Home Cart Sign in  
Chemical Structure| 169048-83-3 Chemical Structure| 169048-83-3

Structure of 169048-83-3

Chemical Structure| 169048-83-3

*Storage: {[sel_prStorage]}

*Shipping: {[sel_prShipping]}

,{[proInfo.pro_purity]}

4.5 *For Research Use Only !

{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]} Purity: {[proInfo.pro_purity]}

Change View

Size Price VIP Price

US Stock

Global Stock

In Stock
{[ item.pr_size ]} Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]}

US Stock: ship in 0-1 business day
Global Stock: ship in 5-7 days

  • {[ item.pr_size ]}

In Stock

- +

Please Login or Create an Account to: See VIP prices and availability

US Stock: ship in 0-1 business day
Global Stock: ship in 2 weeks

  • 1-2 Day Shipping
  • High Quality
  • Technical Support
Product Citations

Alternative Products

Product Details of [ 169048-83-3 ]

CAS No. :169048-83-3
Formula : C4H6ClNO2
M.W : 135.55
SMILES Code : O=C1O[C@H](CCl)CN1
MDL No. :MFCD08706410
InChI Key :FNOZCEQRXKPZEZ-GSVOUGTGSA-N
Pubchem ID :7058042

Safety of [ 169048-83-3 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302
Precautionary Statements:P280-P305+P351+P338

Computational Chemistry of [ 169048-83-3 ] Show Less

Physicochemical Properties

Num. heavy atoms 8
Num. arom. heavy atoms 0
Fraction Csp3 0.75
Num. rotatable bonds 1
Num. H-bond acceptors 2.0
Num. H-bond donors 1.0
Molar Refractivity 32.41
TPSA ?

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

38.33 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

0.99
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

0.38
Log Po/w (WLOGP)?

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

-0.05
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.

0.03
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

1.03
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.

-0.85
Solubility 19.0 mg/ml ; 0.14 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.

-0.75
Solubility 24.1 mg/ml ; 0.178 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

-1.15
Solubility 9.6 mg/ml ; 0.0708 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.

-6.86 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

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)

2.41

Application In Synthesis of [ 169048-83-3 ]

* 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 [ 169048-83-3 ]

[ 169048-83-3 ] Synthesis Path-Downstream   1~21

  • 1
  • [ 113420-81-8 ]
  • [ 169048-83-3 ]
  • 3
  • [ 67-56-1 ]
  • [ 169048-83-3 ]
  • [ 205437-21-4 ]
  • 5-chloromethyl-3-methoxymethyl-2-oxazolidinone [ No CAS ]
  • 4
  • [ 67-56-1 ]
  • [ 169048-83-3 ]
  • (4S,5S)-5-Chloromethyl-4-methoxy-oxazolidin-2-one [ No CAS ]
  • (4R,5S)-5-Chloromethyl-4-methoxy-oxazolidin-2-one [ No CAS ]
  • 5
  • [ 67-56-1 ]
  • [ 169048-83-3 ]
  • (4S,5S)-5-Chloromethyl-4-methoxy-oxazolidin-2-one [ No CAS ]
  • (4R,5S)-5-Chloromethyl-4-methoxy-oxazolidin-2-one [ No CAS ]
  • 5-chloromethyl-3-methoxymethyl-2-oxazolidinone [ No CAS ]
  • 6
  • [ 67-56-1 ]
  • [ 169048-83-3 ]
  • 5-chloromethyl-3-methoxymethyl-2-oxazolidinone [ No CAS ]
  • 7
  • [ 75-89-8 ]
  • [ 169048-83-3 ]
  • 5-chloromethyl-4-(2',2',2'-trifluorethoxy)-2-oxazolidinone [ No CAS ]
  • 8
  • [ 175158-38-0 ]
  • [ 169048-83-3 ]
  • 9
  • [ 93-97-0 ]
  • [ 169048-83-3 ]
  • (S)-3-benzoyl-5-chloromethyl-oxazolidin-2-one [ No CAS ]
  • 10
  • [ 336628-55-8 ]
  • [ 169048-83-3 ]
  • 11
  • [ 590-28-3 ]
  • [ 67843-74-7 ]
  • [ 169048-83-3 ]
YieldReaction ConditionsOperation in experiment
60% With water; for 15.0h;Reflux; Potassium cyanate (4.38 g) was dissolved in 220 ml of water, and (S)-epichlorohydrin was slowly added (2.50 g). The solution was stirred overnight (15 h) at reflux. The reaction mixture was then extracted with ethyl acetate (while still moderately warm) (5 x 200 ml). The combined organic layers were dried over sodium sulfate and concentrated in vacuo to provide the title compound as a wax (which upon standing overnight in vacuo became an off-white solid) (2.18 g, 60%).
41% With magnesium sulfate; In water; at 100℃; for 5.0h; (S)-Epichlorohydrin [(S)-5, 390 muL, 4.99 mmol] and MgSO4 (1.2 g,10 mmol) were added to a solution of potassium cyanate(KOCN, 811 mg, 10 mmol) in H2O (5 mL). After stirring at100C for 5 h, the reaction mixture was diluted with H2O(5 mL) and then extracted with EtOAc (3×20 mL). The combinedextract was washed with brine (20 mL), dried, andconcentrated in vacuo to give a residue (304 mg). Chromatographyon a silica gel column with n-hexane-EtOAc (1 : 2) asthe eluent gave (S)-6 (275.7 mg, 41%) as a colorless powder.1H-NMR (300 MHz, CDCl3) delta: 6.37 (1H, br s, NH), 4.92-4.81(1H, m), 3.76 (1H, td, J=9.2, 0.7 Hz), 3.72-3.70 (2H, m), 3.54(1H, ddd, J=9.2, 5.9, 0.9 Hz).20) HR-EI-MS m/z 135.0087 [M]+(Calcd for C4H6ClNO2: 135.0087). [alpha]D25 +10.0 (c=1.0, CHCl3).
In water; for 19.0h;Reflux; To a solution of (2S)-2-(chloromethyl)oxirane (0.813 g, 8.79 mmol) in water (70 mL) was added potassium cyanate (1.43 g, 17.63 mmol) at room temperature and the resulting mixture was refluxed with stirring for 19 h. The reaction mixture was allowed to cool to room temperature and extracted with ethyl acetate (50 mL, three times). The organic layers were combined, dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated by evaporation to yield (5S)-5-(chloromethyl)-1,3-oxazolidin-2-one along with ethyl acetate as colorless oil (87% in ethyl acetate, 0.242 g, 18%,). 1H NMR (270 MHz, CDCl3) delta: 3.52-3.58 (1H, m), 3.63-3.80 (3H, m), 4.81-4.91 (1H, m), 5.56 (1H, br s). MS (ESI+) m/z: 136, 138 [M+H]+.
  • 12
  • 3-chloro-(2R)-2-[(phenyloxycarbonyl)-oxy]propyl azide [ No CAS ]
  • [ 169048-83-3 ]
  • 15
  • [ 169048-83-3 ]
  • [ 1029018-42-5 ]
  • 16
  • [ 67843-74-7 ]
  • [ 917-61-3 ]
  • [ 169048-83-3 ]
  • 17
  • [ 917-61-3 ]
  • [ 106-89-8 ]
  • [ 169048-83-3 ]
  • [ 169048-79-7 ]
  • 18
  • [ 40473-01-6 ]
  • [ 169048-83-3 ]
  • [ 1093752-54-5 ]
YieldReaction ConditionsOperation in experiment
61% With caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene;tris-(dibenzylideneacetone)dipalladium(0); In 1,4-dioxane; at 85℃; for 12.0h; A mixture of (5S)-5-(chloromethyl)-l,3-oxazolidin-2-one (2.15 g, INTERMEDIATE 4), 2- bromo-5-chloropyridine (3.05 g), cesium carbonate (20.67 g), bispalladium tribenzylideneacetone (2.18 g) and (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (2.07 g) in 16 ml of dioxane was stirred at 850C for 12 h. The sample was then cooled to room temperature, and purified was purified via column chromatography (2x) on a Biotage Horizon 65i column eluting with 0% ethyl acetate in hexanes (1 column volumes), followed by a gradient to 60% ethyl acetate in hexanes (over 10 column volumes), and held at 60% ethyl acetate for 4 column volumes to provide the title compound (2.44 g, 61%).
  • 19
  • [ 959762-95-9 ]
  • [ 169048-83-3 ]
  • [ 1547298-44-1 ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 70℃; for 2.5h; General procedure: To the solution of 4-amino-6-{7-chloro-3-oxatricyclo[7.3.1.05,13]trideca-1(13),5,7,9,11-pentaen-8-yl}-1,3,5-triazine-2-thiol (17, 399 mg, 1.21 mmol) and N-(2-chloroethyl)methanesulfonamide (381 mg, 2.41 mmol) in N,N-dimethylformamide (20 mL) was added N-ethyldiisopropylamine (631 muL, 3.14 mmol) at room temperature. The resulting mixture was stirred for 2.5 h at 70 C. After cooling to room temperature, the mixture was extracted between ethylacetate and water. The organic layer was washed with water and brine successively, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated by evaporation and the resulting residue was purified by preparative HPLC to give the title compound 62%, a light brown solid). H NMR (400 MHz, DMSO-d6) delta: 3.26 (1H, dd, J = 6.6, 8.8 Hz), 3.38 (1H, dd, J = 14.0, 6.0 Hz), 3.47 (1H, dd, J = 14.0, 6.0 Hz), 3.57 (1H, dd, J = 8.8, 8.8 Hz), 4.79-4. 87 (1H, m), 5.05 (2H, s), 5.06 (2H, s), 7.35 (1H, d, J = 7.1 Hz), 7.43 (1H, d, J = 8.8 Hz), 7.45 (1H, s), 7.53 (1H, dd, J = 8.8, 7.1 Hz), 7.57 (1H, s), 7.91 (2H, s). MS (ESI+) m/z: 430, 432 [M+H]+. HRMS (ESI+) m/z: [M+H]+ calcd for C19H1735ClN5O3S, 430.07351; found, 430.07277, [M+H]+ calcd for C19H1737ClN5O3S, 432.07056; found, 432.06954.
  • 20
  • [ 590-28-3 ]
  • [ 51594-55-9 ]
  • [ 169048-83-3 ]
YieldReaction ConditionsOperation in experiment
41% With magnesium sulfate; In water; at 100℃; for 5.0h; (R)-Epichlorohydrin [(R)-5, 390 muL, 4.99 mmol] and MgSO4(1.2 g, 10 mmol) were added to a solution of KOCN (811 mg,10 mmol) in H2O (5 mL). After stirring at 100C for 5 h, thereaction mixture was diluted with H2O (5 mL) and then extractedwith EtOAc (3×20 mL). The combined extract waswashed with brine (20 mL), dried, and concentrated in vacuo to give a residue (320 mg). Chromatography on a silica gelcolumn with n-hexane-EtOAc (1 : 2) as the eluent gave (R)-6(272.8 mg, 40%) as a colorless powder. 1H-NMR (300 MHz,CDCl3) delta: 6.37 (1H, br s, NH), 4.92-4.81 (1H, m), 3.76 (1H,td, J=9.2, 0.7 Hz), 3.72-3.70 (2H, m), 3.54 (1H, ddd, J=9.2,5.9, 0.9 Hz).20) HR-EI-MS m/z 135.0086 [M]+ (Calcd forC4H6ClNO2: 135.0087). [alpha]D25 -9.9 (c=1.0, CHCl3).
  • 21
  • [ 62372-09-2 ]
  • [ 169048-83-3 ]
  • methyl [2-(3,5-dibromo-4-[(5S)-2-oxo-1,3-oxazolidin-5-yl]methoxy}phenyl)ethyl]carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
48% With potassium carbonate; In N,N-dimethyl-formamide; at 140℃; for 0.75h; (S)-6(21.7 mg, 160 mumol) in N,N-dimethylformamide (DMF)(4.0 mL) was added to a solution of 4 (43.5 mg, 123 mumol).K2CO3 (204 mg, 1.48 mmol) was added, and the reactionmixture was stirred at 140C for 45 min. The mixture wasfiltered, and the filtrate was diluted with H2O (5 mL) and thenextracted with CHCl3 (3×30 mL). The combined extract waswashed with brine (20 mL), dried, and concentrated in vacuoto give a residue (60 mg). Chromatography on a silica gel columnwith n-hexane-EtOAc (1 : 2-1 : 1) as the eluent gave (S)-1(26.8 mg, 48%) as a colorless powder. 1H-NMR (400 MHz,CDCl3) delta: 7.35 (2H, s), 5.79 (1H, br), 5.02 (1H, ddt, J=8.7, 6.2,5.0 Hz), 4.82 (1H, br), 4.20 (2H, d, J=5.0 Hz), 3.91 (1H, dd,J=8.7, 6.2 Hz), 3.82 (1H, t, J=8.7 Hz), 3.67 (3H, s), 3.39 (2H, q,J=6.7 Hz), 2.74 (2H, t, J=6.7 Hz). HR-FAB-MS m/z 450.9498[M+H]+ (Calcd for C14H17Br2N2O5: 450.9504). [alpha]D25 +21.4(c=0.1, MeOH).
 

Historical Records

Technical Information

• Acyl Group Substitution • Alkyl Halide Occurrence • Baeyer-Villiger Oxidation • Barbier Coupling Reaction • Baylis-Hillman Reaction • Bucherer-Bergs Reaction • Chan-Lam Coupling Reaction • Clemmensen Reduction • Complex Metal Hydride Reductions • Corey-Bakshi-Shibata (CBS) Reduction • Corey-Chaykovsky Reaction • Fischer Indole Synthesis • General Reactivity • Grignard Reaction • Henry Nitroaldol Reaction • Hiyama Cross-Coupling Reaction • Horner-Wadsworth-Emmons Reaction • Hydride Reductions • Kinetics of Alkyl Halides • Kumada Cross-Coupling Reaction • Lawesson's Reagent • Leuckart-Wallach Reaction • McMurry Coupling • Meerwein-Ponndorf-Verley Reduction • Passerini Reaction • Paternò-Büchi Reaction • Petasis Reaction • Peterson Olefination • Pictet-Spengler Tetrahydroisoquinoline Synthesis • Preparation of Aldehydes and Ketones • Preparation of Amines • Prins Reaction • Reactions of Aldehydes and Ketones • Reactions of Alkyl Halides with Reducing Metals • Reactions of Amines • Reformatsky Reaction • Robinson Annulation • Schlosser Modification of the Wittig Reaction • Schmidt Reaction • Specialized Acylation Reagents-Carbodiimides and Related Reagents • Specialized Acylation Reagents-Ketenes • Stille Coupling • Stobbe Condensation • Substitution and Elimination Reactions of Alkyl Halides • Suzuki Coupling • Tebbe Olefination • Ugi Reaction • Wittig Reaction • Wolff-Kishner Reduction

Categories

Related Functional Groups of
[ 169048-83-3 ]

Chlorides

Chemical Structure| 71999-74-1

A164103 [71999-74-1]

N-Boc-2-chloroethylamine

Similarity: 0.73

Chemical Structure| 118753-70-1

A295462 [118753-70-1]

tert-Butyl bis(2-chloroethyl)carbamate

Similarity: 0.66

Chemical Structure| 154874-94-9

A181953 [154874-94-9]

tert-Butyl 4-chloropiperidine-1-carboxylate

Similarity: 0.66

Chemical Structure| 162536-40-5

A691852 [162536-40-5]

tert-Butyl ((2S,3R)-4-chloro-3-hydroxy-1-phenylbutan-2-yl)carbamate

Similarity: 0.64

Chemical Structure| 208167-83-3

A333376 [208167-83-3]

tert-Butyl 4-(2-chloroethyl)piperazine-1-carboxylate

Similarity: 0.63

Amides

Chemical Structure| 7517-99-9

A810218 [7517-99-9]

5-(Hydroxymethyl)oxazolidin-2-one

Similarity: 0.77

Chemical Structure| 95656-86-3

A385329 [95656-86-3]

tert-Butyl (2-hydroxypropyl)carbamate

Similarity: 0.77

Chemical Structure| 183059-24-7

A222680 [183059-24-7]

tert-Butyl 2-hydroxy-2-methylpropylcarbamate

Similarity: 0.75

Chemical Structure| 144912-84-5

A679901 [144912-84-5]

tert-Butyl (3-amino-2-hydroxypropyl)carbamate

Similarity: 0.75

Chemical Structure| 137618-48-5

A138890 [137618-48-5]

tert-Butyl (2,3-dihydroxypropyl)carbamate

Similarity: 0.73

Related Parent Nucleus of
[ 169048-83-3 ]

Oxazolidines

Chemical Structure| 7517-99-9

A810218 [7517-99-9]

5-(Hydroxymethyl)oxazolidin-2-one

Similarity: 0.77

Chemical Structure| 497-25-6

A342282 [497-25-6]

Oxazolidin-2-one

Similarity: 0.69

Chemical Structure| 4042-43-7

A125191 [4042-43-7]

(R)-4-Methyloxazolidin-2-one

Similarity: 0.67

Chemical Structure| 4042-35-7

A791172 [4042-35-7]

(S)-4-Methyloxazolidin-2-one

Similarity: 0.67

Chemical Structure| 695-53-4

A181810 [695-53-4]

5,5-Dimethyloxazolidine-2,4-dione

Similarity: 0.64