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[ CAS No. 109073-77-0 ] {[proInfo.proName]}

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Product Details of [ 109073-77-0 ]

CAS No. :109073-77-0 MDL No. :MFCD06202808
Formula : C12H12N2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :RRXGRDMHWYLJSY-UHFFFAOYSA-N
M.W : 216.24 Pubchem ID :11160239
Synonyms :

Calculated chemistry of [ 109073-77-0 ]

Physicochemical Properties

Num. heavy atoms : 16
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.17
Num. rotatable bonds : 3
Num. H-bond acceptors : 4.0
Num. H-bond donors : 2.0
Molar Refractivity : 59.72
TPSA : 66.24 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -7.82 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.06
Log Po/w (XLOGP3) : -0.29
Log Po/w (WLOGP) : 0.82
Log Po/w (MLOGP) : -0.25
Log Po/w (SILICOS-IT) : 2.15
Consensus Log Po/w : 0.9

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.35
Solubility : 9.55 mg/ml ; 0.0442 mol/l
Class : Very soluble
Log S (Ali) : -0.64
Solubility : 49.4 mg/ml ; 0.228 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -3.84
Solubility : 0.0315 mg/ml ; 0.000146 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.24

Safety of [ 109073-77-0 ]

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

Application In Synthesis of [ 109073-77-0 ]

* 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 [ 109073-77-0 ]
  • Downstream synthetic route of [ 109073-77-0 ]

[ 109073-77-0 ] Synthesis Path-Upstream   1~12

  • 1
  • [ 109073-77-0 ]
  • [ 99970-84-0 ]
Reference: [1] Journal of Heterocyclic Chemistry, 1990, vol. 27, # 2, p. 163 - 165
[2] Journal of the Chemical Society, Chemical Communications, 1992, # 8, p. 602 - 604
[3] Tetrahedron Letters, 1990, vol. 31, # 35, p. 5069 - 5072
  • 2
  • [ 1762-42-1 ]
  • [ 109073-77-0 ]
YieldReaction ConditionsOperation in experiment
91% With sodium tetrahydroborate In ethanol for 3 h; Reflux Sodium borohydride (1.87g, 49mmol) was added to a suspension of diethyl [2,2'-bipyridine]-4,4'-dicarboxylate 7 (567mg, 1.89mmol) dissolved in absolute ethanol (34mL). The solution was refluxed for 3h. After cooling to room temperature, a saturated ammonium chloride solution (24mL/g of NH4Cl) was added to decompose the excess of sodium borohydride. Ethanol was evaporated under vacuum and the resulting solid was dissolved in a minimum of water using ultrasonic bath. The solution was extracted with ethyl acetate (5×34mL), dried on sodium sulfate and concentrated under vacuum to give a white powder. Yield: 91percent,
89% With sodium tetrahydroborate In ethanol for 3 h; Reflux to a suspension of the diester 4 ( 10.0 g, 33.3 mmol) in 300 ml of absolute ethanol was added sodium borohydride (25.19 g, 665.9 mmol) in one portion. The mixture was refluxed for 3 h and cooled to RT, and excess borohydride was decomposed by the dropwise addition saturated ammonium chloride solution (300 ml). Ethanol was removed under vacuum and the precipitated solid was filtered and the solid was dissolved in ethyl acetate (400 ml), washed with water ( 100 ml), dried over anhy. Na2S04and the solvent was removed under vacuum to yield the diol [2,2'-bipyridine]-4,4'-diyldimethanol 5 as awhite powder (5.9 g, 82percent).
88% With sodium tetrahydroborate In ethanol at 90℃; for 3 h; Ligand 2(1.02 g, 3.40 mmol) was suspended in 200 proof ethanol (67 mL).Sodium borohydride (2.80 g, 74.0 mmol) was added and the suspension was refluxed at 90 C for 3 h. After cooling, saturated aqueous ammonium chloride (75 mL) was added and ethanol was removed in vacuo. Water was added until all white solid was dissolved.The aqueous layer was extracted with ethyl acetate (450 mL) and the combined organic layers were dried over anhydrous Na2SO4. The solvent was removed in vacuo to yielda white solid
75% With sodium tetrahydroborate In ethanol for 3 h; Reflux To a suspension of compound 4 (6.0 g, 22.0 mmol) in 200 ml of absolute ethanol was added 16.4 g (0.434 mol) of sodium borohydride. The mixture was refluxed for 3 h and cooled to room temperature, and then 200 mL of an ammonium chloride saturated water solution was added to decompose the excess borohydride. The reaction mixture was evaporated to removed the ethanol, and a minimal amount of water was added to dissolve the precipitated solid. The resulting solution was extracted with ethyl acetate (5 × 200 mL), dried overMgSO4, and evaporated to dryness product 5 (3.56 g, 75percent yield).

Reference: [1] Chemical Communications, 2009, # 48, p. 7545 - 7547
[2] Electrochimica Acta, 2016, vol. 207, p. 313 - 320
[3] Journal of Physical Chemistry B, 1999, vol. 103, # 38, p. 8067 - 8079
[4] Patent: CN105793241, 2016, A, . Location in patent: Paragraph 0129; 0159
[5] Tetrahedron, 2014, vol. 70, # 36, p. 6271 - 6275
[6] Dalton Transactions, 2015, vol. 44, # 12, p. 5577 - 5586
[7] Polyhedron, 2013, vol. 57, p. 52 - 56
[8] Inorganic Chemistry, 2017, vol. 56, # 3, p. 1366 - 1374
[9] Tetrahedron Letters, 2010, vol. 51, # 47, p. 6161 - 6165
[10] Journal of Chemical Sciences, 2011, vol. 123, # 1, p. 37 - 46
[11] Inorganic Chemistry, 2015, vol. 54, # 9, p. 4512 - 4519
[12] Journal of the American Chemical Society, 2012, vol. 134, # 2, p. 968 - 978
[13] Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy, 2016, vol. 165, p. 150 - 154
[14] Green Chemistry, 2014, vol. 16, # 9, p. 4179 - 4189
[15] Chemistry - A European Journal, 2017, vol. 23, # 72, p. 18239 - 18251
  • 3
  • [ 71071-46-0 ]
  • [ 109073-77-0 ]
Reference: [1] Tetrahedron Asymmetry, 2013, vol. 24, # 8, p. 515 - 525
[2] Chemical Communications, 2010, vol. 46, # 13, p. 2256 - 2258
[3] Helvetica Chimica Acta, 2018, vol. 101, # 5,
[4] Journal of Heterocyclic Chemistry, 1990, vol. 27, # 2, p. 163 - 165
[5] Chemical Communications, 2015, vol. 51, # 53, p. 10746 - 10749
[6] Tetrahedron Letters, 1990, vol. 31, # 35, p. 5069 - 5072
[7] Angewandte Chemie - International Edition, 2013, vol. 52, # 38, p. 9956 - 9960[8] Angew. Chem., 2013,
[9] Chemical Communications, 2015, vol. 51, # 27, p. 5840 - 5843
[10] Chemical Communications, 2016, vol. 52, # 46, p. 7398 - 7401
[11] Journal of the American Chemical Society, 2007, vol. 129, # 18, p. 5919 - 5925
[12] Tetrahedron Letters, 1997, vol. 38, # 25, p. 4389 - 4392
[13] Polymer, 2011, vol. 52, # 15, p. 3318 - 3324
[14] Patent: CN106188151, 2016, A, . Location in patent: Paragraph 0023; 0025; 0029
  • 4
  • [ 1134-35-6 ]
  • [ 109073-77-0 ]
Reference: [1] Journal of the American Chemical Society, 2007, vol. 129, # 18, p. 5919 - 5925
[2] Heterocycles, 2002, vol. 56, # 1-2, p. 157 - 170
[3] Tetrahedron Letters, 1990, vol. 31, # 35, p. 5069 - 5072
[4] Journal of Heterocyclic Chemistry, 1990, vol. 27, # 2, p. 163 - 165
[5] Journal of Chemical Sciences, 2011, vol. 123, # 1, p. 37 - 46
[6] Journal of the American Chemical Society, 2012, vol. 134, # 2, p. 968 - 978
[7] Tetrahedron Asymmetry, 2013, vol. 24, # 8, p. 515 - 525
[8] Angewandte Chemie - International Edition, 2013, vol. 52, # 38, p. 9956 - 9960[9] Angew. Chem., 2013,
[10] Green Chemistry, 2014, vol. 16, # 9, p. 4179 - 4189
[11] Chemical Communications, 2015, vol. 51, # 27, p. 5840 - 5843
[12] Chemical Communications, 2016, vol. 52, # 46, p. 7398 - 7401
[13] Tetrahedron, 2014, vol. 70, # 36, p. 6271 - 6275
[14] Chemical Communications, 2015, vol. 51, # 53, p. 10746 - 10749
[15] Dalton Transactions, 2015, vol. 44, # 12, p. 5577 - 5586
[16] Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy, 2016, vol. 165, p. 150 - 154
[17] Patent: CN105294773, 2016, A, . Location in patent: Paragraph 0031; 0033
[18] Patent: CN105793241, 2016, A,
[19] Patent: CN106188151, 2016, A,
[20] Chemistry - A European Journal, 2017, vol. 23, # 72, p. 18239 - 18251
[21] Helvetica Chimica Acta, 2018, vol. 101, # 5,
  • 5
  • [ 6813-38-3 ]
  • [ 109073-77-0 ]
Reference: [1] Journal of the American Chemical Society, 2007, vol. 129, # 18, p. 5919 - 5925
[2] Tetrahedron Letters, 1990, vol. 31, # 35, p. 5069 - 5072
[3] Journal of Heterocyclic Chemistry, 1990, vol. 27, # 2, p. 163 - 165
[4] Journal of Chemical Sciences, 2011, vol. 123, # 1, p. 37 - 46
[5] Journal of the American Chemical Society, 2012, vol. 134, # 2, p. 968 - 978
[6] Polymer, 2011, vol. 52, # 15, p. 3318 - 3324
[7] Tetrahedron Asymmetry, 2013, vol. 24, # 8, p. 515 - 525
[8] Polyhedron, 2013, vol. 57, p. 52 - 56
[9] Angewandte Chemie - International Edition, 2013, vol. 52, # 38, p. 9956 - 9960[10] Angew. Chem., 2013,
[11] Green Chemistry, 2014, vol. 16, # 9, p. 4179 - 4189
[12] Tetrahedron, 2014, vol. 70, # 36, p. 6271 - 6275
[13] Chemical Communications, 2015, vol. 51, # 53, p. 10746 - 10749
[14] Dalton Transactions, 2015, vol. 44, # 12, p. 5577 - 5586
[15] Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy, 2016, vol. 165, p. 150 - 154
[16] Patent: CN105793241, 2016, A,
[17] Chemical Communications, 2016, vol. 52, # 46, p. 7398 - 7401
[18] Inorganic Chemistry, 2017, vol. 56, # 3, p. 1366 - 1374
[19] Patent: CN106188151, 2016, A,
[20] Chemistry - A European Journal, 2017, vol. 23, # 72, p. 18239 - 18251
[21] Helvetica Chimica Acta, 2018, vol. 101, # 5,
  • 6
  • [ 99970-84-0 ]
  • [ 109073-77-0 ]
Reference: [1] European Journal of Inorganic Chemistry, 2001, # 4, p. 1019 - 1029
[2] Angewandte Chemie - International Edition, 2013, vol. 52, # 38, p. 9956 - 9960[3] Angew. Chem., 2013,
  • 7
  • [ 279681-06-0 ]
  • [ 109073-77-0 ]
Reference: [1] Heterocycles, 2002, vol. 56, # 1-2, p. 157 - 170
[2] Tetrahedron Letters, 2000, vol. 41, # 16, p. 2787 - 2789
  • 8
  • [ 134457-14-0 ]
  • [ 109073-77-0 ]
Reference: [1] Tetrahedron Letters, 2000, vol. 41, # 16, p. 2787 - 2789
[2] Tetrahedron Letters, 2000, vol. 41, # 16, p. 2787 - 2789
  • 9
  • [ 138219-98-4 ]
  • [ 109073-77-0 ]
Reference: [1] Tetrahedron Letters, 2000, vol. 41, # 16, p. 2787 - 2789
  • 10
  • [ 72460-28-7 ]
  • [ 109073-77-0 ]
Reference: [1] Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy, 2016, vol. 165, p. 150 - 154
[2] Inorganic Chemistry, 2017, vol. 56, # 3, p. 1366 - 1374
  • 11
  • [ 199282-52-5 ]
  • [ 109073-77-0 ]
Reference: [1] Tetrahedron Letters, 2000, vol. 41, # 16, p. 2787 - 2789
[2] Tetrahedron Letters, 2000, vol. 41, # 16, p. 2787 - 2789
  • 12
  • [ 87855-83-2 ]
  • [ 109073-77-0 ]
Reference: [1] Heterocycles, 2002, vol. 56, # 1-2, p. 157 - 170
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