Home Cart 0 Sign in  
X

[ CAS No. 6931-16-4 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
3d Animation Molecule Structure of 6931-16-4
Chemical Structure| 6931-16-4
Chemical Structure| 6931-16-4
Structure of 6931-16-4 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Search after Editing

* Storage: {[proInfo.prStorage]}

* Shipping: {[proInfo.prShipping]}

Quality Control of [ 6931-16-4 ]

Related Doc. of [ 6931-16-4 ]

Alternatived Products of [ 6931-16-4 ]
Product Citations

Product Details of [ 6931-16-4 ]

CAS No. :6931-16-4 MDL No. :MFCD01070847
Formula : C10H9NO Boiling Point : -
Linear Structure Formula :- InChI Key :ZTQNUTNKGQGWCM-UHFFFAOYSA-N
M.W : 159.19 Pubchem ID :138869
Synonyms :

Calculated chemistry of [ 6931-16-4 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 10
Fraction Csp3 : 0.1
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 48.24
TPSA : 22.12 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) : -5.48 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.28
Log Po/w (XLOGP3) : 2.52
Log Po/w (WLOGP) : 2.24
Log Po/w (MLOGP) : 1.9
Log Po/w (SILICOS-IT) : 2.46
Consensus Log Po/w : 2.28

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.97
Solubility : 0.172 mg/ml ; 0.00108 mol/l
Class : Soluble
Log S (Ali) : -2.63
Solubility : 0.373 mg/ml ; 0.00234 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.82
Solubility : 0.0243 mg/ml ; 0.000153 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.49

Safety of [ 6931-16-4 ]

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 [ 6931-16-4 ]

* 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 [ 6931-16-4 ]
  • Downstream synthetic route of [ 6931-16-4 ]

[ 6931-16-4 ] Synthesis Path-Upstream   1~22

  • 1
  • [ 612-62-4 ]
  • [ 124-41-4 ]
  • [ 6931-16-4 ]
Reference: [1] Tetrahedron, 2002, vol. 58, # 6, p. 1125 - 1129
[2] Journal of Organic Chemistry, 2007, vol. 72, # 4, p. 1341 - 1346
[3] European Journal of Medicinal Chemistry, 2010, vol. 45, # 4, p. 1657 - 1662
[4] Chemische Berichte, 1882, vol. 15, p. 335
[5] Journal of the American Chemical Society, 1983, vol. 105, p. 1204
[6] Australian Journal of Chemistry, 2003, vol. 56, # 9, p. 913 - 916
  • 2
  • [ 67-56-1 ]
  • [ 213334-93-1 ]
  • [ 6931-16-4 ]
Reference: [1] Organic Letters, 1999, vol. 1, # 12, p. 1977 - 1979
  • 3
  • [ 67-56-1 ]
  • [ 2005-43-8 ]
  • [ 6931-16-4 ]
Reference: [1] Chemistry - A European Journal, 2012, vol. 18, # 9, p. 2498 - 2502
  • 4
  • [ 4295-05-0 ]
  • [ 6931-16-4 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 1980, vol. 28, # 2, p. 493 - 499
  • 5
  • [ 615-43-0 ]
  • [ 6931-16-4 ]
Reference: [1] Organic Letters, 1999, vol. 1, # 12, p. 1977 - 1979
  • 6
  • [ 74857-00-4 ]
  • [ 6931-16-4 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 1980, vol. 28, # 2, p. 493 - 499
[2] Chemical and Pharmaceutical Bulletin, 1980, vol. 28, # 2, p. 493 - 499
  • 7
  • [ 103529-16-4 ]
  • [ 6931-16-4 ]
Reference: [1] Organic Letters, 1999, vol. 1, # 12, p. 1977 - 1979
  • 8
  • [ 112671-40-6 ]
  • [ 6931-16-4 ]
Reference: [1] Organic Letters, 1999, vol. 1, # 12, p. 1977 - 1979
  • 9
  • [ 612-62-4 ]
  • [ 3315-60-4 ]
  • [ 91-22-5 ]
  • [ 6931-16-4 ]
  • [ 50-00-0 ]
Reference: [1] Journal of the American Chemical Society, 1982, vol. 104, # 7, p. 1979 - 1986
[2] Journal of the American Chemical Society, 1982, vol. 104, # 7, p. 1979 - 1986
  • 10
  • [ 2005-43-8 ]
  • [ 865-33-8 ]
  • [ 6931-16-4 ]
  • [ 15793-81-4 ]
Reference: [1] Journal of the American Chemical Society, 2018, vol. 140, # 35, p. 10970 - 10974
  • 11
  • [ 59-31-4 ]
  • [ 74-88-4 ]
  • [ 6931-16-4 ]
  • [ 606-43-9 ]
Reference: [1] Heterocycles, 1993, vol. 36, # 2, p. 315 - 322
  • 12
  • [ 73087-48-6 ]
  • [ 6931-16-4 ]
Reference: [1] Zeitschrift fuer Naturforschung, B: Chemical Sciences, 1987, vol. 42, # 2, p. 217 - 220
  • 13
  • [ 91-22-5 ]
  • [ 67-56-1 ]
  • [ 78948-09-1 ]
  • [ 6931-16-4 ]
  • [ 30074-79-4 ]
Reference: [1] Journal of Organic Chemistry, 1991, vol. 56, # 22, p. 6298 - 6301
  • 14
  • [ 111888-31-4 ]
  • [ 6931-16-4 ]
Reference: [1] Zeitschrift fuer Naturforschung, B: Chemical Sciences, 1987, vol. 42, # 2, p. 217 - 220
[2] Zeitschrift fuer Naturforschung, B: Chemical Sciences, 1987, vol. 42, # 2, p. 217 - 220
[3] Chemische Berichte, 1988, vol. 121, p. 2147 - 2150
  • 15
  • [ 67-56-1 ]
  • [ 1613-37-2 ]
  • [ 6931-16-4 ]
Reference: [1] Heterocycles, 1990, vol. 31, # 7, p. 1325 - 1331
[2] Heterocycles, 1990, vol. 31, # 7, p. 1325 - 1331
  • 16
  • [ 186581-53-3 ]
  • [ 59-31-4 ]
  • [ 6931-16-4 ]
Reference: [1] Monatshefte fuer Chemie, 1905, vol. 26, p. 1314
  • 17
  • [ 59-31-4 ]
  • [ 6931-16-4 ]
Reference: [1] Chemische Berichte, 1882, vol. 15, p. 335
  • 18
  • [ 59-31-4 ]
  • [ 77-78-1 ]
  • [ 6931-16-4 ]
Reference: [1] Monatshefte fuer Chemie, 1905, vol. 26, p. 1314
  • 19
  • [ 67-56-1 ]
  • [ 612-62-4 ]
  • [ 124-41-4 ]
  • [ 6931-16-4 ]
Reference: [1] Chemische Berichte, 1882, vol. 15, p. 335
  • 20
  • [ 6931-16-4 ]
  • [ 1810-66-8 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1993, # 2, p. 181 - 184
  • 21
  • [ 6931-16-4 ]
  • [ 5419-55-6 ]
  • [ 886853-93-6 ]
YieldReaction ConditionsOperation in experiment
95%
Stage #1: With lithium diisopropyl amide In tetrahydrofuran at -78 - 20℃;
Stage #2: With water; ammonium chloride In tetrahydrofuran
Stage #3: With hydrogenchloride In tetrahydrofuran; water
[00235] To a solution of to 2-methoxyquinoline (10.0 g, 62.8 mmol) and triisiopropylborate (17.86 g, 95.1 mmol) in THF (140 mL) at -78 0C was added LDA solution (75.4 mmol, prepared from Pr'2NH and n-BuLi). The mixture was stirred at -78 0C for over 4 hours and slowly warmed to rt overnight. The mixture was quenched with saturated NH4Cl (68 mL) and acidified to a pH=5 with 3M HCl. The organic solvent THF and hexanes were evaporated under vacuum and EPO <DP n="133"/>boronic acid was precipitated as a white solid. The mixture was filtered through a Buchner funnel and the solid was washed thoroughly with H2O to afford the product after dried under high vacuum (12.11 g, 95 percent). 1H NMR (400 MHz, CDCl3) δ 8.64 (IH, s), 7.85 (IH, d, J= 8.3 Hz), 7.80 (IH, dJ= 7.9 Hz), 7.68 (IH, dd, 7=14.1, 1.1 Hz), 7.41 (IH, J= 7.5 Hz), 5.91 (2H, s, br), 4.18 (3H, s). 13C NMR (400 MHz, CDCl3) δ 164.9, 149.8, 148.I5 131.1, 128.6, 127.4, 125.5, 124.7, 53.9. HRMS (EI) calc'd for C10H10BNO3 ([M]+) 203.0754. Found: 203.0758.
77% With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; for 9 h; 2-methoxy-quinoline (20.0g, 126mmol), triisopropoxy borane(59.1g, 314mmol,Mixture of tetrahydrofuran (dehydrated) (200mL) and cooled to -78 .There was added n- butyllithium (in hexanes 1.6M, 86mL, 138mmol), stirred for 4 hours at -78 ,The temperature was raised to room temperature over 5 hours.After the reaction, the addition of saturated NH4Cl solution (100mL), and was added until the pH of HCl (3M) solution be 5. Then, the suspended solids obtained by concentration of the organic layer was washed with water, and filtered to give the number of 2-methoxy-3-boronic acid (19.7g, 97.0mmol) (yield 77percent).
Reference: [1] Patent: WO2006/47888, 2006, A1, . Location in patent: Page/Page column 73; 131-132
[2] Patent: KR2016/18458, 2016, A, . Location in patent: Paragraph 0309; 0312; 0313
[3] European Journal of Medicinal Chemistry, 2010, vol. 45, # 4, p. 1657 - 1662
  • 22
  • [ 6931-16-4 ]
  • [ 886853-93-6 ]
Reference: [1] Journal of Organic Chemistry, 2007, vol. 72, # 4, p. 1341 - 1346
Recommend Products
Same Skeleton Products
Historical Records

Related Functional Groups of
[ 6931-16-4 ]

Ethers

Chemical Structure| 40335-00-0

[ 40335-00-0 ]

2,4-Dimethoxyquinoline

Similarity: 0.83

Chemical Structure| 14300-45-9

[ 14300-45-9 ]

2,4-Dihydroxy-6-methoxyquinoline

Similarity: 0.81

Chemical Structure| 1260663-96-4

[ 1260663-96-4 ]

2-Methoxy-5-methylpyridin-4-amine

Similarity: 0.79

Chemical Structure| 87199-83-5

[ 87199-83-5 ]

7-Methoxyquinolin-3-amine

Similarity: 0.78

Chemical Structure| 4964-76-5

[ 4964-76-5 ]

7-Methoxyquinoline

Similarity: 0.78

Related Parent Nucleus of
[ 6931-16-4 ]

Quinolines

Chemical Structure| N/A

[ N/A ]

2,7-Dihydroxyquinoline

Similarity: 0.88

Chemical Structure| 84909-43-3

[ 84909-43-3 ]

4-Methylquinolin-2-ol

Similarity: 0.87

Chemical Structure| 40335-00-0

[ 40335-00-0 ]

2,4-Dimethoxyquinoline

Similarity: 0.83

Chemical Structure| 14300-45-9

[ 14300-45-9 ]

2,4-Dihydroxy-6-methoxyquinoline

Similarity: 0.81

Chemical Structure| 70254-42-1

[ 70254-42-1 ]

Quinolin-2-ol

Similarity: 0.79