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Structure of 62037-46-1

Chemical Structure| 62037-46-1

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Product Details of [ 62037-46-1 ]

CAS No. :62037-46-1
Formula : C3H9Cl2NO
M.W : 146.02
SMILES Code : OC(CCl)CN.[H]Cl
MDL No. :MFCD01697322
InChI Key :ZCPJBHYNOFIAPJ-UHFFFAOYSA-N
Pubchem ID :147580

Safety of [ 62037-46-1 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Computational Chemistry of [ 62037-46-1 ] Show Less

Physicochemical Properties

Num. heavy atoms 7
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 32.17
TPSA ?

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

46.25 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

0.0
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.

0.35
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.

0.23
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

-0.07
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

0.11

Water Solubility

Log S (ESOL):?

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

-0.65
Solubility 32.6 mg/ml ; 0.223 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.

-0.58
Solubility 38.0 mg/ml ; 0.26 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

-0.36
Solubility 64.3 mg/ml ; 0.441 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.

-7.15 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)

2.0

Application In Synthesis of [ 62037-46-1 ]

* 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 [ 62037-46-1 ]

[ 62037-46-1 ] Synthesis Path-Downstream   1~16

  • 1
  • [ 62037-46-1 ]
  • [ 89034-17-3 ]
  • 2
  • [ 62037-46-1 ]
  • Thiophosphorsaeure-S-<3-amino-2-hydroxy-propylester> Dilithiumsalz [ No CAS ]
  • 3
  • 3-benzylidenamino-1-chloropropan-2-ol [ No CAS ]
  • [ 62037-46-1 ]
  • 4
  • [ 62037-46-1 ]
  • [ 98026-24-5 ]
  • 5
  • [ 7732-18-5 ]
  • [ 62037-46-1 ]
  • silver oxide [ No CAS ]
  • [ 616-30-8 ]
  • 6
  • [ 108-24-7 ]
  • [ 62037-46-1 ]
  • [ 53460-78-9 ]
  • 8
  • [ 19667-37-9 ]
  • [ 62037-46-1 ]
YieldReaction ConditionsOperation in experiment
EXAMPLE 5 (+-)-1-Amino-3-chloro-2-propanol hydrochloride (+-)-(V) A slurry of (+-)-1-phthalimido-3-chloro-2-propanol (IVC, 40.018 g, 166.98 mmol) in hydrochloric acid (37.5 wt %, 79 ml, 968 mmol, 5.80 eq) and water (82 ml) is stirred at 109 for 5 hrs. The mixture is cooled to 22 and the precipitate is removed by filtration with reduced pressure and washed with water (40 ml). The filtrate is concentrated under reduced pressure to 26 g net weight and ethanol (100 ml) added. The mixture is warmed to 75 to give a solution then cooled to -12 and the resultant precipitate collected by filtration with reduced pressure, washed with ethanol cooled to -12 and dried to give the title compound, mp=101-104; NMR (CD3 OD) 2.96, 3.21, 3.57-3.64 and 4.03-4.09 delta; CMR (CD3 OD) 43.54, 46.95 and 68.71 delta; MS (CI, NH3), M/Z (relative intensity) 129 (12), 127 (39), 112 (56), 110 (100).
  • 10
  • [ 34619-03-9 ]
  • [ 62037-46-1 ]
  • [ 570390-94-2 ]
  • 11
  • [ 62037-46-1 ]
  • [ 594-44-5 ]
  • N-(3-chloro-2-hydroxypropyl)ethane sulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With dipotassium hydrogenphosphate; In tetrahydrofuran; water; at 0 - 20℃; A three-necked flask was charged with <strong>[62037-46-1]1-amino-3-chloropropyl-2-ol hydrochloride</strong> (14.60 g, 100 mmol) and tetrahydrofuran(73 mL), water (73 mL), stirred and cooled to 0 to 5 C, added with dipotassium hydrogen phosphate (34.84 g, 200 mmol), stirred for 5 minAfter the clockwise drop of ethyl sulfonyl chloride (13.50g, 105mm0l), plus the temperature after warming to room temperature for 3-4 hours, the end of the reaction0.5mol / L dilute hydrochloric acid 73mL quenching reaction, stirring and dispensing, water and then extracted with ethyl acetate 35mL 2 times, combined organic saturatedAnd washed with salt (73 mL), dried over anhydrous sodium sulfate and concentrated to give N-(3-chloro-2-hydroxypropyl) ethane sulfonamide Followed by the next step (GC purity of about 92%).
  • 12
  • [ 24424-99-5 ]
  • [ 62037-46-1 ]
  • [ 570390-94-2 ]
YieldReaction ConditionsOperation in experiment
96.71% With sodium hydrogencarbonate; In methanol; water; at 20℃; for 3h; The reaction flask was charged with 116.8 g of compound II (0.80 mol)191.8 g of Boc2O (0.88 mol) and 1500 ml of methanol, stirred,And 1200 ml of an aqueous solution containing 80.6 g of sodium hydrogencarbonate (0.96 mol)And then reacted at room temperature for 3 hours. After the reaction was complete, the methanol was removed by concentration,The residue was extracted with 2000 ml of methylene chloride and the dichloromethane layer was washed with water,And finally dried over anhydrous sodium sulfate; filtered, the filtrate was concentrated to dryness,174.3 g of an oil was obtained, and 1200 ml of petroleum ether was added to the oil to freeze the crystals,The filter cake was washed with petroleum ether to give 161.7 g of the white solid, compound III; mp 48-51 C, molar yield: 96.71% (calculated as compound II).
  • 13
  • [ 106-89-8 ]
  • [ 62037-46-1 ]
YieldReaction ConditionsOperation in experiment
74.04% The reaction flask was charged with 1200 ml of ethanol and 111.3 g of benzaldehyde (1.05 mol)110 ml of 25% aqueous ammonia (1.60 mol) was added, and after stirring for 15 minutes, 92 g of epichlorohydrin (1.00 mol)The control temperature was lower than 40 C, the addition was completed, reacted at 35-40 C for 8 hours, and then reacted at room temperature for 15 hours,After vapor phase detection of epichlorohydrin almost completely disappeared, the reaction solution was concentrated to remove about 1/3 volume of ethanol,Then, 800 ml of toluene was added, and the mixture was stirred at a temperature of 35 to 40 C and 270 ml of 6N hydrochloric acid (1.62 mol)After completion of the dropwise addition, the reaction was continued for 6 hours at this temperature, and after the completion of the reaction,The upper layer was washed with water, the aqueous layers were combined, concentrated to dryness, and the residue was concentrated by adding absolute ethanol,Finally, toluene was added to concentrate to remove the contained water, and the resulting residue was recrystallized from ethanol and ethyl acetate,To give 108.1 g of a white solid, compound II; mp: 127-130 C, molar yield: 74.04% (calculated as epichlorohydrin).
  • 14
  • (E)-3-(4-chlorophenyl)-2-phenylacryloyl chloride [ No CAS ]
  • [ 62037-46-1 ]
  • (E)-N-(3-chloro-2-hydroxypropyl)-3-(4-chlorophenyl)-2-phenylacrylamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
172.2 mg With pyridine; In dichloromethane; at 0 - 23℃;Inert atmosphere; To a suspension of <strong>[62037-46-1]1-amino-3-chloropropan-2-ol hydrochloride</strong> (175.2 mg, 1.2 mmol, 1.0 eq) and pyridine (0.49 mL, 6.0 mmol, 5.0 eq) in DCM (3 mL) at 0 C was added the crude acid chloride 16 from the above reaction. The reaction mixture was allowed to warm to 23 C over 2 h, and then stirred overnight at rt. The resultant mixture was partitioned between DCM (3 mL) and water (5 mL). The organic layer was washed with saturated NaHCO3 (aq, 5 mL) and brine (5 mL), dried over anhydrous MgSO4, filtered, and concentrated in vacuo. The crude material was purified by column chromatography on silica gel, using a mobile phase gradient of 15 to 40% of EtOAc/hexanes to yield the acrylamide 17 (172.2 mg, 0.49 mmol, 41% from 15) as a white solid. 1H NMR (500 MHz, DMSO-d6) delta 7.44 - 7.39 (m, 4H), 7.37 (t, J= 5.6 Hz, 1H), 7.24 (d, J= 8.6 Hz, 2H), 7.21 - 7.17 (m, 2H), 6.99 (d, J= 8.7 Hz, 2H), 5.35 (d, J= 5.3 Hz, 1H), 3.83 - 3.74 (m, 1H), 3.58 (dd, J= 11.2, 4.4 Hz, 1H), 3.47 (dd, J= 11.2, 6.0 Hz, 1H), 3.34 - 3.28 (m, 1H), 3.19 (ddd, J = 13.4, 6.7, 5.6 Hz, 1H); 13C NMR (126 MHz, DMSO-d6) delta 167.32, 137.21, 135.65, 133.96, 132.78, 132.71, 131.30, 129.40, 129.07, 128.27, 128.23, 69.06, 47.88, 43.19; HRMS m/z calcd. for C18H18Cl2NO2 [M+H]+ 350.07091, found 350.06477.
  • 15
  • C16H16ClNO [ No CAS ]
  • [ 62037-46-1 ]
  • 16
  • [ 5807-30-7 ]
  • [ 62037-46-1 ]
  • FNL-0010 [ No CAS ]
YieldReaction ConditionsOperation in experiment
General procedure: [0445] Certain compounds disclosed herein with an amide moiety, without a triazole moiety, were synthesized according to the above scheme, over two steps. In the first step, <strong>[62037-46-1]1- amino-3-chloropropan-2-ol hydrochloride</strong> was combined with R-COOH, 1-ethyl-3-(3- dimethylaminopropyl)carbodiimide hydrochloride (EDC.HCl), hydroxybenzotriazole hydrate (HOBt.H2O), triethylamine (Et3N), and dichloromethane (DCM), and the mixture stirred at room temperature for 18 h. In the second step, the product from the first step was reacted with NaOH (1N) and acetone at room temperature for 30 minutes to produce the final compound comprising an amide moiety, without a triazole.
 

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Technical Information

Categories

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