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Chemical Structure| 5683-31-8 Chemical Structure| 5683-31-8

Structure of 5683-31-8

Chemical Structure| 5683-31-8

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Product Details of [ 5683-31-8 ]

CAS No. :5683-31-8
Formula : C6H10O2Si
M.W : 142.23
SMILES Code : C[Si](C)(C)C#CC(O)=O
MDL No. :MFCD00190216
InChI Key :IPEATTYBFBRNEB-UHFFFAOYSA-N
Pubchem ID :2760863

Safety of [ 5683-31-8 ]

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

Computational Chemistry of [ 5683-31-8 ] Show Less

Physicochemical Properties

Num. heavy atoms 9
Num. arom. heavy atoms 0
Fraction Csp3 0.5
Num. rotatable bonds 0
Num. H-bond acceptors 2.0
Num. H-bond donors 1.0
Molar Refractivity 38.76
TPSA ?

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

37.3 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

1.76
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

2.22
Log Po/w (WLOGP)?

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

1.03
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.

1.17
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

-0.76
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

1.08

Water Solubility

Log S (ESOL):?

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

-2.12
Solubility 1.08 mg/ml ; 0.00758 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.

-2.64
Solubility 0.327 mg/ml ; 0.0023 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

-0.58
Solubility 37.7 mg/ml ; 0.265 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.

-5.59 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.

0.56

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)

3.31

Application In Synthesis of [ 5683-31-8 ]

* 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 [ 5683-31-8 ]

[ 5683-31-8 ] Synthesis Path-Downstream   1~35

  • 1
  • [ 5683-31-8 ]
  • [ 16205-84-8 ]
  • 2
  • [ 186581-53-3 ]
  • [ 5683-31-8 ]
  • [ 42201-71-8 ]
  • 4
  • [ 75-77-4 ]
  • [ 54620-69-8 ]
  • [ 5683-31-8 ]
  • 5
  • [ 6829-40-9 ]
  • [ 5683-31-8 ]
  • [ 135726-07-7 ]
  • 6
  • [ 5683-31-8 ]
  • [ 53704-09-9 ]
  • [ 135726-06-6 ]
  • 7
  • [ 5683-31-8 ]
  • [ 134322-93-3 ]
  • [ 135726-08-8 ]
  • 8
  • [ 5683-31-8 ]
  • [ 114298-66-7 ]
  • Trimethylsilanyl-propynoic acid 2,4,4-trimethyl-3-vinyl-cyclohex-2-enyl ester [ No CAS ]
  • 9
  • [ 5683-31-8 ]
  • [ 148680-86-8 ]
  • 1'-methyl-4'-chloro-2'(Z)-butenyl 3-(trimethylsilyl)-2-propynoate [ No CAS ]
  • 10
  • [ 5683-31-8 ]
  • [ 76355-71-0 ]
  • [ 148680-98-2 ]
  • 12
  • [ 5683-31-8 ]
  • [ 5683-30-7 ]
  • [ 88946-47-8 ]
  • 13
  • [ 5683-31-8 ]
  • [ 88946-47-8 ]
  • 15
  • [ 5683-31-8 ]
  • [ 542-92-7 ]
  • [ 88946-53-6 ]
  • 16
  • [ 5683-31-8 ]
  • [ 542-92-7 ]
  • [ 88946-53-6 ]
  • 18
  • [ 5683-31-8 ]
  • [ 142-29-0 ]
  • [ 115377-00-9 ]
  • 19
  • [ 5683-31-8 ]
  • [ 110-83-8 ]
  • [ 115377-03-2 ]
  • 21
  • [ 5683-31-8 ]
  • [ 78-79-5 ]
  • [ 591-47-9 ]
  • 22
  • [ 5683-31-8 ]
  • [ 78-79-5 ]
  • [ 88946-55-8 ]
  • [ 88946-54-7 ]
  • 23
  • [ 5683-31-8 ]
  • [ 78-79-5 ]
  • [ 88946-60-5 ]
  • [ 88946-65-0 ]
  • [ 99-94-5 ]
  • [ 99-04-7 ]
  • 24
  • [ 5683-31-8 ]
  • [ 5680-79-5 ]
  • [ 80050-37-9 ]
  • 25
  • [ 5683-31-8 ]
  • [ 2491-20-5 ]
  • [ 80050-36-8 ]
  • 26
  • [ 5683-31-8 ]
  • [ 6638-79-5 ]
  • N-Methoxy-N-methyl-3-(trimethylsilyl)prop-2-ynamide [ No CAS ]
  • 27
  • [ 74-85-1 ]
  • [ 5683-31-8 ]
  • 2-iodoethyl trimethylsilylpropynoate [ No CAS ]
  • 28
  • [ 5683-31-8 ]
  • [ 358-23-6 ]
  • [ 1026856-11-0 ]
  • 29
  • [ 5683-31-8 ]
  • [ 97589-09-8 ]
  • 2-hydroxy-3-(trimethylsilylpropynoyloxy)octan-1-ol [ No CAS ]
  • 30
  • [ 5683-31-8 ]
  • [ 171231-63-3 ]
  • (2S,3S)-2-Hydroxy-3-(3-trimethylsilanyl-propynoyloxy)-octanoic acid [ No CAS ]
  • 31
  • [ 5683-31-8 ]
  • [ 100-39-0 ]
  • benzyl 3-(trimethylsilyl)propiolate [ No CAS ]
  • 32
  • [ 5683-31-8 ]
  • [ 180862-79-7 ]
  • [ 180862-80-0 ]
  • 34
  • [ 5683-31-8 ]
  • [ 66224-70-2 ]
YieldReaction ConditionsOperation in experiment
With oxalyl dichloride; N,N-dimethyl-formamide; In dichloromethane; at 0℃; for 0.25h; In a 10 mL flask, the <strong>[5683-31-8]3-(trimethylsilyl)propiolic acid</strong> (3.24 mmol, 0.460 g) was dissolved in dry DCM (1 mL) under argon atmosphere. Oxalyl chloride (3.24 mmol, 0.27 mL) and DMF (0.03 mL) were successively added to the reaction mixture at 0C. After 15 minutes of stirring, the apparition of bubbles stopped. Oxalyl chloride and DCM were evaporated under vacuum. (0115) To a solution of this resulting 100 3-(trimethylsilyl)propynoyl chloride in dry 8 DCM (1 mL) were added dropwise at 0C 33 4-amino-N-(2,5-dimethoxyphenyl) benzenesulfonamide (1.62 mmol, 0.500 g) dissolved in 11 mL of dry DCM and 49 Et3N (0.23 mL, 1.62 mmol). After stirring overnight, the reaction mixture was quenched with a saturated solution of 13 NaCl. The aqueous layer was extracted three times with DCM. The combined organic layers were dried over Na2SO4. After removal under vacuum of the solvent, the crude was purified by chromatography over silica gel (DCM/EP: 60/40 to 100/0) affording the expected 96 compound (28) as a white solid (0.45 g, 1.04 mmol) with 64% yield. (Rf: 0.29 (DCM); mp: 84C). RMN 1H (300 MHz, CDCl3): 7.74 (d, 2H, Har), 7.58 (s, 1 H, NH), 7.56 (d, 2H, Har), 7.15 (d, 1 H, H7), 7.01 (s, 1 H, NH), 6.65 (d, 1H, H5), 6.56 (dd, 1 H, H6), 3.75 (s, 3H, CH3), 3.60 (s, 3H, CH3), 0.25 (s, 9H, Si-CH3). RMN 13C (75 MHz, CDCl3): 154.0 (s, CO), 150.3 (s, CO), 143.7 (s, CO), 141.3 (s, Car), 134.8 (s, Car), 128.8 (s, Car), 126.5 (s, Car), 119.3 (s, Car), 111.6 (s, C5), 110.1 (s, C6), 107.4 (s, C7), 97.3 (s, Calk), 94.4 (s, Calk), 56.3 (s, CH3), 55.9 (s, CH3), -0.67 (s, Si-CH3). HRMS: Calculated for [M+ H]+: 433.1253; Measured: 433.1248. IR: 3232 (v N-H), 2956 (v Car-H), 2835 (v OC-H), 1648 (v C=O), 1313 (vas SO2), 1152 (vs SO2)
With oxalyl dichloride; In dichloromethane; N,N-dimethyl-formamide; at 0℃; for 0.25h;Inert atmosphere; In a 10 mL flask, the <strong>[5683-31-8]3-(trimethylsilyl)propiolic acid</strong> (3.24 mmol, 0.460 g) was dissolved in dry DCM (1 mL) underargon atmosphere. Oxalyl chloride (3.24 mmol, 0.27 mL) and DMF (0.03 mL) were successively added to the reactionmixture at 0C. After 15 minutes of stirring, the apparition of bubbles stopped. Oxalyl chloride and DCM were evaporatedunder vacuum.
With oxalyl dichloride; In N,N-dimethyl-formamide; at 0 - 20℃; for 0.5h; [1435] 3-(trimethylsilyl)propioloyl chloride : To a stirred solution of <strong>[5683-31-8]3-(trimethylsilyl)propiolic acid</strong> (0.080 g, 0.562 mmol, 1 eq) in DMF (0.002 mL, 0.022 mmol, 0.04 eq) was added oxalyl chloride (0.053 mL, 0618 mmol, 1.1 eq) at 0C. The mixture was allowed to warm room temperature and stirred 30 minutes. Then, the reaction mixture was concentrated under reduced pressure to obtain 3-(trimethylsilyl)propioloyl chloride. The crude was taken as such to next step.
 

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