Home Cart Sign in  
Chemical Structure| 924894-85-9 Chemical Structure| 924894-85-9

Structure of 924894-85-9

Chemical Structure| 924894-85-9

*Storage: {[sel_prStorage]}

*Shipping: {[sel_prShipping]}

,{[proInfo.pro_purity]}

4.5 *For Research Use Only !

{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]} Purity: {[proInfo.pro_purity]}

Change View

Size Price VIP Price

US Stock

Global Stock

In Stock
{[ item.pr_size ]} Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]}

US Stock: ship in 0-1 business day
Global Stock: ship in 5-7 days

  • {[ item.pr_size ]}

In Stock

- +

Please Login or Create an Account to: See VIP prices and availability

US Stock: ship in 0-1 business day
Global Stock: ship in 2 weeks

  • 1-2 Day Shipping
  • High Quality
  • Technical Support
Product Citations

Alternative Products

Product Details of [ 924894-85-9 ]

CAS No. :924894-85-9
Formula : C18H26B2O4S2
M.W : 392.15
SMILES Code : CC1(C)C(C)(C)OB(C(S2)=CC3=C2C=C(B4OC(C)(C)C(C)(C)O4)S3)O1
MDL No. :MFCD22200472
Boiling Point : No data available
InChI Key :SIWCRHWJNFQUSJ-UHFFFAOYSA-N
Pubchem ID :58825499

Safety of [ 924894-85-9 ]

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

Computational Chemistry of [ 924894-85-9 ] Show Less

Physicochemical Properties

Num. heavy atoms 26
Num. arom. heavy atoms 8
Fraction Csp3 0.67
Num. rotatable bonds 2
Num. H-bond acceptors 4.0
Num. H-bond donors 0.0
Molar Refractivity 112.65
TPSA ?

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

93.4 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

4.75
Log Po/w (WLOGP)?

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

3.56
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.

1.94
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

4.14
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

2.88

Water Solubility

Log S (ESOL):?

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

-5.36
Solubility 0.00171 mg/ml ; 0.00000437 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Moderately soluble
Log S (Ali)?

Ali: Topological method implemented from
Ali J. et al. 2012 J. Chem. Inf. Model.

-6.44
Solubility 0.000142 mg/ml ; 0.000000362 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Poorly 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

-5.74
Solubility 0.000717 mg/ml ; 0.00000183 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Moderately 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

Yes
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

Yes
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

Yes
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

Yes
Log Kp (skin permeation)?

Skin permeation: QSPR model implemented from
Potts RO and Guy RH. 1992 Pharm. Res.

-5.32 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<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)

4.12

Application In Synthesis of [ 924894-85-9 ]

* 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.

  • Upstream synthesis route of [ 924894-85-9 ]

[ 924894-85-9 ] Synthesis Path-Upstream   1~3

  • 1
  • [ 251-41-2 ]
  • [ 61676-62-8 ]
  • [ 924894-85-9 ]
YieldReaction ConditionsOperation in experiment
61.25%
Stage #1: With n-butyllithium In tetrahydrofuran; hexanes at -78℃; for 1.16667 h; Inert atmosphere; Cooling with ice
Stage #3: With ammonium chloride In tetrahydrofuran; hexanes; water
To a solution of thieno[3,2-b]thiophene (1 .5 g, 10.70 mmol) in THF (25.5 mL) at -78 °C under N 2 is added dropwise a solution of BuLi in hexanes (8.988 mL of 2.5 M, 22.47 mmol), stirred for 20 min, cooling bath is replaced with ice bath and stirred for 50 min. The resultant thick suspension is quenched with 2- isopropoxy-4,4,5,5-tetramethyl-1 ,3,2-dioxaborolane (4.181 g, 4.584 mL, 22.47 mmol). The reaction mixture is kept for overnight and then quenched with saturated aq. NH4Cl solution. After extraction with CH2Cl2 (2 x 100 mL), the combined extracts are washed with brine and dried (Na2S04). Organic solution is diluted with -20 mL of ethyl acetate, concentrated slowly on rotary evaporator until CH2Cl2 is removed. The resultant white fine crystals are collected by filtration. The solid is washed with heptanes and dried under high vacuum to afford 4,4,5,5-tetramethyl-2-[5-(4,4,5,5-tetramethyl-1 ,3,2- dioxaborolan-2-yl)thieno[3,2-b]thiophen-2-yl]-1 ,3,2-dioxaborolane (2.57 g, 6.554 mmol, 61.25percent) as half-white solid. 1H NMR (400 MHz, CDCl3) δ 7.75 (s, 2H), 1.343 (s, 12H).
References: [1] Patent: WO2011/119853, 2011, A1, . Location in patent: Page/Page column 126-127.
[2] Patent: WO2011/119858, 2011, A1, . Location in patent: Page/Page column 86.
  • 2
  • [ 251-41-2 ]
  • [ 25015-63-8 ]
  • [ 924894-85-9 ]
References: [1] Dalton Transactions, 2015, vol. 44, # 29, p. 13007 - 13016.
  • 3
  • [ 25121-87-3 ]
  • [ 61676-62-8 ]
  • [ 924894-85-9 ]
References: [1] Journal of Materials Chemistry, 2011, vol. 21, # 25, p. 9224 - 9231.
 

Historical Records

Categories

Related Functional Groups of
[ 924894-85-9 ]

Organoborons

Chemical Structure| 476004-80-5

A164313 [476004-80-5]

4,4,5,5-Tetramethyl-2-(5-methylthiophen-2-yl)-1,3,2-dioxaborolane

Similarity: 0.89

Chemical Structure| 1040281-83-1

A118648 [1040281-83-1]

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

Similarity: 0.82

Chemical Structure| 193978-23-3

A261566 [193978-23-3]

4,4,5,5-Tetramethyl-2-(2-thienyl)-1,3,2-dioxaborolane

Similarity: 0.79

Chemical Structure| 175361-81-6

A292442 [175361-81-6]

2,5-Bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene

Similarity: 0.78

Chemical Structure| 885692-91-1

A555944 [885692-91-1]

4,4,5,5-Tetramethyl-2-(3-methylthiophen-2-yl)-1,3,2-dioxaborolane

Similarity: 0.73