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[ CAS No. 122334-36-5 ] {[proInfo.proName]}

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Chemical Structure| 122334-36-5
Chemical Structure| 122334-36-5
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Product Details of [ 122334-36-5 ]

CAS No. :122334-36-5 MDL No. :MFCD02684311
Formula : C10H13NO2 Boiling Point : -
Linear Structure Formula :- InChI Key :JFLVXYRFUSRSCR-UHFFFAOYSA-N
M.W : 179.22 Pubchem ID :5133773
Synonyms :

Calculated chemistry of [ 122334-36-5 ]

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.3
Num. rotatable bonds : 3
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 50.39
TPSA : 29.54 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.14 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.31
Log Po/w (XLOGP3) : 1.77
Log Po/w (WLOGP) : 1.63
Log Po/w (MLOGP) : 2.08
Log Po/w (SILICOS-IT) : 1.29
Consensus Log Po/w : 1.82

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.21
Solubility : 1.11 mg/ml ; 0.00617 mol/l
Class : Soluble
Log S (Ali) : -2.01
Solubility : 1.76 mg/ml ; 0.00981 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.58
Solubility : 0.468 mg/ml ; 0.00261 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.51

Safety of [ 122334-36-5 ]

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

Application In Synthesis of [ 122334-36-5 ]

* 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 [ 122334-36-5 ]
  • Downstream synthetic route of [ 122334-36-5 ]

[ 122334-36-5 ] Synthesis Path-Upstream   1~15

  • 1
  • [ 693-25-4 ]
  • [ 122334-36-5 ]
  • [ 1669-33-6 ]
Reference: [1] Synthetic Communications, 1999, vol. 29, # 8, p. 1249 - 1255
  • 2
  • [ 99-94-5 ]
  • [ 1117-97-1 ]
  • [ 122334-36-5 ]
YieldReaction ConditionsOperation in experiment
98%
Stage #1: at 0℃; for 0.166667 h;
Stage #2: With phosphorus trichloride In toluene at 20 - 60℃; for 0.5 h;
General procedure: A solution of NHMe(OMe) (0.360 g, 6.0 mmol) and benzoic acid (0.244 g, 2.0 mmol) was stirred in dry toluene (10 mL) at 0 °C for 10 min. A solution of PCl3 (0.137 g, 1.0 mmol) in dry toluene (2 mL) was then added dropwise to the mixture. The mixture was warmed to r.t. slowly and then stirred at 60 °C for 0.5 h. When the reaction was complete (TLC monitoring), the mixture was cooled to r.t. The mixture was then quenched with sat. NaHCO3 soln (20 mL) and extracted with EtOAc (3 × 10 mL). The combined organic layers were dried (anhyd MgSO4). The solvent was removed in vacuo.The product was purified by column chromatography (silica gel, petroleum ether–EtOAc, 3:2) to give pure 3a as a colorless oil; yield: 320 mg (97percent).
Reference: [1] Synthesis (Germany), 2014, vol. 46, # 3, p. 320 - 330
[2] Organic Letters, 2000, vol. 2, # 25, p. 4091 - 4093
[3] Chimia, 1995, vol. 49, # 10, p. 381 - 385
  • 3
  • [ 589-18-4 ]
  • [ 6638-79-5 ]
  • [ 122334-36-5 ]
YieldReaction ConditionsOperation in experiment
87% With tert.-butylhydroperoxide; copper(II) acetate monohydrate; calcium carbonate In acetonitrile at 80℃; for 24 h; General procedure: An oven-dried 15 mL glass vial with a magnetic stirrer bar was charged with Cu(OAc)2·H2O (12 mg, 6 molpercent), N,O-dimethylhydroxylamine hydrochloride (2; 117 mg, 1.2 mmol), the respective benzyl alcohol 1 (1 mmol), aq 70percent TBHP (0.17 mL, 1.2 mmol), CaCO3 (120 mg, 1.2 mmol) in MeCN (1 mL). The glass vial was flushed with N2 three times and the contents were stirred at r.t. for 1 h. Then the reaction mixture was stirred for 24 h at 80 °C. After completion of the reaction, the mixture was cooled to r.t. All volatiles were removed under vacuum. The product was extracted with EtOAc (20 mL) and the organic layer was washed with sat. aq NaHCO3 (20 mL), dried (Na2SO4), and the solvent removed under vacuum. The Weinreb amide product 3 was purified by column chromatography (silica gel, 100–200 mesh) using a gradient of petroleum ether (bp 60–80 °C) and EtOAc. All the amides were identified by GC-MS, 1H, and 13C NMR spectroscopic analysis.
Reference: [1] Synthesis (Germany), 2015, vol. 47, # 4, p. 526 - 532
  • 4
  • [ 6638-79-5 ]
  • [ 874-60-2 ]
  • [ 122334-36-5 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 4, p. 1415 - 1419
[2] Synlett, 2007, # 18, p. 2841 - 2846
[3] Patent: EP1400518, 2004, A1, . Location in patent: Page 29
[4] Patent: WO2016/192083, 2016, A1, . Location in patent: Page/Page column 55
[5] European Journal of Organic Chemistry, 2018, vol. 2018, # 12, p. 1416 - 1425
[6] Journal of Organic Chemistry, 2017, vol. 82, # 2, p. 1114 - 1126
  • 5
  • [ 201230-82-2 ]
  • [ 624-31-7 ]
  • [ 6638-79-5 ]
  • [ 122334-36-5 ]
Reference: [1] RSC Advances, 2014, vol. 4, # 57, p. 30019 - 30027
[2] Chemistry - A European Journal, 2014, vol. 20, # 20, p. 5885 - 5889
  • 6
  • [ 201230-82-2 ]
  • [ 106-38-7 ]
  • [ 6638-79-5 ]
  • [ 122334-36-5 ]
Reference: [1] RSC Advances, 2014, vol. 4, # 57, p. 30019 - 30027
  • 7
  • [ 6638-79-5 ]
  • [ 99-94-5 ]
  • [ 122334-36-5 ]
Reference: [1] Synthetic Communications, 2003, vol. 33, # 23, p. 4013 - 4018
  • 8
  • [ 1062512-43-9 ]
  • [ 99-94-5 ]
  • [ 122334-36-5 ]
Reference: [1] Organic Letters, 2009, vol. 11, # 19, p. 4474 - 4477
  • 9
  • [ 31614-66-1 ]
  • [ 30289-28-2 ]
  • [ 122334-36-5 ]
Reference: [1] Chemistry Letters, 1998, # 2, p. 163 - 164
  • 10
  • [ 6638-79-5 ]
  • [ 93131-73-8 ]
  • [ 13939-06-5 ]
  • [ 122334-36-5 ]
Reference: [1] Australian Journal of Chemistry, 2017, vol. 70, # 1, p. 44 - 51
  • 11
  • [ 99-94-5 ]
  • [ 122334-36-5 ]
Reference: [1] Synlett, 2007, # 18, p. 2841 - 2846
[2] Patent: WO2016/192083, 2016, A1,
[3] Journal of Organic Chemistry, 2017, vol. 82, # 2, p. 1114 - 1126
  • 12
  • [ 10347-11-2 ]
  • [ 6638-79-5 ]
  • [ 122334-36-5 ]
Reference: [1] Journal of the American Chemical Society, 2009, vol. 131, # 43, p. 15608 - 15609
  • 13
  • [ 874-60-2 ]
  • [ 1117-97-1 ]
  • [ 122334-36-5 ]
Reference: [1] Tetrahedron Letters, 1998, vol. 39, # 12, p. 1509 - 1512
  • 14
  • [ 4294-57-9 ]
  • [ 223570-55-6 ]
  • [ 122334-36-5 ]
Reference: [1] Synthetic Communications, 1999, vol. 29, # 8, p. 1249 - 1255
  • 15
  • [ 1613-85-0 ]
  • [ 6214-19-3 ]
  • [ 122334-36-5 ]
Reference: [1] Canadian Journal of Chemistry, 1991, vol. 69, # 5, p. 798 - 810
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