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[ CAS No. 17016-83-0 ] {[proInfo.proName]}

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Chemical Structure| 17016-83-0
Chemical Structure| 17016-83-0
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Product Details of [ 17016-83-0 ]

CAS No. :17016-83-0 MDL No. :MFCD00010847
Formula : C6H11NO2 Boiling Point : -
Linear Structure Formula :- InChI Key :YBUPWRYTXGAWJX-RXMQYKEDSA-N
M.W : 129.16 Pubchem ID :7157133
Synonyms :
(S)-4-Isopropyl-2-oxazolidinone

Calculated chemistry of [ 17016-83-0 ]

Physicochemical Properties

Num. heavy atoms : 9
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.83
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 37.23
TPSA : 38.33 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.29 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.51
Log Po/w (XLOGP3) : 1.12
Log Po/w (WLOGP) : 0.37
Log Po/w (MLOGP) : 0.41
Log Po/w (SILICOS-IT) : 0.83
Consensus Log Po/w : 0.85

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -1.28
Solubility : 6.77 mg/ml ; 0.0524 mol/l
Class : Very soluble
Log S (Ali) : -1.52
Solubility : 3.92 mg/ml ; 0.0303 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -0.94
Solubility : 14.7 mg/ml ; 0.114 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.22

Safety of [ 17016-83-0 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 17016-83-0 ]

* 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.

  • Upstream synthesis route of [ 17016-83-0 ]
  • Downstream synthetic route of [ 17016-83-0 ]

[ 17016-83-0 ] Synthesis Path-Upstream   1~6

  • 1
  • [ 17016-83-0 ]
  • [ 16369-05-4 ]
Reference: [1] Tetrahedron Letters, 2002, vol. 43, # 4, p. 557 - 559
  • 2
  • [ 17016-83-0 ]
  • [ 123-62-6 ]
  • [ 77877-19-1 ]
YieldReaction ConditionsOperation in experiment
99%
Stage #1: With triethylamine; lithium chloride In tetrahydrofuran at 0℃; for 0.5 h;
Stage #2: at 0 - 20℃; for 1.5 - 2 h;
Example 2: Preparation of (S)-4-isopropyl-3-propionyloxazolidin-2-one (3) <n="15"/>The compound (2) prepared in Example 1 (10Og) was dissolved in tetrahydrofuran (300mNo.), and cooled to 0°C . Lithium chloride (36g) was added, triethylamine (10Ig) was then slowly added, and the resulting mixture was stirred for 30 min. Propionic acid anhydride (106g) was slowly added over a 30 min. time period. The reaction mixture was slowly warmed to room temperature, and stirred for 1-1.5 h. The reaction solution was cooled, IN aqueous sodium chloride solution (300mNo.) was added, and the mixture was stirred for 30 min. Ethyl acetate (300mf) was added, the phases were separated, and extracted once again by ethyl acetate (300m.pound.). After washing with 1.5 N hydrochloric acid (300m.pound.), the organic phase was washed once again with aqueous sodium chloride solution (300mNo.), dried, filtered and distilled to produce the title compound (142g, Yieldpercent). 1H NMR (300MHz, CDCl3) δ 4.4 (m, IH), 4.3-4.2 (m, 2H), 2.97 (m, 2H), 2.3 (m,IH), 1.2 (t, 3H), 0.93 (dd, 6H)
Reference: [1] Patent: WO2008/127070, 2008, A1, . Location in patent: Page/Page column 13-14
[2] Organic Letters, 2013, vol. 15, # 3, p. 472 - 475
  • 3
  • [ 79-03-8 ]
  • [ 17016-83-0 ]
  • [ 77877-19-1 ]
Reference: [1] Synthesis, 1998, # SPEC. ISS. APR., p. 603 - 612
[2] Bioorganic and Medicinal Chemistry, 2011, vol. 19, # 12, p. 3831 - 3844
[3] Journal of Organic Chemistry, 2017, vol. 82, # 1, p. 353 - 371
[4] Chemische Berichte, 1996, vol. 129, # 11, p. 1361 - 1368
[5] Organic Syntheses, 2008, vol. 85, p. 158 - 171
[6] Organic Letters, 2010, vol. 12, # 22, p. 5258 - 5261
[7] Tetrahedron Asymmetry, 2002, vol. 13, # 7, p. 675 - 680
[8] Tetrahedron, 2008, vol. 64, # 24, p. 5637 - 5644
[9] Journal of Fluorine Chemistry, 2007, vol. 128, # 10, p. 1271 - 1279
[10] Journal of the American Chemical Society, 1990, vol. 112, # 13, p. 5290 - 5313
[11] Journal of Organic Chemistry, 1991, vol. 56, # 7, p. 2489 - 2498
[12] Journal of the American Chemical Society, 1981, vol. 103, # 8, p. 2127 - 2129
[13] Tetrahedron Letters, 1995, vol. 36, # 45, p. 8315 - 8318
[14] Journal of the Chemical Society, Perkin Transactions 1, 2000, # 20, p. 3406 - 3416
[15] Angewandte Chemie - International Edition, 2016, vol. 55, # 42, p. 13240 - 13243[16] Angew. Chem., 2016, vol. 128, # 42, p. 13434 - 13437,4
[17] Organic and Biomolecular Chemistry, 2018, vol. 16, # 26, p. 4807 - 4815
  • 4
  • [ 4122-52-5 ]
  • [ 17016-83-0 ]
  • [ 77877-19-1 ]
Reference: [1] Angewandte Chemie - International Edition, 2012, vol. 51, # 33, p. 8304 - 8308
  • 5
  • [ 17016-83-0 ]
  • [ 851913-12-7 ]
  • [ 17016-83-0 ]
  • [ 136436-80-1 ]
  • [ 95530-58-8 ]
Reference: [1] Tetrahedron Asymmetry, 2008, vol. 19, # 9, p. 1068 - 1077
  • 6
  • [ 17016-83-0 ]
  • [ 95530-58-8 ]
Reference: [1] Chemistry Letters, 1992, # 6, p. 991 - 994
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