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Chemical Structure| 77-85-0 Chemical Structure| 77-85-0

Structure of 77-85-0

Chemical Structure| 77-85-0

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Product Details of [ 77-85-0 ]

CAS No. :77-85-0
Formula : C5H12O3
M.W : 120.15
SMILES Code : CC(CO)(CO)CO
MDL No. :MFCD00004687
InChI Key :QXJQHYBHAIHNGG-UHFFFAOYSA-N
Pubchem ID :6502

Safety of [ 77-85-0 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P301+P312-P302+P352-P304+P340-P305+P351+P338

Computational Chemistry of [ 77-85-0 ] Show Less

Physicochemical Properties

Num. heavy atoms 8
Num. arom. heavy atoms 0
Fraction Csp3 1.0
Num. rotatable bonds 3
Num. H-bond acceptors 3.0
Num. H-bond donors 3.0
Molar Refractivity 29.37
TPSA ?

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

60.69 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

0.9
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

-1.17
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.

-0.65
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

-0.44
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

-0.48

Water Solubility

Log S (ESOL):?

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

0.35
Solubility 269.0 mg/ml ; 2.24 mol/l
Class?

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

Highly soluble
Log S (Ali)?

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

0.39
Solubility 294.0 mg/ml ; 2.45 mol/l
Class?

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

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

0.24
Solubility 211.0 mg/ml ; 1.75 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.

-7.86 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)

1.09

Application In Synthesis of [ 77-85-0 ]

* 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 [ 77-85-0 ]

[ 77-85-0 ] Synthesis Path-Downstream   1~7

  • 1
  • [ 51792-34-8 ]
  • [ 77-85-0 ]
  • [ 426263-16-3 ]
YieldReaction ConditionsOperation in experiment
toluene-4-sulfonic acid; In toluene; at 100℃; for 48h; Synthesis of (3-methyl-3,4-dihydro-2H-thieno[3,4-b][1 ,4]dioxepin-3-yl)-methanol; <strong>[51792-34-8]3,4-dimethoxythiophene</strong> (4 g, 27.8 mmol) was taken with 1500 mL of toluene and to this trimethylol ethane (4.32 g, 36.10 mmol) was added followed by p-TSA (0.52 g, 2.78 mmol). The mixture was stirred at 100 0C with a continuous flow of argon for 48 h. Excess toluene was evaporated and the greenish black residue was extracted with ethyl acetate, washed repeatedly with water, dried over sodium sulphate and ethyl acetate was removed under vacuum. The crude product was purified by silica gel column chromatography eluting with pet ether-ethyl acetate (80:20) to get colourless viscous oil which solidified over a period of two days to a white solid. 1H NMR (CDCI3): 0.95 (s, 3H), 1.70 (s, 1H), 3.73 (d, 2H), 3.74 (s, 2H), 4.08 (d, 2H), 6.48 (s, 2H). Mass: 200 [M]+
With toluene-4-sulfonic acid; In toluene; at 110℃; for 36h; ProDOT-OH and ProDOT-N3 were synthesized as described inthe literature [35]. 3-Methyl-3-(hydroxymethyl)-3,4-dihydro-2H-thieno[3,4-b][1,4]dioxepine, ProDOT-OH: <strong>[51792-34-8]3,4-dimethoxythiophene</strong> (2.5 g,17.5 mmol) was dissolved in 100 mL of toluene. 2-Hydroxymethyl-2-methylpropan-1,3-diol (4.2 g, 2 eq, 35 mmol) and para-toluenesulfonic acid monohydrate (635 mg, 0.2 eq, 3.5 mmol) were added. The mixture was warmed at 110 °C over 36 h. The mixture was allowed to cool at room temperature. The toluene phase was extracted with NaHCO3 5 percent in water (230 mL) and brine (30 mL), and finally dried (Na2SO4). The solvents were removed under reduced pressure. The compound was finallypurified on column (8/2, cyclohexane/ethyl acetate). 3-(Azidomethyl)-3-methyl-3,4-dihydro-2H-thieno[3,4-b][1,4]dioxepine, ProDOT-N3: ProDOT-OH (2.6 g, 11.5 mmol) wasdissolved in 50 mL of dichloromethane. Triethylamine (2.3 g, 2eq, 23 mmol) was added. The mixture was cooled at 0 C.Methanesulfonyl chloride (1.58 g, 1.2 eq, 13.8 mmol) was addeddropwise. The mixture was allowed to warm up at room temperature. After 4 h, 10 mL of methanol was added. The mixture was stirred for 30 additional min. All volatiles were removed under reduced pressure. The residual oil was dissolved in 100 mL of N,N-dimethylformamide (DMF) and NaN3 (3.7 g, 5 eq, 44.5 mmol) was added. The mixture was heated at 95 °C overnight. The reaction was then allowed to cool at room temperature and most part of the DMF was removed under reduced pressure. 100 mL of dichloromethane was added. The organic layer was washed with water (230 mL) and brine (30 mL), dried over Na2SO4. The solvents were removed under reduced pressure. ProDOT-1N3 is finally purified on column (80/20, cyclohexane/dichloromethane). All yields and spectroscopic data agreed with the literature.
  • 2
  • [ 77-85-0 ]
  • [ 78385-26-9 ]
YieldReaction ConditionsOperation in experiment
A 2-lErlenmeyer flask was charged with metriol (300 g, 2.5 mol),48% hydrobromic acid (1030 ml, 1524.4 g, 9 mol), andglacial acetic acid (140 ml, 147.1 g, 2.45 mol). The stirredmixture was carefully treated by addition of sulfuric acid(380 ml, 696.9 g, 3.9 mol) and refluxed for 4 h. After that,the reaction mixture was cooled to ~15 and the lower(organic) layer was separated in a separatory funnel, andthe upper (aqueous) layer was extracted with chloroform(200 ml and 3×100 ml). The extracts were combined withthe organic layer, the obtained solution was washed withwater (3×75 ml), then with aqueous 15% Na2CO3 solution(50 ml), and again with water (2×75 ml). The chloroformsolution was then evaporated, giving a mixture of products1 and 1b (550.4 g) in the ratio of 46.0 and 46.8% as abrown liquid with low viscosity.3-Bromo-2-(bromomethyl)-2-methylpropan-1-ol (1a).1 NMR spectrum (DMSO-d6), delta, ppm (J, Hz): 1.01 (3,s, 3); 3.33 (2, d, J = 5.3, CH2OH); 3.48 (4, s,CH2Br); 4.97 (1H, t, J = 5.3, OH).3-Bromo-2-(bromomethyl)-2-methylpropyl acetate(1b). 1 NMR spectrum (DMSO-d6), delta, ppm: 1.09 (3, s,3); 2.04 (3, s, OC(O)CH3); 3.55 (4, s, CH2Br); 3.99(2, s, CH2OC(O)CH3). 13C NMR spectrum (CDCl3), delta, ppm:170.60; 67.20; 66.25; 40.59; 39.13; 38.32; 20.82; 20.23;19.87 (for mixture 1a and 1b).A three-neck one liter flask equipped with an overheadstirrer was charged with a mixture of compounds 1a and 1b(524.2 g, 2 mol) and TBAB (8.4 g, 26 mmol). The reactionmixture was vigorously stirred and treated by the additionof a solution prepared from NaOH (109.5 g, 2.6 mol) andwater (190 ml). The reaction mixture was thenthermostated at 50 while vigorously stirring for 1.5 h.After that, the reaction flask was connected through anintermediate vessel to steam generator and compound 2awas steam-distilled from the reaction mixture. The organicphase (bottom layer) was obtained with a yield of 174.0 gand contained 84.0% of 3-bromomethyl-3-methyloxetane(2a) according to 1H NMR spectrum. Distillation allowedto separate the main fraction (144.7 g) as a colorless liquidwith bp 47.5-48 / 6 Torr (62-64 / 10 Torr54), thecontent of compound 2a was 137.47 g (95%), the yield ofcyclization step was 43.8%.3-Bromomethyl-3-methyloxetane (2). 1 NMRspectrum (DMSO-d6), delta, ppm (J, Hz): 1.34 (3, s, 3);3.78 (2, s, CH2Br); 4.24 (2, d, J = 5.9) and 4.33 (2, d,J = 5.9, CH2O). 13C NMR spectrum (75.47 MHz, CDCl3),delta, ppm: 80.68; 41.31; 40.60; 22.44.
  • 3
  • [ 77-85-0 ]
  • [ 1119249-30-7 ]
  • [ 1119249-31-8 ]
  • 4
  • [ 77-85-0 ]
  • [ 325142-82-3 ]
  • Na(3-(CF3)C6H4B(OCH2)3CCH3) [ No CAS ]
  • 5
  • [ 77-85-0 ]
  • [ 374790-93-9 ]
  • C4H3OB(OCH2)3CCH3(1-)*Na(1+)=NaC4H3OB(OCH2)3CCH3 [ No CAS ]
  • 6
  • [ 77-85-0 ]
  • [ 1310-73-2 ]
  • [ 325142-82-3 ]
  • Na(3-(CF3)C6H4B(OCH2)3CCH3) [ No CAS ]
  • 7
  • [ 77-85-0 ]
  • [ 1310-73-2 ]
  • [ 374790-93-9 ]
  • C4H3OB(OCH2)3CCH3(1-)*Na(1+)=NaC4H3OB(OCH2)3CCH3 [ No CAS ]
 

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