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Chemical Structure| 60827-45-4 Chemical Structure| 60827-45-4

Structure of 60827-45-4

Chemical Structure| 60827-45-4

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Product Details of [ 60827-45-4 ]

CAS No. :60827-45-4
Formula : C3H7ClO2
M.W : 110.54
SMILES Code : OC[C@H](O)CCl
MDL No. :MFCD00210270
InChI Key :SSZWWUDQMAHNAQ-GSVOUGTGSA-N
Pubchem ID :148904

Safety of [ 60827-45-4 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H301-H312-H318
Precautionary Statements:P264-P270-P280-P301+P310-P302+P352-P305+P351+P338-P310-P322-P330-P363-P405-P501
Class:6.1
UN#:2689
Packing Group:

Computational Chemistry of [ 60827-45-4 ] Show Less

Physicochemical Properties

Num. heavy atoms 6
Num. arom. heavy atoms 0
Fraction Csp3 1.0
Num. rotatable bonds 2
Num. H-bond acceptors 2.0
Num. H-bond donors 2.0
Molar Refractivity 23.65
TPSA ?

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

40.46 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

1.17
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

-0.49
Log Po/w (WLOGP)?

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

-0.42
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.

-0.18
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

0.16
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

0.05

Water Solubility

Log S (ESOL):?

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

-0.08
Solubility 91.0 mg/ml ; 0.823 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.

0.11
Solubility 142.0 mg/ml ; 1.28 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

-0.14
Solubility 79.7 mg/ml ; 0.721 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.

-7.32 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

2.0
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)

2.32

Application In Synthesis of [ 60827-45-4 ]

* 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 [ 60827-45-4 ]

[ 60827-45-4 ] Synthesis Path-Downstream   1~35

  • 1
  • 1-O-β-D-glucosyl-(2S)-3-chloropropylene glycol [ No CAS ]
  • [ 60827-45-4 ]
  • 2
  • barium D-3-chloropropane-1,2-diol-1-phosphate [ No CAS ]
  • [ 57090-45-6 ]
  • [ 60827-45-4 ]
  • 3
  • barium D-3-chloropropane-1,2-diol-1-phosphate [ No CAS ]
  • [ 60827-45-4 ]
  • 4
  • [ 96-24-2 ]
  • [ 57090-45-6 ]
  • [ 60827-45-4 ]
  • D-3-chloropropane-1,2-diol-1-phosphate [ No CAS ]
  • 5
  • [ 96-24-2 ]
  • [ 60827-45-4 ]
  • 6
  • [ 78692-88-3 ]
  • [ 60827-45-4 ]
  • 7
  • [ 869-50-1 ]
  • [ 57090-45-6 ]
  • [ 60827-45-4 ]
  • 8
  • [ 78692-88-3 ]
  • [ 57090-45-6 ]
  • [ 60827-45-4 ]
  • 10
  • [ 60827-45-4 ]
  • [ 60456-23-7 ]
YieldReaction ConditionsOperation in experiment
With potassium phosphate; In dichloromethane; for 3h;Heating / reflux;Product distribution / selectivity; To 1.2 L of a methylene chloride solution of (S)-3-chloro-l,2-propanediol (200 g, 99.5% ee) was added 519 g of potassium phosphate tribasic, and then the obtained solution was refluxed, under stirring, for 3 hours. The resulting solution was cooled to 0C, and 220 g of trie thy lamine, 4 g of 4-(dimethylamino)pyridine, and 315 g of butanoic acid anhydride were dropwisely added to the solution. After additional stirring for 1 hour at a room temperature, the reaction mixture was successively washed with 2.2 L of 5% aqueous potassium carbonate solution, 2 L of IN aqueous hydrogen chloride solution, and 1 L of water. The organic layer was dried with 50 g of anhydrous sodium sulfate and filtrated. The methylene chloride was evaporated under reduced pressure. Fractional distillation (90C/19 mmHg) of the resulting residue gave 242 g of the targeted compound:- Yield: 92.7%- Chemical purity: 99.4%- Optical purity (GC) 99.5% ee.
With potassium carbonate; In dichloromethane; for 25h;Heating / reflux;Product distribution / selectivity; To 1.2 L of a methylene chloride solution of (S)-3-chloro-l,2-propanediol (200 g, 99.5% ee) was added 338 g of potassium carbonate, and then the obtained solution was refluxed, under stirring, for 25 hours. The resulting solution was cooled to 0C, and 220 g of triethylamine, 4 g of 4-(dimethylamino)pyridine, and 315 g of butanoic acid anhydride were dropwisely added to the solution. After additional stirring for 1 hour at a room temperature, the reaction mixture was successively washed with 2.2 L of 5% aqueous potassium carbonate solution, 2 L of IN aqueous hydrogen chloride solution, and 1 L of water. The organic layer was dried with 50 g of anhydrous sodium sulfate and filtrated. The methylene chloride was evaporated under reduced pressure. Fractional distillation (90C/19 mmHg) of the resulting residue gave ID g of the targeted compound:- Yield: 65.0%- Chemical purity: 97.4%- Optical purity (GC) 98.1% ee.
With potassium carbonate; In dichloromethane; at 20℃; for 17.5h; 200 g of 3-chloro-1,2-propanediol was dissolved in 2000 mL of dichloromethane, 625 g of potassium carbonate was added, and the mixture was stirred at room temperature for 17.5 hours.The precipitated insoluble materials were filtered,By washing the filtration residue with 1,000 mL of dichloromethane,(S) -oxiran-2-ylmethanolWas obtained.To the obtained solution,198 g of dihydropyran was added,After cooling to 0 C.,5.16 g of p-toluenesulfonic acid monohydrate was added at 10 C. or less,And the mixture was stirred at room temperature for 1.5 hours. 408 g of a 7.5% sodium bicarbonate aqueous solution was added,After stirring, the organic layer and the aqueous layer were separated. The obtained organic layer was concentrated,Distillation gave 247.8 g of the title compound as a colorless oil.
  • 11
  • [ 96-24-2 ]
  • [ 57090-45-6 ]
  • [ 60827-45-4 ]
  • 12
  • [ 106-89-8 ]
  • [ 67843-74-7 ]
  • [ 57090-45-6 ]
  • [ 60827-45-4 ]
YieldReaction ConditionsOperation in experiment
26% With Aspergillus niger epoxide hydrolases immobilized onto modified Eupergit C; In aq. phosphate buffer; dimethyl sulfoxide; at 25℃; for 3h;pH 6.5;Enzymatic reaction;Kinetics; General procedure: Asymmetric hydrolysis of (R/S)-SO, (R/S)-PO and (R/S)-ECH were examined in a batch type reactor (1.1 cm × 5 cm). To 1.5 mL of 100 mM phosphate buffer (pH = 7.0 for the free and EHIL; pH = 6.5 for EHIF and EHIE), 100 L of the free EH solution (1 mg mL-1) or 30 mg of each immobilized EH was loaded and the mixture kept at 25 C for 2 min. The reaction was initiated by the addition 0.4 mL of each racemic epoxide solution (0.5 M in DMSO). A hundred microliters of aliquots withdrawn at different time intervals (15, 30,60, 90, 120, 180 and 240 min) were mixed with 400 L of diethylether and analyzed by a Shodex ORpak CDC-453 HQ chiral HPLC column (4.6 mm × 150 mm) according to Yildirim et al. [23]. The enantiomers of styrene oxide and their vicinal diols were detected at 220 nm. The enantiomers of propylene oxide, epichlorohydrin and their vicinal diols were detected using a refractive index detector (Shimadzu RID-10A). The optical configurations of remaining epoxides and formed diols were identified by comparing the retention time of these compounds with their optically active standard forms. The enantiomeric excess (ee) values of formed vicinal diol and remaining epoxide were calculated from the equations: eeepoxide=([S-R]epoxide)/([S+R]epoxide) and eediol=([R-S]diol)/([R+S]diol) The enantiomeric ratio values (E) of free and immobilized EHs were calculated from the equation proposed by Chen et al. [27]. E=(Vmax(R)/Km(R))/(Vmax(S)/Km(S)) where Vmax(R) and Km(R) values are maximum velocity and Michealis-Menten constant of free and immobilized EH preparations toward (R)-enantiomer of epoxide and Vmax(S) and Km(S) are corresponding values toward (S)-enantiomer of epoxide.
  • 14
  • [ 616-23-9 ]
  • [ 57090-45-6 ]
  • [ 60827-45-4 ]
  • (S)-1,3-dichloro-1-propanol [ No CAS ]
  • [ 106-89-8 ]
YieldReaction ConditionsOperation in experiment
EXAMPLE 3 This Example shows the conversion of (S)-3-amino-1,2-dihydroxypropane isopropylidene acetal 11 to (S)-1-chloro-2,3-dihydroxypropane 3.
EXAMPLE 2 Sodium periodate (9.31 g) was added slowly to a cooled and stirred solution of 6,6'-dichloro-6,6'-dideoxy-sucrose (5.0 g) in water (250 ml). After stirring at room temperature for 2 hours, the solution was diluted with ethanol (750 ml) and the resulting suspension was stirred at room temperature for a further 2 hours. The suspension was then filtered and the filtrate was concentrated to a syrup (25 ml) which was diluted with water (100 ml). A solution of sodium borohydride (2.04 g) in water (50 ml) was added slowly with cooling to the solution of oxidised product. After the addition, the reaction mixture was stirred at room temperature for 20 hours, and then a few drops of acetic acid were added. Concentration in vacuo at 40 gave a semi-solid mass which was then dissolved in ethyl acetate (AR):ethanol (9:1) and eluted through a column of silica gel. Evaporation of the elude yielded a semi-solid mass (5.1 g). T.l.c. showed that this was a mixture. The components were identified by g.l.c. to be alpha-chlorohydrin, dihydroxyacetone (dimer) and hydroxyacetaldehyde. Chromatography and distillation of the product mixture gave S-3-chloro-1,2-propanediol identical with that obtained in Example 1.
EXAMPLE 3 This Example shows the conversion of (S)-3-amino-1,2-dihydroxypropane isopropylidene acetal 11 to (S)-1-chloro-2,3-dihydroxypropane 3 .
  • 16
  • [ 60827-45-4 ]
  • (Coα-cyano)(Coβ-hydroxo)[1'-O-(p-tolyl)cobamide] [ No CAS ]
  • {Coβ-[(S)-2,3-dihydroxypropyl][1'-O-(p-tolyl)cobamide] [ No CAS ]
  • 17
  • [ 60827-45-4 ]
  • hydroxocobalamin [ No CAS ]
  • [(S)-2,3-dihydroxypropyl]cob(III)alamin [ No CAS ]
  • 20
  • [ 60827-45-4 ]
  • [ 431-03-8 ]
  • [ 149-73-5 ]
  • [ 371161-05-6 ]
  • 21
  • [ 60827-45-4 ]
  • [ 431-03-8 ]
  • [ 149-73-5 ]
  • [ 371160-90-6 ]
  • 24
  • [ 60827-45-4 ]
  • [ 288570-67-2 ]
  • [ 444335-16-4 ]
YieldReaction ConditionsOperation in experiment
With potassium tert-butylate; acetic acid; In tetrahydrofuran; hexane; water; ethyl acetate; To a solution of 1056 g (3.64 mol) of 2-Methylpropyl (4-bromo-3-fluorophenyl)carbamate in 6.65 L of THF cooled to -15 C. in a 22 L round bottom flask was added a solution of 428 g (4.55 mol, 1.25 equiv.) of lithium t-amylate over 10 min via an addition funnel, maintaining -15 to -12 C. In a separate 5 L flask, a solution of 438 g (4.37 mol, 1.20 equiv.) of (S)-3-chloro-1,2-propanediol in 1.75 L of THF was cooled to -25 C. and treated with a 20% t-BuOK solution in THF (2645 mL, 4.29 mol, 1.18 equiv) over 25 min, resulting in a thick but stirrable slurry. This was allowed to warm to 10 over 75 min and then poured into the 22 L flask containing the carbamate solution. The resulting slurry was allowed to warm from -7 to 7 over 1.5 h, monitoring reaction progress by HPLC. Upon completion (~2.5% each of remaining 2-Methylpropyl (4-bromo-3-fluorophenyl)carbamate and the over addition product) a quench solution composed of 1.05 AcOH and 3.5 L of water was added. The layers were separated. The aqueous layer was back-extracted with 1 L of THF, and the combined organic layers were washed with brine. The volatile were removed, giving white solids wet with acetic acid. This material was slurried in 1.6 L of EtOAc. Hexane (4L) was added over 1 h. The resulting slurry was cooled to 2 over 1 h and filtered, giving 916 g (87%) of (5R)-3-(4-bromo-3-fluorophenyl)-5-(hydroxymethyl)-1,3-oxazolidin-2-one as coarse white crystals: TLC Rf=0.008 (50% EtOAc/hexane); HPLC rt=2.55 min; mp 114-121 ; [alpha]D=+52.2 c. =1, MeOH); 1H NMR (DMSO) delta7.49 (m, 2H), 7.15 (d,1H, J=8.5 Hz), 5.30 (br s, 1H), 4.54 (m,1H), 3.89 (t, 1H, J=8.6 Hz), 3.67 (m, 1H), 3.50 (dd, 1H, J=3.0, 11.8 Hz), 3.39 (dd, 1H, 3.8, 11.8 Hz); 13C NMR (DMSO) delta158.1 (s, JCF=241 hz), 154.2 (S), 139.7 (S, JCF=10 hz), 133.3 (D), 114.9 (D), 105.9 (d, JCF=29 Hz), 100.9 (s, JCF=21 Hz), 73.3(d), 61.5(t), 45.9 (t); Anal. calc'd for C10H9BrFNO3: C, 41.40; H, 3.13; N, 4.83: Br, 27.55; found: C, 41.11; H, 3.06; N, 4.83: Br, 26.97.
  • 26
  • [ 60827-45-4 ]
  • [ 506-59-2 ]
  • [ 666234-81-7 ]
  • 27
  • [ 60827-45-4 ]
  • [ 761442-96-0 ]
  • (S)-4-(5-chloro-2-hydroxyphenyl)-3-(2,3-dihydroxypropylsulfanyl)-6-trifluoromethyl-1H-quinolin-2-one [ No CAS ]
  • 28
  • [ 145387-82-2 ]
  • [ 106-89-8 ]
  • [ 60827-45-4 ]
  • C13H28ClNO5SSi [ No CAS ]
  • 29
  • [ 198572-71-3 ]
  • [ 106-89-8 ]
  • [ 60827-45-4 ]
  • C14H19ClN2O7S [ No CAS ]
  • 30
  • [ 110-87-2 ]
  • [ 60827-45-4 ]
  • (S)-1-Chloro-3-(tetrahydro-pyran-2-yloxy)-propan-2-ol [ No CAS ]
  • 31
  • [ 60827-45-4 ]
  • [ 108-24-7 ]
  • acetic acid-3-chloro-(S)-2-hydroxy-propyl ester [ No CAS ]
  • 33
  • [ 1011475-45-8 ]
  • [ 60827-45-4 ]
  • (S)-3-{4-[5-(5,6-diethyl-pyridin-3-yl)-[1,2,4]oxadiazol-3-yl]-2-ethyl-6-methyl-phenoxy}-propane-1,2-diol [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium hydroxide; In water; isopropyl alcohol; at 60℃; for 72h; Example 14 To a solution of 4-[5-(5,6-diethyl-pyridin-3-yl)-[1,2,4]oxadiazol-3-yl]-2-ethyl-6-methyl-phenol (100 mg, 0.296 mmol) in isopropanol (10 mL) and 3 N aq. NaOH (3 mL), (S)-3-chloro-1,2-propanediol (98 mg, 0.89 mmol) is added. The mixture is stirred at 60 C. for 24 h before another portion of (S)-3-chloro-1,2-propanediol (98 mg, 0.89 mmol) is added. Stirring is continued at 60 C. for 2 days. The mixture is diluted with EA and washed with sat. aq. NaHCO3 solution. The org. extract is dried over MgSO4, filtered and evaporated. The crude product is purified by chromatography on prep. TLC plates with EA-heptane to give (S)-3-{4-[5-(5,6-diethyl-pyridin-3-yl)-[1,2,4]oxadiazol-3-yl]-2-ethyl-6-methyl-phenoxy}-propane-1,2-diol (14 mg) as a red oil; LC-MS: tR=0.93 min, [M+1]+=412.16.
With sodium hydroxide; In water; isopropyl alcohol; at 60℃; for 72h; To a solution of 4-[5-(5,6-diethyl-pyridin-3-yl)-[1 ,2,4]oxadiazol-3-yl]-2-ethyl-6-methyl-phenol (100 mg, 0.296 mmol) in isopropanol (10 ml.) and 3 N aq. NaOH (3 ml_), (S)-3-chloro-1 ,2- propanediol (98 mg, 0.89 mmol) is added. The mixture is stirred at 600C for 24 h before another portion of (S)-3-chloro-1 ,2-propanediol (98 mg, 0.89 mmol) is added. Stirring is continued at 600C for 2 days. The mixture is diluted with EA and washed with sat. aq. NaHCOs solution. The org. extract is dried over MgSO4, filtered and evaporated. The crude product is purified by chromatography on prep. TLC plates with EA-heptane to give (S)-3- {4-[5-(5,6-diethyl-pyridin-3-yl)-[1 ,2,4]oxadiazol-3-yl]-2-ethyl-6-methyl-phenoxy}-propane-1 ,2- diol (14 mg) as a red oil; LC-MS: tR = 0.93 min, [M+1]+ = 412.16.
  • 34
  • [ 60827-45-4 ]
  • [ 767-00-0 ]
  • [ 148460-02-0 ]
  • 35
  • [ 23010-10-8 ]
  • [ 60827-45-4 ]
  • (S)-3-(2-tert-butoxyphenoxy)-propane-1,2-diol [ No CAS ]
  • (R)-3-(2-tert-butoxyphenoxy)-propane-1,2-diol [ No CAS ]
 

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Technical Information

Categories

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[ 60827-45-4 ]

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