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[ CAS No. 18962-05-5 ] {[proInfo.proName]}

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Chemical Structure| 18962-05-5
Chemical Structure| 18962-05-5
Structure of 18962-05-5 * Storage: {[proInfo.prStorage]}
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Product Details of [ 18962-05-5 ]

CAS No. :18962-05-5 MDL No. :
Formula : C10H12O2 Boiling Point : -
Linear Structure Formula :- InChI Key :WDANSDASCKBVKH-UHFFFAOYSA-N
M.W : 164.20 Pubchem ID :250077
Synonyms :

Calculated chemistry of [ 18962-05-5 ]

Physicochemical Properties

Num. heavy atoms : 12
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 : 47.94
TPSA : 26.3 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) : 2.12
Log Po/w (XLOGP3) : 2.56
Log Po/w (WLOGP) : 2.29
Log Po/w (MLOGP) : 1.74
Log Po/w (SILICOS-IT) : 2.49
Consensus Log Po/w : 2.24

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.64
Solubility : 0.374 mg/ml ; 0.00228 mol/l
Class : Soluble
Log S (Ali) : -2.76
Solubility : 0.285 mg/ml ; 0.00174 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.9
Solubility : 0.207 mg/ml ; 0.00126 mol/l
Class : Soluble

Medicinal Chemistry

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

Safety of [ 18962-05-5 ]

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 [ 18962-05-5 ]

* 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 [ 18962-05-5 ]
  • Downstream synthetic route of [ 18962-05-5 ]

[ 18962-05-5 ] Synthesis Path-Upstream   1~8

  • 1
  • [ 75-30-9 ]
  • [ 123-08-0 ]
  • [ 18962-05-5 ]
YieldReaction ConditionsOperation in experiment
77% With Ki; potassium carbonate In hexane; ethyl acetate; N,N-dimethyl-formamide REFERENCE EXAMPLE 3
4-Isopropoxybenzaldehyde
To a solution of 2 g (16.38 mmol) of 4-hydroxybenzaldehyde in 100 mL of DMF, 2.72 g (19.69 mmol) of K2CO3, 2.74 g (16.52 mmol) of KI and 3.94 mL (39.38 mmol) of 2-iodopropane was added under argon.
The mixture was stirred at 80° C. overnight, concentrated and the residue obtained was partitioned between CHCl3 and H2O.
The phases were separated, the aqueous phase was extracted with CHCl3 and the combined organic phases were dried over MgSO4 and concentrated.
The crude product obtained was purified by chromatography on silica gel using EtOAc/hexane mixtures of increasing polarity as eluent, to give 2.08 g of the title compound of the example as an oil (77percent yield).
1H-NMR (300 MHz, CDCl3 δ TMS): 1.39 (d, J=6 Hz, 6H), 4.67 (m, 1H), 6.96 (d, J=8.7 Hz, 2H), 7.81 (d, J=8.7 Hz, 2H), 9.87 (s, 1H).
Reference: [1] Patent: US2003/176481, 2003, A1,
[2] Journal fuer Praktische Chemie (Leipzig), 1940, vol. <2>155, p. 332,340
[3] Patent: US4622342, 1986, A,
[4] CrystEngComm, 2016, vol. 18, # 2, p. 222 - 229
  • 2
  • [ 123-08-0 ]
  • [ 75-26-3 ]
  • [ 18962-05-5 ]
Reference: [1] Synthesis, 2011, # 16, p. 2671 - 2683
[2] Synthesis (Germany), 2012, vol. 44, # 24, p. 3757 - 3764
[3] Macromolecules, 2012, vol. 45, # 17, p. 6840 - 6849,10
[4] Molecules, 2015, vol. 20, # 7, p. 12512 - 12524
[5] Tetrahedron, 2003, vol. 59, # 18, p. 3315 - 3321
[6] Russian Journal of General Chemistry, 2005, vol. 75, # 7, p. 1113 - 1124
[7] Chemical and Pharmaceutical Bulletin, 2010, vol. 58, # 5, p. 752 - 754
[8] Organic and Biomolecular Chemistry, 2013, vol. 11, # 4, p. 549 - 554
[9] Tetrahedron, 2013, vol. 69, # 2, p. 933 - 941
[10] Chemistry - A European Journal, 2018, vol. 24, # 12, p. 2832 - 2836
  • 3
  • [ 683-60-3 ]
  • [ 104-88-1 ]
  • [ 18962-05-5 ]
YieldReaction ConditionsOperation in experiment
75% With hemicucurbituril supported [Bmim]Cl In toluene for 10 h; Reflux General procedure: A mixture of aryl halide (1 mmol) and sodium alkoxide(3.0 mmol) was refluxed in the presence of 200 mg ofHmCucSILP catalyst in toluene (5 mL) for an appropriatetime as indicated in Table 2. After completion of thereaction, the reaction mixture was filtered and solvent wasevaporated in vacuo to give the crude product, which waspurified by column chromatography over silica gel usinghexane/EtOAc as the eluent.
Reference: [1] Catalysis Letters, 2016, vol. 146, # 12, p. 2485 - 2494
  • 4
  • [ 683-60-3 ]
  • [ 15164-44-0 ]
  • [ 18962-05-5 ]
YieldReaction ConditionsOperation in experiment
76% With hemicucurbituril supported [Bmim]Cl In toluene for 8 h; Reflux General procedure: A mixture of aryl halide (1 mmol) and sodium alkoxide(3.0 mmol) was refluxed in the presence of 200 mg ofHmCucSILP catalyst in toluene (5 mL) for an appropriatetime as indicated in Table 2. After completion of thereaction, the reaction mixture was filtered and solvent wasevaporated in vacuo to give the crude product, which waspurified by column chromatography over silica gel usinghexane/EtOAc as the eluent.
Reference: [1] Catalysis Letters, 2016, vol. 146, # 12, p. 2485 - 2494
  • 5
  • [ 683-60-3 ]
  • [ 1122-91-4 ]
  • [ 18962-05-5 ]
YieldReaction ConditionsOperation in experiment
72% With hemicucurbituril supported [Bmim]Cl In toluene for 10 h; Reflux General procedure: A mixture of aryl halide (1 mmol) and sodium alkoxide(3.0 mmol) was refluxed in the presence of 200 mg ofHmCucSILP catalyst in toluene (5 mL) for an appropriatetime as indicated in Table 2. After completion of thereaction, the reaction mixture was filtered and solvent wasevaporated in vacuo to give the crude product, which waspurified by column chromatography over silica gel usinghexane/EtOAc as the eluent.
Reference: [1] Catalysis Letters, 2016, vol. 146, # 12, p. 2485 - 2494
  • 6
  • [ 459-57-4 ]
  • [ 67-63-0 ]
  • [ 18962-05-5 ]
Reference: [1] Synthetic Communications, 2010, vol. 40, # 14, p. 2122 - 2129
  • 7
  • [ 100-97-0 ]
  • [ 40141-12-6 ]
  • [ 18962-05-5 ]
Reference: [1] Journal fuer Praktische Chemie (Leipzig), 1956, vol. <4> 3, p. 274,275
  • 8
  • [ 18962-05-5 ]
  • [ 82657-71-4 ]
YieldReaction ConditionsOperation in experiment
97% With hydrogen In methanol at 20℃; for 4.1 h; General procedure: A mixture of 1a (196 mg, 1 mmol) and 1percentPd/Ni bimetallic catalyst9 (60 mg, 30 wt percent) in MeOH (10 mL) was stirred underH2 at room temperature and atmospheric pressure (on an atmosphericpressure hydrogenation apparatus) until the absorption of hydrogen ceased(3.5 h). After the catalyst was removed off by a magnetic stirring bar, thesolution was evaporated in a vaporator to give the product 2a
81%
Stage #1: With sodium tetrahydroborate In methanol at 0 - 35℃; for 4 h;
Stage #2: With hydrogenchloride; water In methanol
Reference Example 110
(4-Isopropoxyphenyl)methanol
With ice cooling, to a solution of 4-isopropoxybenzaldehyde (0.93 g, 5.6 mmol) in methanol (20 mL) was added a solution of sodium tetrahydroborate (0.32 g, 11 mmol) in methanol (10 mL), and the mixture was stirred at room temperature for 4 hours.
The mixture was acidified by adding 2 N hydrochloric acid to the reaction solution, and extracted with diethyl ether.
The extract was washed with water, and then concentrated under reduced pressure.
The residue was purified with silica gel column chromatography (hexane/ethyl acetate = 7: 3) to give the title compound (0.76 g, yield 81percent) as an oily matter.
1H NMR: 1.33 (6H, d, J=6.1), 4.55 (1H, quintet, J=6.1), 4.61 (2H, s), 6.85-6.91 (2H, m), 7.25-7.30 (2H, m).
Reference: [1] Tetrahedron Letters, 2015, vol. 56, # 46, p. 6460 - 6462
[2] ChemMedChem, 2016, vol. 11, # 13, p. 1415 - 1427
[3] Patent: EP1688138, 2006, A1, . Location in patent: Page/Page column 106
[4] Tetrahedron, 2013, vol. 69, # 2, p. 933 - 941
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