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Chemical Structure| 2914-69-4 Chemical Structure| 2914-69-4

Structure of 2914-69-4

Chemical Structure| 2914-69-4

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Product Details of [ 2914-69-4 ]

CAS No. :2914-69-4
Formula : C4H6O
M.W : 70.09
SMILES Code : C[C@H](O)C#C
MDL No. :MFCD00190166
InChI Key :GKPOMITUDGXOSB-BYPYZUCNSA-N
Pubchem ID :6995470

Safety of [ 2914-69-4 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H225-H300-H310-H315-H317-H319-H330
Precautionary Statements:P260-P264-P280-P284-P301+P310-P302+P350
Class:6.1(3)
UN#:2929
Packing Group:

Computational Chemistry of [ 2914-69-4 ] Show Less

Physicochemical Properties

Num. heavy atoms 5
Num. arom. heavy atoms 0
Fraction Csp3 0.5
Num. rotatable bonds 0
Num. H-bond acceptors 1.0
Num. H-bond donors 1.0
Molar Refractivity 20.67
TPSA ?

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

20.23 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

1.43
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

0.06
Log Po/w (WLOGP)?

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

0.08
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.

0.6
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

0.09
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

0.45

Water Solubility

Log S (ESOL):?

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

-0.31
Solubility 34.1 mg/ml ; 0.487 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.

-0.04
Solubility 64.2 mg/ml ; 0.916 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

0.32
Solubility 147.0 mg/ml ; 2.09 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

Low
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.

-6.68 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

3.0
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)

2.86

Application In Synthesis of [ 2914-69-4 ]

* 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 [ 2914-69-4 ]

[ 2914-69-4 ] Synthesis Path-Downstream   1~35

  • 1
  • [ 2914-69-4 ]
  • [ 75-07-0 ]
  • (<i>S</i>)-3-(1-chloro-ethoxy)-but-1-yne [ No CAS ]
  • 2
  • [ 2914-69-4 ]
  • [ 124-63-0 ]
  • [ 59967-06-5 ]
YieldReaction ConditionsOperation in experiment
99% With triethylamine; In dichloromethane; at 0 - 20℃; for 2.5h; I(S(at)I-1-methylprop-2-ynyl methanesulfonate To a stirred solution of (S) -but-3-yn-2-ol (15g, 16.8ml, 0.2143mol), triethylamine (32.5g, 44.7ml, 0.3218mol) in dichloromethane (150ml) at 0C, was added dropwise over 30 minutes methanesulfonylchloride (29.4g, 19.9ml, 0.257mmol). The mixture was stirred for a further 2 hours before warming to ambient temperature. Water (150m.) was then added and the DCM layer was separated and the aqueous phase was extracted twice more (2 x 1 00ml). The combined organics were washed with brine (1 00ml) before drying over Na2S04. The solvent was removed under vacuo to yield a pale yellow oil/solid as the product (31.6g, 99%). GC-MS single peak Rt 1.4 minutes MS: 121, 120, 106, 77,68, 54,53, 51, 41 (No molecular ion)
95% With dmap; triethylamine; In dichloromethane; at 20℃; for 3h;Inert atmosphere; To a stirred solution of 15 (2.0 g, 28.5 mmol) in CH2Cl2 (50 mL) were added Et3N (6.0 mL, 42.8 mmol), MsCl (2.6 mL, 34.2 mmol) and DMAP (206 mg, 1.43 mmol) under the room temperature. After being stirred for 3 h, water (50 mL) was added at 0 C. The mixture was extracted with Et2O, washed with saturated NaHCO3 and brine, dried, concentrated and chromatographed (SiO2 58 g, hexane:Et2O = 3:2) to give 9 (4.0 g, 27.2 mmol, 95%) as a colorless oil. [alpha]D17-119.7 (c 1.11, CHCl3); 1H NMR (400 MHz, CDCl3) delta 5.29 (ddd, J = 2.0, 6.8, 13.2 Hz, 1H), 3.13 (s, 3H), 2.72 (d, J = 2.0 Hz, 1H), 1.66 (d, J = 6.8 Hz, 3H); 13C NMR (100 MHz, CDCl3) delta 80.1, 76.3, 67.4, 39.1, 22.4; FT-IR (KBr) 3283, 3029, 2998, 2942, 2125, 1358, 1177, 1123, 1090, 1017 cm-1; HRMS (EI) calcd for C5H7O3S [(M-H)+] 147.0116, found 147.0116.
  • 5
  • [ 110-87-2 ]
  • [ 50-00-0 ]
  • [ 2914-69-4 ]
  • [ 114419-91-9 ]
  • [ 114419-87-3 ]
  • 6
  • [ 110-87-2 ]
  • [ 2914-69-4 ]
  • [ 114352-05-5 ]
  • [ 114351-88-1 ]
  • 7
  • [ 67-56-1 ]
  • <2S-(2α(R*),3aα,4α,7α,7aα)>-Octahydro-7,8,8-trimethyl-2-(1-methyl-2-propinyloxy)-4,7-methanobenzofuran [ No CAS ]
  • [ 2914-69-4 ]
  • 8
  • [ 50-00-0 ]
  • [ 2914-69-4 ]
  • [ 65032-23-7 ]
  • 9
  • [ 1450-14-2 ]
  • [ 2914-69-4 ]
  • [ 100244-12-0 ]
  • 10
  • [ 74213-24-4 ]
  • [ 2914-69-4 ]
  • [ 119596-03-1 ]
  • 12
  • [ 5930-98-3 ]
  • [ 2914-69-4 ]
  • [ 42969-65-3 ]
  • 13
  • [ 2914-69-4 ]
  • [ 150406-34-1 ]
  • 14
  • [ 128241-50-9 ]
  • [ 2914-69-4 ]
  • [ 42969-65-3 ]
  • 18
  • [ 2028-63-9 ]
  • [ 2914-69-4 ]
YieldReaction ConditionsOperation in experiment
With vinyl benzoate;Europa lipase E2 (Candida rugosa lipase); at 23℃; for 48h;Resolution of racemate; Enzymic Resolution of but-3-yn-2-ol A substrate solution is prepared containing racemic but-3-yn-2-ol (10g, 0.143 mol) and vinyl benzoate (41.53g, 0.28 mol). The total volume is 50ml. To the solution is added 2.5g Europa lipase E2 (Candida rugosa lipase). The solution is mixed by agitation on a shaker at 23C (ambient temp). The reaction is monitored by chiral GC on a Varian CP7503 Chiralsil Dex CB column, 30m x 0.32um, helium carrier gas at 9.52psi and initial flow of 2ml/min. Initial oven temp 50C for 5 min then 20C/min to 180C and hold for 2 min. Run time 13.5 min. Retention times 5.6min (R 3-butyn-2-ol), 5.9 min (S 3-butyn-2- ol), 11.51 min (R Benzyl ester) and 11.56 min (S Benzyl ester). After 48h incubation, (S) -3-butyn-2-ol of 96% ee was obtained at 75% conversion.
  • 19
  • [ 100837-08-9 ]
  • [ 2914-69-4 ]
  • 20
  • [ 153123-06-9 ]
  • [ 2914-69-4 ]
  • [ 107647-75-6 ]
  • 21
  • [ 2914-69-4 ]
  • [ 39637-99-5 ]
  • [ 133796-97-1 ]
  • 22
  • [ 2914-69-4 ]
  • [ 18162-48-6 ]
  • [ 150406-34-1 ]
YieldReaction ConditionsOperation in experiment
96% With 1H-imidazole; In dichloromethane; at 0 - 20℃; for 8h;Inert atmosphere; (S)-3-Butyn-2-ol (99% ee) (1.2 mL, 15 mmol) and imidazole (2.0 g, 30mmol) were dissolved in DCM (30 mL) at 0 C. Then, TBSCl (3.4 g, 22mmol) was added to the mixture, and the solution was stirred at rt for 8 h. The reaction was quenched with H2O and the mixture was extracted with DCM (3 × 15 mL). The combined organic layer was dried over MgSO4. Then, the drying agent was removed by filtration, and the filtrate was concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel (0-5% EtOAc/hexane) to give the TBS-protected alcohol derivative (2.6 g, 14 mmol) in 96% yield.
73% To a flask containing (S)-but-3-yn-2-ol (5, 1.40 g, 20 mmol) in dry CH2Cl2 (16 mL) was added at 0 C imidazole (1.50 g, 22 mmol) and the mixture was stirred for 10 min. TBDMSCl (3.01 g, 20 mmol) was added and the reaction mixture was stirred at 0 C for 15 min and then at 23 C for 3 h (formation of a white precipitate after 1 h). The reaction mixture was diluted with H2O (10 mL) and extracted with pentane (3 × 30 mL). The combined organic extracts were dried over MgSO4, filtered and the solvents removed under reduced pressure. The crude product was purified by column chromatography (pentane) to give 34 (2.70 g, 73% yield). Spectral data for 34 match those previously reported.
  • 24
  • (1R,4R,5S)-6,6-Dimethyl-4-<(S)-3-(but-1-ynyloxy)>-3-oxabicyclo<3.1.0>hexan-2-one [ No CAS ]
  • [ 2914-69-4 ]
  • 25
  • [ 2914-69-4 ]
  • [ 144282-55-3 ]
  • [ 144282-56-4 ]
  • 26
  • [ 2914-69-4 ]
  • [ 141580-65-6 ]
  • [ 176966-00-0 ]
  • 27
  • [ 141783-42-8 ]
  • [ 2914-69-4 ]
  • 30
  • [ 615-37-2 ]
  • [ 2914-69-4 ]
  • (S)-(-)-4-o-toluyl-3-butyn-2-ol [ No CAS ]
  • 31
  • [ 625-95-6 ]
  • [ 2914-69-4 ]
  • (S)-(-)-4-m-toluyl-3-butyn-2-ol [ No CAS ]
  • 35
  • [ 2914-69-4 ]
  • [ 126347-88-4 ]
  • (S)-5,15-hexadeca-1,11-dien-13-yn-2-ol [ No CAS ]
 

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Technical Information

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