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[ CAS No. 59718-84-2 ] {[proInfo.proName]}

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Chemical Structure| 59718-84-2
Chemical Structure| 59718-84-2
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Product Details of [ 59718-84-2 ]

CAS No. :59718-84-2 MDL No. :MFCD03789583
Formula : C8H9NO2 Boiling Point : -
Linear Structure Formula :- InChI Key :CCQFKEITVOTHIW-UHFFFAOYSA-N
M.W : 151.16 Pubchem ID :12264487
Synonyms :

Calculated chemistry of [ 59718-84-2 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.25
Num. rotatable bonds : 2
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 40.48
TPSA : 39.19 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.23 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.83
Log Po/w (XLOGP3) : 1.4
Log Po/w (WLOGP) : 1.18
Log Po/w (MLOGP) : 0.66
Log Po/w (SILICOS-IT) : 1.64
Consensus Log Po/w : 1.34

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.93
Solubility : 1.77 mg/ml ; 0.0117 mol/l
Class : Very soluble
Log S (Ali) : -1.83
Solubility : 2.25 mg/ml ; 0.0149 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.47
Solubility : 0.512 mg/ml ; 0.00339 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.53

Safety of [ 59718-84-2 ]

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 [ 59718-84-2 ]

* 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 [ 59718-84-2 ]
  • Downstream synthetic route of [ 59718-84-2 ]

[ 59718-84-2 ] Synthesis Path-Upstream   1~16

  • 1
  • [ 583-61-9 ]
  • [ 67-56-1 ]
  • [ 55589-47-4 ]
  • [ 59718-84-2 ]
Reference: [1] Organic Preparations and Procedures International, 1999, vol. 31, # 1, p. 120 - 123
  • 2
  • [ 3430-17-9 ]
  • [ 67-56-1 ]
  • [ 201230-82-2 ]
  • [ 59718-84-2 ]
YieldReaction ConditionsOperation in experiment
93.6% at 80℃; for 16 h; A mixture of 2-bromo-3-methylpyridine (5.0 g, 29.0 mmol), Pd(dppf)C12 (2.1 g, 2.9 mmol), and triethylamine (8.8 g, 87 mmol) in methanol (250 mL) was stirred at 80 °C under CO atmosphere (50 psi) for 16 h. The mixture was filtered and the filtrate concentrated in vacuo, then purified by column chromatography on Si02 to give the desired product (4.1 g, 93.6percent). LCMS (mlz): 152.0 (M+1).
Reference: [1] Patent: WO2015/200677, 2015, A2, . Location in patent: Paragraph 00470; 00471
  • 3
  • [ 67-56-1 ]
  • [ 4021-07-2 ]
  • [ 59718-84-2 ]
YieldReaction ConditionsOperation in experiment
85% Reflux General procedure: To a solution of carboxylic acid 22 or 29–31 (0.1mol) in dry methanol (150mL), concd H2SO4 (20mL) was added. The mixture was refluxed for 15–20h (LC–MS control). The solvent was removed in vacuo, and the residue was dissolved in H2O. The solution was made alkaline with cold saturated aq K2CO3 and extracted with CH2Cl2 (4×50mL). The combined organic extracts were dried over Na2SO4 and evaporated in vacuo. The residue was purified by flash chromatography (EtOAc as eluent) or distilled in vacuo to give 17–20.
Reference: [1] Tetrahedron, 2013, vol. 69, # 33, p. 6799 - 6803
  • 4
  • [ 124-38-9 ]
  • [ 13737-07-0 ]
  • [ 74-88-4 ]
  • [ 59718-84-2 ]
Reference: [1] Patent: US2017/240485, 2017, A1, . Location in patent: Paragraph 0129
[2] Chemistry - A European Journal, 2016, vol. 22, # 9, p. 2930 - 2934
  • 5
  • [ 594-27-4 ]
  • [ 157865-84-4 ]
  • [ 59718-84-2 ]
Reference: [1] Tetrahedron Letters, 1996, vol. 37, # 4, p. 459 - 462
  • 6
  • [ 1071068-55-7 ]
  • [ 59718-84-2 ]
Reference: [1] Organic Syntheses, 2003, vol. 80, p. 133 - 143
  • 7
  • [ 67-56-1 ]
  • [ 1071068-55-7 ]
  • [ 59718-84-2 ]
Reference: [1] Journal of Organic Chemistry, 1998, vol. 63, # 22, p. 7840 - 7850
  • 8
  • [ 874-24-8 ]
  • [ 59718-84-2 ]
Reference: [1] Tetrahedron Letters, 1996, vol. 37, # 4, p. 459 - 462
  • 9
  • [ 62733-99-7 ]
  • [ 59718-84-2 ]
Reference: [1] Tetrahedron Letters, 1996, vol. 37, # 4, p. 459 - 462
  • 10
  • [ 3430-17-9 ]
  • [ 59718-84-2 ]
Reference: [1] Chemistry - A European Journal, 2016, vol. 22, # 9, p. 2930 - 2934
  • 11
  • [ 20970-75-6 ]
  • [ 59718-84-2 ]
Reference: [1] Tetrahedron, 2013, vol. 69, # 33, p. 6799 - 6803
  • 12
  • [ 583-61-9 ]
  • [ 67-56-1 ]
  • [ 55589-47-4 ]
  • [ 59718-84-2 ]
Reference: [1] Organic Preparations and Procedures International, 1999, vol. 31, # 1, p. 120 - 123
  • 13
  • [ 59718-84-2 ]
  • [ 116986-09-5 ]
YieldReaction ConditionsOperation in experiment
80.6% With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In tetrachloromethane at 90℃; for 16 h; Inert atmosphere A mixture of methyl 3-methylpicolinate (4.1 g, 27.1 mmol), NBS (5.8 g, 32.5 mmol), and AIBN (100 mg, 0.61 mmol) in carbon tetrachloride (55 mL) was stuffed at 90 °C for 16 h under nitrogen. The mixture was filtered and concentrated before being purified by column chromatography to give the desired product (5.0 g, 80.6percent). ‘H NMR (400 MHz, CDC13, ): 8.67 (dd, J= 1.6, 4.6 Hz, 1 H), 7.91 (dd, J= 1.5, 7.9 Hz, 1 H), 7.48 (dd, J= 4.6, 7.9 Hz, 1 H), 4.95 (s, 2 H), 4.07 — 4.03 (m, 3 H). LCMS (mlz): 229.9 (M+1).
Reference: [1] Patent: WO2015/200677, 2015, A2, . Location in patent: Paragraph 00472; 00473
[2] Journal fuer Praktische Chemie (Leipzig), 1987, vol. 329, # 4, p. 557 - 562
[3] Organic Letters, 2017, vol. 19, # 14, p. 3895 - 3898
  • 14
  • [ 59718-84-2 ]
  • [ 878207-92-2 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 6, p. 1736 - 1739
[2] Patent: WO2014/209727, 2014, A1,
[3] Patent: WO2014/205593, 2014, A1,
[4] Patent: US2015/57260, 2015, A1,
[5] Patent: WO2015/25026, 2015, A1,
[6] Patent: WO2015/94912, 2015, A1,
  • 15
  • [ 59718-84-2 ]
  • [ 1201924-32-4 ]
Reference: [1] Patent: WO2015/94912, 2015, A1,
  • 16
  • [ 59718-84-2 ]
  • [ 1029720-23-7 ]
YieldReaction ConditionsOperation in experiment
83% With N-Bromosuccinimide In tetrachloromethane for 16 h; Reflux To a solution of ester 17–20 (13.7g, 0.100mol) in dry CCl4 (400mL), N-bromosuccinimide (35.6g, 0.200mol) was added. The mixture was slowly heated to reflux, then refluxed for 16h (monitored by LC–MS), and then cooled to rt. The succinimide was filtered off, and the filtrate was concentrated under reduced pressure to give gem-dibromomethyl compound 25–28. Analytical samples were prepared by chromatography (hexanes–EtOAc (1:9)).
Reference: [1] Tetrahedron, 2013, vol. 69, # 33, p. 6799 - 6803
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