into a 250 mL round-bottom flask equipped with a magnetic stir bar and under nitrogen was weighed isopropyl boronic acid (12.5 g, 142 mmol, 1.1 equiv). The solid was taken up in diethyl ether (100 mL), affording a yellow suspension. To this suspension was added over 4 equal portions (1S,2S,3R,5S)-2,6,6-trimethylbicyclo[3 .1.1 ]heptane-2,3 -diol (22.0 g, 129 mmol, 1.0 equiv) [NOTE: Slight exotherm observed]. The resulting yellow suspension became a light white opaque solution. The reaction mixture was stirred for 16 h. The mixture was concentrated under reduced pressure and the crude yellow oil poured onto a pad of silica gel (10 cm wide x 6 cm high) on a sintered glass funnel and the product eluted with 2% EtOAc in hexanes (500 mL). The clear filtrate was concentration under reduced pressure to afford a clear oil (23.7 g, 83%).
  • 9
  • [ 80041-89-0 ]
  • [ 35804-44-5 ]
  • [ 184649-44-3 ]
  • 10
  • [ 80041-89-0 ]
  • [ 98-88-4 ]
  • [ 611-70-1 ]
  • 11
  • [ 781650-19-9 ]
  • [ 80041-89-0 ]
  • C17H22N2O3 [ No CAS ]
  • 12
  • [ 60-29-7 ]
  • [ 150-46-9 ]
  • [ 1068-55-9 ]
  • [ 80041-89-0 ]
YieldReaction ConditionsOperation in experiment
a) Preparation of isopropylboronic acid A solution of 149 g of triethyl borate (1 mol) in 300 cm3 of ether and a 2M solution of 103 g of isopropylmagnesium chloride (1 mol) in 500 cm3 of ether, are added simultaneously, under a nitrogen atmosphere and with vigorous stirring, into ethyl ether (500 cm3) stirred under nitrogen at -78° C., while maintaining the temperature below -70° C. for 2 hours. The temperature of the reaction mixture is allowed to rise to room temperature and stirring is continued for a further 24 hours. The mixture is then acidified with cold dilute 40percent sulphuric acid (250 cm3) and is stirred. while maintaining the temperature below 15° C. Stirring is carried out for a further 16 hours and the mixture is diluted again with water (250 cm3) in order to remove the emulsion. The ether phase is separated out and the aqueous phase is extracted with ether (3*200 cm3). The ether phases are combined, dried (magnesium sulphate) and then concentrated. The resulting solid is crystallized from water. The desired product is obtained (wet); this product needs to be kept wet or in ether in order to prevent autoxidation.
  • 13
  • [ 150-46-9 ]
  • [ 1068-55-9 ]
  • [ 80041-89-0 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; In tetrahydrofuran; g. 2-Isopropyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolidine. A dry, 5 L, three-necked flask was equipped with a mechanical stirrer, a Claisen adapter holding a low-temperature thermometer and an addition funnel, and a second Claisen adapter holding an addition funnel and a nitrogen inlet. Isopropylmagnesium chloride (1.60 L, 2.0M in tetrahydrofuran) was transferred via cannula into one addition funnel, and triethylborate (467.1 g) was placed into the other addition funnel. Tetrahydrofuran (1 L) was placed in the reaction flask and was cooled to -78° C. The triethylborate and the Grignard reagent were simultaneously added dropwise over a 2 hour period, while maintaining an internal temperature of less than -50° C. Upon completion of the addition, the mixture was stirred for an additional 2 hours at -78° C. The reaction was quenched by dropwise addition of concentrated hydrochloric acid (600 mL) over 1 hour. The temperature of the mixture rose from -78° C. to -20° C., and the dark amber solution became colorless. The mixture was stirred overnight, evaporated, and extracted with ether. The combined extracts were washed with brine and dried (MgSO4). Evaporation gave crude (dihydroxy)isopropylborane as a white semi-solid (360.2 g). This material was dissolved in ethyl acetate (1 mL) and the solution was placed in a 3 L, 3-necked flask equipped with a mechanical stirrer and a nitrogen inlet.
  • 14
  • [ 80041-89-0 ]
  • [ 109785-53-7 ]
  • [ 137332-23-1 ]
  • 15
  • [ 288-13-1 ]
  • [ 80041-89-0 ]
  • [ 40958-82-5 ]
  • [ 80041-71-0 ]
  • 16
  • [ 24347-58-8 ]
  • [ 80041-89-0 ]
  • C2H2BO2(CH3)2CH(CH3)2 [ No CAS ]
  • 17
  • [ 80041-89-0 ]
  • [ 156574-61-7 ]
  • C15H20O [ No CAS ]
  • 18
  • [ 80041-89-0 ]
  • [ 585-79-5 ]
  • [ 6526-74-5 ]
  • 19
  • [ 80041-89-0 ]
  • [ 769-92-6 ]
  • [ 1019532-61-6 ]
  • 20
  • [ 80041-89-0 ]
  • [ 106-47-8 ]
  • [ 770-40-1 ]
  • 21
  • [ 80041-89-0 ]
  • [ 104-94-9 ]
  • [ 16495-67-3 ]
  • 23
  • [ 80041-89-0 ]
  • [ 1353643-28-3 ]
  • [ 875550-90-6 ]
  • 24
  • potassium trifluoro(isopropenyl)borate(1-) [ No CAS ]
  • [ 7732-18-5 ]
  • [ 80041-89-0 ]
  • 25
  • potassium trifluoro(isopropenyl)borate(1-) [ No CAS ]
  • [ 80041-89-0 ]
  • 26
  • [ 80041-89-0 ]
  • potassium trifluoro(isopropenyl)borate(1-) [ No CAS ]
  • 27
  • [ 80041-89-0 ]
  • [ 5720-05-8 ]
  • [ 618-39-3 ]
  • [ 1410809-28-7 ]
  • 28
  • [ 80041-89-0 ]
  • [ 107-21-1 ]
  • 2-(propan-2-yl)-1,3,2-dioxaborolane [ No CAS ]
  • 29
  • [ 80041-89-0 ]
  • [ 55-21-0 ]
  • [ 5440-69-7 ]
  • 30
  • [ 80041-89-0 ]
  • [ 75747-28-3 ]
  • [ 1453815-03-6 ]
  • 31
  • [ 80041-89-0 ]
  • [ 126-30-7 ]
  • [ 61727-48-8 ]
  • 32
  • [ 19404-18-3 ]
  • [ 80041-89-0 ]
  • [ 22105-89-1 ]
  • 33
  • [ 80041-89-0 ]
  • [ 95-66-9 ]
  • [ 4706-89-2 ]
  • 34
  • [ 323580-68-3 ]
  • [ 80041-89-0 ]
  • tert-butyl 6-isopropyl-1H-indole-1-carboxylate [ No CAS ]
  • 35
  • [ 80041-89-0 ]
  • [ 100-00-5 ]
  • [ 1817-47-6 ]
 

Historical Records

Technical Information

Categories

Related Functional Groups of
[ 80041-89-0 ]

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