Home Cart 0 Sign in  
X

[ CAS No. 13026-23-8 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
3d Animation Molecule Structure of 13026-23-8
Chemical Structure| 13026-23-8
Chemical Structure| 13026-23-8
Structure of 13026-23-8 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Quality Control of [ 13026-23-8 ]

Related Doc. of [ 13026-23-8 ]

Alternatived Products of [ 13026-23-8 ]

Product Details of [ 13026-23-8 ]

CAS No. :13026-23-8 MDL No. :MFCD00014010
Formula : C15H12O2 Boiling Point : -
Linear Structure Formula :- InChI Key :DMJDEZUEYXVYNO-DHZHZOJOSA-N
M.W : 224.25 Pubchem ID :5842785
Synonyms :

Calculated chemistry of [ 13026-23-8 ]

Physicochemical Properties

Num. heavy atoms : 17
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.0
Num. rotatable bonds : 3
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 68.55
TPSA : 37.3 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) : -5.0 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.14
Log Po/w (XLOGP3) : 3.76
Log Po/w (WLOGP) : 3.34
Log Po/w (MLOGP) : 3.32
Log Po/w (SILICOS-IT) : 3.45
Consensus Log Po/w : 3.2

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -3.92
Solubility : 0.0267 mg/ml ; 0.000119 mol/l
Class : Soluble
Log S (Ali) : -4.24
Solubility : 0.013 mg/ml ; 0.000058 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -4.38
Solubility : 0.00924 mg/ml ; 0.0000412 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 2.21

Safety of [ 13026-23-8 ]

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 [ 13026-23-8 ]

* 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 [ 13026-23-8 ]
  • Downstream synthetic route of [ 13026-23-8 ]

[ 13026-23-8 ] Synthesis Path-Upstream   1~17

  • 1
  • [ 13026-23-8 ]
  • [ 35888-99-4 ]
Reference: [1] Journal of Medicinal Chemistry, 2012, vol. 55, # 2, p. 824 - 836
[2] Bioorganic and Medicinal Chemistry Letters, 2005, vol. 15, # 5, p. 1333 - 1336
  • 2
  • [ 64-19-7 ]
  • [ 3218-36-8 ]
  • [ 13026-23-8 ]
YieldReaction ConditionsOperation in experiment
99%
Stage #1: With titanium tetrachloride In dichloromethane at 25℃; for 0.333333 h; Inert atmosphere
Stage #2: With triethylamine In dichloromethane at 25℃; Inert atmosphere
General procedure: To a mixture of an aldehyde (0.1 mol) and acetic acid(0.1 mol) in dichloromethane (15 mL) was added TiCl4 (0.21 mol). The resulting reaction mixture was stirred at room temperature for 20 min under nitrogen atmosphere. To this was added Et3N (0.25 mol) dropwise over aperiod of 10 min and the mixture was stirred for further 3-4 h at room temperature. When the reaction was complete as confirmed by TLC, the mixture was diluted with water (25 mL) and the organic layer was separated. The organic phase was dried over anhydrous Na2SO4 and evaporated under reduced pressure to afford the corresponding (E)-α,β-unsaturated carboxylicacid (1) in excellent yield and purity.
Reference: [1] Tetrahedron Letters, 2014, vol. 55, # 24, p. 3503 - 3506
  • 3
  • [ 141-82-2 ]
  • [ 3218-36-8 ]
  • [ 13026-23-8 ]
YieldReaction ConditionsOperation in experiment
75% Reflux General procedure: A solution of suitably substituted carbaldehyde (200mmol), propenedioic acid (20.8g, 200mmol) in pyridine (10mL, 120mmol) and piperidine (1mL) was warmed at reflux for 2h. The resultant solution was poured into 2M HCl aq. and cooled to room temperature. The solid was filtered, washed with water and recrystallized in ethanol/water
Reference: [1] European Journal of Medicinal Chemistry, 2018, vol. 149, p. 56 - 68
[2] Bioorganic and Medicinal Chemistry, 2018, vol. 26, # 20, p. 5479 - 5493
[3] Journal of the American Chemical Society, 1957, vol. 79, p. 3514,3516
[4] Bioorganic and Medicinal Chemistry Letters, 2005, vol. 15, # 5, p. 1333 - 1336
[5] Bioorganic and Medicinal Chemistry, 2010, vol. 18, # 14, p. 4991 - 4996
[6] Journal of Organic Chemistry, 2018, vol. 83, # 7, p. 4190 - 4196
  • 4
  • [ 20883-99-2 ]
  • [ 13026-23-8 ]
YieldReaction ConditionsOperation in experiment
84% With potassium hydroxide In tetrahydrofuran; methanol for 3 h; Reflux Step 2: To a suspension of 3-biphenyl-4-yl-acrylic acid methyl ester (9.384 g, 39.38 mmol) in THF (120 ml) and MeOH (80 ml) was added 1N KOH (79 ml) and the mixture refluxed. After 3 h, heating was stopped. The reaction mixture was concentrated to about 50 ml, diluted with water (200 ml) and acidified with 2N HCl (80 ml). EtOAc (1000 ml) was added and the whole mixture heated to boiling to dissolve all solids. After cooling, the layers were separated and the organic layer washed with 1N HCl (2.x.70 ml), water (3.x.70 ml), brine (2.x.50 ml), dried over Na2SO4, filtered, concentrated and dried to give 3-biphenyl-4-yl-acrylic acid (7.393 g, 32.966 mmol, 84percent) as a white solid, dec. 223-226° C. 1H NMR (DMSO-d6) δ 6.58 (d, 1H), 7.37-7.53 (m, 3H), 7.62 (d, 1H), 7.70-7.84 (m, 6H), 12.40 (s, 1H); mass spectrum [ES(-)], m/z 223 (M-H)-.
Reference: [1] Patent: US2005/70584, 2005, A1, . Location in patent: Page/Page column 25
  • 5
  • [ 81069-41-2 ]
  • [ 13026-23-8 ]
Reference: [1] Tetrahedron, 1997, vol. 53, # 17, p. 6045 - 6056
  • 6
  • [ 558-13-4 ]
  • [ 2350-89-2 ]
  • [ 13026-23-8 ]
Reference: [1] RSC Advances, 2017, vol. 7, # 19, p. 11233 - 11243
  • 7
  • [ 141-82-2 ]
  • [ 3218-36-8 ]
  • [ 13026-23-8 ]
  • [ 63974-15-2 ]
Reference: [1] Tetrahedron, 2002, vol. 58, # 37, p. 7449 - 7461
  • 8
  • [ 1667-11-4 ]
  • [ 13026-23-8 ]
Reference: [1] Journal of the American Chemical Society, 1957, vol. 79, p. 3514,3516
  • 9
  • [ 3218-36-8 ]
  • [ 13026-23-8 ]
Reference: [1] Journal of the Chemical Society, 1931, p. 2476,2477
[2] RSC Advances, 2017, vol. 7, # 19, p. 11233 - 11243
  • 10
  • [ 76985-08-5 ]
  • [ 13026-23-8 ]
Reference: [1] ChemCatChem, 2018, vol. 10, # 12, p. 2627 - 2633
  • 11
  • [ 644-08-6 ]
  • [ 13026-23-8 ]
Reference: [1] Chemische Berichte, 1935, vol. 68, p. 453
[2] Journal of the Chemical Society, 1931, p. 2476,2477
[3] Journal of the Chemical Society, 1931, p. 2476,2477
  • 12
  • [ 113538-22-0 ]
  • [ 13026-23-8 ]
Reference: [1] Tetrahedron Letters, 2008, vol. 49, # 3, p. 543 - 547
  • 13
  • [ 6287-94-1 ]
  • [ 13026-23-8 ]
Reference: [1] Journal of the Chemical Society, 1931, p. 2476,2477
  • 14
  • [ 108-24-7 ]
  • [ 3218-36-8 ]
  • [ 13026-23-8 ]
  • [ 79913-05-6 ]
Reference: [1] Journal of the Chemical Society, 1931, p. 2476,2477
[2] Chemische Berichte, 1939, vol. 72, p. 1064,1067
  • 15
  • [ 141-78-6 ]
  • [ 3218-36-8 ]
  • [ 13026-23-8 ]
Reference: [1] Chemische Berichte, 1935, vol. 68, p. 453
  • 16
  • [ 623-11-0 ]
  • [ 35888-99-4 ]
  • [ 13026-23-8 ]
Reference: [1] Chemische Berichte, 1933, vol. 66, p. 1464,1467
  • 17
  • [ 13026-23-8 ]
  • [ 155760-02-4 ]
Reference: [1] ChemCatChem, 2018, vol. 10, # 12, p. 2627 - 2633
Same Skeleton Products
Historical Records

Related Functional Groups of
[ 13026-23-8 ]

Aryls

Chemical Structure| 1866-39-3

[ 1866-39-3 ]

3-(p-Tolyl)acrylic acid

Similarity: 0.93

Chemical Structure| 28010-12-0

[ 28010-12-0 ]

(2E,4E)-5-Phenylpenta-2,4-dienoic acid

Similarity: 0.93

Chemical Structure| 140-10-3

[ 140-10-3 ]

(2E)-2-Phenyl-2-propenoic acid

Similarity: 0.93

Chemical Structure| 940-61-4

[ 940-61-4 ]

(E)-3-(p-Tolyl)acrylic acid

Similarity: 0.93

Chemical Structure| 16089-48-8

[ 16089-48-8 ]

Potassium cinnamate

Similarity: 0.90

Alkenes

Chemical Structure| 1866-39-3

[ 1866-39-3 ]

3-(p-Tolyl)acrylic acid

Similarity: 0.93

Chemical Structure| 28010-12-0

[ 28010-12-0 ]

(2E,4E)-5-Phenylpenta-2,4-dienoic acid

Similarity: 0.93

Chemical Structure| 140-10-3

[ 140-10-3 ]

(2E)-2-Phenyl-2-propenoic acid

Similarity: 0.93

Chemical Structure| 940-61-4

[ 940-61-4 ]

(E)-3-(p-Tolyl)acrylic acid

Similarity: 0.93

Chemical Structure| 16089-48-8

[ 16089-48-8 ]

Potassium cinnamate

Similarity: 0.90

Carboxylic Acids

Chemical Structure| 1866-39-3

[ 1866-39-3 ]

3-(p-Tolyl)acrylic acid

Similarity: 0.93

Chemical Structure| 28010-12-0

[ 28010-12-0 ]

(2E,4E)-5-Phenylpenta-2,4-dienoic acid

Similarity: 0.93

Chemical Structure| 140-10-3

[ 140-10-3 ]

(2E)-2-Phenyl-2-propenoic acid

Similarity: 0.93

Chemical Structure| 940-61-4

[ 940-61-4 ]

(E)-3-(p-Tolyl)acrylic acid

Similarity: 0.93

Chemical Structure| 130036-17-8

[ 130036-17-8 ]

2-Formylcinnamic acid

Similarity: 0.88