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Structure of 3112-85-4

Chemical Structure| 3112-85-4

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Product Citations

Product Citations

Morningstar, John Tanner ;

Abstract: Molecular electronics is a continuously growing field which attempts to solve the problem that their solid-state counterparts encounter with continuing to grow smaller while maintaining the same functionality. Although successful molecular electronics have been created, their level of functionality does not yet match solid states. Furthering the field involves elucidating the mechanism of rectification and continuing to grow the library of compounds available. To accomplish this, we have successfully synthesized twenty new alkylsilanes which exhibit rectification behavior. We were able to draw several conclusions about promising scaffolds through examination of terminal groups with electron withdrawing and donating substituents, nitrogen heterocycles, and sterically hindered substituents. Additionally, our compounds were subjected to doping of the selfassembled monolayer devices which we found to benefit rectification. It was hypothesized that adding electron withdrawing groups, large and soft atoms, and groups with non-bonding electrons would also boost rectification. We obtained compounds with R ratios as high as 8500. This value is the highest our group has achieved to date. Biopolymers are commonly used as drug delivery scaffolds due to their safety and resistance to environmental stimuli. Alginate is one such polymer which has garnered increased attention as of late. To improve the properties of alginate for this purpose, we have developed a method to quantitatively modify the backbone of alginate with small molecules via sodium periodate oxidation and reductive amination of the corresponding oxidized product. Examining the difference in modified alginate with a small unsubstituted aromatic ring as well as an aromatic ketone, ester, and carboxylic acid allowed us to determine which molecules are beneficial to environmental pH sensitivity. xiv We successfully synthesized three new quantitatively modified alginates and examined their pH sensitivity using hydrogel beading studies. Each new compound shows distinct pH response; however, our expectations were met as our original benzoic acid modified product still holds the most desirable degradation profile.

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Alternative Products

Product Details of [ 3112-85-4 ]

CAS No. :3112-85-4
Formula : C7H8O2S
M.W : 156.20
SMILES Code : O=S(C1=CC=CC=C1)(C)=O
MDL No. :MFCD00014741
InChI Key :JCDWETOKTFWTHA-UHFFFAOYSA-N
Pubchem ID :18369

Safety of [ 3112-85-4 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302
Precautionary Statements:P280-P305+P351+P338

Computational Chemistry of [ 3112-85-4 ] Show Less

Physicochemical Properties

Num. heavy atoms 10
Num. arom. heavy atoms 6
Fraction Csp3 0.14
Num. rotatable bonds 1
Num. H-bond acceptors 2.0
Num. H-bond donors 0.0
Molar Refractivity 39.54
TPSA ?

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

42.52 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

1.26
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.

2.17
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.

1.51
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

1.12
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

1.31

Water Solubility

Log S (ESOL):?

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

-1.5
Solubility 4.92 mg/ml ; 0.0315 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.

-0.96
Solubility 17.0 mg/ml ; 0.109 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

-2.69
Solubility 0.315 mg/ml ; 0.00202 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.

-6.9 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

0.0 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)

1.63

Application In Synthesis of [ 3112-85-4 ]

* 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 [ 3112-85-4 ]

[ 3112-85-4 ] Synthesis Path-Downstream   1~5

  • 1
  • [ 6704-31-0 ]
  • [ 3112-85-4 ]
  • [ 1221819-46-0 ]
YieldReaction ConditionsOperation in experiment
82% To a solution of (methylsulfonyl)benzene (2.2 g, 13.9 mmol) in THF (38 mL) at 0 was added n-BuLi (2.5 M in hexanes, 12.2 mL, 30.6 mmol) dropwise over 10 minutes. After the mixture was stirred for 30 min, chlorodiethylphosphonate (2.4 mL, 16.7 mmol) was added dropwise to the reaction. After 30 minutes, a solution of oxetan-3-one (1.0 g, 13.9 mmol) in THF (2 mL) was added dropwise to the reaction mixture at -78 . The reaction mixture was stirred at -78 for 2 hours, then diluted with aqueous NH4Cl (100 mL) and extracted with EtOAc (100 mL x 2) . The combined organic layers were concentrated and the residue was purified by silica gel chromatxography column (petroleum ether/EtOAc = 3/1) to give the title compound (2.4 g, 82%) as a colorless oil. 1H NMR (400 MHz, CDCl3) : delta7.90-7.88 (m, 2H) , 7.68-7.64 (m, 1H) , 7.57 (t, J= 7.6 Hz, 2H) , 6.13-6.11 (m, 1H) , 5.66-5.64 (m, 2H) , 5.30-5.27 (m, 2H).
75% 3-((Phenylsulfonyl)methylene)oxetane To an oven-dried vial was added (methylsulfonyl)benzene (0.570 g, 3.65 mmol) and the vial was evacuated with argon 3 times. The dry THF (17 mL) was added and the reaction was cooled to 0 C. The 2.5 M BuLi in hexanes (3.21 mL, 8.03 mmol) was added dropwise and the reaction began to stir at 0 C. and stirred for 45 minutes. The diethyl chlorophosphate (0.528 mL, 3.65 mmol) was then added at 0 C. and the reaction stirred for 30 minutes. The reaction was then cooled to -78 C. and the oxetan-3-one (0.330 mL, 5.15 mmol) was then added dropwise and the reaction stirred for 2 h. The reaction was then warmed to rt and filtered through a silica plug. The reaction was then concentrated onto silica and purified by MPLC (20 min, 0-40% EtOAc:hex) to provide pure 3-((phenylsulfonyl)methylene)oxetane (0.579 g, 2.75 mmol, 75% yield). 1H NMR (400 MHz, CDCl3): delta 7.91-7.87 (m, 2H), 7.69-7.64 (m, 1H), 7.60-7.55 (m, 2H), 6.12 (quintet, J=2.3 Hz, 1H), 5.66-5.63 (m, 2H), 5.30-5.27 (m, 2H).
74% To a stirred solution of methyiphenylsulfone (3 g, 19.2 mmol) in dry tetrahydrofuran (15 mL) was added n-butyllithium (2.5 M in tetrahydrofuran; 15.4 mL, 38.4 mmol) at 0 C. Thereaction mixture was stirred for 30 mi Diethyl chiorophosphate (4 mL, 27.8 mmol) wasadded, and the mixture was stirred at 0 C for an additional 30 mm. It was then cooled to -78C, and a solution of 3-oxetanone (1.38 g, 19.2 mmol) in dry tetrahydrofuran (3 mL) wasadded. The mixture was stirred at -78 C for 1.5 h and filtered through a silica plug to give 3-((phenylsulfonyl)methylene)oxetane as a white solid (3 g, 74%). ?H NMR (400 MHz, CDC13)oe 7.90 - 7.87 (m, 2H), 7.66 - 7.64 (m, 1H), 7.59 - 7.56 (m, 2H), 6.12 (s, 1H), 5.65 (d, J =6.0Hz, 2H), 5.29 (d, J =5.6 Hz, 2H).
Example 1313-A. 3-((Phenylsulfonyl)methylene)oxetane.A solution of BuLi (2.5 M in hexanes, 22.5 mL, 56.3 mmol) was added over 10 min to a solution of methylphenylsulfone (4.00 g, 25.6 mmol) in THF (70 mL) at 0 C. The solution went from clear to light green to a heterogeneous yellow suspension. The mixture was stirred for 30 min at 0 C and then chlorodiethylphosphonate (4.46 mL, 30.7 mmol) was added dropwise and the stirring was continued for 30 min, at which point the solution turned clear orange. The reaction mixture was then cooled to -78 C and oxetan-3-one (1.85 g, 25.6 mmol) was added in THF (3 mL). The reaction mixture turned pale brown/yellow in color. After stirring for another 1.5 h, the reaction mixture was filtered through a plug of silica gel. The filtrate was triturated with solid NH4C1 until pH reached 7. The mixture was then filtered and the filtrate was concentrated. The residue was purified by silica gel chromatography (0-60%EtOAc/heptane) to provide 3-((phenylsulfonyl)methylene)oxetane. 1H NMR (400 MHz, CD2C12) delta ppm 7.86 - 7.99 (m, 2 H) 7.68 - 7.77 (m, 1 H) 7.57 - 7.68 (m, 2 H) 6.18 (t, J=2.40 Hz, 1 H) 5.59 - 5.70 (m, 2 H) 5.30 (td, J=3.41, 2.27 Hz, 2 H)
Example 34 Preparation of 3-(phenylsulfonylmethylene)oxetane [0275] In a dry 100 mL flask, methylsulfonylbenzene (1.00 g, 6.41 mmoles) in a solution of dry tetrahydrofuran was 2.5 M n-buLi added at 0C over 10 mins then stirred for 30 mins. Chlorodiethylphosphonate (1.1 mL) was added dropwise and continued to stir for 30 mins before cooling to -78C. Oxetan-3-one (0.65 g, 9.04 mmoles) in dry diethylether (1.0 mL) was added and stirred for 1.5h. The reaction was filtered through a silica plug and to get pure product.

  • 2
  • [ 606-83-7 ]
  • [ 7605-28-9 ]
  • [ 2286-54-6 ]
  • [ 3112-85-4 ]
YieldReaction ConditionsOperation in experiment
62% With aluminum (III) chloride; at 200℃; for 3h;Inert atmosphere; General procedure: In a 10 mL round-bottomed flask, (phenylsulfonyl)acetonitrile (544mg, 3.0 mmol, 1.0 equiv) was added to a mixture of acid 1(3.0mmol) and AlCl3(8 mg, 0.06 mmol, 0.02 equiv). The mixture was then stirred under argon at 200 C for 3 h. After completion of the reaction, the crude mixture was diluted with CH2Cl2(5 mL + 5 mL),silica gel (3 g) was then added to make a solid deposit after evaporation of the solvent. A silica gel column chromatography (eluent:PE-EtOAc, 95:5) finally afforded the pure nitrile together with methyl phenyl sulfone.
  • 3
  • [ 2215-77-2 ]
  • [ 7605-28-9 ]
  • [ 3112-85-4 ]
  • [ 3096-81-9 ]
YieldReaction ConditionsOperation in experiment
53% With aluminum (III) chloride; at 200℃; for 3h;Inert atmosphere; General procedure: In a 10 mL round-bottomed flask, (phenylsulfonyl)acetonitrile (544mg, 3.0 mmol, 1.0 equiv) was added to a mixture of acid 1(3.0mmol) and AlCl3(8 mg, 0.06 mmol, 0.02 equiv). The mixture was then stirred under argon at 200 C for 3 h. After completion of the reaction, the crude mixture was diluted with CH2Cl2(5 mL + 5 mL),silica gel (3 g) was then added to make a solid deposit after evaporation of the solvent. A silica gel column chromatography (eluent:PE-EtOAc, 95:5) finally afforded the pure nitrile together with methyl phenyl sulfone.
  • 4
  • [ 3112-85-4 ]
  • [ 1805-32-9 ]
  • [ 2039-83-0 ]
  • 5
  • [ 3112-85-4 ]
  • [ 35216-39-8 ]
 

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